TURNING POINT BRANDS, INC.

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			Page No.
PART I—FINANCIAL INFORMATION

	ITEM 1	Financial Statements (Unaudited)

		Consolidated Balance Sheets as of June 30, ~~2022,~~2023, and December 31, ~~2021~~2022	56

		Consolidated Statements of Income for the three months ended June 30, ~~2022~~2023 and ~~2021~~2022	67

		Consolidated Statements of Income for the six months ended June 30, ~~2022~~2023 and ~~2021~~2022	78

		Consolidated Statements of Comprehensive Income for the three months ended June 30, 2023 and 2022	9

		Consolidated Statements of Comprehensive Income for the six months ended June 30, ~~2022~~2023 and ~~2021~~2022	89

		Consolidated Statements of Cash Flows for the six months ended June 30, ~~2022~~2023 and ~~2021~~2022	910

		Consolidated Statements of Changes in Stockholders’ Equity for the three months ended June 30, ~~2022~~2023 and ~~2021~~2022	1011

		Consolidated Statements of Changes in Stockholders’ Equity for the six months ended June 30, ~~2022~~2023 and ~~2021~~2022	11

		Notes to Consolidated Financial Statements	12

	ITEM 2	Management’s Discussion and Analysis of Financial Condition and Results of Operations	3735

	ITEM 3	Quantitative and Qualitative Disclosures about Market Risk	4846

	ITEM 4	Controls and Procedures	4846

PART II—OTHER INFORMATION

	ITEM 1	Legal Proceedings	4947

	ITEM 1A	Risk Factors	4947

	ITEM 2	Unregistered Sales of Equity Securities and Use of Proceeds	4948

	ITEM 3	Defaults Upon Senior Securities	4948

	ITEM 4	Mine Safety Disclosures	4948

	ITEM 5	Other Information	4948

	ITEM 6	Exhibits	5049

	Signatures		5150

Cautionary Note Regarding Forward-Looking Statements

This Quarterly Report on Form 10-Q contains forward-looking statements within the meaning of the federal securities laws. Forward-looking statements may generally be identified by the use of words such as “anticipate,” “believe,” “expect,” “intend,” “plan,” and “will” or, in each case, their negative, or other variations or comparable terminology. These forward-looking statements include all matters that are not historical facts. By their nature, forward-looking statements involve risks and uncertainties because they relate to events, and depend on circumstances, that may or may not occur in the future. As a result, actual events may differ materially from those expressed in, or suggested by, the forward-looking statements. Any forward-looking statement made by Turning Point Brands, Inc. (“TPB”), in this Quarterly Report on Form 10-Q speaks only as of the date hereof. New risks and uncertainties ~~arise~~come up from time to time, and it is impossible for TPB to predict these events or how they may affect it. TPB has no obligation, and does not intend, to update any forward-looking statements after the date hereof, except as required by federal securities laws. Factors that could cause these differences include, but are not limited to:

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declining sales of tobacco products, and expected continuing decline of sales, in the tobacco industry overall;

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our dependence on a small number of third-party suppliers and producers;

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the possibility that we will be unable to identify or contract with new suppliers or producers in the event of a supply or product disruption, as well as other supply chain concerns, including delays in product shipments and increases in freight cost;

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the possibility that our licenses to use certain brands or trademarks will be terminated, challenged or restricted;

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failure to maintain consumer brand recognition and loyalty of our customers;

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our reliance on relationships with several large retailers and national chains for distribution of our products;

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intense competition and our ability to compete effectively;

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competition from illicit sources and the damage caused by illicit products to brand equity;

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contamination of our tobacco supply or products;

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uncertainty and continued evolution of the markets for our ~~NewGen and cigar~~Creative Distribution Solutions products;

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complications with the design or implementation of our new enterprise resource planning system could adversely impact our business and operations;

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substantial and increasing U.S. regulation;

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regulation or marketing denials of our products by the ~~FDA,~~U.S. Food and Drug Administration, which has broad regulatory powers;

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many of our products contain nicotine, which is considered to be a highly addictive substance;

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requirement to maintain compliance with master settlement agreement escrow ~~agreement;~~account;

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possible significant increases in federal, state and local municipal tobacco- and vapor-related taxes;

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our products are subject to developing and unpredictable regulation, such as court actions that impact obligations;

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increase in state and local regulation of our ~~NewGen~~Creative Distribution Solutions products has been proposed or enacted;

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increase in tax of our ~~NewGen~~Creative Distribution Solutions products could adversely affect our business;

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sensitivity of end-customers to increased sales taxes and economic conditions including significant increases in the rate of inflation and other declines in purchasing power;

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uncertainty surrounding FDA compliance policy;

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possible increasing international control and regulation;

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failure to comply with environmental, health and safety regulations;

●

imposition of significant tariffs on imports into the U.S.;

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the scientific community’s lack of information regarding the long-term health effects of certain substances contained in some of our products;

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significant product liability litigation;

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~~the effect of the COVID-19 pandemic on our business;~~

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our amount of indebtedness;

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the terms of our indebtedness, which may restrict our current and future operations;

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our ability to comply with required disclosure requirements;

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identification of a material ~~weakness~~weaknesses in our internal control ~~related to ineffective information technology general controls~~over financial reporting, which, if not remediated appropriately or timely, could result in loss of investor confidence and adversely impact our stock price;

●

~~Changes in the method for determining LIBOR or the replacement of LIBOR with an alternative reference rate, may adversely affect interest expense related to outstanding debt;~~

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our certificate of incorporation and bylaws, as well as Delaware law and certain regulations, could discourage or prohibit acquisition bids or merger proposals, which may adversely affect the market price of our common stock;

●

our certificate of incorporation limits the ownership of our common stock by individuals and entities that are Restricted Investors. These restrictions may affect the liquidity of our common stock and may result in Restricted Investors (as defined in our Certificate of Incorporation) being required to sell or redeem their shares at a loss or relinquish their voting, dividend and distribution rights;

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future sales of our common stock in the public market could reduce our stock price, and any additional capital raised by us through the sale of equity or convertible securities may dilute your ownership in us;

●

we may issue preferred stock whose terms could adversely affect the voting power or value of our common stock;

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our business may be damaged by events outside of our suppliers’ control, such as the impact of epidemics (e.g., coronavirus), political upheavals, or natural disasters;

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adverse impact of climate change;

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our reliance on information technology;

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cybersecurity and privacy breaches;

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failure to manage our growth;

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failure to successfully integrate our acquisitions or otherwise be unable to benefit from pursuing acquisitions;

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fluctuations in our results;

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exchange rate fluctuations;

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adverse U.S. and global economic conditions;

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departure of key management personnel or our inability to attract and retain talent;

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infringement on or misappropriation of our intellectual property;

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third-party claims that we infringe on their intellectual property; and

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failure to meet expectations ~~relating~~relating to environmental, social and governance factors.

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PART I—FINANCIAL INFORMATION

Item 1. Financial Statements

Turning Point Brands, Inc.

Consolidated Balance Sheets

(dollars in thousands except share data)

							(unaudited)
							June 30,			December 31,
ASSETS	(unaudited) June 30, 2022			December 31, 2021			2023			2022
Current assets:
Cash	$	107,429		$	128,320		$	100,507		$	106,403
Accounts receivable, net of allowances of $161 in 2022 and $262 in 2021		9,177			6,496
Accounts receivable, net of allowances of $103 in 2023 and $114 in 2022								7,920			8,377
Inventories		115,129			87,607			125,056			119,915
Other current assets		27,353			26,746			18,216			22,959
Total current assets		259,088			249,169			251,699			257,654
Property, plant, and equipment, net		22,376			18,650			24,128			22,788
Deferred income taxes		2,111			1,363			7,966			8,443
Right of use assets		13,749			15,053			10,923			12,465
Deferred financing costs, net		335			388			229			282
Goodwill		162,385			162,333			136,244			136,253
Other intangible assets, net		86,566			87,485			82,048			83,592
Master Settlement Agreement (MSA) escrow deposits		29,224			31,720			28,229			27,980
Other assets		28,475			35,399			18,208			22,649
Total assets	$	604,309		$	601,560		$	559,674		$	572,106

LIABILITIES AND STOCKHOLDERS’ EQUITY
Current liabilities:
Accounts payable	$	14,436		$	7,361		$	10,802		$	8,355
Accrued liabilities		34,560			32,937			30,898			33,001
Other current liabilities		38			38			5			20
Total current liabilities		49,034			40,336			41,705			41,376
Notes payable and long-term debt		415,410			414,172			379,195			406,757
Lease liabilities		11,934			13,336			9,528			10,593
Total liabilities		476,378			467,844			430,428			458,726

Commitments and contingencies

Stockholders’ equity:
Preferred stock; $0.01 par value; authorized shares 40,000,000; issued and outstanding shares -0-		0			0			-			-
Common stock, voting, $0.01 par value; authorized shares, 190,000,000; 19,797,735 issued shares and 17,890,441 outstanding shares at June 30, 2022, and 19,690,884 issued shares and 18,395,476 outstanding shares at December 31, 2021		198			197
Common stock, voting, $0.01 par value; authorized shares, 190,000,000; 19,912,039 issued shares and 17,595,579 outstanding shares at June 30, 2023, and 19,801,623 issued shares and 17,485,163 outstanding shares at December 31, 2022								199			198
Common stock, nonvoting, $0.01 par value; authorized shares, 10,000,000; issued and outstanding shares -0-		0			0			-			-
Additional paid-in capital		110,563			108,811			115,272			113,242
Cost of repurchased common stock (1,907,294 shares at June 30, 2022, and 1,295,408 shares at December 31, 2021)		(68,287	)		(48,869	)
Cost of repurchased common stock (2,316,460 shares at June 30, 2023 and December 31, 2022)								(78,093	)		(78,093	)
Accumulated other comprehensive loss		(2,064	)		(195	)		(3,181	)		(2,393	)
Accumulated earnings		85,641			71,460			93,873			78,691
Non-controlling interest		1,880			2,312			1,176			1,735
Total stockholders’ equity		127,931			133,716			129,246			113,380
Total liabilities and stockholders’ equity	$	604,309		$	601,560		$	559,674		$	572,106

The accompanying notes are an integral part of the consolidated financial statements.

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Turning Point Brands, Inc.

Consolidated Statements of Income

(dollars in thousands except share data)

(unaudited)

	Three Months Ended June 30,						Three Months Ended June 30,
	2022			2021			2023			2022

Net sales	$	102,925		$	122,643		$	105,595		$	102,925
Cost of sales		51,456			62,670			53,117			51,456
Gross profit		51,469			59,973			52,478			51,469
Selling, general, and administrative expenses		33,323			35,094			31,933			33,323
Operating income		18,146			24,879			20,545			18,146
Interest expense, net		5,144			5,522			4,019			5,144
Investment loss (income)		6,227			(110	)
Investment loss								4,080			6,227
Gain on extinguishment of debt								(600	)		-
Income before income taxes		6,775			19,467			13,046			6,775
Income tax expense		1,569			4,424			3,338			1,569
Consolidated net income		5,206			15,043			9,708			5,206
Net loss attributable to non-controlling interest		(218	)		(312	)		(217	)		(218	)
Net income attributable to Turning Point Brands, Inc.	$	5,424		$	15,355		$	9,925		$	5,424

Basic income per common share:
Net income attributable to Turning Point Brands, Inc.	$	0.30		$	0.81		$	0.56		$	0.30
Diluted income per common share:
Net income attributable to Turning Point Brands, Inc.	$	0.30		$	0.73		$	0.53		$	0.30
Weighted average common shares outstanding:
Basic		18,063,259			18,975,522			17,584,241			18,063,259
Diluted		21,443,279			22,489,662			20,409,943			21,443,279

The accompanying notes are an integral part of the consolidated financial statements.

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Turning Point Brands, Inc.

Consolidated Statements of Income

(dollars in thousands except share data)

(unaudited)

	Six Months Ended June 30,						Six Months Ended June 30,
	2022			2021			2023			2022

Net sales	$	203,819		$	230,284		$	206,551		$	203,819
Cost of sales		100,556			117,050			105,456			100,556
Gross profit		103,263			113,234			101,095			103,263
Selling, general, and administrative expenses		65,888			64,006			62,708			65,888
Operating income		37,375			49,228			38,387			37,375
Interest expense, net		10,340			10,009			8,029			10,340
Investment loss (income)		6,149			(135	)
Loss on extinguishment of debt		0			5,706
Investment loss								8,879			6,149
Gain on extinguishment of debt								(1,377	)		-
Income before income taxes		20,886			33,648			22,856			20,886
Income tax expense		4,909			7,078			5,806			4,909
Consolidated net income		15,977			26,570			17,050			15,977
Net loss attributable to non-controlling interest		(445	)		(567	)		(472	)		(445	)
Net income attributable to Turning Point Brands, Inc.	$	16,422		$	27,137		$	17,522		$	16,422

Basic income per common share:
Net income attributable to Turning Point Brands, Inc.	$	0.90		$	1.43		$	1.00		$	0.90
Diluted income per common share:
Net income attributable to Turning Point Brands, Inc.	$	0.86		$	1.30		$	0.94		$	0.86
Weighted average common shares outstanding:
Basic		18,159,940			19,034,415			17,556,030			18,159,940
Diluted		21,603,113			22,559,087			20,538,947			21,603,113

The accompanying notes are an integral part of the consolidated financial statements.

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Turning Point Brands, Inc.

Consolidated Statements of Comprehensive Income

(dollars in thousands)

(unaudited)

	Three Months Ended June 30,					Three Months Ended June 30,
	2022			2021		2023			2022
Consolidated net income	$	5,206		$	15,043	$	9,708		$	5,206

Other comprehensive income (loss), net of tax
Unrealized (loss) gain on MSA investments, net of tax of $244 in 2022 and $83 in 2021		(768	)		260
Foreign currency translation, net of tax of $0 in 2022 and 2021		45			642
Unrealized gain on derivative instruments, net of tax of $0 in 2022 and $126 in 2021		0			178
Unrealized loss on MSA investments, net of tax of $116 in 2023 and $244 in 2022							(365	)		(768	)
Foreign currency translation, net of tax of $0 in 2023 and 2022							(169	)		45
Unrealized loss on derivative instruments, net of tax of $150 in 2023 and $0 in 2022							(472	)		-
		(723	)		1,080		(1,006	)		(723	)
Consolidated comprehensive income		4,483			16,123		8,702			4,483
Comprehensive income (loss) attributable to non-controlling interest		(203	)		9
Comprehensive loss attributable to non-controlling interest							(217	)		(203	)
Comprehensive income attributable to Turning Point Brands, Inc.	$	4,686		$	16,114	$	8,919		$	4,686

	Six Months Ended June 30,						Six Months Ended June 30,
	2022			2021			2023			2022
Consolidated net income	$	15,977		$	26,570		$	17,050		$	15,977

Other comprehensive income (loss), net of tax
Unrealized loss on MSA investments, net of tax of $602 in 2022 and $61 in 2021		(1,894	)		(192	)
Foreign currency translation, net of tax of $0 in 2022 and 2021		38			960
Unrealized gain on derivative instruments, net of tax of $0 in 2022 and $810 in 2021		0			2,626
Unrealized gain (loss) on MSA investments, net of tax of $60 in 2023 and $602 in 2022								188			(1,894	)
Foreign currency translation, net of tax of $0 in 2023 and 2022								(248	)		38
Unrealized loss on derivative instruments, net of tax of $259 in 2023 and $0 in 2022								(815	)		-
		(1,856	)		3,394			(875	)		(1,856	)
Consolidated comprehensive income		14,121			29,964			16,175			14,121
Comprehensive loss attributable to non-controlling interest		(432	)		(87	)		(472	)		(432	)
Comprehensive income attributable to Turning Point Brands, Inc.	$	14,553		$	30,051		$	16,647		$	14,553

The accompanying notes are an integral part of the consolidated financial statements.

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Turning Point Brands, Inc.

Consolidated Statements of Cash Flows

(dollars in thousands)

(unaudited)

	Six Months Ended June 30,						Six Months Ended June 30,
	2022			2021			2023			2022
Cash flows from operating activities:
Consolidated net income	$	15,977		$	26,570		$	17,050		$	15,977
Adjustments to reconcile net income to net cash provided by operating activities:
Loss on extinguishment of debt		0			5,706
Gain on sale of property, plant, and equipment		(8	)		(2	)
Gain on extinguishment of debt								(1,377	)		-
Loss (gain) on sale of property, plant, and equipment								44			(8	)
Depreciation expense		1,750			1,546			1,535			1,750
Amortization of other intangible assets		919			954			1,542			919
Amortization of deferred financing costs		1,291			1,251			1,225			1,291
Deferred income tax (benefit) expense		(146	)		1,027
Deferred income tax expense (benefit)								659			(146	)
Stock compensation expense		2,661			4,263			2,836			2,661
Noncash lease income		(6	)		(19	)		(29	)		(6	)
Loss (gain) on investments		6,258			(34	)
Loss on investments								8,989			6,258
Changes in operating assets and liabilities:
Accounts receivable		(2,673	)		3,955			456			(2,673	)
Inventories		(27,499	)		(12,007	)		(5,146	)		(27,499	)
Other current assets		(598	)		813			3,769			(598	)
Other assets		624			599			(4,548	)		624
Accounts payable		7,240			1,423			2,500			7,240
Accrued liabilities and other		1,359			1,370			(1,972	)		1,359
Net cash provided by operating activities	$	7,149		$	37,415		$	27,533		$	7,149

Cash flows from investing activities:
Capital expenditures	$	(5,694	)	$	(2,170	)	$	(2,993	)	$	(5,694	)
Acquisitions, net of cash acquired		0			(3,419	)
Payments for investments		0			(8,657	)
Restricted cash, MSA escrow deposits		(10,078	)		(20,147	)	$	-		$	(10,078	)
Proceeds on the sale of property, plant and equipment		63			2			3			63
Net cash used in investing activities	$	(15,709	)	$	(34,391	)	$	(2,990	)	$	(15,709	)

Cash flows from financing activities:
Proceeds from Senior Secured Notes	$	0		$	250,000
Payments of 2018 first lien term loan		0			(130,000	)
Settlement of interest rate swaps		0			(3,573	)
Convertible Senior Notes repurchased							$	(27,357	)	$	-
Proceeds from call options								70			-
Payment of dividends		(2,181	)		(2,006	)		(2,209	)		(2,181	)
Payments of financing costs		0			(6,921	)
Exercise of options		475			886			406			475
Redemption of options		(155	)		(2,111	)		(346	)		(155	)
Redemption of performance restricted stock units		(1,228	)		0			(995	)		(1,228	)
Common stock repurchased		(19,418	)		(14,086	)		-			(19,418	)
Net cash provided by (used in) financing activities	$	(22,507	)	$	92,189
Net cash used in financing activities							$	(30,431	)	$	(22,507	)

Net (decrease) increase in cash	$	(31,067	)	$	95,213
Net decrease in cash							$	(5,888	)	$	(31,067	)
Effect of foreign currency translation on cash	$	56		$	315		$	(8	)	$	56

Cash, beginning of period:
Unrestricted		128,320			41,765			106,403			128,320
Restricted		15,155			35,074			4,929			15,155
Total cash at beginning of period		143,475			76,839			111,332			143,475

Cash, end of period:
Unrestricted		107,429			157,474			100,507			107,429
Restricted		5,035			14,893			4,929			5,035
Total cash at end of period	$	112,464		$	172,367		$	105,436		$	112,464

Supplemental schedule of noncash investing activities:
Accrued capital expenditures	$	19		$	242		$	42		$	19

Supplemental schedule of noncash financing activities:
Dividends declared not paid	$	1,110		$	1,241		$	1,188		$	1,110
Accrued consideration for acquisition	$	0		$	402

The accompanying notes are an integral part of the consolidated financial statements.

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Turning Point Brands, Inc.

Consolidated Statements of Changes in Stockholders’ Equity

For the Three and Six Months Ended June 30, ~~2022~~2023 and ~~2021~~2022

(dollars in thousands except share data)

(unaudited)

												Accumulated																							Accumulated
				Common		Additional			Cost of			Other						Non-									Common		Additional			Cost of			Other						Non-
	Voting			Stock,		Paid-In			Repurchased			Comprehensive			Accumulated			Controlling						Voting			Stock,		Paid-In			Repurchased			Comprehensive			Accumulated			Controlling
																								Shares			Voting		Capital			Common Stock			Income (Loss)			Earnings			Interest			Total

Beginning balance April 1, 2023																									17,585,529		$	199	$	113,477		$	(78,093	)	$	(2,234	)	$	85,133		$	1,452		$	119,934

Unrealized loss on MSA investments, net of tax of $116																									-			-		-			-			(365	)		-			-			(365	)
Unrealized loss on derivative instruments, net of tax of $150																									-			-		-			-			(472	)		-			-			(472	)
Foreign currency translation, net of tax of $0																									-			-		-			-			(110	)		-			(59	)		(169	)
Stock compensation expense																									-			-		2,093			-			-			-			-			2,093
Exercise of options																									4,416			-		49			-			-			-			-			49
Redemption of options																									(15,985	)		-		(346	)		-			-			-			-			(346	)
Performance restricted stock units issuance																									26,050			-		78			-			-			-			-			78
Performance restricted stock units redeemed																									(4,431	)		-		(105	)		-			-			-			-			(105	)
Settlement of call options, net of tax of $9																									-			-		26			-			-			-			-			26
Dividends																									-			-		-			-			-			(1,185	)		-			(1,185	)
Net income																									-			-		-			-			-			9,925			(217	)		9,708
Ending balance June 30, 2023																									17,595,579		$	199	$	115,272		$	(78,093	)	$	(3,181	)	$	93,873		$	1,176		$	129,246
	Shares			Voting		Capital			Common Stock			Income (Loss)			Earnings			Interest			Total

Beginning balance April 1, 2022		18,180,174		$	198	$	109,073		$	(59,491	)	$	(1,326	)	$	81,327		$	2,083		$	131,864			18,180,174		$	198	$	109,073		$	(59,491	)	$	(1,326	)	$	81,327		$	2,083		$	131,864

Unrealized loss on MSA investments, net of tax of $244		-			0		0			0			(768	)		0			0			(768	)		-			-		-			-			(768	)		-			-			(768	)
Foreign currency translation, net of tax of $0		-			0		0			0			30			0			15			45			-			-		-			-			30			-			15			45
Stock compensation expense		-			0		1,502			0			0			0			0			1,502			-			-		1,502			-			-			-			-			1,502
Exercise of options		7,175			0		230			0			0			0			0			230			7,175			-		230			-			-			-			-			230
Redemption of options		-			0		(155	)		0			0			0			0			(155	)		-			-		(155	)		-			-			-			-			(155	)
Performance restricted stock units issuance		4,754			0		0			0			0			0			0			0			4,754			-		-			-			-			-			-			-
Redemption of restricted stock units		-			0		(87	)		0			0			0			0			(87	)
Performance restricted stock units redeemed																									-			-		(87	)		-			-			-			-			(87	)
Cost of repurchased common stock		(301,662	)		0		0			(8,796	)		0			0			0			(8,796	)		(301,662	)		-		-			(8,796	)		-			-			-			(8,796	)
Dividends		-			0		0			0			0			(1,110	)		0			(1,110	)		-			-		-			-			-			(1,110	)		-			(1,110	)
Net income		-			0		0			0			0			5,424			(218	)		5,206			-			-		-			-			-			5,424			(218	)		5,206
Ending balance June 30, 2022		17,890,441		$	198	$	110,563		$	(68,287	)	$	(2,064	)	$	85,641		$	1,880		$	127,931			17,890,441		$	198	$	110,563		$	(68,287	)	$	(2,064	)	$	85,641		$	1,880		$	127,931


Beginning balance April 1, 2021		19,059,120		$	196	$	102,879		$	(15,924	)	$	(480	)	$	34,357		$	3,954		$	124,982

Unrealized gain on MSA investments, net of tax of $83		-			0		0			0			260			0			0			260
Unrealized gain on derivative instruments, net of tax of $126		-			0		0			0			178			0			0			178
Foreign currency translation, net of tax of $0		-			0		0			0			321			0			321			642
Stock compensation expense		-			0		2,764			0			0			0			0			2,764
Exercise of options		39,403			0		462			0			0			0			0			462
Redemption of options		-			0		(645	)		0			0			0			0			(645	)
Cost of repurchased common stock		(175,000	)		0		0			(8,353	)		0			0			0			(8,353	)
Dividends		-			0		0			0			0			(1,065	)		0			(1,065	)
Net income		-			0		0			0			0			15,355			(312	)		15,043
Ending balance June 30, 2021		18,923,523		$	196	$	105,460		$	(24,277	)	$	279		$	48,647		$	3,963		$	134,268

~~The accompanying notes are an integral part of the consolidated financial statements.~~

~~Table of Contents~~

~~Turning Point Brands, Inc.~~

~~Consolidated Statements of Changes in Stockholders’ Equity~~

~~For the Six Months Ended June 30, 2022 and 2021~~

~~(dollars in thousands except share data)~~

~~(unaudited)~~

												Accumulated																							Accumulated
				Common		Additional			Cost of			Other						Non-									Common		Additional			Cost of			Other						Non-
	Voting			Stock,		Paid-In			Repurchased			Comprehensive			Accumulated			Controlling						Voting			Stock,		Paid-In			Repurchased			Comprehensive			Accumulated			Controlling
																								Shares			Voting		Capital			Common Stock			Income (Loss)			Earnings			Interest			Total
Beginning balance January 1, 2023																									17,485,163		$	198	$	113,242		$	(78,093	)	$	(2,393	)	$	78,691		$	1,735		$	113,380

Unrealized gain on MSA investments, net of tax of $60																									-			-		-			-			188			-			-			188
Unrealized loss on derivative instruments, net of tax of $259																									-			-		-			-			(815	)		-			-			(815	)
Foreign currency translation, net of tax of $0																									-			-		-			-			(161	)		-			(87	)		(248	)
Stock compensation expense																									-			-		2,836			-			-			-			-			2,836
Exercise of options																									29,371			-		406			-			-			-			-			406
Redemption of options																									(15,985	)		-		(346	)		-			-			-			-			(346	)
Performance restricted stock units issuance																									140,324			1		77			-			-			-			-			78
Performance restricted stock units redeemed																									(43,294	)		-		(995	)		-			-			-			-			(995	)
Settlement of call options, net of tax of $17																									-			-		52			-			-			-			-			52
Dividends																									-			-		-			-			-			(2,340	)		-			(2,340	)
Net income																									-			-		-			-			-			17,522			(472	)		17,050
Ending balance June 30, 2023																									17,595,579		$	199	$	115,272		$	(78,093	)	$	(3,181	)	$	93,873		$	1,176		$	129,246
	Shares			Voting		Capital			Common Stock			Income (Loss)			Earnings			Interest			Total

Beginning balance January 1, 2022		18,395,476		$	197	$	108,811		$	(48,869	)	$	(195	)	$	71,460		$	2,312		$	133,716			18,395,476		$	197	$	108,811		$	(48,869	)	$	(195	)	$	71,460		$	2,312		$	133,716

Unrealized loss on MSA investments, net of tax of $602		-			0		0			0			(1,894	)		0			0			(1,894	)		-			-		-			-			(1,894	)		-			-			(1,894	)
Foreign currency translation, net of tax of $0		-			0		0			0			25			0			13			38			-			-		-			-			25			-			13			38
Stock compensation expense		-			0		2,661			0			0			0			0			2,661			-			-		2,661			-			-			-			-			2,661
Exercise of options		32,341			0		475			0			0			0			0			475			32,341			-		475			-			-			-			-			475
Redemption of options		-			0		(155	)		0			0			0			0			(155	)		-			-		(155	)		-			-			-			-			(155	)
Issuance of performance restricted stock units		74,510			1		(1	)		0			0			0			0			0
Redemption of performance restricted stock units		-			0		(1,141	)		0			0			0			0			(1,141	)
Performance restricted stock units issuance																									74,510			1		(1	)		-			-			-			-			-
Performance restricted stock units redeemed																									-			-		(1,141	)		-			-			-			-			(1,141	)
Redemption of restricted stock units		-			0		(87	)		0			0			0			0			(87	)		-			-		(87	)		-			-			-			-			(87	)
Cost of repurchased common stock		(611,886	)		0		0			(19,418	)		0			0			0			(19,418	)		(611,886	)		-		-			(19,418	)		-			-			-			(19,418	)
Dividends		-			0		0			0			0			(2,241	)		0			(2,241	)		-			-		-			-			-			(2,241	)		-			(2,241	)
Net income		-			0		0			0			0			16,422			(445	)		15,977			-			-		-			-			-			16,422			(445	)		15,977
Ending balance June 30, 2022		17,890,441		$	198	$	110,563		$	(68,287	)	$	(2,064	)	$	85,641		$	1,880		$	127,931			17,890,441		$	198	$	110,563		$	(68,287	)	$	(2,064	)	$	85,641		$	1,880		$	127,931


Beginning balance January 1, 2021		19,133,794		$	195	$	102,423		$	(10,191	)	$	(2,635	)	$	23,645		$	4,050		$	117,487

Unrealized loss on MSA investments, net of tax of $61		-			0		0			0			(192	)		0			0			(192	)
Unrealized gain on derivative instruments, net of tax of $810		-			0		0			0			2,626			0			0			2,626
Foreign currency translation, net of tax of $0		-			0		0			0			480			0			480			960
Stock compensation expense		-			0		4,263			0			0			0			0			4,263
Exercise of options		83,760			1		885			0			0			0			0			886
Redemption of options		-			0		(2,111	)		0			0			0			0			(2,111	)
Cost of repurchased common stock		(294,031	)		0		0			(14,086	)		0			0			0			(14,086	)
Dividends		-			0		0			0			0			(2,135	)		0			(2,135	)
Net income		-			0		0			0			0			27,137			(567	)		26,570
Ending balance June 30, 2021		18,923,523		$	196	$	105,460		$	(24,277	)	$	279		$	48,647		$	3,963		$	134,268

The accompanying notes are an integral part of the consolidated financial statements.

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Turning Point Brands, Inc.

Notes to Consolidated Financial Statements

(dollars in thousands, except where designated and per share data)

Note 1. Description of Business and Basis of Presentation

Description of Business

T~~urning~~

Turning Point Brands, Inc. and its subsidiaries (collectively referred to herein as the “Company,” “we,” “our,” or “us”) is a leading manufacturer, marketer and distributor of branded consumer products. The Company sells a wide range of products to adult consumers consisting of staple products with its iconic brands Zig-Zag^®and Stoker’s^®and its next generation products to fulfill evolving consumer preferences. ~~The Company’s~~ 3 ~~focus~~Its segments are led by its core, proprietary brands: Zig-Zag^® and CLIPPER^® in the Zig-Zag Products segment; Stoker’s^® along with Beech-Nut^® and Trophy^® in the Stoker’s Products ~~segment; and its distribution platforms (~~segment.~~Vapor Beast~~^®~~, VaporFi~~^® ~~and~~ ~~Direct Vapor~~^®)~~and~~ ~~Solace~~^® ~~in the NewGen Products segment.~~The Company’s products are available in more than 217~~215,000~~,000 retail outlets in North America. The Company operates in 3three segments: (i) Zig-Zag Products, (ii) Stoker’s Products, and (iii) ~~NewGen Products.~~Creative Distribution Solutions (formerly known as NewGen).

Basis of Presentation

TheThe accompanying unaudited interim, consolidated financial statements have been prepared in accordance with the accounting practices described in the Company’s audited, consolidated financial statements as of and for the year ended December 31, ~~2021, included in its Annual Report on Form 10-K for the year then ended.~~2022. In the opinion of management, the unaudited, interim, consolidated financial statements included herein contain all adjustments necessary to present fairly the financial position, results of operations, and cash flows of the Company for the periods indicated. Such adjustments, other than nonrecurring adjustments separately disclosed, are of a normal and recurring nature. The operating results for interim periods are not necessarily indicative of results to be expected for a full year or future interim periods. The unaudited, interim, consolidated financial statements should be read in conjunction with the Company’s audited, consolidated financial statements and accompanying notes as of and for the year ended December 31, ~~2021.~~2022. The accompanying interim, consolidated financial statements are presented in accordance with the rules and regulations of the Securities and Exchange Commission (the “SEC”) and, accordingly, do not include all the disclosures required by generally accepted accounting principles in the United States (“GAAP”) with respect to annual financial ~~statements.~~statements.

Note 2. Summary of Significant Accounting Policies

Consolidation

The consolidated financial statements include the accounts of the Company, its subsidiaries, all of which are wholly-owned, and variable interest entities (“VIEs”) for which the Company is considered the primary beneficiary. All significant intercompany transactions have been eliminated.

Revenue Recognition

The Company recognizes revenues in accordance with Accounting Standards Codification (“ASC”) 606, Revenue from Contracts with Customers (Topic 606), which includes excise taxes and shipping and handling charges billed to customers, net of cash discounts for prompt payment, sales returns and incentives, upon delivery of goods to the customer – at which time the Company’s performance obligation is satisfied - at an amount that the Company expects to be entitled to in exchange for those goods in accordance with the five-step analysis outlined in Topic 606: (i) identify the contract with the customer, (ii) identify the performance obligations in the contract, (iii) determine the transaction price, (iv) allocate the transaction price to the performance obligations, and (v) recognize revenue when (or as) performance obligations are satisfied. The Company excludes from the transaction price, sales taxes and value-added taxes imposed at the time of sale (which do not include excise taxes on smokeless tobacco, cigars or vaping products billed to customers).

The Company records an allowance for sales returns, based principally on historical volume and return rates, which is included in accrued liabilities on the consolidated balance sheets. The Company records sales incentives, which consist of consumer incentives and trade promotion activities, as a reduction in revenues (a portion of which is based on amounts estimated ~~as being~~to be due to wholesalers, retailers and consumers at the end of the period) based principally on historical volume and utilization rates. Expected payments for sales incentives are included in accrued liabilities on the consolidated balance sheets.

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A further requirement of ASC 606 is for entities to disaggregate revenue recognized from contracts with customers into categories that depict how the nature, amount, timing, and uncertainty of revenue and cash flows are affected by economic factors. The Company’s management views business performance through segments that closely resemble the performance of major product lines. Thus, the primary and most useful disaggregation of the Company’s contract revenue for decision making purposes is the disaggregation by segment which can be found in Note ~~17.~~16, “Segment Information”. An additional disaggregation of contract revenue by sales channel can be found within Note 1716 as well.

~~Table of Contents~~

Shipping Costs

The Company records shipping costs incurred as a component of selling, general, and administrative expenses. Shipping costs incurred were approximately ~~$6.0~~$5.7 million and ~~$8.1~~ $6.0 million for the three months ~~ended~~ ending June 30, 2023 and 2022, ~~and 2021,~~ respectively. Shipping costs incurred were approximately ~~$12.1~~$11.9 million and ~~$14.1~~$12.1 million for the six months ~~ended~~ending June 30, 2023 and 2022, ~~and 2021,~~ respectively.

Inventories

~~Inventories~~

Inventories are stated at the lower of cost or net realizable value using the ~~first-in, first-out~~first-in, first-out (“FIFO”) method. Leaf tobacco is presented in current assets in accordance with standard industry practice, notwithstanding the fact that such tobaccos are carried longer than one year for the purpose of curing.

Fair Value

GAAP establishes a framework for measuring fair value. That framework provides a fair value hierarchy that prioritizes the inputs to valuation techniques used to measure fair value. The hierarchy gives the highest priority to unadjusted quoted prices in active markets for identical assets or liabilities ~~(level~~(Level 1) and the lowest priority to unobservable inputs ~~(level~~(Level 3).

The three levels of the fair value hierarchy under GAAP are described below:

●

Level 1 – Inputs to the valuation methodology are unadjusted quoted prices for identical assets or liabilities in active markets at the measurement date.

●

Level 2 – Inputs to the valuation methodology include quoted prices for similar assets or liabilities in active markets, quoted prices for identical or similar assets or liabilities in inactive markets, inputs other than quoted prices that are observable for the asset or liability, and inputs that are derived principally from or corroborated by observable market data by correlation or other means.

●

Level 3 – Unobservable inputs that reflect management’s best estimate of what market participants would use in pricing the asset or liability at the measurement date.

Derivative Instruments

~~Foreign Currency Forward Contracts:~~The ~~Company~~Company enters into foreign currency ~~forward~~forward contracts to hedge a portion of its exposure to changes in foreign currency exchange rates on inventory purchase commitments. The Company accounts for its forward contracts under the provisions of ASC 815, Derivatives and Hedging. Under the Company’s policy, the Company may hedge up to 100% of its anticipated purchases of inventory in the denominated invoice currency over a ~~forward~~forward period not to exceed twelve months. The Company may also, from time to time, hedge up to ~~90percent~~100% of its non-inventory purchases in the denominated invoice currency. Forward contracts that qualify as hedges are adjusted to their fair value through other comprehensive income as determined by market prices on the measurement date, except any hedge ineffectiveness which is recognized currently in income. Gains and losses on these forward contracts are ~~transferred~~reclassified from other comprehensive income into inventory as the related inventories are received and are transferred to net income as inventory is sold. Changes in fair value of any contracts that do not qualify for hedge accounting or are not designated as hedges are recognized currently in income.

~~Interest Rate Swap Agreements:~~ The Company enters into interest rate swap contracts to manage interest rate risk and reduce the volatility of future cash flows. The Company accounts for its interest rate swap contracts under the provisions of ASC 815, Derivatives and Hedging. Swap contracts that qualify as hedges are adjusted to their fair value through other comprehensive income as determined by market prices on the measurement date, except any hedge ineffectiveness which is recognized currently in income. Gains and losses on these swap contracts are transferred from other comprehensive income into net income upon settlement of the derivative position or at maturity of the interest rate swap contract. Changes in fair value of any contracts that do not qualify for hedge accounting or are not designated as hedges are recognized currently in income.

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Risks and Uncertainties

Manufacturers and sellers of tobacco products are subject to regulation at the federal, state, and local levels. Such regulations include, among others, labeling requirements, limitations on advertising, and prohibition of sales to minors. The tobacco industry is likely to continue to be heavily regulated. There can be no assurance as to the ultimate content, timing, or effect of any regulation of tobacco products by any federal, state, or local legislative or regulatory body, nor can there be any assurance that any such legislation or regulation would not have a material adverse effect on the Company’s financial position, results of operations, or cash flows. In a number of states, targeted flavor bans have been proposed or enacted legislatively or by the administrative process. Depending on the number and location of such bans, that legislation or regulation could have a material adverse effect on the Company’s financial position, results of operations or cash flows. The U.S. Food and Drug Administration (“FDA”) continues to consider various restrictive regulations around our products, including targeted flavor bans; however, the details, timing, and ultimate implementation of such measures remain unclear.

The tobacco industry has experienced, and is experiencing, significant product liability litigation. Most tobacco liability lawsuits have been brought against manufacturers and sellers of cigarettes for injuries allegedly caused by smoking or exposure to smoke. However, several lawsuits have been brought against manufacturers and sellers of smokeless products for injuries to health allegedly caused by use of smokeless products. Typically, such claims assert that use of smokeless products is addictive and causes oral cancer. Additionally, several lawsuits have been brought against manufacturers and distributors of ~~NewGen~~Creative Distribution Solutions products due to malfunctioning devices. There can be no assurance the Company will not sustain losses in connection with such lawsuits and that such losses will not have a material adverse effect on the Company’s financial position, results of operations, or cash flows.

Master Settlement Agreement (MSA): Pursuant to the Master Settlement Agreement (the “MSA”) entered into in November 1998 by most states (represented by their attorneys general acting through the National Association of Attorneys General) and subsequent states’ statutes, a “cigarette manufacturer” (which is defined to include a manufacturer of make-your-own (“MYO”) cigarette tobacco) has the option of either becoming a signatory to the MSA or opening, funding, and maintaining an escrow account to have funds available for certain potential tobacco-related liabilities with sub-accounts on behalf of each settling state. Such companies are entitled to direct the investment of the escrowed funds and withdraw any appreciation but cannot withdraw the principal for twenty-five years from the year of each annual deposit, except to withdraw funds deposited pursuant to an individual state’s escrow statute to pay a final judgement to that state’s plaintiffs in the event of such a final judgement against the Company. The Company chose to open and fund an escrow account as its method of compliance. It is the Company’s policy to record amounts on deposit in the escrow account for prior years as a non-current asset.As of June 30, 2023, the Company had on deposit approximately $32.1 million, the fair value of which was approximately $28.2 million. At December 31, 2022, the Company had on deposit approximately $32.1 million, the fair value of which was approximately ~~$29.2 million. At December 31, 2021, the Company had on deposit approximately $32.1 million, the fair value of which was approximately $31.7~~$28.0 million. The Company discontinued its generic category of MYO in 2019 and its Zig-Zagbranded MYO cigarette smoking tobacco in 2017. Thus, pending a change in MSA legislation, the Company has no remaining product lines covered by the MSA and will not be required to make future escrow deposits.

The Company has chosen to invest a portion of the MSA escrow, from time to time, in U.S. Government securities including TIPS, Treasury Notes, and Treasury Bonds. These investments are classified as available-for-sale and carried at fair value. Realized losses are prohibited under the MSA; any investment in an unrealized loss position will be held until the value is recovered, or until maturity.

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Fair values for the U.S. Governmental agency obligations are Level 2 in the fair value hierarchy. The following tables show cost and estimated fair value of the assets held in the MSA account, respectively, as well as the maturities of the U.S. Governmental agency obligations held in such account for the periods indicated.

	As of June 30, 2023							As of December 31, 2022
			Gross			Estimated				Gross			Estimated
			Unrealized			Fair				Unrealized			Fair
	Cost		Losses			Value		Cost		Losses			Value
Cash and cash equivalents	$	1,929	$	-		$	1,929	$	1,929	$	-		$	1,929
U.S. Governmental agency obligations (unrealized position < 12 months)		746		(59	)		687		10,226		(1,251	)		8,975
U.S. Governmental agency obligations (unrealized position > 12 months)		29,398		(3,785	)		25,613		19,918		(2,842	)		17,076
	$	32,073	$	(3,844	)	$	28,229	$	32,073	$	(4,093	)	$	27,980

As of June 30, 2022
As of December 31, 2021
Cost
Gross
Unrealized
Gains

Gross
Unrealized
Losses

Estimated
Fair
Value
Cost

Gross
Unrealized
Gains

Gross
Unrealized
Losses

Estimated
Fair
Value

Cash and cash equivalents $ 2,035 $ 0 $ 0 $ 2,035 $ 12,155 $ 0 $ 0 $ 12,155
U.S. Governmental agency obligations
(unrealized position < 12 months)
21,090 0 (1,772 ) 19,318 19,918
4 (357 ) 19,565
U.S. Governmental agency obligations
(unrealized position > 12 months)
8,948 0 (1,077 ) 7,871 0 0 0 0
$ 32,073 $ 0 $ (2,849 ) $ 29,224 $ 32,073 $
4 $
(357 ) $
31,720

	As of		As of
	June 30, 2022		June 30, 2023
Less than one year	$	0	$	2,199
One to five years		7,443		9,242
Five to ten years		20,640		16,748
Greater than ten years		1,955		1,955
Total	$	30,038	$	30,144

The following ~~table~~ shows the amount of deposits by sales year for the MSA escrow account:

	Deposits as of				Deposits as of
Sales Year	June 30, 2022		December 31, 2021		June 30, 2023		December 31, 2022
1999	$	211	$	211	$	211	$	211
2000		1,017		1,017		1,017		1,017
2001		1,673		1,673		1,673		1,673
2002		2,271		2,271		2,271		2,271
2003		4,249		4,249		4,249		4,249
2004		3,714		3,714		3,714		3,714
2005		4,553		4,553		4,553		4,553
2006		3,847		3,847		3,847		3,847
2007		4,167		4,167		4,167		4,167
2008		3,364		3,364		3,364		3,364
2009		1,619		1,619		1,619		1,619
2010		406		406		406		406
2011		193		193		193		193
2012		199		199		199		199
2013		173		173		173		173
2014		143		143		143		143
2015		101		101		101		101
2016		91		91		91		91
2017		82		82		82		82

Total	$	32,073	$	32,073	$	32,073	$	32,073

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~~Food and Drug Administration (FDA):~~FDA: On June 22, 2009, the Family Smoking Prevention and Tobacco Control Act (the “~~FSPTCA~~”“FSPTCA”) authorized the FDA to immediately regulate the manufacturing, sale, and marketing of 4four categories of tobacco products – cigarettes, cigarette tobacco, roll-your-own tobacco, and smokeless tobacco. On August 8, 2016, the FDA deeming regulation became effective. The deeming regulation gave the FDA the authority to also regulate cigars, pipe tobacco, e-cigarettes, vaporizers, and e-liquids as “deemed” tobacco products under the FSPTCA.

The FDA currently assesses tobacco product user fees on ~~6 classes~~six classes of regulated tobacco products and computes user fees using a methodology similar to the methodology used by the U.S Department of Agriculture to compute the Tobacco Transition Payment Program (“TTPP,” also known as the “Tobacco Buyout”) assessment. First, the total, annual, congressionally established user fee assessment is allocated among the various classes of tobacco products using the federal excise tax weighted market share of tobacco products subject to regulation. Then, the assessment for each class of tobacco products is divided among individual manufacturers and ~~importers~~.importers.

In August 2016, the FDA’s regulatory authority under the Tobacco Control Act (the “TCA”) was extended to all tobacco products not previously covered, including: (i) certain ~~NewGen~~Creative Distribution Solutions products (such as electronic cigarettes, vaporizers and e-liquids) and their components or parts (such as tanks, coils and batteries);; (ii) cigars and their components or parts (such as cigar tobacco and wraps);; (iii) pipe ~~tobacco;~~tobacco; (iv) hookah ~~products;~~products; and (v) any other tobacco product “newly deemed” by the FDA. These “deeming regulations” apply to all products made or derived from tobacco intended for human consumption, but excluding accessories of tobacco products (such as lighters). Accordingly, the FDA has since regulated our cigar and cigar wrap products as well as our vapor products containing tobacco-derived nicotine and products intended or reasonably expected to be used to consume such e-liquids.

As a result of the deeming regulations, the FDA regulates our cigar and cigar wrap products as well as our vapor products containing tobacco-derived nicotine and products intended or reasonably expected to be used to consume.

Subsequently, on April 14, 2022, the FDA Center for Tobacco Products also obtained jurisdiction over non-tobacco nicotine products (“NTN Products”), including synthetic nicotine. ~~This~~That law subjects NTN Products to the same requirements as tobacco-derived products, including not selling these products to persons under 21 years of age, not marketing these products as modified risk tobacco products without authorization, and not distributing free samples of these products. Additionally, NTN Products became subject to premarket filing requirements. Under the new law, manufacturers were required to file a ~~PMTA~~Premarket Tobacco Application (“PMTA”) by May 14, 2022, in order to continue selling products currently on the market. NTN Products subject of a timely-filed PMTA, and not in receipt of a negative action, were allowed to remain on the market until July 13, 2022, at which time these products became subject to enforcement, similar to tobacco-derived products remaining under review.

A successful PMTA must demonstrate that the subject product is “appropriate for the protection of public health,” taking into account the effect of the marketing of the product on all sub-populations while a Substantial Equivalence Report must demonstrate that a new product either has the same characteristics as its predicate product or different characteristics but does not raise different questions of public health. We submitted premarket filings ~~prior to the September 9, 2020 deadline~~ for certain of our ~~tobacco and tobacco-derived~~regulated products ~~all of which~~in order to continue selling these products while they remain under review. ~~We likewise filed premarket submissions for certain of our NTN Products ahead of the May 14, 2022 deadline.~~ We have continued to supplement these applications with additional ~~information;~~information and have responded to information requests from the FDA; however, there can be no guarantee that the FDA will accept such amendments and responses or that the applications will meet the standard of “appropriate for the protection of public ~~health.~~health” or “substantially equivalent,” as appropriate. The FDA has indicated its enforcement priority is those applicants who have received negative action on their application, such as a Marketing Denial Order or Refuse to File notification and who continue to illegally sell those unauthorized products, as well as products for which manufacturers failed to submit a marketing application. Despite these stated enforcement priorities, given the FDA’s limited resources we expect that for a period of time there may be a lack of enforcement, which may adversely impact our ability to compete in the marketplace against those who continue to sell unauthorized products. There can be no guarantee that the FDA will not shift its enforcement priorities or that it will increase in ability to enforce against unauthorized products over time.

~~The FDA has issued a number of proposed rules related to premarket filings; however, those rules were not finalized prior to the September 9, 2020, filing deadline.~~

On October 5, 2021, the FDA finalized 2 two rules related to the Substantial Equivalence process and the ~~PMTA~~Premarket Tobacco Product Application process, respectively, which both became effective November 4, 2021. Both final rules (collectively, the “Rules”) indicate that any new or additional requirements will not retroactively apply to currently pending PMTAs for tobacco and tobacco-derived products; however, the information outlined in the rule remains important to the FDA’s substantive review of an application. The FDA has yet to indicate how it might apply these Rules to NTN Product filings. We believe we have products that meet the Rules and have filed premarket filings supporting a showing of the respective required standards. However, there is no assurance that the FDA’s guidance or regulations will not change, or that the FDA will not prioritize its enforcement in a manner that negatively affects our pending applications, or that unforeseen circumstances will not arise that prevent us from sufficiently supplementing or completing our applications or otherwise ~~increase~~increases the amount of time and money we are required to spend to receive all necessary marketing orders. Although we filed many premarket applications in a timely manner, no assurance can be given that the applications will ultimately be successful. This may result in the prioritization of supplementing or completing applications for high priority SKUs in our inventory position, which could adversely impact future revenues generated by lower priority SKUs.

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In addition, we currently distribute many third-party manufactured vapor products for which we ~~will be~~are completely dependent on the manufacturer complying with the premarket filing requirements. There can be no assurance that these third-party products will receive a marketing order or otherwise remain in compliance with relevant legal requirements. While we will take measures to pursue regulatory compliance for our own privately-branded or proprietary vape products that compete with these third-party products, there is no assurance that such proprietary products would be as successful in the marketplace or can fully displace third-party products that are currently being distributed by us, which could adversely affect our results of operations and liquidity. ~~For a period of time after the filing deadline, we expect there~~Additionally, FDA has limited resources, which may impact its ability to ~~be a lack of enforcement, which~~meaningfully enforce these provisions. This may adversely affect our ability to compete in the marketplace against those who continue to sell unauthorized ~~products.~~products; however, regulatory uncertainty in the FDA’s enforcement policies may likewise affect operations or sales of our proprietary products if the FDA’s policies or priorities shift.

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On May 4, 2022, the FDA proposed 2 two tobacco product standards related to combusted tobacco products: (1) a ban on menthol as a characterizing flavor in cigarettes; and (2) a ban on all characterizing flavors (including menthol) in cigars. On June 21, 2022, the FDA also issued a proposed product standard related to restricting the level of nicotine in traditional cigarettes. These product standards are required to go through the formal rulemaking process where we ~~would~~ have had the opportunity to ~~comment on the proposed rule~~provide comments with regard to ~~any~~the impact such standards would have on ~~any of~~ our products. These proposed rules remain pending. The FDA’s policy on these and other regulated products may change or expand over time in ways not yet known and may significantly impact our products or our premarket ~~filings~~filings.

Prevent All Cigarette Trafficking Act (“PACT Act”): On December 27, 2020, President Trump signed the Further Consolidated Appropriations Act, 2021, into law. This law included an amendment to the Jenkins Act expanding the definition of “cigarette” to include “electronic nicotine delivery systems,” or ENDS, and required that the United States Postal Service ~~(USPS)~~(“USPS”) promulgate regulations clarifying the applicability of the prohibition on delivery sales of cigarettes to ENDS. USPS issued its final rule on October 21, 2021. We have received appropriate shipping exemptions from carrier services we use to carry the affected freight. Failure to comply with the PACT Act could result in significant financial or criminal penalties. To the extent we are unable to respond to, or comply with, these new requirements, we could lose our shipping exemptions, be subject to civil or criminal penalties, or there could be a material adverse effect on our business, results of operations and financial condition.

~~Note 3. Acquisitions~~

~~Unitabac~~

In July 2021, the Company acquired certain assets of Unitabac, a marketer of mass-market cigars, for $10.7 million in total consideration, comprised of $9.6 million in cash and $1.1 million of capitalized transaction costs. The acquisition is comprised of a portfolio of cigarillo products and all related intellectual property, including Cigarillo Non-Tip (“NT”) Homogenized Tobacco Leaf (“HTL”) products and Rolled Leaf and Natural Leaf Cigarillo Products. The transaction was accounted for as an asset purchase with $10.0 million assigned to intellectual property, which has an indefinite life, and $0.7 million assigned to inventory. The intellectual property asset is deductible for tax purposes.

~~Direct Value Wholesale~~

In April 2021, Turning Point Brands Canada, a VIE for which the Company is considered the primary beneficiary, purchased 100% of the equity interests of Westhem Ventures LTD d/b/a Direct Value Wholesale (“DVW”) for $3.9 million, net of cash acquired, with $3.5 million paid in cash at closing and $0.5 million in accrued consideration to be paid during 2021. DVW is a Canadian distribution entity that operates in markets not primarily served by Turning Point Brands Canada. The acquisition expands Turning Point Brands Canada’s markets in Canada. On April 13, 2021, in connection with the acquisition of DVW, the Company provided a $3.7 million unsecured loan to Turning Point Brands Canada bearing interest at 8% per annum and maturing April 13, 2023. The unsecured loan is eliminated in the consolidation of Turning Point Brands Canada. The following table summarizes the consideration transferred and calculation of goodwill based on excess of the acquisition price over the estimated fair value of the identifiable net assets acquired:

Total consideration transferred $ 3,462
Adjustments to consideration transferred:
Cash acquired (43 )
Accrued consideration 472
Adjusted consideration transferred 3,891
Assets acquired:
Working capital (primarily AR and inventory) 1,334
Fixed assets and Other long term assets 27
Net assets acquired $ 1,361

Goodwill $ 2,530

~~The goodwill of $2.5 million consists of the synergies expected from combining the operations and is deductible for tax purposes.~~

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~~Turning Point Brands Canada~~

In July 2021, the Company invested an additional $2.3 million in Turning Point Brands Canada increasing its ownership interest to 65%. The Company received board seats aligned with its ownership position. The Company has determined that Turning Point Brands Canada continues to be a VIE due to its required subordinated financial support. The Company has determined it remains the primary beneficiary due to its 65% equity interest, additional subordinated financing and distribution agreement with Turning Point Brands Canada for the sale of the Company’s products. As a result of the Company remaining the primary beneficiary, the increase in ownership interest resulted in a decrease in Non-controlling interest of $1.1 million and a decrease in Additional paid-in capital of $1.1 million

Note 4.3. Derivative Instruments

Foreign Currency

The Company’s policy is to manage the risks associated with foreign exchange rate movements. The policy allows hedging of up to 100% of its anticipated purchases of inventory over a forward period that will not exceed 12 rolling and consecutive months. The Company may, from time to time, hedge currency for non-inventory purchases, e.g., production equipment, ~~not~~up to ~~exceed~~ ~~90%~~100% of the purchase price. At During the six months ended June 30, ~~2022 and December 31, 2021, the Company had 0 forward contracts outstanding.~~2023

~~Interest Rate Swaps~~

~~The Company’s policy is to manage interest rate risk relating to the volatility of future cash flows associated with debt instruments bearing interest at variable rates. In March 2018,~~, the Company executed various ~~interest rate swap agreements for a notional amount of $70 million with an expiration of December 2022. The swap agreements fixed LIBOR at 2.755%. The swap agreements~~foreign exchange contracts, which met ~~the~~ hedge accounting ~~requirements; thus, any change in~~requirements for the purchase of €10.9 million and the sale of €6.0 million.

At June 30, 2023, the Company had foreign currency contracts for the purchase of €10.9 million and sale of €6.0 million. The foreign currency contracts’ fair value ~~was recorded to other comprehensive income.~~at ~~The~~June 30, 2023, resulted in an asset of $0.2 million included in Other current assets and a liability of $0.1 million included in Accrued liabilities. At December 31, 2022, the Company ~~used the Shortcut Method to account~~had foreign currency contracts for the ~~swap agreements.~~purchase of €18.5 million and sale of €18.5 million. The ~~Shortcut Method assumes the hedge to be perfectly effective; thus, there is~~ no ~~ineffectiveness to be recorded~~foreign currency contracts’ fair value at December 31, 2022, resulted in ~~earnings. The Company terminated the interest rate swap agreement~~an asset of $1.2 million included in ~~conjunction with the prepayment~~Other current assets and a liability of ~~all outstanding amounts under the~~ ~~2018 First~~ ~~Lien Credit Facility (as defined below)~~$0.0 million included in ~~the~~ Accrued liabilities.~~first~~ ~~quarter of~~ ~~2021 with the early termination payment made by the Company~~ ~~in the amount of $3.6~~ ~~million which was reclassified out of accumulated other comprehensive loss into loss on extinguishment of debt.~~

Note 5.4. Fair Value of Financial Instruments

The estimated fair value amounts have been determined by the Company using the methods and assumptions described below. However, considerable judgment is required to interpret market data to develop estimates of fair value. Accordingly, the estimates presented herein are not necessarily indicative of the amounts the Company could realize in a current market exchange. The use of different market assumptions and/or estimation methodologies may have a material effect on the estimated fair value amounts.

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Cash and Cash Equivalents

Cash and cash equivalents are, by definition, short-term. Thus, the carrying amount is a reasonable estimate of fair value.

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Accounts Receivable

The fair value of accounts receivable approximates their carrying value due to their short-term nature.

Long-Term Debt

The Company’s Senior Secured Notes (as defined ~~below)~~in Note 10) bear interest at a rate of 5.625% per year. As of June 30, 2023, the fair value approximated $228.3 million, with a carrying value of $250 million. As of December 31, 2022, the fair value of the Senior Secured Notes approximated ~~$230.9~~$226.4 million, with a carrying value of ~~$250~~$250 million. ~~As of December 31, 2021, the fair value of the Senior Secured Notes approximated their carrying value of $250 million due to the recency of the notes’ issuance, related to December 31, 2021.~~

The Convertible Senior Notes (as ~~defined)~~defined in Note 10) bear interest at a rate of 2.50% per year, and the fair value of the Convertible Senior Notes without the conversion feature approximated $~~147.2~~ 124.9 million,, with a carrying value of $~~172.5~~ 133.5 million as of June 30, ~~2022~~2023. As of December 31, ~~2021~~,2022, the fair value of the Convertible Senior Notes without the conversion feature approximated $~~159.8~~ 139.2 million,, with a carrying value of $~~172.5 million~~162.5 .million.

See Note ~~11,~~10, “Notes Payable and Long-Term Debt”, for further information regarding the Company’s long-term debt.

Note 6.5. Inventories

The components of inventories are as follows:

					June 30,		December 31,
	June 30, 2022		December 31, 2021		2023		2022
Raw materials and work in process	$	7,853	$	6,936	$	5,552	$	7,283
Leaf tobacco		49,163		35,900		55,794		43,468
Finished goods - Zig-Zag Products		37,435		25,663		42,855		42,279
Finished goods - Stoker’s Products		10,798		8,959		9,671		9,667
Finished goods - NewGen products		8,379		8,591
Finished goods - Creative Distribution Solutions						9,410		15,431
Other		1,501		1,558		1,774		1,787
Inventories	$	115,129	$	87,607	$	125,056	$	119,915

The inventory valuation allowance was ~~$4.8~~$4.2 million and ~~$7.7~~$4.5 million as of June 30, ~~2022,~~2023, and December 31, ~~2021,~~2022, respectively.

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Note 7.6. Other Current Assets

Other current assets consist of:

					June 30,		December 31,
	June 30, 2022		December 31, 2021		2023		2022
Inventory deposits	$	3,223	$	12,091	$	4,969	$	6,395
Insurance deposit		3,000		3,000		3,000		3,000
Prepaid taxes		3,036		0		976		448
Other		18,094		11,655		9,271		13,116
Total	$	27,353	$	26,746	$	18,216	$	22,959

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Note 8.7. Property, Plant, and Equipment

Property, plant, and equipment consists of:

							June 30,			December 31,
	June 30, 2022			December 31, 2021			2023			2022
Land	$	22		$	22		$	22		$	22
Buildings and improvements		3,096			3,096			3,096			3,096
Leasehold improvements		5,391			5,374			5,409			5,404
Machinery and equipment		23,927			19,591			28,451			25,832
Furniture and fixtures		9,194			9,402			9,403			9,264
Gross property, plant and equipment		41,630			37,485			46,381			43,618
Accumulated depreciation		(19,254	)		(18,835	)		(22,253	)		(20,830	)
Net property, plant and equipment	$	22,376		$	18,650		$	24,128		$	22,788

Note 9.8. Other Assets

Other assets consist of:

					June 30,		December 31,
	June 30, 2022		December 31, 2021		2023		2022
Equity investments	$	19,300	$	25,649	$	4,627	$	13,376
Debt security investment		8,000		8,000		7,488		7,820
Other		1,175		1,750		6,093		1,453
Total	$	28,475	$	35,399	$	18,208	$	22,649

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The Company records its equity investments without a readily determinable fair value, that are not accounted for under the equity method, at cost, with adjustments for impairment and observable price changes.

In June 2022, based on a contemplated sale of the assets of dosist, the Company deemed its investment was impaired resulting in decreasing of the fair value of the investment to $1.6 million. Fair value was determined using a valuation derived from the contemplated purchase price (Level 3). This resulted in a loss of $6.3 million which is recorded in investment loss for the three and six months ended June 30, 2022.

In July 2021, the Company invested $8.0 million in Old Pal Holding Company LLC (“Old Pal”). In July 2022, the Company invested an additional $1.0 million in Old Pal. The Company invested in the form of a convertible note which includes additional follow-on investment rights. The accrued interest of $0.2 million from July 2021 to July 2022 was rolled into the convertible note in July 2022 resulting in a total investment of $9.2 million. Old Pal is a leading brand in the cannabis lifestyle space that operates a non-plant touching licensing model. The Company’s investment will enable Old Pal to expand product offerings in existing states, which include California, Nevada, Michigan, Oklahoma, Ohio, Washington and Massachusetts, and will help create the infrastructure necessary to support continued territory and product expansion. The convertible note bears an interest rate of 3.0% per year and matures July 31, 2026.Interest and principal not paid to date are ~~payable~~receivable at maturity. Old Pal has the option to extend the maturity date in one-year increments. The interest rate is subject to change based on ~~sales levels of~~ Old Pal ~~meeting~~reaching certain sales thresholds. The weighted average interest rate on the convertible note was 3% 3.0% for the three and six months ended June 30, ~~2022.~~2023. Old Pal has the option to convert the note into shares once sales reach a certain threshold.~~Additionally, the Company has the right to convert the note into shares at any time.~~ The conditions required to allow Old Pal to convert the note were not met as of June 30, 2023. Additionally, the Company has the right to convert the note into shares at any time after January 1, 2022. The Company has classified the debt security with Old Pal as available for sale. The Company records the debt security at fair value and includes unrealized gains and losses recorded in stockholders’ equity as a component of accumulated other comprehensive income on our Consolidated Balance Sheets. The Company reports interest income on available for sale debt securities in interest ~~expense, net~~income in our Consolidated Statements of Income. ~~The~~Quarterly, we perform a qualitative assessment to determine if the fair value of the ~~debt security approximated its carrying~~investment could be less than the amortized cost basis. The fourth quarter 2022 qualitative assessment determined that the fair value of ~~$8.0~~the investment could be less than the amortized cost basis and therefore the Company performed a quantitative assessment of the fair value of the investment. The fair value as of December 31, 2022 was determined to be $7.9 million atbased on a Monte Carlo simulation (Level 3). The Company determined that the impairment was a result of credit related factors and, as such, recorded an allowance for credit losses of $1.4 million which is included in investment loss for the year ended December 31, 2022. In the second quarter of 2023, based on a subsequent quantitative assessment of the fair value using a Monte Carlo simulation, the Company determined the fair value to be $7.7 million and recorded an additional allowance for credit losses of $0.3 million which is included in investment loss for the quarter ended June 30, ~~2022~~ ~~and December 31, 2021, due to the recency of the debt security’s purchase, related to each such date.~~2023. The Company has recorded accrued interest receivable of ~~$0.2~~$0.3 million and $0.1 million at June 30, ~~2022~~2023 and December 31, ~~2021,~~2022, respectively,, in other current assets on our Consolidated Balance Sheets.

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In April 2021, the Company invested $8.7 million in Docklight Brands, Inc., a pioneering consumer products company with celebrated brands including Marley Natural® cannabis and Marley™ CBD. The Company has additional follow-on investment rights. As part of the investment, the Company has obtained exclusive U.S. distribution rights for Docklight’s Marley™ CBD topical products. In the first quarter of 2023, based on Docklight’s financial results and other operating difficulties, and the decline in the revenue multiples for public companies comparable to Docklight, the Company deemed the investment in Docklight was impaired resulting in the fair value of the Company’s investment decreasing to $3.8 million resulting in a loss of $4.9 million which was recorded for the three months ended March 31, 2023. In the second quarter of 2023, based on a significant change in Docklight’s business model, the Company deemed its investment in Docklight fully impaired resulting in an additional loss of $3.8 million bringing the fair value of the Company’s investment in Docklight to zero. Impairment losses for the Company’s investment in Docklight are recorded in Investment loss on our Consolidated Statements of Income. Fair value for both periods was determined using a valuation derived from relevant revenue multiples (Level 3).

Note ~~10.~~9. Accrued Liabilities

Accrued liabilities consist of:

					June 30,		December 31,
	June 30, 2022		December 31, 2021		2023		2022
Accrued payroll and related items	$	5,637	$	6,974	$	4,729	$	7,685
Customer returns and allowances		7,759		6,497		7,444		7,291
Taxes payable		1,911		2,053		2,008		1,867
Lease liabilities		3,068		2,976		2,596		3,102
Accrued interest		7,318		7,318		6,830		7,277
Other		8,867		7,119		7,291		5,779
Total	$	34,560	$	32,937	$	30,898	$	33,001

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Note ~~11.~~10. Notes Payable and Long-Term Debt

Notes payable and long-term debt consists of the following in order of preference:

							June 30,			December 31,
	June 30, 2022			December 31, 2021			2023			2022
Senior Secured Notes	$	250,000		$	250,000		$	250,000		$	250,000
Convertible Senior Notes		172,500			172,500			133,541			162,500
Gross notes payable and long-term debt		422,500			422,500			383,541			412,500
Less deferred finance charges		(7,090	)		(8,328	)		(4,346	)		(5,743	)
Notes payable and long-term debt	$	415,410		$	414,172		$	379,195		$	406,757

Senior Secured Notes

On February 11, 2021, the Company closed a private offering (the “Offering”) of $250 million aggregate principal amount of its 5.625% senior secured notes due 2026 (the “Senior Secured Notes”). The Senior Secured Notes bear interest at a rate of 5.625% and will mature on February 15, 2026. Interest on the Senior Secured Notes is payable semi-annually in arrears on February 15 and August 15 of each year, commencing on August 15, 2021.The Company used the proceeds from the Offering (i) to repay all obligations under and terminate the 2018 First Lien Credit Facility, (ii) to pay related fees, costs, and expenses and (iii) for general corporate purposes.

Obligations under the Senior Secured Notes are guaranteed by the Company’s existing and future wholly-owned domestic subsidiaries (the “Guarantors”) that guarantee any Credit Facility (as defined in the Indenture governing the Senior Secured Notes or the “Senior Secured Notes Indenture”) or capital markets debt securities of the Company or Guarantors in excess of $15.0 million. The Senior Secured Notes and the related guarantees are secured by first-priority liens on substantially all of the assets of the Company and the Guarantors, subject to certain exceptions.

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The Company may redeem the Senior Secured Notes, in whole or in part, at any time ~~prior to~~on or after February 15, 2023, at the redemption prices (expressed as a ~~price equal to 100%~~percentage of the principal amount ~~of the Notes redeemed~~to be redeemed) set forth below, plus accrued and unpaid interest, if any, to, but excluding the applicable redemption date, plus a “make-whole” premium. Thereafter, the Company may redeem the Senior Secured Notes, in whole or in part, at established redemption prices set forth in the Senior Secured Notes Indenture, plus accrued and unpaid interest, if any. In addition, on or prior to February 15, 2023, the Company may redeem up to 40% of the aggregate principal amount of the Senior Secured Notes with the net cash proceeds from certain equity offerings at a redemption price equal to 105.625%, plus accrued and unpaid interest, if any to the redemption date; provided, however, that at least 50% of the original aggregate principal amount of the Senior Secured Notes (calculated after giving effect to the issuance of any additional notes) remains outstanding. In addition, at any time and from time to time prior to February 15, 2023, but not more than once in any twelve-month period, the Company may redeem up to 10% of the aggregate principal amount of the Senior Secured Notes at a redemption price of 103% of the aggregate principal amount of Senior Secured Notes redeemed plus accrued and unpaid interest, if any to but not including the redemption date, on the Senior Secured Notes to be ~~redeemed.~~redeemed to (but not including) the applicable redemption date if redeemed during the period indicated below:

On or after February 15, 2023	102.813	%
On or after February 15, 2024	101.406	%
On or after February 15, 2025 and thereafter	100.000	%

If the Company experiences a change of control (as defined in the Senior Secured Notes Indenture), the Company must offer to repurchase the Senior Secured Notes at a repurchase price equal to 101% of the principal amount of the Notes to be repurchased, plus accrued and unpaid interest.

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The Indenture contains covenants that, among other things, restrict the ability of the Company and its restricted subsidiaries to: (i) grant or incur liens; (ii) incur, assume or guarantee additional indebtedness; (iii) sell or otherwise dispose of assets, including capital stock of subsidiaries; (iv) make certain investments; (v) pay dividends, make distributions or redeem or repurchase capital stock; (vi) engage in certain transactions with affiliates; and (vii) consolidate or merge with or into, or sell substantially all of our assets to another entity. These covenants are subject to a number of limitations and exceptions set forth in the Indenture. The Indenture provides for customary events of default. The Company was in compliance with all covenants as of June 30, ~~2022.~~2023.

The Company incurred debt issuance costs attributable to the issuance of the Senior Secured Notes of $6.4 million which are amortized to interest expense using the effective interest method over the expected life of the Senior Secured Notes.

2021 Revolving Credit Facility

In connection with the Offering, the Company also entered into a new ~~$25~~$25.0 million senior secured revolving credit facility (the “2021 Revolving Credit Facility”) with the lenders party thereto (the “Lenders”) and Barclays Bank PLC, as administrative agent and collateral agent (in such capacity, the “Agent”). ~~The~~ On May 10, 2023, the Company and certain of its subsidiaries, as guarantors, entered into an amendment (the “Amendment”) to the 2021 Revolving Credit Facility ~~provides for~~(as amended, the “Amended Revolving Credit Facility”). The Amendment includes certain modifications to the 2021 Revolving Credit Facility relating to the replacement of the London Inter-Bank Offered Rate with a ~~revolving line of credit of up~~Secured Overnight Financing Rate (“SOFR”) as the interest rate benchmark under the 2021 Revolving Credit Facility and adjusts certain other provisions to $~~25.0~~reflect current documentation standards and other agreed modifications.

~~million.~~ Letters of credit are limited to $1010.0 million (and are a part of, and not in addition to, the revolving line of credit). The Company has 0not drawn any borrowings under the ~~2021~~Amended Revolving Credit Facility but does have letters of credit of approximately $~~3.6~~1.4 million outstanding under the ~~facility.~~facility as of June 30, 2023. The ~~2021~~Amended Revolving Credit Facility will mature on August 11, 2025, if none of the Company’s Convertible Senior Notes are outstanding, and if any Convertible Senior Notes are outstanding, the date which is 91 days prior to the maturity date of July 15, 2024, for such Convertible Senior Notes.

Interest is payable on the ~~2021~~Amended Revolving Credit Facility at a fluctuating rate of interest determined by reference to the Eurodollar rate or the Term SOFR rate, as applicable, plus an applicable margin of 3.50% (with step-downs upon de-leveraging). The Company also has the option to borrow at a rate determined by reference to the base rate.

The obligations under the ~~2021~~Amended Revolving Credit Agreement are guaranteed on a joint and several basis by the Guarantors. The Company’s and Guarantors’ obligations under the ~~2021~~Amended Revolving Credit Facility are secured on a pari passu basis with the Senior Secured Notes.

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The ~~2021~~Amended Revolving Credit Agreement contains covenants that are substantially the same as the covenants in the Senior Secured Notes Indenture. The ~~2021~~Amended Revolving Credit Facility also requires the maintenance of a Consolidated Leverage Ratio (as defined in the ~~2021~~Amended Revolving Credit Agreement) of 5.50 to 1.00 (with a step down to 5.25 to 1.00 beginning with the fiscal quarter ending March 31, 2023) at the end of each fiscal quarter when extensions of credit under the ~~2021~~Amended Revolving Credit Facility and certain drawn and undrawn letters of credit (excluding (a) letters of credit that have been cash collateralized and (b) letters of credit having an aggregate face amount less than ~~$5,000,000)~~$5.0 million) in the aggregate outstanding exceeds 35% of the total commitments under the ~~2021~~Amended Revolving Credit Facility. The ~~2021~~Amended Revolving Credit Agreement provides for customary events of default. The Company was in compliance with all covenants as of June 30, ~~2022.~~2023.

The Company incurred debt issuance costs attributable to the issuance of the ~~2021~~Amended Revolving Credit Facility of $0.5 million which are amortized to interest expense using the effective interest method over the expected life of the ~~2021~~Amended Revolving Credit Facility.

~~2018 First Lien Credit Facility~~

The 2018 First Lien Term Loan and the 2018 Revolving Credit Facility bore interest at LIBOR plus a spread of 2.75% to 3.50% based on the Company’s senior leverage ratio. The Company used a portion of the proceeds from the issuance of the Senior Secured Notes to prepay all outstanding amounts under and terminate the 2018 First Lien Credit Facility in the first quarter of 2021 in the amount of $130.0 million, and the transaction resulted in a $5.7 million loss on extinguishment of debt.

~~Table of Contents~~

Convertible Senior Notes

In July 2019, the Company closed an offering of $172.5 million in aggregate principal amount of its 2.50% Convertible Senior Notes due July 15, 2024 (the “Convertible Senior Notes”). The Convertible Senior Notes bear interest at a rate of 2.50% per year, payable semiannually in arrears on January 15 and July 15 of each year, beginning on January 15, 2020. The Convertible Senior Notes will mature on July 15, 2024, unless earlier repurchased, redeemed or converted. The Convertible Senior Notes are senior unsecured obligations of the Company.

In the fourth quarter of 2022, a wholly owned subsidiary of the Company repurchased $10.0 million in aggregate principal amount of the Convertible Senior Notes on the open market resulting in a $0.9 million gain on extinguishment of debt. Subsequent repurchases occurred in the first and second quarters of 2023 for $13.9 million and $15.1 million, respectively, in aggregate principal amounts resulting in gains on extinguishment of debt of $0.7 million and $0.6 million, respectively. The repurchased notes continue to be held by our subsidiary and may be resold subject to compliance with applicable securities law. As of June 30, 2023, $133.5 million aggregate principal remains outstanding and held by third parties.

The Convertible Senior Notes held by third parties are convertible into approximately ~~3,211,484~~2,455,360 shares of TPB Common Stock under certain circumstances prior to maturity at a conversion rate of ~~18.617~~18.6789 shares per $1,000 principal amount of the Convertible Senior Notes, which represents a conversion price of approximately ~~$53.71~~$53.54 per share, subject to adjustment under certain conditions, but will not be adjusted for any accrued and unpaid interest. The conversion price is adjusted periodically as a result of dividends paid by the Company in excess of pre-determined thresholds of $0.04 per share. Upon conversion, the Company may pay cash, shares of common stock or a combination of cash and stock, as determined by the Company at its discretion. The conditions required to allow the holders to convert their Convertible Senior Notes were not met as of June 30, ~~2022.~~

2023. Subsequent to the balance sheet date the Convertible Senior Notes became current in the amount of $133.5 million. Based on the current liquidity, free cash flow generation and other financing options, the Company believe there will be adequate liquidity to address the maturity of the Convertible Senior Notes. The Company incurred debt issuance costs attributable to the Convertible Senior Notes of $5.9 million which are amortized to interest expense using the effective interest method over the expected life of the Convertible Senior Notes.

In connection with the Convertible Senior Notes offering, the Company entered into privately negotiated capped call transactions with certain financial institutions. The capped call transactions have a strike price of ~~$53.71~~$53.54 per and a cap price of $82.86 per share, and are exercisable when, and if, the Convertible Senior Notes are converted. The Company paid $20.53 million for these capped calls at the time they were entered into and charged that amount to additional paid-in capital.

~~Promissory Note~~

On ~~June 10, 2020, in connection with the acquisition of certain Durfort assets, the Company issued the Promissory Note in the principal amount of $10.0~~ ~~million, with an annual interest rate of~~ ~~7.5%, payable~~ ~~quarterly, with the~~ ~~first~~ ~~interest payment due~~ ~~September 10, 2020~~. The Company prepaid all outstanding amounts under and terminated the Promissory Note in the third quarter of 2021 in the amount of $9.6 million. The transaction resulted in a $0.4 million gain on extinguishment of debt.

~~Unsecured Loan~~

On ~~April 6, 2020, the~~ ~~2018 First~~ ~~Lien Credit Facility was amended to allow for an unsecured loan under the Coronavirus Aid, Relief, and Economic Security Act of~~ ~~2020~~ ~~(“CARES”). On~~ ~~April 17, 2020, National Tobacco Company, L.P., a subsidiary of the Company, entered into a loan agreement with Regions Bank guaranteed by the Small Business Administration for a $7.5~~ ~~million unsecured loan. The proceeds of the loan were received on~~ ~~April 27, 2020. The loan was scheduled to mature on~~ ~~April 17, 2022~~ ~~and had a~~ ~~1.00%~~ ~~interest rate~~. ~~During 2021, the Company applied for forgiveness for the loan. On October 15, 2021,~~ the Company received notice that its application for forgiveness was fully approved. The extinguishment of the unsecured loan occurred in the fourth quarter of 2021, resulting in a $7.5 million gain on extinguishment of debt. The Company is subject to audit relating to the unsecured loan until 2027 which could result in repayment of some or all of the unsecured loan previously forgiven. However, the Company believes that repayment of any amount is not probable.

2422

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Note ~~12.~~11. Leases

The Company’s leases consist primarily of leased property for manufacturing, warehouse, corporate offices and ~~head offices~~retail space as well as vehicle leases. At lease inception, the Company recognizes a lease right of use asset and lease liability calculated as the present value of future minimum lease payments. In general, the Company does not recognize any renewal periods within the lease terms as there are no significant barriers to ending the lease at the initial term. Lease and non-lease components are accounted for as a single lease component.

Leases with an initial term of 12 months or less are not recorded on the balance sheet. Lease expense for these leases is recognized on a straight-line basis over the lease term.

The components of lease expense consisted of the following:

	Three Months Ended June 30,					Three Months Ended June 30,
	2022		2021			2023		2022
Operating lease cost
Cost of sales	$	233	$	232		$	129	$	233
Selling, general and administrative		683		762			503		386
Variable lease cost (1)		211		535			407		211
Short-term lease cost		11		11			7		11
Sublease income		0		(30	)
Total	$	1,138	$	1,510		$	1,046	$	841

(1)	Variable lease cost includes elements of a contract that do not represent a good or service but for which the lessee is responsible for paying.

	Three Months Ended June 30,
	2023		2022
Financing lease cost
Selling, general and administrative	$	348	$	297
Total	$	348	$	297

	Six Months Ended June 30,					Six Months Ended June 30,
	2022		2021			2023		2022
Operating lease cost
Cost of sales	$	460	$	457		$	257	$	460
Selling, general and administrative		1,373		1,514			1,024		785
Variable lease cost (1)		323		740			632		323
Short-term lease cost		25		22			13		25
Sublease income		0		(60	)
Total	$	2,181	$	2,673		$	1,926	$	1,593

	Six Months Ended June 30,
	2023		2022
Financing lease cost
Selling, general and administrative	$	686	$	588
Total	$	686	$	588

~~(1)~~

~~Variable lease cost includes elements of a contract that do not represent a good or service but for which the lessee is responsible for paying.~~

~~Table of Contents~~

					June 30,		December 31,
	June 30, 2022		December 31, 2021		2023		2022
Assets:
Right of use assets	$	13,749	$	15,053
Right of use assets - Operating					$	9,983	$	10,967
Right of use assets - Financing						940		1,498
Total lease assets	$	13,749	$	15,053	$	10,923	$	12,465

Liabilities:
Current lease liabilities (2)	$	3,068	$	2,976
Long-term lease liabilities		11,934		13,336
Current lease liabilities - Operating (2)					$	1,947	$	2,007
Current lease liabilities - Financing (2)						649		1,095
Long-term lease liabilities - Operating						9,272		10,243
Long-term lease liabilities - Financing						256		350
Total lease liabilities	$	15,002	$	16,312	$	12,124	$	13,695

(2)	Reported within accrued liabilities on the balance sheet.

As of June 30,
2022 2021
Weighted-average remaining lease term - operating leases 6.36 years 7.0 years
Weighted-average discount rate - operating leases 4.87 % 4.93 %

~~Nearly all the lease contracts for the Company do not provide a readily determinable implicit interest rate. For these contracts, the Company~~ ~~uses a discount rate that approximates its incremental borrowing rate at the time of the lease commencement.~~

~~As of June 30, 2022, maturities of lease liabilities consisted of the following:~~

June 30,
2022

2022 $ 1,851
2023 3,632
2024 2,501
2025 2,187
2026 2,101
Years thereafter 5,344
Total lease payments $ 17,616
Less: Imputed interest 2,614
Present value of lease liabilities $ 15,002

2623

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Note ~~13.~~12. Income Taxes

The Company’s effective income tax rate for the three and six months ended June 30, 2023 was 25.6% and 25.4%, respectively. The Company’s effective income tax rate for the three and six months ended June 30, 2022, was 23.2% and 23.5%, respectively, which includes a discrete tax deduction of $0.3 million and $0.7 million, ~~for the three and six months ended June 30, 2022,~~ respectively, relating to stock option ~~exercises. The Company’s effective income tax rate for the three and six months ended June 30, 2~~exercise~~021, was 22.7% and 21.0%,~~ ~~respectively, which includes a discrete tax deduction of $2.0 million and $5.2 million for the three and six months ended June 30, 202~~1, ~~respectively, relating to stock option exercises~~s.

The Company follows the provisions of ASC 740-10-25, which prescribes a recognition threshold and measurement attribute for the financial statement recognition and measurement of a tax position taken or expected to be taken in a tax return. For those benefits to be recognized, a tax position must be more-likely-than-not to be sustained upon examination by taxing authorities. The amount recognized is measured as the largest amount of benefit that is greater than 50 percent likely of being realized upon ultimate settlement. The Company has determined that the Company did not have any uncertain tax positions requiring recognition under the provisions of ASC 740-10-25. The Company’s policy is to recognize interest and penalties accrued on uncertain tax positions, if any, as part of interest expense. The Company files income tax returns in the U.S. federal jurisdiction and various state jurisdictions. In general, the Company is no longer subject to U.S. federal and state tax examinations for years prior to ~~2018.~~2019.

Note ~~14.~~13. Share Incentive Plans

On March 22, 2021, the Company’s Board of Directors adopted the Turning Point Brands, Inc. 2021 Equity Incentive Plan (the “2021 Plan”), pursuant to which awards may be granted to employees, non-employee directors, and consultants. In addition, the 2021 Plan provides for the granting of nonqualified stock options to employees of the Company or any subsidiary of the Company. Pursuant to the 2021 Plan, 1,290,000 shares, plus 100,052 shares remaining available for issuance under the 2015 Equity Incentive Plan (the “2015 Plan”), of TPB Common Stock are reserved for issuance as awards to employees, non-employee directors, and consultants as compensation for past or future services or the attainment of certain performance goals. The 2021 Plan is scheduled to terminate on March 21, 2031. The 2021 Plan is administered by the compensation committee (the “Committee”) of the Company’s Board of Directors. The Committee determines the vesting criteria for the awards, with such criteria to be specified in the award agreement. As of June 30, ~~2022,~~2023, net of forfeitures, there were ~~103,340~~277,397 Restricted Stock Units (“RSUs”), ~~109,010~~120,746 options and ~~17,029~~30,559 Performance-Based Restricted Stock Units (“PRSUs”) granted under the 2021 Plan. There are ~~1,160,673~~961,350 shares available for grant under the 2021 Plan.

On April 28, 2016, the Board of Directors of the Company adopted the 2015 Plan, pursuant to which awards could have been granted to employees, non-employee directors, and consultants. In addition, the 2015 Plan provided for the granting of nonqualified stock options to employees of the Company or any subsidiary of the Company. Pursuant to the 2015 Plan, 1,400,000 shares of TPB Common Stock were reserved for issuance as awards to employees, non-employee directors, and consultants as compensation for past or future services or the attainment of certain performance goals. The 2015 Plan was scheduled to terminate on April 27, 2026. Upon adoption of the 2021 Plan, the 2015 Plan was terminated, and the Company determined no additional grants would be made under the 2015 Plan. However, all awards issued under the 2015 Plan that have not been previously terminated or forfeited remain outstanding and continue unaffected. There are 0no shares available for grant under the 2015 Plan. The 2015 Plan was administrated by the Committee.

On February 8, 2006, the Board of Directors of the Company adopted the 2006 Equity Incentive Plan (the “2006 Plan”) of North Atlantic Holding Company, Inc., pursuant to which awards may be granted to employees. The 2006 Plan provides for the granting of nonqualified stock options and restricted stock awards to employees. Upon the adoption of the Company’s 2015 Equity Incentive Plan in connection with its IPO, the Company determined no additional grants would be made under the 2006 Plan. However, all awards issued under the 2006 Plan that have not been previously terminated or forfeited remain outstanding and continue unaffected. There are 0no shares available for grant under the 2006 Plan.

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Stock option activity for the 2006, 2015 and 2021 Plans is summarized below:

	Stock Option Shares			Weighted Average Exercise Price		Weighted Average Grant Date Fair Value					Weighted		Weighted
Outstanding, December 31, 2020		711,060		$	19.58	$	6.42
								Stock			Average		Average
Granted		119,500			50.93		13.58
Exercised		(202,768	)		10.22		6.35
Forfeited		(7,957	)		33.22		9.63
								Option			Exercise		Grant Date
								Shares			Price		Fair Value
Outstanding, December 31, 2021		619,835			28.51		8.70		619,835		$	28.51	$	8.70

Granted		114,827			30.58		10.34		114,827			30.58		10.34
Exercised		(37,278	)		12.75		4.14		(40,331	)		12.49		4.08
Forfeited		(8,263	)		31.35		8.77		(11,117	)		32.60		9.35
Outstanding, June 30, 2022		689,121		$	29.67	$	9.22
Outstanding, December 31, 2022									683,214		$	29.74	$	9.24

Granted									77,519			20.71		6.45
Exercised									(29,371	)		13.84		4.37
Forfeited									(62,987	)		26.61		9.00
Outstanding, June 30, 2023									668,375		$	29.68	$	9.15

Under the 2006, 2015 and 2021 Plans, the total intrinsic value of options exercised during the six months ended June 30, 2023 and 2022, ~~and 2021,~~ was ~~$0.5~~$0.2 million, and ~~$5.3~~$0.5 million, respectively.

At June 30, ~~2022,~~2023, under the 2006 Plan, the exercise price for the ~~75,945~~46,824 outstanding options is $3.83 per share, all of which are exercisable. The weighted average of the remaining lives of the outstanding stock options with an exercise price of $3.83 is approximately ~~1.94~~1.11 years. The Company estimates the expected life of these stock options is ten years from the date of grant. For the $3.83 per share options, the weighted average fair value of options at the date of grant was determined using the Black-Scholes model with the following ~~assumptions~~assumptions: a ten-year life from grant date, a current share price and exercise price of $3.83, a risk-free interest rate of 3.57%, volatility of 40%, and 0no assumed dividend yield. Based on these assumptions, the fair value of these options is approximately $2.17 per share option granted.

At June 30, ~~2022,~~2023, under the 2015 and 2021 Plans, the risk-free interest rate is based on the U.S. Treasury rate for the expected life at the time of grant. The expected volatility is based on the average long-term historical volatilities of peer companies. We intend to continue to consistently use the same group of publicly traded peer companies to determine expected volatility until sufficient information regarding volatility of our share price becomes available or until the selected companies are no longer suitable for this purpose. Due to our limited trading history, we are using the simplified method presented by SEC Staff Accounting Bulletin No. 107 to calculate expected holding periods, which represent the periods of time for which options granted are expected to be outstanding. We will continue to use this method until we have sufficient historical exercise experience to give us confidence in the reliability of our calculations. The fair values of these options were determined using the Black-Scholes option pricing model.

The following table outlines the assumptions based on the number of options granted under the 2015 Plan.

																									February 10,			May 17,			March 7,			March 20,			October 24,			March 18,			February 18,			May 3,
	February 10, 2017			May 17, 2017			March 7, 2018			March 20, 2019			October 24, 2019			March 18, 2020			February 18, 2021			May 3, 2021			2017			2017			2018			2019			2019			2020			2021			2021
Number of options granted		40,000			93,819			98,100			155,780			25,000			155,000			100,000			12,000			40,000			93,819			98,100			155,780			25,000			155,000			100,000			12,000
Options outstanding at June 30, 2022		20,000			45,733			58,067			141,784			25,000			94,117			94,148			12,000
Number exercisable at June 30, 2022		20,000			45,733			58,067			141,784			25,000			61,818			39,335			4,080
Options outstanding at June 30, 2023																										20,000			39,983			51,567			125,984			25,000			82,068			91,287			12,000
Number exercisable at June 30, 2023																										20,000			39,983			51,567			125,984			25,000			82,068			64,564			8,040
Exercise price	$	13.00		$	15.41		$	21.21		$	47.58		$	20.89		$	14.85		$	51.75		$	47.76		$	13.00		$	15.41		$	21.21		$	47.58		$	20.89		$	14.85		$	51.75		$	47.76
Remaining lives		4.62			4.88			5.69			6.73			7.32			7.72			8.64			8.85			3.62			3.88			4.69			5.73			6.32			6.72			7.64			7.85
Risk free interest rate		1.89	%		1.76	%		2.65	%		2.34	%		1.58	%		0.79	%		0.56	%		0.84	%		1.89	%		1.76	%		2.65	%		2.34	%		1.58	%		0.79	%		0.56	%		0.84	%
Expected volatility		27.44	%		26.92	%		28.76	%		30.95	%		31.93	%		35.72	%		28.69	%		29.03	%		27.44	%		26.92	%		28.76	%		30.95	%		31.93	%		35.72	%		28.69	%		29.03	%
Expected life		6.000			6.000			6.000			6.000			6.000			6.000			6.000			6.000			6.000			6.000			6.000			6.000			6.000			6.000			6.000			6.000
Dividend yield		0			0			0.83	%		0.42	%		0.95	%		1.49	%		0.55	%		0.59	%		-			-			0.83	%		0.42	%		0.95	%		1.49	%		0.55	%		0.59	%
Fair value at grant date	$	3.98		$	4.60		$	6.37		$	15.63		$	6.27		$	4.41		$	13.77		$	13.06		$	3.98		$	4.60		$	6.37		$	15.63		$	6.27		$	4.41		$	13.77		$	13.06

Table of Contents

The following table outlines the assumptions based on the number of options granted under the 2021 Plan.

										May 17,			March 14,			April 29,			May 12,
	May 17, 2021			March 14, 2022			April 29, 2022			2021			2022			2022			2023
Number of options granted		7,500			100,000			14,827			7,500			100,000			14,827			77,519
Options outstanding at June 30, 2022		7,500			100,000			14,827
Number exercisable at June 30, 2022		2,550			0			0
Options outstanding at June 30, 2023											7,500			73,816			14,827			77,519
Number exercisable at June 30, 2023											5,100			25,295			5,042			38,760
Exercise price	$	45.05		$	30.46		$	31.39		$	45.05		$	30.46		$	31.39		$	20.71
Remaining lives		8.88			9.71			9.84			7.88			8.71			8.84			9.87
Risk free interest rate		0.84	%		2.10	%		2.92	%		0.84	%		2.10	%		2.92	%		3.41	%
Expected volatility		31.50	%		35.33	%		35.33	%		31.50	%		35.33	%		35.33	%		34.51	%
Expected life		6.000			6.000			6.000			6.000			6.000			6.000			5.186
Dividend yield		0.63	%		1.01	%		0.98	%		0.63	%		1.01	%		0.98	%		1.61	%
Fair value at grant date	$	13.23		$	10.23		$	11.07		$	13.23		$	10.23		$	11.07		$	6.45

The Company has recorded compensation expense related to the options based on the provisions of ASC 718 under which the fixed portion of such expense is determined as the fair value of the options on the date of grant and amortized over the vesting period. The Company recorded compensation expense related to the options of approximately ~~$0.3~~$0.5 million and ~~$1.4~~$0.3 million for the three months ended June 30, ~~2022~~2023 and ~~2021,~~2022, respectively. The Company recorded compensation expense related to the options of approximately $0.5 million and ~~$1.7~~$0.5 million for the six months ended June 30, ~~2022~~2023 and ~~2021,~~2022, respectively. Total unrecognized compensation expense related to options at June 30, ~~2022,~~2023, is ~~$1.3~~$0.7 million, which will be expensed over ~~2.2 years.~~1.23 years.

PRSUs are restricted stock units subject to both performance-based and service-based vesting conditions. The number of shares of TPB Common Stock a recipient will receive upon vesting of a PRSU will be calculated by reference to certain performance metrics related to the Company’s performance over a five-year period. PRSUs will vest on the measurement date, which is no more than 65 days after the performance period provided the applicable service and performance conditions are satisfied. As of June 30, ~~2022~~2023, there are ~~476,347~~460,334 PRSUs ~~outstanding, all of which are unvested.~~outstanding. The following table outlines the PRSUs granted and outstanding as of June 30, ~~2022~~2023.

															March 20,		March 18,		December 28,		February 18,		March 14,		May 4,
	March 7, 2018		March 20, 2019		July 19, 2019		March 18, 2020		December 28, 2020		February 18, 2021		March 14, 2022		2019		2020		2020		2021		2022		2023
Number of PRSUs granted		96,000		92,500		88,582		94,000		88,169		100,000		49,996		92,500		94,000		88,169		100,000		49,996		133,577
PRSUs outstanding at June 30, 2022		89,600		77,380		21,342		86,110		58,779		93,140		49,996
PRSUs outstanding at June 30, 2023																77,380		85,410		31,040		88,490		44,437		133,577
Fair value as of grant date	$	21.21	$	47.58	$	52.15	$	14.85	$	46.42	$	51.75	$	30.46	$	47.58	$	14.85	$	46.42	$	51.75	$	30.46	$	22.25
Remaining lives		0.50		1.50		0.50		2.50		1.50		3.50		4.50		0.50		1.50		0.50		2.50		3.50		2.75

The Company recorded compensation expense related to the PRSUs of approximately ~~$0.8~~$0.6 million and ~~$1.3~~$0.8 million in the consolidated statements of income for the three months ended June 30, ~~2022~~2023 and ~~2021~~,2022, respectively, based on the probability of achieving the performance condition. The Company recorded compensation expense related to the PRSUs of approximately ~~$1.6~~$1.1 million and ~~$2.5~~$1.6 million in the consolidated statements of income for the six months ended June 30, ~~2022~~2023 and ~~2021,~~2022, respectively, based on the probability of achieving the performance condition. Total unrecognized compensation expense related to these awards at June 30, ~~2022~~,2023, is ~~$5.5~~$7.3 million which will be expensed over the service periods based on the probability of achieving the performance ~~condition.~~condition.

Table of Contents

The Company has granted ~~95,804~~229,553 RSUs which vest over one to five years. The following table outlines the RSUs granted and outstanding as of June 30, ~~2022.~~2023.

											March 14,		March 14,		April 29,		May 5,		May 5,		May 8,
	July 23, 2021		March 14, 2022		March 14, 2022		April 29, 2022		April 29, 2022		2022		2022		2022		2023		2023		2023
Number of RSUs granted		1,159		50,004		28,726		11,393		4,522		50,004		28,726		4,522		130,873		22,472		20,101
RSUs outstanding at June 30, 2022		1,159		50,004		28,726		11,393		4,522
RSUs outstanding at June 30, 2023												43,860		18,961		4,522		130,873		11,236		20,101
Fair value as of grant date	$	51.81	$	30.46	$	30.46	$	31.39	$	31.39	$	30.46	$	30.46	$	31.39	$	22.25	$	22.25	$	21.77
Remaining lives		0.06		4.50		2.50		0.82		4.50		3.50		1.50		3.50		2.75		0.50		0.86

The Company has recorded compensation expense related to the RSUs based on the provisions of ASC 718 under which the fixed portion of such expense is determined as the fair value of the RSUs on the date of grant and amortized over the vesting period. The Company recorded compensation expense related to the RSUs of approximately ~~$0.4~~$1.0 million and ~~$0.1~~$0.4 million for the three months ended June 30, ~~2022~~2023 and ~~2021, respectively.~~2022. The Company recorded compensation expense related to the RSUs of approximately ~~$0.6~~$1.3 million and ~~$0.1~~$0.6 million for the six months ended June 30, ~~2022~~2023 and ~~2021,~~2022, respectively. Total unrecognized compensation expense related to RSUs at June 30, ~~2022,~~2023, is ~~$2.5~~$4.3 million, which will be expensed over ~~3.55~~2.56 years.

Note ~~15.~~14. Contingencies

On October 9, 2020, a purported stockholder of Turning Point Brands, Inc. (“TPB” or the “Company”), Paul-Emile Berteau (the “Plaintiff”), filed a complaint in the Delaware Court of Chancery (the “Court”) relating to the merger of ~~SDI~~Standard Diversified, Inc. (“SDI”) with a TPB subsidiary pursuant to the Agreement and Plan of Merger and Reorganization, dated as of April 7, 2020, by and among TPB, SDI and Merger ~~Sub.~~Sub (“Action”). The complaint purports to assert 2two derivative counts for breach of fiduciary duty on TPB’s behalf and against the TPB Board of Directors and certain SDI ~~affiliates.~~affiliates (collectively, the “Defendants”). The third count purports to assert a direct claim against TPB and its Board of Directors based on allegations that TPB’s Amended and Restated Bylaws are inconsistent with TPB’s certificate of incorporation. On October 26,2020, the TPB Board of Directors adopted Amendment No. 1 to TPB’s Amended and Restated Bylaws, which amended the challenged section of the bylaws. On June 30,2021, the ~~court~~Court granted in part and denied in part the ~~defendants’~~Defendants’ motions to dismiss. Among other things, the ~~court~~Court dismissed TPB director H.C. Charles Diao as a defendant in the action and dismissed the third count of the ~~plaintiff’s~~Plaintiff’s complaint as moot. ~~The remaining defendants answered the complaint on August~~ ~~23,2021, and continue to litigate.~~ While the Company believes it has good and valid defenses to the claims, there can be no assurance that the Company will prevail in this case, and it could have a material adverse effect on the Company’s business and results of operations.

The Defendants and the Company deny any wrongdoing but following a mediation in November 2022, the Defendants agreed to settle with the Plaintiff to eliminate the distraction, burden, expense, risks and potential delay of further litigation involving the asserted claims. The parties entered into a Stipulation and Agreement of Compromise, Settlement and Release, dated and filed with the Court on June 27, 2023 (together with the exhibits thereto, the “Settlement Stipulation”). The material terms of the proposed settlement of the Action include, among other things, that the Defendants’ insurers will pay or cause to be paid an aggregate of $5,000,000 into an escrow account (the “Settlement Payment”) in exchange for a release of all claims. Plaintiff also intends to seek an award of attorneys’ fees and expenses to Plaintiff’s counsel of up to $1,000,000 and an additional mootness fee of up to $500,000 in connection with the third count of the complaint that will be paid out of the Settlement Payment with the remaining funds paid to the Company. The proposed settlement is subject to, and conditioned on approval by the Court, and no assurances can be given that such Court approval will be obtained. The impact to the Company is not expected to be material.

Other major tobacco companies are defendants in product liability claims. In a number of these cases, the amounts of punitive and compensatory damages sought are significant and, if such a claim were brought against the Company, could have a material adverse effect on our business and results of operations. The Company is subject to several lawsuits alleging personal injuries resulting from malfunctioning vaporizer devices or batteries and may be subject to claims in the future relating to other ~~NewGen~~Creative Distribution Solutions products. The Company is still evaluating these claims and the potential defenses to ~~them.~~them and may from time to time settle some such suits in order to eliminate distraction, burden, expense, risks and potential delay of further litigation involving the asserted claims. For example, the Company did not design or manufacture the products at issue; rather, the Company was merely the distributor. Nonetheless, there can be no assurance that the Company will prevail in these cases, and they could have a material adverse effect on the financial position, results of operations, or cash flows of the ~~Company~~.Company.

~~Table of Contents~~

We have several subsidiaries engaged in making, distributing, and selling vapor products. As a result of the overall publicity and controversy surrounding the vapor industry generally, many companies have received informational subpoenas from various regulatory bodies and in some jurisdictions regulatory lawsuits have been filed regarding marketing practices and possible underage sales. ~~We expect that our subsidiaries will be subject to~~ While we have received some such ~~cases and~~ investigative ~~requests.~~requests with regard to the marketing of our vapor products, no regulatory bodies have taken action against us with regard to our marketing practices. In the acquisition of the vapor businesses, we negotiated financial “hold-backs”, which we ~~have used~~expect to be able to use to defray expenses associated with the information production and the cost of defending any such lawsuits as well as the franchisee ~~matter.~~matters discussed below. To the extent that litigation becomes necessary, we believe that the subsidiaries have strong factual and legal defenses against claims that they unfairly marketed vapor products.

We have 2two franchisor ~~subsidiaries, one of which no longer has any franchisees.~~subsidiaries. Like many franchise businesses, in the ordinary course of their business, these subsidiaries are from ~~time to time~~time-to-time responding parties to arbitration demands brought by franchisees.

We have reached an agreement to arbitrate a claim brought by a former franchisee. This matter relates to the termination of the franchise agreement by the franchisor for failure to pay franchising fees and our subsequent demand that the franchisee cease using our marks and de-image locations formerly housing the franchises. The franchisee is claiming tortious interference and conversion. We believe the franchisor’s ultimate termination of the franchise agreement for multiple uncured material defaults by the franchisee was proper. We are party to another franchise arbitration with breach of contract and negligence allegations, among others. We believe we have good and valid substantive defenses against the claims and intend on vigorously defending our interests in ~~this matter.~~these matters.

Note ~~16.~~15. Income Per Share

The following is a reconciliation of the numerators and denominators of the basic and diluted EPS computations of net income:

														Three Months Ended June 30,
	Three Months Ended June 30,													2023						2022
	2022						2021											Per						Per
	Income		Shares		Per Share		Income		Shares		Per Share			Income		Shares		Share		Income		Shares		Share
Basic EPS:
Numerator
Net income attributable to Turning Point Brands, Inc.	$	5,424					$	15,355						$	9,925					$	5,424

Denominator
Weighted average				18,063,259	$	0.30				18,975,522	$	0.81					17,584,241	$	0.56				18,063,259	$	0.30

Diluted EPS:
Numerator
Net income attributable to Turning Point Brands, Inc.	$	5,424					$	15,355						$	9,925					$	5,424
Interest expense related to Convertible Senior Notes, net of tax		1,054						1,054							846						1,054
Diluted net income attributable to Turning Point Brands. Inc.	$	6,478					$	16,409						$	10,771					$	6,478

Denominator
Basic weighted average				18,063,259						18,975,522							17,584,241						18,063,259
Convertible Senior Notes				3,211,484						3,206,637							2,625,714						3,211,484
Stock options				168,536						307,503
Stock options and restricted stock units																	199,988						168,536
				21,443,279	$	0.30				22,489,662	$	0.73	��				20,409,943	$	0.53				21,443,279	$	0.30

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													Six Months Ended June 30,
	Six Months Ended June 30,												2023						2022
	2022						2021										Per						Per
	Income		Shares		Per Share		Income		Shares		Per Share		Income		Shares		Share		Income		Shares		Share
Basic EPS:
Numerator
Net income attributable to Turning Point Brands, Inc.	$	16,422					$	27,137					$	17,522					$	16,422

Denominator
Weighted average				18,159,940	$	0.90				19,034,415	$	1.43				17,556,030	$	1.00				18,159,940	$	0.90

Diluted EPS:
Numerator
Net income attributable to Turning Point Brands, Inc.	$	16,422					$	27,137					$	17,522					$	16,422
Interest expense related to Convertible Senior Notes		2,108						2,108						1,800						2,108
Diluted net income attributable to Turning Point Brands. Inc.	$	18,530					$	29,245					$	19,322					$	18,530

Denominator
Basic weighted average				18,159,940						19,034,415						17,556,030						18,159,940
Convertible Senior Notes				3,211,484						3,206,637						2,799,434						3,211,484
Stock options				231,689						318,035
Stock options and restricted stock units																183,483						231,689
				21,603,113	$	0.86				22,559,087	$	1.30				20,538,947	$	0.94				21,603,113	$	0.86

Note ~~17.~~16. Segment Information

In accordance with ASC 280, Segment Reporting, the Company has 3three reportable segments: (1) Zig-Zag Products; (2) Stoker’s Products; and (3) ~~NewGen Products.~~Creative Distribution Solutions. The Zig-Zag Products segment markets and distributes (a) rolling papers, tubes, and related products; and (b) finished cigars and MYO cigar ~~wraps.~~wraps and (c) CLIPPER reusable lighters. The Stoker’s Products segment (a) manufactures and markets moist snuff and (b) contracts for and markets loose leaf chewing tobacco products. The ~~NewGen Products~~Creative Distribution Solutions segment (a) markets and distributes liquid vapor products and certain other products without tobacco and/or nicotine; (b) distributes a wide assortment of products to non-traditional retail outlets via VaporBeast; and (c) markets and distributes a wide assortment of products to individual consumers via the VaporFi B2C online platform. Products in the Zig-Zag Products and Stoker’s Products segments are distributed primarily through wholesale distributors in the ~~United States~~U.S. and Canada while products in the ~~NewGen Products~~Creative Distribution Solutions segment are distributed primarily through e-commerce to non-traditional retail outlets and direct to consumers in the ~~United States.~~U.S. Corporate unallocated includes the costs and assets of the Company not assigned to one of the 3three reportable segments such as intercompany transfers, deferred taxes, deferred financing fees, and investments in subsidiaries. As a result of a change in the Company’s chief operating decision maker (“CODM”), resulting from the hiring of a new Chief Executive Officer in the first quarter of 2022, certain general and administrative costs previously included to the NewGen Products segment are now included in Corporate unallocated to align with new management and reporting structures in the Company and better reflect how performance is now evaluated and resources are allocated by the CODM. Amounts in the prior year period have not been adjusted. Had such prior period amounts been adjusted, approximately $1.1 million and $2.0 million of costs for the three and six months ended June 30, 2021 previously reported in the ~~NewGenProducts~~ ~~segment would have been reported in Corporate unallocated~~.

The accounting policies of these segments are the same as those of the Company. Corporate costs are not directly charged to the 3three reportable segments in the ordinary course of operations. The Company evaluates the performance of its segments and allocates resources to them based on operating income.

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The tables below present financial information about reported segments:

							Three Months Ended June 30,
	Three Months Ended June 30,						2023			2022
	2022			2021
Net sales
Zig-Zag products	$	46,226		$	47,202		$	46,722		$	46,226
Stoker’s products		33,588			33,369			36,056			33,588
NewGen products		23,111			42,072
Total Zig-Zag and Stoker’s products							$	82,778		$	79,814
Creative Distribution Solutions								22,817			23,111
Total	$	102,925		$	122,643		$	105,595		$	102,925

Gross profit
Zig-Zag products	$	26,430		$	27,743		$	26,422		$	26,430
Stoker’s products		18,079			18,146			19,968			18,079
NewGen products		6,960			14,084
Total Zig-Zag and Stoker’s products							$	46,390		$	44,509
Creative Distribution Solutions								6,088			6,960
Total	$	51,469		$	59,973		$	52,478		$	51,469

Operating income (loss)
Zig-Zag products	$	18,503		$	21,338		$	17,000		$	18,503
Stoker’s products		13,378			13,826			15,110			13,378
NewGen products		552			1,657
Corporate unallocated ⁽¹⁾⁽²⁾		(14,287	)		(11,942	)		(12,025	)		(14,287	)
Total Zig-Zag and Stoker’s products							$	20,085		$	17,594
Creative Distribution Solutions								460			552
Total	$	18,146		$	24,879		$	20,545		$	18,146

Interest expense, net		5,144			5,522			4,019			5,144
Investment income		6,227			(110	)
Investment loss								4,080			6,227
Gain on extinguishment of debt								(600	)		-

Income before income taxes	$	6,775		$	19,467		$	13,046		$	6,775

Capital expenditures
Zig-Zag products	$	2,237		$	98		$	112		$	2,237
Stoker’s products		670			1,177			446			670
NewGen products		0			53
Total Zig-Zag and Stoker’s products							$	558		$	2,907
Creative Distribution Solutions								-			-
Total	$	2,907		$	1,328		$	558		$	2,907

Depreciation and amortization
Zig-Zag products	$	93		$	93		$	267		$	93
Stoker’s products		770			629			709			770
NewGen products		472			515
Total Zig-Zag and Stoker’s products							$	976		$	863
Creative Distribution Solutions								554			472
Total	$	1,335		$	1,237		$	1,530		$	1,335

(1)	Includes corporate costs that are not allocated to any of the 3three reportable segments.

(2)	Includes costs related to PMTA of $0.7 million in 2023 and $2.0 million in ~~2022 and $3.3 milion in 2021.~~2022.

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							Six Months Ended June 30,
	Six Months Ended June 30,						2023			2022
	2022			2021
Net sales
Zig-Zag products	$	91,898		$	88,206		$	88,609		$	91,898
Stoker’s products		65,291			62,624			69,718			65,291
NewGen products		46,630			79,454
Total Zig-Zag and Stoker’s products							$	158,327		$	157,189
Creative Distribution Solutions								48,224			46,630
Total	$	203,819		$	230,284		$	206,551		$	203,819

Gross profit
Zig-Zag products	$	52,773		$	52,639		$	48,812		$	52,773
Stoker’s products		35,765			34,038			39,433			35,765
NewGen products		14,725			26,557
Total Zig-Zag and Stoker’s products							$	88,245		$	88,538
Creative Distribution Solutions								12,850			14,725
Total	$	103,263		$	113,234		$	101,095		$	103,263

Operating income (loss)
Zig-Zag products	$	37,240		$	40,775		$	30,641		$	37,240
Stoker’s products		26,883			26,081			29,672			26,883
NewGen products		1,230			3,663
Corporate unallocated ⁽¹⁾⁽²⁾		(27,978	)		(21,291	)		(22,647	)		(27,978	)
Total Zig-Zag and Stoker’s products							$	37,666		$	36,145
Creative Distribution Solutions								721			1,230
Total	$	37,375		$	49,228		$	38,387		$	37,375

Interest expense, net		10,340			10,009			8,029			10,340
Investment income		6,149			(135	)
Loss on extinguishment of debt		0			5,706
Investment loss								8,879			6,149
Gain on extinguishment of debt								(1,377	)		-

Income before income taxes	$	20,886		$	33,648		$	22,856		$	20,886

Capital expenditures
Zig-Zag products	$	4,560		$	98		$	1,085		$	4,560
Stoker’s products		1,134			2,017			1,908			1,134
NewGen products		0			55
Total Zig-Zag and Stoker’s products							$	2,993		$	5,694
Creative Distribution Solutions								-			-
Total	$	5,694		$	2,170		$	2,993		$	5,694

Depreciation and amortization
Zig-Zag products	$	185		$	207		$	534		$	185
Stoker’s products		1,537			1,263			1,415			1,537
NewGen products		947			1,030
Total Zig-Zag and Stoker’s products							$	1,949		$	1,722
Creative Distribution Solutions								1,128			947
Total	$	2,669		$	2,500		$	3,077		$	2,669

(1)	Includes corporate costs that are not allocated to any of the 3three reportable segments.

(2)	Includes costs related to PMTA of $~~3.1~~0.8 million in ~~2022~~2023 and ~~$9.2~~$3.1 million in ~~2021.~~2022.

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					June 30,		December 31,
	June 30, 2022		December 31, 2021		2023		2022
Assets
Zig-Zag products	$	175,509	$	227,554	$	191,672	$	225,893
Stoker’s products		232,285		142,334		168,326		151,241
NewGen products		58,532		72,746
Corporate unallocated ⁽¹⁾		137,983		158,926		167,190		155,348
Total Zig-Zag and Stoker’s products					$	527,188	$	532,482
Creative Distribution Solutions						32,486		39,624
Total	$	604,309	$	601,560	$	559,674	$	572,106

(1)	Includes assets not assigned to the 3three reportable segments. All goodwill has been allocated to the reportable segments.

Revenue Disaggregation—Sales Channel

Revenues of the Zig-Zag Products and Stoker’s Products segments are primarily comprised of sales made to wholesalers while ~~NewGen~~Creative Distribution Solutions sales are made business to business and business to consumer, both online and through our corporate retail stores. ~~NewGen~~Creative Distribution Solutions net sales are broken out by sales channel below.

					Creative Distribution Solutions Segment
	NewGen Segment				Three Months Ended
	Three Months Ended June 30,				June 30,
	2022		2021		2023		2022
Business to Business	$	17,674	$	30,715	$	20,038	$	17,674
Business to Consumer - Online		5,336		11,263		2,525		5,336
Other		101		94		254		101
Total	$	23,111	$	42,072	$	22,817	$	23,111

					Creative Distribution Solutions Segment
	NewGen Segment				Six Months Ended
	Six Months Ended June 30,				June 30,
	2022		2021		2023		2022
Business to Business	$	36,798	$	57,972	$	42,531	$	36,798
Business to Consumer - Online		9,569		21,296		5,335		9,569
Other		263		186		358		263
Total	$	46,630	$	79,454	$	48,224	$	46,630

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Net Sales—Domestic vs. Foreign

The following table shows a breakdown of consolidated net sales between domestic and foreign customers.

					Three Months Ended
	Three Months Ended June 30,				June 30,
	2022		2021		2023		2022
Domestic	$	95,442	$	116,843	$	98,121	$	95,442
Foreign		7,483		5,800		7,474		7,483
Total	$	102,925	$	122,643	$	105,595	$	102,925

					Six Months Ended
	Six Months Ended June 30,				June 30,
	2022		2021		2023		2022
Domestic	$	189,208	$	215,911	$	191,981	$	189,208
Foreign		14,611		14,373		14,570		14,611
Total	$	203,819	$	230,284	$	206,551	$	203,819

Note 17. Additional Information with Respect to Unrestricted Subsidiary

Under the terms of the Indenture and Senior Secured Notes, the Company has designated its subsidiaries, South Beach Brands LLC, TPB Beast LLC and Intrepid Brands, LLC as “Unrestricted Subsidiaries”. South Beach Brands LLC is a holding company under which our vape business TPB Beast LLC operating as Creative Distribution Solutions sits. The Company is required under the terms of the Indenture and the Senior Secured Notes to present additional information that reflects the financial condition and results of operations of the Company and its Restricted Subsidiaries separate from the financial condition and results of operations of the Company’s Unrestricted Subsidiaries as of and for the periods presented. This additional information is below.

Income Statement for the Three Months Ended June 30, 2023 and 2022 (unaudited):

	Three Months Ended June 30
	2023								2022
	Company and Restricted Subsidiaries			Unrestricted Subsidiaries		Consolidated			Company and Restricted Subsidiaries			Unrestricted Subsidiaries		Consolidated
Net sales	$	82,778		$	22,817	$	105,595		$	79,814		$	23,111	$	102,925
Cost of sales		36,388			16,729		53,117			35,305			16,151		51,456
Gross profit		46,390			6,088		52,478			44,509			6,960		51,469
Selling, general, and administrative expenses		26,305			5,628		31,933			26,915			6,408		33,323
Operating income		20,085			460		20,545			17,594			552		18,146
Interest expense, net		4,019			-		4,019			5,144			-		5,144
Investment loss		4,080			-		4,080			6,227			-		6,227
Gain on extinguishment of debt		(600	)		-		(600	)		-			-		-
Income before income taxes		12,586			460		13,046			6,223			552		6,775
Income tax expense		3,220			118		3,338			1,441			128		1,569
Consolidated net income		9,366			342		9,708			4,782			424		5,206
Net loss attributable to non-controlling interest		(217	)		-		(217	)		(218	)		-		(218	)
Net income attributable to Turning Point Brands, Inc.	$	9,583		$	342	$	9,925		$	5,000		$	424	$	5,424

Income Statement for the Six Months Ended June 30, 2023 and 2022 (unaudited):

	Six Months Ended June 30
	2023								2022
	Company and Restricted Subsidiaries			Unrestricted Subsidiaries		Consolidated			Company and Restricted Subsidiaries			Unrestricted Subsidiaries		Consolidated

Net sales	$	158,327		$	48,224	$	206,551		$	157,189		$	46,630	$	203,819
Cost of sales		70,082			35,374		105,456			68,651			31,905		100,556
Gross profit		88,245			12,850		101,095			88,538			14,725		103,263
Selling, general, and administrative expenses		50,579			12,129		62,708			52,393			13,495		65,888
Operating income		37,666			721		38,387			36,145			1,230		37,375
Interest expense, net		8,029			-		8,029			10,340			-		10,340
Investment loss		8,879			-		8,879			6,149			-		6,149
Gain on extinguishment of debt		(1,377	)		-		(1,377	)		-			-		-
Income before income taxes		22,135			721		22,856			19,656			1,230		20,886
Income tax expense		5,623			183		5,806			4,620			289		4,909
Consolidated net income		16,512			538		17,050			15,036			941		15,977
Net loss attributable to non-controlling interest		(472	)		-		(472	)		(445	)		-		(445	)
Net income attributable to Turning Point Brands, Inc.	$	16,984		$	538	$	17,522		$	15,481		$	941	$	16,422

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Balance Sheet as of June 30, 2023 (unaudited):

ASSETS	Company and Restricted Subsidiaries		Unrestricted Subsidiaries		Eliminations			Consolidated
Current assets:
Cash	$	96,701	$	3,806	$	-		$	100,507
Accounts receivable, net		7,550		370		-			7,920
Inventories		115,646		9,410		-			125,056
Other current assets		15,103		3,113		-			18,216
Total current assets		235,000		16,699		-			251,699
Property, plant, and equipment, net		23,808		320		-			24,128
Deferred income taxes		7,966		-		-			7,966
Right of use assets		10,888		35		-			10,923
Deferred financing costs, net		229		-		-			229
Goodwill		136,244		-		-			136,244
Other intangible assets, net		66,646		15,402		-			82,048
Master Settlement Agreement (MSA) escrow deposits		28,229		-		-			28,229
Other assets		18,178		30		-			18,208
Investment in unrestricted subsidiaries		51,836		-		(51,836	)		-
Total assets	$	579,024	$	32,486	$	(51,836	)	$	559,674

LIABILITIES AND STOCKHOLDERS’ EQUITY
Current liabilities:
Accounts payable	$	9,449	$	1,353	$	-		$	10,802
Accrued liabilities		29,018		1,880		-			30,898
Other current liabilities		5		-		-			5
Total current liabilities		38,472		3,233		-			41,705
Notes payable and long-term debt		379,195		-		-			379,195
Lease liabilities		9,528		-		-			9,528
Total liabilities		427,195		3,233		-			430,428

Commitments and contingencies

Stockholders’ equity:
Total Turning Point Brands Inc. Stockholders’ Equity/Net parent investment in unrestricted subsidiaries		150,653		29,253		(51,836	)		128,070
Non-controlling interest		1,176		-		-			1,176
Total stockholders’ equity		151,829		29,253		(51,836	)		129,246
Total liabilities and stockholders’ equity	$	579,024	$	32,486	$	(51,836	)	$	559,674

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Balance Sheet as of December 31, 2022:

ASSETS	Company and Restricted Subsidiaries		Unrestricted Subsidiaries		Eliminations			Consolidated
Current assets:
Cash	$	103,990	$	2,413	$	-		$	106,403
Accounts receivable, net		7,374		1,003		-			8,377
Inventories		104,883		15,032		-			119,915
Other current assets		18,828		4,131		-			22,959
Total current assets		235,075		22,579		-			257,654
Property, plant, and equipment, net		22,261		527		-			22,788
Deferred income taxes		8,443		-		-			8,443
Right of use assets		12,328		137		-			12,465
Deferred financing costs, net		282		-		-			282
Goodwill		136,253		-		-			136,253
Other intangible assets, net		67,241		16,351		-			83,592
Master Settlement Agreement (MSA) escrow deposits		27,980		-		-			27,980
Other assets		22,619		30		-			22,649
Investment in unrestricted subsidiaries		60,120		-		(60,120	)		-
Total assets	$	592,602	$	39,624	$	(60,120	)	$	572,106

LIABILITIES AND STOCKHOLDERS’ EQUITY
Current liabilities:
Accounts payable	$	7,628	$	727	$	-		$	8,355
Accrued liabilities		31,118		1,883		-			33,001
Other current liabilities		20		-		-			20
Total current liabilities		38,766		2,610		-			41,376
Notes payable and long-term debt		406,757		-		-			406,757
Lease liabilities		10,593		-		-			10,593
Total liabilities		456,116		2,610		-			458,726

Commitments and contingencies

Stockholders’ equity:
Total Turning Point Brands Inc. Stockholders’ Equity/Net parent investment in unrestricted subsidiaries		134,751		37,014		(60,120	)		111,645
Non-controlling interest		1,735		-		-			1,735
Total stockholders’ equity		136,486		37,014		(60,120	)		113,380
Total liabilities and stockholders’ equity	$	592,602	$	39,624	$	(60,120	)	$	572,106

Note 18. Dividends and Share ~~Repurchase~~Repurchases

~~The most recent~~A dividend of ~~$0.06~~$0.065 per common share was paid on July ~~8, 2022,~~7, 2023, to shareholders of record at the close of business on June ~~17, 2022.~~16, 2023.

The Company currently pays a quarterly cash dividend. Dividends are considered restricted payments under the Senior Secured Notes Indenture and 2021 Revolving Credit Facility. The Company is generally permitted to make restricted payments provided that, at the time of payment, or as a result of payment, the Company is not in default on its debt covenants. Additional earnings and market capitalization restrictions limit the aggregate amount of restricted, quarterly dividends during a fiscal year.

On February 25, 2020, the Company’s Board of Directors approved a $50.0 million share repurchase program which is intended for opportunistic execution based upon a variety of factors including market dynamics. ~~On October~~ ~~25,2021,~~ ~~the Board increased the approved share repurchase program by~~ ~~$30.7 million. On February~~ ~~24,2022,~~ ~~the Board increased the approve share repurchase program by~~ ~~$24.6 million~~. The program is subject to the ongoing discretion of the ~~Board. The total number~~Board of ~~shares repurchased for~~Directors. On October 25, 2021, the ~~three~~Board ~~months ended June~~ of Directors~~30,~~ increased the approved share repurchase program by $30.7 million and by an additional $24.6 million on February 24, 2022 ~~was~~, in each case bringing the aggregate approval back to $50.0 million. ~~301,662~~ ~~shares for a total cost of~~ $~~8.8~~27.2 million ~~and an average price per share of~~ ~~$29.16.$37.0 million~~ remains available for share repurchases under the program at June 30,~~2022.~~ 2023.

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Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations

You should read the following discussion of the historical financial condition and results of operations in conjunction with our historical consolidated financial statements and accompanying notes, which are included elsewhere in this Quarterly Report on Form 10-Q. In addition, this discussion includes forward-looking statements subject to risks and uncertainties that may result in actual results differing from statements we make. See “Cautionary Note Regarding Forward-Looking Statements.” Factors that could cause actual results to differ include those risks and uncertainties discussed in “Risk Factors.”

The following ~~discussion~~Management’s Discussion and Analysis (“MD&A”) relates to the unaudited financial statements of Turning Point Brands, Inc., included elsewhere in this Quarterly Report on Form 10-Q. The MD&A is intended to enable the reader to understand the Company’s financial condition and results of operations, including any material changes in the Company’s financial condition and results of operations since December 31, 2022, and as compared with the three and six months ended June 30, 2022. The MD&A is provided as a supplement to and should be read in conjunction with the unaudited consolidated financial statements and notes thereto included in the Quarterly report on Form 10-Q, as well as “Management’s Discussion and Analysis of Financial Condition and Results of Operations” contained in the 2022 Annual Report.

In this ~~discussion,~~MD&A, unless the context requires otherwise, references to “our Company” “we,” “our,” or “us” refer to Turning Point Brands, Inc., and its consolidated subsidiaries. References to “TPB” refer to Turning Point Brands, Inc., without any of its subsidiaries. We were incorporated in 2004 under the name North Atlantic Holding Company, Inc. On November 4, 2015, we changed our name to Turning Point Brands, Inc. Many of the amounts and percentages in this discussion have been rounded for convenience of presentation.

Overview

Turning Point Brands, Inc. (the “Company,” “we,” “our,” or “us”) is a leading manufacturer, marketer and distributor of branded consumer products. We sell a wide range of products to adult consumers consisting of staple products with our iconic brands Zig-Zag^®and Stoker’s^®and our next generation products to fulfill evolving consumer preferences. Among other markets, we compete in the alternative smoking accessories and Other Tobacco Products (“OTP”) industries. The alternative smoking accessories market is a dynamic market experiencing robust secular growth driven by cannabinoid legalization in the U.S. and Canada, and positively evolving consumer perception and acceptance in North America. The OTP industry, which consists of non-cigarette tobacco products, exhibited mid-single-digit consumer unit annualized growth over the ~~year~~three-year period ~~ending 2021~~ended 2022 as reported by Management Science Associates, Inc. (“MSAi”), a third-party analytics and information company. Our ~~three focus~~ segments are led by our core, proprietary brands: Zig-Zag^® and CLIPPER^® in the Zig-Zag Products segment; Stoker’s^® along with Beech-Nut^® and Trophy^® in the Stoker’s ~~Products segment; and our distribution platforms (Vapor Beast~~^®~~, VaporFi~~^® ~~and~~ ~~Direct Vapor~~^®) ~~along with~~ ~~Solace~~^® ~~in the NewGen~~ Products segment. Our businesses generate solid cash flows which we use to invest in our business, finance acquisitions, increase brand support, expand our distribution infrastructure, and strengthen our capital position. We currently ship to approximately 800 distributors with an additional 200 secondary, indirect wholesalers in the U.S. that carry and sell our products. Under the leadership of a senior management team with extensive experience in the consumer products, alternative smoking accessories and tobacco industries, we have grown and diversified our business through new product launches, category expansions, and acquisitions while concurrently improving operational efficiency.

We believe there are meaningful opportunities to grow through acquisitions and joint ventures across all product categories. ~~As of December 31, 2021, our~~Our products are currently available in approximately ~~195,000~~197,000 U.S. retail locations which, with the addition of retail stores in Canada, brings our total North American retail presence to an estimated ~~215,000~~217,000 points of distribution. Our sales team targets widespread distribution to all traditional retail channels, including convenience stores, and we have a growing e-commerce business.

In the fourth quarter of 2022, we contributed our NewGen Products business to South Beach Holdings LLC doing business as Creative Distribution Solutions (“CDS”), a newly-formed wholly-owned subsidiary. CDS is separately operated and reports to its own Board of Directors. During the first quarter of 2023, the business was designated an unrestricted subsidiary under the Senior Secured Notes and concurrently we renamed what we previously referred to as our NewGen Products segment as our Creative Distribution Solutions segment as we believe this name better aligns with the goals and strategies of the segment.

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Products

We operate in three segments: Zig-Zag Products, Stoker’s Products and ~~NewGen Products.~~Creative Distribution Solutions. In our Zig-Zag Products segment, we principally market and distribute (i) rolling papers, tubes, and related products; and (ii) finished cigars and make-your-own (“MYO”) cigar ~~wraps.~~wraps and (iii) lighters and other accessories. In addition, we have a majority stake in Turning Point Brands Canada which markets and distributes cannabis accessories and tobacco products throughout Canada. In our Stoker’s Products segment, we (i) manufacture and market moist snuff tobacco (“MST”) and (ii) contract for and market loose leaf chewing tobacco products. In our ~~NewGen Products~~Creative Distribution Solutions segment, we (i) market and distribute liquid vapor products and certain other products without tobacco and/or nicotine; (ii) distribute a wide assortment of products to non-traditional retail via VaporBeast; and (iii) market and distribute a wide assortment of products to individual consumers via the VaporFi and Direct Vapor B2C online platform.

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Operations

Our core Zig-Zag Products and Stoker’s Products segments primarily generate revenues from the sale of our products to wholesale distributors who, in turn, resell the products to retail operations. Our acquisition of VaporBeast in 2016 expanded our revenue streams as we began selling directly to non-traditional retail outlets. Our acquisition of IVG in 2018 enhanced our B2C revenue stream with the addition of the Vapor-Fi online platform. The acquisition of Solace in 2019 provided us with a line of leading liquids and a powerful new product development platform. Our net sales, which include federal excise taxes, consist of gross sales net of cash discounts, returns, and selling and marketing allowances.

We rely on long-standing relationships with high-quality, established manufacturers to provide the majority of our produced products. More than ~~80%~~75% of our production, as measured by net sales, is outsourced to suppliers. The remaining production consists primarily of our moist snuff tobacco operations located in Dresden, Tennessee, and Louisville, Kentucky. Our principal operating expenses include the cost of raw materials used to manufacture the limited number of our products which we produce in-house; the cost of finished products, which are generally purchased goods; federal excise taxes; legal expenses; and compensation expenses, including benefits and costs of salaried personnel. Our other principal expenses include interest expense and other expenses.

Key Factors Affecting Our Results of Operations

We consider the following to be the key factors affecting our results of operations:

●

~~Our ability to further penetrate markets with our existing products;~~

●

~~Our ability to introduce new products and product lines that complement our core business;~~

●

~~Decreasing interest in some tobacco products among consumers;~~

●

~~Marketing and promotional initiatives, which cause variability in our results;~~

●

~~General economic conditions, including consumer access to disposable income and other conditions affecting purchasing power such as inflation;~~

●

~~Price sensitivity in our end-markets;~~

●

~~Cost and increasing regulation of promotional and advertising activities;~~

●

~~Cost of complying with regulation, including the “deeming regulation”;~~

●

~~Increasing and unpredictable regulation of NewGen products;~~

●

~~Counterfeit and other illegal products in our end-markets;~~

●

~~Currency fluctuations;~~

●

~~Our ability to identify attractive acquisition opportunities; and~~

●

Our ability to further penetrate markets with our existing products;

Our ability to introduce new products and product lines that complement our core business;

Decreasing interest in some tobacco products among consumers;

Price sensitivity in our end-markets;

Marketing and promotional initiatives, which cause variability in our results;

Cost and increasing regulation of promotional and advertising activities;

General economic conditions, including consumer access to disposable income and other conditions affecting purchasing power such as inflation;

Labor and production costs;

Cost of complying with regulation, including the “deeming regulation”;

Increasing and unpredictable regulation of Creative Distribution Solutions products;

Counterfeit and other illegal products in our end-markets;

Currency fluctuations;

Our ability to identify attractive acquisition opportunities; and

Our ability to successfully integrate acquisitions.

~~Recent Developments~~

~~Non-Tobacco Nicotine Included Under Jurisdiction of FDA’s Center for Tobacco Products~~

New legislation enacted on March 15, 2022, provides authority for the FDA to regulate tobacco products containing nicotine from any source (“NTN Products”). This law took effect April 14, 2022, and requires NTN Products to comply with applicable requirements under the Federal Food, Drug, and Cosmetic Act, such as not selling to persons under 21 years of age, not marketing these products as modified risk tobacco products without FDA’s authorization, and not distributing free samples. Additionally, companies with NTN Products in the market between March 15, 2022, and April 14, 2022, were required to file a premarket tobacco application by May 14, 2022. NTN Products subject of a timely-filed PMTA, and not in receipt of a negative action, were allowed to remain on the market until July 13, 2022, at which time these products became subject to enforcement, similar to tobacco-derived products remaining under review. We submitted premarket filings for certain of our NTN Products prior to the May 14, 2022, deadline. While these applications remain under review, we will continue to supplement these filings with additional information to support a finding that the marketing of these products is “appropriate for the protection of public health.”

~~CLIPPER~~^®~~Lighters~~

~~In February 2022, we entered into an agreement with Flamagas, a renowned lighter manufacturer, for exclusive distribution of CLIPPER~~^® ~~lighters in the United States and Canada.~~

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~~Final Rule Related to PACT Act Published~~

On October 21, 2021, the United States Postal Service (“USPS”) published a Final Rule entitled “Treatment of E-Cigarettes in the Mail,” which followed its earlier publication of the Proposed Rule on February 19, 2021. This Final Rule was required as a result of the inclusion of Division FF, Title VI (Preventing Online Sales of E-Cigarettes to Children or “POSECA”) in the Further Consolidated Appropriations Act, 2021. POSECA, among other things, expanded the definition of “cigarettes” in the Jenkins Act and Prevent All Cigarette Trafficking (“PACT”) Act to expressly capture “electronic nicotine delivery systems,” i.e., ENDS. Consistent with the Proposed Rule, the Final Rule extends the existing prohibition on and exceptions to the mailing of “cigarettes” via USPS to ENDS products, other than the Consumer Testing and Public Health exceptions. Specifically, the Final Rule extends the following exceptions to the prohibition on mailing of ENDS products: the Business/Regulatory Purposes Exception, the Certain Individuals Exception, and the exception for intra-Alaska and intra-Hawaii shipments. We have received certain shipping exemptions from carrier services to carry the affected freight and have created a supplemental logistical network for those shipments not covered by the exemptions.

Critical Accounting Policies and Uses of Estimates

There have been no material changes to our critical accounting policies and estimates from the information provided in “Management’s Discussion and Analysis of Financial Condition and Results of Operations” included in our ~~2021~~2022 Annual Report on Form 10-K.

Recent Accounting Pronouncements

There are no recent accounting pronouncements that impact the Company.

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Results of Operations

Comparison of the Three Months Ended June 30, ~~2022,~~2023, to the Three Months Ended June 30, ~~2021~~2022

The table and discussion set forth below displays our consolidated results of operations (in thousands):

	Three Months Ended June 30,									Three Months Ended June 30,
	2022			2021			% Change			2023			2022			% Change
Consolidated Results of Operations Data:
Net sales
Zig-Zag products	$	46,226		$	47,202			-2.1	%	$	46,722		$	46,226			1.1	%
Stoker's products		33,588			33,369			0.7	%
NewGen products		23,111			42,072			-45.1	%
Stoker’s products											36,056			33,588			7.3	%
Total Zig-Zag and Stoker’s products											82,778			79,814			3.7	%
Creative Distribution Solutions											22,817			23,111			-1.3	%
Total net sales		102,925			122,643			-16.1	%		105,595			102,925			2.6	%
Cost of sales		51,456			62,670			-17.9	%		53,117			51,456			3.2	%
Gross profit
Zig-Zag products		26,430			27,743			-4.7	%		26,422			26,430			0.0	%
Stoker's products		18,079			18,146			-0.4	%
NewGen products		6,960			14,084			-50.6	%
Stoker’s products											19,968			18,079			10.4	%
Total Zig-Zag and Stoker’s products											46,390			44,509			4.2	%
Creative Distribution Solutions											6,088			6,960			-12.5	%
Total gross profit		51,469			59,973			-14.2	%		52,478			51,469			2.0	%

Selling, general, and administrative expenses		33,323			35,094			-5.0	%		31,933			33,323			-4.2	%
Operating income		18,146			24,879			-27.1	%		20,545			18,146			13.2	%
Interest expense, net		5,144			5,522			-6.8	%		4,019			5,144			-21.9	%
Investment loss (income)		6,227			(110	)		-5760.9	%
Investment loss											4,080			6,227			-34.5	%
Gain on extinguishment of debt											(600	)		-		NM
Income before income taxes		6,775			19,467			-65.2	%		13,046			6,775			92.6	%
Income tax expense		1,569			4,424			-64.5	%		3,338			1,569			112.7	%
Consolidated net income		5,206			15,043			-65.4	%		9,708			5,206			86.5	%
Net loss attributable to non-controlling interest		(218	)		(312	)		-30.1	%		(217	)		(218	)		-0.5	%
Net income attributable to Turning Point Brands, Inc.	$	5,424		$	15,355			-64.7	%	$	9,925		$	5,424			83.0	%

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Net Sales: For the three months ended June 30, ~~2022,~~2023, consolidated net sales ~~decreased~~increased to ~~$102.9~~$105.6 million from ~~$122.6~~$102.9 million for the three months ended June 30, ~~2021, a decrease~~2022, an increase of ~~$19.7~~$2.7 million or ~~16.1%~~2.6%. ~~The decrease in net sales was primarily driven by decreased sales volume in the NewGen Products segment.~~

For the three months ended June 30, ~~2022,~~2023, net sales in the Zig-Zag Products segment ~~decreased~~increased to ~~$46.2~~$46.7 million from ~~$47.2~~$46.2 million for the three months ended June 30, ~~2021, a decrease~~2022, an increase of ~~$1.0~~$0.5 million or ~~2.1%~~1.1%. ~~For the three months ended June 30, 2022, volume decreased 2.3%~~The increase in net sales was driven by strong growth in our Canadian and ~~price/mix increased 0.2%. Our U.S. rolling papers business grew double-digits, primarily through our e-commerce channels. However, these increases were~~other smoking accessories businesses partially offset by declines in the ~~cigar~~U.S. rolling papers and wraps ~~business driven partially by a trade inventory reduction during the current period compared with a trade inventory load in the prior year period.~~businesses.

For the three months ended June 30, ~~2022,~~2023, net sales in the Stoker’s Products segment increased to ~~$33.6~~$36.1 million from ~~$33.4~~$33.6 million for the three months ended June 30, ~~2021,~~2022, an increase of ~~$0.2~~$2.5 million or ~~0.7%~~7.3%. For the three months ended June 30, ~~2022,~~2023, volume ~~decreased 6.1%~~increased 0.7% and price/product mix increased ~~6.8%~~6.6%. The increase in net sales was driven by ~~mid-single digit~~double-digit growth of Stoker’s^® ~~MST. However, this was~~MST partially offset by a decline in loose-leaf chewing tobacco.

For the three months ended June 30, ~~2022,~~2023, net sales in the ~~NewGen products~~Creative Distribution Solutions segment decreased to ~~$23.1~~$22.8 million from ~~$42.1~~$23.1 million for the three months ended June 30, ~~2021,~~2022, a decrease of ~~$19.0~~$0.3 million or ~~45.1%~~1.3%. The decrease in net sales was primarily the result of ~~declines~~lower volumes in the vape distribution ~~businesses which continues to be impacted by the regulatory environment.~~businesses.

Gross Profit: For the three months ended June 30, ~~2022,~~2023, consolidated gross profit ~~decreased~~increased to ~~$51.5~~$52.5 million from ~~$60.0~~$51.5 million for the three months ended June 30, ~~2021, a decrease~~2022, an increase of ~~$8.5~~$1.0 million or ~~14.2%~~2.0%. Gross profit as a percentage of ~~revenue increased~~net sales decreased to 49.7% for the three months ended June 30, 2023, compared to 50.0% for the three months ended June 30, 2022 ~~compared to 48.9% for the three months ended June 30, 2021~~ driven by ~~mix as~~increased margin in the ~~NewGen~~Stoker’s Products segment ~~which experienced~~offset by decreased margin in the Zig-Zag Products and Creative Distribution Solutions segments as a ~~significant revenue decrease generates lower margins.~~result of price/product mix.

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For the three months ended June 30, ~~2022,~~2023, gross profit in the Zig-Zag Products segment ~~decreased to~~remained unchanged at $26.4 million ~~from $27.7 million for~~compared to the three months ended June 30, ~~2021, a decrease of $1.3 million or 4.7%.~~2022. Gross profit as a percentage of net sales decreased to 56.6% of net sales for the three months ended June 30, 2023, from 57.2% of net sales for the three months ended June 30, 2022, driven primarily by product mix.

For the three months ended June 30, 2023, gross profit in the Stoker’s Products segment increased to $20.0 million from ~~58.8%~~$18.1 million for the three months ended June 30, 2022, an increase of $1.9 million or 10.4%. Gross profit as a percentage of net sales increased to 55.4% of net sales for the three months ended June 30, ~~2021, as a result of strong growth in lower gross margin products.~~

~~For the three months ended June 30, 2022, gross profit in the Stoker’s Products segment was flat at $18.1 million. Gross profit as a percentage of net sales decreased to~~2023, from 53.8% of net sales for the three months ended June 30, 2022, primarily as a result of strong market share and pricing gains in MST.

For the three months ended June 30, 2023, gross profit in the Creative Distribution Solutions segment decreased to $6.1 million from ~~54.4%~~$7.0 million for the three months ended June 30, 2022, a decrease of $0.9 million or 12.5%. Gross profit as a percentage of net sales decreased to 26.7% of net sales for the three months ended June 30, 2021, primarily as a result of an inventory write-down of certain FRE nicotine pouch products due to rationalization of the product line ahead of the regulatory filing deadline for non-tobacco nicotine products in May 2022.

~~For the three months ended June 30, 2022, gross profit in the NewGen products segment decreased to $7.0 million~~2023, from ~~$14.1 million for the three months ended June 30, 2021, a decrease of $7.1 million or 50.6%. Gross profit as a percentage of net sales decreased to~~ 30.1% of net sales for the three months ended June 30, 2022, ~~from 33.5% of net sales for the three months ended June 30, 2021,~~ primarily as a result of product ~~mix and the competitive environment.~~mix.

Selling, General, and Administrative Expenses: For the three months ended June 30, ~~2022,~~2023, selling, general, and administrative expenses decreased to ~~$33.3~~$31.9 million from ~~$35.1~~$33.3 million for the three months ended June 30, ~~2021,~~2022, a decrease of ~~$1.8~~$1.4 million or ~~5.0%~~4.2%. Selling, general and administrative expenses in the three months ended June 30, 2023, included $2.1 million of stock options, restricted stock and incentives expense, $0.7 million of expense related to PMTA, $0.1 million of transaction costs and $0.1 million of expense related to the new ERP and CRM systems. Selling, general and administrative expenses in the three months ended June 30, 2022, included $1.5 million of stock ~~options,~~option, restricted stock and incentives expense, $0.4 million of transaction ~~expense,~~costs, $2.0 million of expense related to PMTA, $0.3 million of expense related to corporate restructuring and $0.9 million of consulting expense related to the scoping of the new ERP and CRM systems. Selling, general and administrative expenses in the three months ended June 30, 2021, included $2.8 million of stock option, restricted stock and incentives expense (including $1.1 million for accelerated vesting of options for a departing executive), $0.7 million of transaction costs and $0.6 million of expense related to PMTA.

Interest Expense, net: For the three months ended June 30, ~~2022,~~2023, interest expense, net decreased to ~~$5.1~~$4.0 million from ~~$5.5~~$5.1 million for the three months ended June 30, ~~2021~~2022 as a result of the ~~repayment~~repurchase of $39.0 million of Convertible Senior Notes in the ~~Promissory Note~~fourth quarter of 2022 and ~~forgiveness~~the first half of ~~the Unsecured Loan each discussed in Note 11.~~2023, and increased interest income on cash as a result of rising interest rates.

Investment ~~Loss (Income):~~Loss: For the three months ended June 30, ~~2022,~~2023, investment loss ~~increased~~decreased to ~~$6.2~~$4.1 million compared to ~~$0.1~~a $6.2 million ~~of investment income~~loss for the three months ended June 30, ~~2021, primarily~~2022. The change is a result of the impairment charge recognized on our investment in Docklight for $3.7 million in the second quarter 2023 compared to an impairment charge of $6.3 million in the second quarter of 2022 related to our investment in Dosist.

Gain on Extinguishment of Debt: There was a gain on extinguishment of debt of $0.6 million for the three months ended June 30, 2023 as a result of repurchasing $15.1 million of Convertible Senior Notes compared to no gain on extinguishment of debt for the ~~$6.3 million impairment of our investment in dosist. See Note 9 Other Assets in the Consolidated Financial Statements for information on the dosist impairment.~~three months ended June 30, 2022.

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Income Tax Expense: Our income tax expense of ~~$1.6~~$3.3 million was ~~23.2%~~25.6% of income before income taxes for the three months ended June 30, ~~2022 and included a discrete tax benefit of $0.3 million~~ ~~relating to stock option exercises~~.2023. Our effective income tax rate was ~~22.7%~~23.2% for the three months ended June 30, ~~2021~~2022 and included a discrete tax benefit ~~$2.0~~$0.3 million relating to stock option exercises.

Net Loss Attributable to Non-Controlling Interest: Net loss attributable to non-controlling interest was $0.2 million for the three months ended June 30, ~~2022~~2023 compared to ~~$0.3~~$0.2 million for the three months ended June 30, ~~2021.~~2022.

Net Income Attributable to Turning Point Brands, Inc.: Due to the factors described above, net income attributable to Turning Point Brands, Inc. for the three months ended June 30, 2023 and 2022, ~~and 2021,~~ was ~~$5.4~~$9.9 million and ~~$15.4~~$5.4 million, respectively.

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Comparison of the Six Months Ended June 30, ~~2022,~~2023, to the Six Months Ended June 30, ~~2021~~2022

The table and discussion set forth below displays our consolidated results of operations (in thousands):

	Six Months Ended June 30,									Six Months Ended June 30,
	2022			2021			% Change			2023			2022			% Change
Consolidated Results of Operations Data:
Net sales
Zig-Zag products	$	91,898		$	88,206			4.2	%	$	88,609		$	91,898			-3.6	%
Stoker's products		65,291			62,624			4.3	%
NewGen products		46,630			79,454			-41.3	%
Stoker’s products											69,718			65,291			6.8	%
Total Zig-Zag and Stoker’s products											158,327			157,189			0.7	%
Creative Distribution Solutions											48,224			46,630			3.4	%
Total net sales		203,819			230,284			-11.5	%		206,551			203,819			1.3	%
Cost of sales		100,556			117,050			-14.1	%		105,456			100,556			4.9	%
Gross profit
Zig-Zag products		52,773			52,639			0.3	%		48,812			52,773			-7.5	%
Stoker's products		35,765			34,038			5.1	%
NewGen products		14,725			26,557			-44.6	%
Stoker’s products											39,433			35,765			10.3	%
Total Zig-Zag and Stoker’s products											88,245			88,538			-0.3	%
Creative Distribution Solutions											12,850			14,725			-12.7	%
Total gross profit		103,263			113,234			-8.8	%		101,095			103,263			-2.1	%

Selling, general, and administrative expenses		65,888			64,006			2.9	%		62,708			65,888			-4.8	%
Operating income		37,375			49,228			-24.1	%		38,387			37,375			2.7	%
Interest expense, net		10,340			10,009			3.3	%		8,029			10,340			-22.4	%
Investment loss (income)		6,149			(135	)		-4654.8	%
Loss on extinguishment of debt		-			5,706			-100.0	%
Investment loss											8,879			6,149			44.4	%
Gain on extinguishment of debt											(1,377	)		-		NM
Income before income taxes		20,886			33,648			-37.9	%		22,856			20,886			9.4	%
Income tax expense		4,909			7,078			-30.6	%		5,806			4,909			18.3	%
Consolidated net income		15,977			26,570			-39.9	%		17,050			15,977			6.7	%
Net loss attributable to non-controlling interest		(445	)		(567	)		-21.5	%		(472	)		(445	)		6.1	%
Net income attributable to Turning Point Brands, Inc.	$	16,422		$	27,137			-39.5	%	$	17,522		$	16,422			6.7	%

Net Sales: For the six months ended June 30, ~~2022,~~2023, consolidated net sales ~~decreased~~increased to ~~$203.8~~$206.6 million from ~~$230.3~~$203.8 million for the six months ended June 30, ~~2021, a decrease~~2022, an increase of ~~$26.5~~$2.7 million or ~~11.5%~~1.3%. ~~The decrease in net sales was driven by decreased sales volume in the NewGen Products segment.~~

For the six months ended June 30, ~~2022,~~2023, net sales in the Zig-Zag Products segment ~~increased~~decreased to ~~$91.9~~$88.6 million from ~~$88.2~~$91.9 million for the six months ended June 30, ~~2021,~~2022, a decrease of $3.3 million or 3.6%. The decrease in net sales was driven by anticipated declines in the U.S. rolling papers and wraps businesses which were impacted by reduction of trade inventory during the period, offset by growth in our Canadian and other smoking accessories businesses.

For the six months ended June 30, 2023, net sales in the Stoker’s Products segment increased to $69.7 million from $65.3 million for the six months ended June 30, 2022, an increase of ~~$3.7~~$4.4 million or ~~4.2%~~6.8%. For the six months ended June 30, ~~2022,~~2023, volume increased ~~1.9%~~0.4% and price/product mix increased ~~2.2%~~6.4%. The increase in net sales was driven by double-digit growth ~~in U.S. rolling papers primarily through our e-commerce channels.~~of Stoker’s^® MST.

For the six months ended June 30, ~~2022,~~2023, net sales in the ~~Stoker’s Products~~Creative Distribution Solutions segment increased to ~~$65.3~~$48.2 million from ~~$62.6~~$46.6 million for the six months ended June 30, ~~2021,~~2022, an increase of ~~$2.7~~$1.6 million or ~~4.3%. For the six months ended June 30, 2022, volume decreased 3.2% and price/mix increased 7.5%~~3.4%. The increase ~~in net sales was driven by high-single digit growth of~~ ~~Stoker’s~~^® ~~MST.~~

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For the six months ended June 30, 2022, net sales in the NewGen products segment decreased to $46.6 million from $79.5 million for the six months ended June 30, 2021, a decrease of $32.8 million or 41.3%. The decrease in net sales was primarily the result of ~~declines~~improved volumes in the vape distribution ~~businesses which continue to be impacted by the regulatory environment.~~businesses.

Gross Profit: For the six months ended June 30, ~~2022,~~2023, consolidated gross profit decreased to ~~$103.3~~$101.1 million from ~~$113.2~~$103.3 million for the six months ended June 30, ~~2021,~~2022, a decrease of ~~$10.0~~$2.2 million or ~~8.8%~~2.1%. Gross profit as a percentage of ~~revenue increased~~net sales decreased to 48.9% for the six months ended June 30, 2023, compared to 50.7% for the six months ended June 30, 2022 ~~compared to 49.2% for the six months ended June 30, 2021~~ driven by increased margin in the Stoker’s Products segment offset by decreased margin in the Zig-Zag Products and ~~mix~~Creative Distribution Solutions segments as ~~the NewGen Products segment generates lower margins.~~a result of product mix.

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For the six months ended June 30, ~~2022,~~2023, gross profit in the Zig-Zag Products segment ~~increased~~decreased to ~~$52.8~~$48.8 million from ~~$52.6~~$52.8 million for the six months ended June 30, ~~2021, an increase~~2022, a decrease of ~~$0.1~~$4.0 million or ~~0.3%~~7.5%. Gross profit as a percentage of net sales decreased to 55.1% of net sales for the six months ended June 30, 2023, from 57.4% of net sales for the six months ended June 30, 2022, ~~from 59.7% of net sales for the six months ended June 30, 2021,~~ as a result of ~~strong growth~~product mix including the decline in net sales of higher margin U.S. rolling paper and wraps products and contribution of CLIPPER lighters, as a result of the exclusive distribution deal entered into in February, 2022, which operates at lower gross ~~margin products.~~profit margins.

For the six months ended June 30, ~~2022,~~2023, gross profit in the Stoker’s Products segment increased to ~~$35.8~~$39.4 million from ~~$34.0~~$35.8 million for the six months ended June 30, 2022, an increase of ~~$1.7~~$3.7 million or ~~5.1%~~10.3%. Gross profit as a percentage of net sales increased to 56.6% of net sales for the six months ended June 30, 2023, from 54.8% of net sales for the six months ended June 30, 2022, ~~from 54.4% of net sales for the six months ended June 30, 2021,~~ primarily as a result of the strong incremental margin contribution of MST.

For the six months ended June 30, ~~2022,~~2023, gross profit in the ~~NewGen products~~Creative Distribution Solutions segment decreased to ~~$14.7~~$12.9 million from ~~$26.6~~$14.7 million for the six months ended June 30, ~~2021,~~2022, a decrease of ~~$11.8~~$1.9 million or ~~44.6%~~12.7%. Gross profit as a percentage of net sales decreased to 26.6% of net sales for the six months ended June 30, 2023, from 31.6% of net sales for the six months ended June 30, 2022, ~~from 33.4% of net sales for the six months ended June 30, 2021,~~primarily as a result of product ~~mix and the competitive environment.~~mix.

Selling, General, and Administrative Expenses: For the six months ended June 30, ~~2022,~~2023, selling, general, and administrative expenses ~~increased~~decreased to ~~$65.9~~$62.7 million from ~~$64.0~~$65.9 million for the six months ended June 30, ~~2021, an increase~~2022, a decrease of ~~$1.9~~$3.2 million or ~~2.9%~~4.8%. Selling, general and administrative expenses ~~for~~in the six months ended June 30, 2023, included $2.8 million of stock options, restricted stock and incentives expense, $0.8 million of expense related to PMTA, $0.3 million of expense related to the new ERP and CRM systems and $0.1 million related to transaction costs. Selling, general and administrative expenses in the six months ended June 30, 2022, included $2.7 million of stock ~~options,~~option, restricted stock and incentives expense, $0.8 million of transaction ~~expense,~~costs, $3.1 million of expense related to PMTA, $1.6 million of expense related to corporate restructuring and $1.2 million of consulting expense related to the scoping of the new ERP and CRM systems. Selling, general and administrative expenses in the six months ended June 30, 2021, included $4.3 million of stock option, restricted stock and incentives expense (including $1.1 million for accelerated vesting of options for a departing executive), $1.3 million of transaction costs and $0.9 million of expense related to PMTA.

Interest Expense, net: For the six months ended June 30, ~~2022,~~2023, interest expense, net ~~increased~~decreased to ~~$10.3~~$8.0 million, from ~~$10.0~~$10.3 million for the six months ended June 30, ~~2021~~2022 as a result of the ~~increase~~repurchases of $39.0 million of Convertible Senior Notes in the ~~Company’s outstanding debt in February 2021.~~fourth quarter of 2022 and the first and second quarters of 2023, and increased interest income on cash as a result of rising interest rates.

Investment ~~Loss (Income):~~Loss: For the six months ended June 30, ~~2022,~~2023, investment ~~income~~loss increased to ~~$6.1~~$8.9 million compared to ~~$0.1~~$6.1 million ~~of investment income~~ for the six months ended June 30, ~~2021, primarily as~~2022. The change is a result of ~~$6.3 million~~the impairment ofcharge recognized on our investment in ~~dosist. See Note 9 Other Assets~~Docklight for $6.5 million in the ~~Consolidated Financial Statements for information on~~first half of 2023 compared to an impairment charge of $6.3 million in the ~~dosist impairment.~~second quarter of 2022 related to our investment in Dosist.

~~Loss~~Gain on Extinguishment of Debt: There was a gain on extinguishment of debt of $1.4 million for the six months ended June 30, 2023 as a result of repurchasing $29.0 million of Convertible Senior Notes during the first and second quarters of 2023 compared to no ~~loss~~gain on extinguishment of debt for the six months ended June 30, ~~2022 compared to $5.7 million for the six months ended June 30, 2021 related to the repayment of the 2018 First Lien Credit Facility.~~2022.

Income Tax Expense: Our income tax expense of ~~$4.9~~$5.8 million was ~~23.5%~~25.4% of income before income taxes for the six months ended June 30, ~~2022 and included a discrete tax benefit of $0.7 million~~ ~~relating to stock option exercises~~.2023. Our effective income tax rate was ~~21.0%~~23.5% for the six months ended June 30, ~~2021~~2022 and included a discrete tax benefit ~~$5.2~~$0.7 million relating to stock option exercises.

Net Loss Attributable to Non-Controlling Interest: Net loss attributable to non-controlling interest was $0.5 million for the six months ended June 30, 2023 compared to $0.4 million for the six months ended June 30, ~~2022 compared to $0.6 million for the six months ended June 30, 2021.~~2022.

Net Income Attributable to Turning Point Brands, Inc.: Due to the factors described above, net income attributable to Turning Point Brands, Inc. for the six months ended June 30, 2023 and 2022, ~~and 2021,~~ was ~~$16.4~~$17.5 million and ~~$27.1~~$16.4 million, respectively.

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EBITDA and Adjusted EBITDA

To supplement our financial information presented in accordance with generally accepted accounting principles in the United States, or U.S. GAAP, we use non-U.S. GAAP financial measures including EBITDA and Adjusted EBITDA. We believe Adjusted EBITDA provides useful information to management and investors regarding certain financial and business trends relating to our financial condition and results of operations. Adjusted EBITDA is used by management to compare our performance to that of prior periods for trend analyses and planning purposes and is presented to our Board of Directors. We believe that EBITDA and Adjusted EBITDA are appropriate measures of operating performance because they eliminate the impact of expenses that do not relate to operating performance. In addition, our debt instruments contain covenants which use Adjusted EBITDA calculations.

We define “EBITDA” as net income before interest expense, ~~loss~~gain (loss) on extinguishment of debt, provision for income taxes, depreciation, and amortization. We define “Adjusted EBITDA” as net income before interest expense, ~~loss~~gain (loss) on extinguishment of debt, provision for income taxes, depreciation, amortization, other non-cash items, and other items we do not consider ordinary course in our evaluation of ongoing operating performance noted in the reconciliation below.

Non-U.S. GAAP measures should not be considered a substitute for, or superior to, financial measures calculated in accordance with U.S. GAAP. Adjusted EBITDA excludes significant expenses required to be recorded in our financial statements by U.S. GAAP and is subject to inherent limitations. Other companies in our industry may calculate this non-U.S. GAAP measure differently than we do or may not calculate it at all, limiting its usefulness as a comparative measure. The tables below provide reconciliations between net income and Adjusted EBITDA.

(in thousands)	Three Months Ended June 30,				Three Months Ended June 30,
	2022		2021		2023			2022
Net income attributable to Turning Point Brands, Inc.	$	5,424	$	15,355	$	9,925		$	5,424
Add:
Interest expense, net		5,144		5,522		4,019			5,144
Gain on extinguishment of debt						(600	)		-
Income tax expense		1,569		4,424		3,338			1,569
Depreciation expense		879		758		759			879
Amortization expense		456		479		771			456
EBITDA	$	13,472	$	26,538	$	18,212		$	13,472
Components of Adjusted EBITDA
Corporate restructuring (a)		270		-		-			270
ERP/CRM (b)		861		-		138			861
Stock options, restricted stock, and incentives expense (c)		1,502		2,764		2,093			1,502
Transactional expenses (d)		364		702		82			364
FDA PMTA (e)		1,957		-		662			1,957
Non-cash asset impairment (f)		6,300		-		4,092			6,300
Adjusted EBITDA	$	24,726	$	30,004	$	25,279		$	24,726

(a)	Represents costs associated with corporate restructuring, including severance.

(b)	Represents cost associated with scoping and mobilization of new ERP and CRM ~~systems.~~systems and cost of duplicative ERP licenses.

(c)	Represents non-cash stock options, restricted stock, incentives expense and Solace performance stock units.

(d)	Represents the fees incurred for transaction expenses.

(e)	Represents costs associated with applications related to FDA premarket tobacco product application ~~("PMTA"~~(“PMTA”).

(f)	Represents impairment of investment ~~in dosist.~~assets.

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(in thousands)	Six Months Ended June 30,				Six Months Ended June 30,
	2022		2021		2023			2022
Net income attributable to Turning Point Brands, Inc.	$	16,422	$	27,137	$	17,522		$	16,422
Add:
Interest expense, net		10,340		10,009		8,029			10,340
Loss on extinguishment of debt		-		5,706
Gain on extinguishment of debt						(1,377	)		-
Income tax expense		4,909		7,078		5,806			4,909
Depreciation expense		1,750		1,546		1,535			1,750
Amortization expense		919		954		1,542			919
EBITDA	$	34,340	$	52,430	$	33,057		$	34,340
Components of Adjusted EBITDA
Corporate restructuring (a)		1,602		-		-			1,602
ERP/CRM (b)		1,191		-		276			1,191
Stock options, restricted stock, and incentives expense (c)		2,661		4,263		2,836			2,661
Transactional expenses (d)		789		1,309		86			789
FDA PMTA (e)		3,096		-		820			3,096
Non-cash asset impairment (f)		6,300		-		8,989			6,300
Adjusted EBITDA	$	49,979	$	58,002	$	46,064		$	49,979

(a)	Represents costs associated with corporate restructuring, including severance.

(b)	Represents cost ~~associated~~assosicated with scoping and mobilization of new ERP and CRM ~~systems.~~systems and cost of duplicative ERP licenses.

(c)	Represents non-cash stock options, restricted stock, incentives expense and Solace performance stock units.

(d)	Represents the fees incurred for transaction expenses.

(e)	Represents costs associated with applications related to FDA premarket tobacco product application ~~("PMTA"~~(“PMTA”).

(f)	Represents impairment of investment ~~in dosist.~~assets.

Liquidity and Capital ~~Reserves~~Resources

Our principal uses for cash are working capital, debt service, and capital expenditures. We believe our cash on hand, cash flows from operations and borrowing availability under our 2021 Revolving Credit Facility are adequate to satisfy our operating cash requirements for the foreseeable future. As of June 30, ~~2022,~~2023, we had ~~$107.4~~$100.5 million of cash on hand and have ~~$21.4~~$23.6 million of availability under the 2021 Revolving Credit Facility. Subsequent to the balance sheet date the Convertible Senior Notes became current in the amount of $133.5 million. Based on the current liquidity, free cash flow generation and other financing options, we believe there will be adequate liquidity to address the maturity of the Convertible Senior Notes.

Our working capital, which we define as current assets less cash and current liabilities, ~~increased $22.1~~decreased $0.4 million to ~~$102.6~~$109.5 million at June 30, ~~2022,~~2023, compared with ~~$80.5~~$109.9 million at December 31, ~~2021 primarily due to increase in inventory as a result of our annual tobacco purchase.~~2022.

	As of				As of
(in thousands)	June 30,		December 31,		June 30, 2023		December 31, 2022
	2022		2021

Current assets	$	151,659	$	120,849	$	151,192	$	151,251
Current liabilities		49,034		40,336		41,705		41,376
Working capital	$	102,625	$	80,513	$	109,487	$	109,875

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Cash Flows from Operating Activities

For the six months ended June 30, ~~2022,~~2023, net cash provided by operating activities was ~~$7.1~~$27.5 million compared to net cash provided by operating activities of ~~$37.4~~$7.1 million for the six months ended June 30, ~~2021, a decrease~~2022, an increase of ~~$30.3~~$20.4 million, primarily due to ~~lower net income due to decreased sales combined with~~ the timing of changes toof inventory and other working ~~capital, primarily as a result of annual tobacco inventory purchase.~~capital.

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Cash Flows from Investing Activities

For the six months ended June 30, ~~2022,~~2023, net cash used in investing activities was ~~$15.7~~$3.0 million compared to net cash used in investing activities of ~~$34.4~~$15.7 million for the six months ended June 30, ~~2021,~~2022, a ~~decrease~~reduction in cash used in investing activities of ~~$18.7~~$12.7 million, primarily due to ~~the lower~~a decrease in purchases of investments of $10.7 million in our MSA escrow ~~account as well as no acquisitions or investments made in the current year period.~~account.

Cash Flows from Financing Activities

For the six months ended June 30, ~~2022,~~2023, net cash used in financing activities was ~~$22.5~~$30.4 million compared to net cash ~~provided by~~used in financing activities of ~~$92.2~~$22.5 million for the six months ended June 30, ~~2021, a decrease~~2022, an increase of ~~$114.7~~$7.9 million, primarily due to $27.4 million in repurchases of Convertible Senior Notes during the ~~increase~~period, offset by a decrease in repurchases of common stock of $19.4 million during ~~2022 compared to net proceeds received from the Senior Secured Notes partially offset by the repayment in full of the 2018 First Lien Term Loan in the first quarter of 2021.~~2023.

Dividends and Share Repurchase

~~The most recent~~A dividend of ~~$0.06~~$0.065 per common share was paid on July ~~8, 2022,~~7, 2023, to shareholders of record at the close of business on June ~~17, 2022.~~16, 2023.

On February 25, 2020, our Board of Directors approved a $50.0 million share repurchase program, which is intended for opportunistic execution based upon a variety of factors including market dynamics. ~~On October 25, 2021, the Board increased the approved share repurchase program by $30.7 million. On February 24, 2022, the Board increased the approve share repurchase program by $24.6 million.~~ The program is subject to the ongoing discretion of the Board. ~~The total number~~On October 25, 2021, the Board of ~~shares repurchased for~~Directors increased the ~~three months ended June 30, 2022, was 301,662 shares for a total cost of $8.8~~approved share repurchase program by $30.7 million and by an ~~average price per share of $29.16. $37.0~~additional $24.6 million on February 24, 2022. $27.2 million remains available for share repurchases under the program at June 30, ~~2022.~~2023.

Long-Term Debt

As of June 30, ~~2022,~~2023, we were in compliance with the financial and restrictive covenants of the Senior Secured Notes and 2021 Revolving Credit Facility. The following table provides outstanding balances of our debt instruments.

	June 30, 2022			December 31, 2021			June 30, 2023			December 31, 2022
Senior Secured Notes	$	250,000		$	250,000		$	250,000		$	250,000
Convertible Senior Notes		172,500			172,500			133,541			162,500
Gross notes payable and long-term debt		422,500			422,500			383,541			412,500
Less deferred finance charges		(7,090	)		(8,328	)		(4,346	)		(5,743	)
Notes payable and long-term debt	$	415,410		$	414,172		$	379,195		$	406,757

Senior Secured Notes

On February 11, 2021, we closed a private offering (the “Offering”) of $250 million aggregate principal amount of our 5.625% senior secured notes due 2026 (the “Senior Secured Notes”). The Senior Secured Notes bear interest at a rate of 5.625% and will mature on February 15, 2026. Interest on the Senior Secured Notes is payable semi-annually in arrears on February 15 and August 15 of each year, commencing on August 15, 2021.We used the proceeds from the Offering (i) to repay all obligations under and terminate the 2018 First Lien Credit Facility, (ii) to pay related fees, costs, and expenses and (iii) for general corporate purposes.

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The Company may redeem the Senior Secured Notes, in whole or in part, at any time ~~prior to~~on or after February 15, 2023, at the redemption prices (expressed as a ~~price equal to 100%~~percentage of the principal amount ~~of the Notes redeemed~~to be redeemed) set forth below, plus accrued and unpaid interest, if any, to, but excluding the applicable redemption date, plus a “make-whole” premium. Thereafter, we may redeem the Senior Secured Notes, in whole or in part, at established redemption prices set forth in the Senior Secured Notes Indenture, plus accrued and unpaid interest, if any. In addition, on or prior to February 15, 2023, we may redeem up to 40% of the aggregate principal amount of the Senior Secured Notes with the net cash proceeds from certain equity offerings at a redemption price equal to 105.625%, plus accrued and unpaid interest, if any to the redemption date; provided, however, that at least 50% of the original aggregate principal amount of the Senior Secured Notes (calculated after giving effect to the issuance of any additional notes) remains outstanding. In addition, at any time and from time to time prior to February 15, 2023, but not more than once in any twelve-month period, we may redeem up to 10% of the aggregate principal amount of the Senior Secured Notes at a redemption price of 103% of the aggregate principal amount of Senior Secured Notes redeemed plus accrued and unpaid interest, if any to but not including the redemption date, on the Senior Secured Notes to be ~~redeemed.~~redeemed to (but not including) the applicable redemption date if redeemed during the period indicated below:

On or after February 15, 2023	102.813%
On or after February 15, 2024	101.406%
On or after February 15, 2025 and thereafter	100.000%

If we experience a change of control (as defined in the Senior Secured Notes Indenture), we must offer to repurchase the Senior Secured Notes at a repurchase price equal to 101% of the principal amount of the Notes to be repurchased, plus accrued and unpaid interest.

The Indenture contains covenants that, among other things, restrict the ability of the Company and its restricted subsidiaries to: (i) grant or incur liens; (ii) incur, assume or guarantee additional indebtedness; (iii) sell or otherwise dispose of assets, including capital stock of subsidiaries; (iv) make certain investments; (v) pay dividends, make distributions or redeem or repurchase capital stock; (vi) engage in certain transactions with affiliates; and (vii) consolidate or merge with or into, or sell substantially all of our assets to another entity. These covenants are subject to a number of limitations and exceptions set forth in the Indenture. The Indenture provides for customary events of default. We were in compliance with all covenants as of June 30, ~~2022.~~2023.

We incurred debt issuance costs attributable to the issuance of the Senior Secured Notes of $6.4 million which are amortized to interest expense using the effective interest method over the expected life of the Senior Secured Notes.

2021 Revolving Credit Facility

In connection with the Offering, we also entered into a new $25.0 million senior secured revolving credit facility (the “2021 Revolving Credit Facility”) with the lenders party thereto (the “Lenders”) and Barclays Bank PLC, as administrative agent and collateral agent (in such capacity, the “Agent”). ~~The~~On May 10, 2023, the Company and certain of its subsidiaries, as guarantors, entered into an amendment (the “Amendment”) to the 2021 Revolving Credit Facility ~~provides for~~(as amended, the “Amended Revolving Credit Facility”). The Amendment includes certain modifications to the 2021 Revolving Credit Facility relating to the replacement of the London Inter-Bank Offered Rate with a ~~revolving line of credit of up~~Secured Overnight Financing Rate as the interest rate benchmark under the 2021 Revolving Credit Facility and adjusts certain other provisions to ~~$25.0 million.~~ reflect current documentation standards and other agreed modifications.

Letters of credit are limited to ~~$10~~$10.0 million (and are a part of, and not in addition to, the revolving line of credit). We have not drawn any borrowings under the ~~2021~~Amended Revolving Credit Facility but do have letters of credit of approximately ~~$3.6~~$1.4 million outstanding under the ~~facility.~~facility as of March 31, 2023. The ~~2021~~Amended Revolving Credit Facility will mature on August 11, 2025 if none of our Convertible Senior Notes are outstanding, and if any Convertible Senior Notes are outstanding, the date which is 91 days prior to the maturity date of July 15, 2024, for such Convertible Senior Notes.

Interest is payable on the Amended 2021 Revolving Credit Facility at a fluctuating rate of interest determined by reference to the Eurodollar rate of Term SOFR rate, as applicable, plus an applicable margin of 3.50% (with step-downs upon de-leveraging). We also have the option to borrow at a rate determined by reference to the base rate.

The ~~2021~~Amended Revolving Credit Agreement contains covenants that are substantially the same as the covenants in the Senior Secured Notes Indenture. The ~~2021~~Amended Revolving Credit Facility also requires the maintenance of a Consolidated Leverage Ratio (as defined in the ~~2021~~Amended Revolving Credit Agreement) of 5.50 to 1.00 (with a step down to 5.25 to 1.00 beginning with the fiscal quarter ending March 31, 2023) at the end of each fiscal quarter when extensions of credit under the ~~2021~~Amended Revolving Credit Facility and certain drawn and undrawn letters of credit (excluding (a) letters of credit that have been cash collateralized and (b) letters of credit having an aggregate face amount less than ~~$5,000,000)~~$5.0 million) in the aggregate outstanding exceeds 35% of the total commitments under the ~~2021~~Amended Revolving Credit Facility. The ~~2021~~Amended Revolving Credit Agreement provides for customary events of default. We were in compliance with all covenants as of June 30, ~~2022.~~2023.

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We incurred debt issuance costs attributable to the issuance of the ~~2021~~Amended Revolving Credit Facility of $0.5 million which are amortized to interest expense using the effective interest method over the expected life of the ~~2021~~Amended Revolving Credit Facility.

~~2018 Credit Facility~~

In the first quarter of 2021, we used a portion of the proceeds from the issuance of the Senior Secured Notes to prepay all outstanding amounts under and terminate the 2018 First Lien Credit Facility in the amount of $130.0 million, and the transaction resulted in a $5.7 million loss on extinguishment of debt. See Note 11~~, “Notes Payable and Long-Term Debt,” in the Notes to Consolidated Financial Statements included in this Quarterly Report~~ ~~for further discussion.~~

Convertible Senior Notes

In July 2019 we closed an offering of $172.5 million in aggregate principal amount of our 2.50% Convertible Senior Notes due July 15, 2024 (the “Convertible Senior Notes”). The Convertible Senior Notes bear interest at a rate of 2.50% per year, payable semiannually in arrears on January 15 and July 15 of each year, beginning on January 15, 2020. The Convertible Senior Notes will mature on July 15, 2024, unless earlier repurchased, redeemed or converted. The Convertible Senior Notes are senior unsecured obligations.

The Convertible Senior Notes held by third parties are convertible into approximately ~~3,211,484~~2,455,360 shares of our voting common stock under certain circumstances prior to maturity at a conversion rate of ~~18.617~~18.6789 shares per $1,000 principal amount of the Convertible Senior Notes, which represents a conversion price of approximately ~~$53.71~~$53.54 per share, subject to adjustment under certain conditions, but will not be adjusted for any accrued and unpaid interest. The conversion price is adjusted periodically as a result of dividends paid by ~~the~~ us in excess of pre-determined thresholds of $0.04 per share. Upon conversion, we may pay cash, shares of our common stock or a combination of cash and stock, as determined by us at our discretion. The conditions required to allow the holders to convert their Convertible Senior Notes were not met as of June 30, ~~2022.~~2023.

We incurred debt issuance costs attributable to the Convertible Senior Notes of $5.9 million which are amortized to the interest expense using the effective interest method over the expected life of the Convertible Senior Notes.

In connection with the Convertible Senior Notes offering, we entered into privately negotiated capped call transactions with certain financial institutions. The capped call transactions have a strike price of ~~$53.71~~$53.54 per and a cap price of $82.86 per share, and are exercisable when, and if, the Convertible Senior Notes are converted. We paid $20.53 million for these capped calls at the time they were entered into and charged that amount to additional paid-in capital.

~~Promissory Note~~

On June 10, 2020, in connection with the acquisition of certain Durfort assets, we issued an unsecured subordinated promissory note (“Promissory Note”) in the principal amount of $10.0 million (the “Principal Amount”), with an annual interest rate of 7.5%, payable quarterly, with the first interest payment due September 10, 2020. We prepaid all outstanding amounts under and terminated the Promissory Note in the third quarter of 2021 in the amount of $9.6 million. The transaction resulted in a $0.4 million gain on extinguishment of debt.

~~Unsecured Loan~~

On April 17, 2020, National Tobacco Company, L.P., a wholly-owned subsidiary of the Company, entered into a loan agreement with Regions Bank guaranteed by the Small Business Administration for a $7.5 million unsecured loan issued pursuant to the CARES Act. The proceeds of the loan were received on April 27, 2020. The loan was scheduled to mature on April 17, 2022 and had a 1.00% interest rate. Under the CARES Act we were permitted to apply for forgiveness of the loan if the proceeds were used as required for certain purposes. During 2021, we applied for forgiveness for the loan. On October 15, 2021, we received notice that our application for forgiveness was fully approved. The extinguishment of the unsecured loan occurred in the fourth quarter of 2021 ~~resulting in a $7.5 million gain on extinguishment of debt~~. We are subject to audit relating to the unsecured loan until 2027 which could result in repayment of some or all of the unsecured loan previously forgiven. However, we believe that repayment of any amount is not probable.

~~Table of Contents~~

Off-balance Sheet Arrangements

During the ~~three~~six months ended June 30, ~~2022~~,2023, we executed various foreign exchange contracts for the ~~Company did not execute any forward contracts. We~~purchase of €10.9 million and sale of €6.0 million with maturity dates ranging from August 2023 to October 2023. At June 30, 2023, we had ~~no forward~~foreign currency contracts for the purchase of €10.9 million and sale of €6.0 million. The fair value of the foreign currency contracts were based on quoted market prices and resulted in an asset of $0.2 million included in Other current assets and a liability of $0.1 million included in Accrued liabilities at June 30, ~~2022.~~ 2023. During ~~2021,~~2022, we ~~did not execute any forward contracts. We~~executed various foreign currency contracts for the purchase of €28.9 million and sale of €28.9 million. At December 31, 2022, we had ~~no forward~~foreign currency contracts for the purchase of €18.5 million and sale of €18.5 million. The fair value of the foreign currency contracts resulted in an asset of $1.2 million included in Other current assets and a liability of $0.0 million included in Accrued liabilities at December 31, ~~2021. The Company had no interest rate swap contracts at June 30,~~ 2022.The Company terminated its interest rate swap agreement in conjunction with the prepayment of all outstanding amounts under to the 2018 First Lien Credit Facility in the first quarter of 2021 in the amount of $3.6 million, and the transaction resulted in a $5.7 million loss recorded in the loss on extinguishment of debt. See Note 11~~, “Notes Payable and Long-Term Debt,” in the Notes to Consolidated Financial Statements included in this Quarterly Report~~ ~~for further discussion.~~

Inflation

Inflation in general and the recent rapid increases in ~~costs of goods and services, such as food and~~ gas prices have had a substantial negative effect on the purchasing power of consumers. While historically, we have been able to ~~pass on most cost~~increase prices at a rate equal to or greater than that of inflation, doing so would be difficult in the current inflationary environment. However, we have implemented price increases ~~to our customers, no assurance can be given that we will continue to be able to do so.~~in areas where doing so has been feasible. In addition, we have been able to maintain a relatively stable variable cost structure for our products due, in part, to our successful procurement ~~with regard to~~regarding our tobacco products and, in part, to our existing contractual agreement for the purchase of our premium cigarette papers.

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Item 3. Quantitative and Qualitative Disclosures about Market Risk

Foreign Currency Sensitivity

There have been no material changes in our exposure to exchange rate fluctuation risk, as reported within our ~~2021~~2022 Annual Report on Form 10-K, during the period. Please refer to our ‘Quantitative and Qualitative Disclosures about Market Risk’ included in our ~~2021~~2022 Annual Report on Form 10-K filed with the SEC.

Credit Risk

There have been no material changes in our exposure to credit risk, as reported within our ~~2021~~2022 Annual Report on Form 10-K, during the six months ended June 30, ~~2022~~2023. Please refer to our ‘Quantitative and Qualitative Disclosures about Market Risk’ included in our ~~2021~~2022 Annual Report on Form 10-K filed with the SEC.

Interest Rate Sensitivity

In February 2021, we issued the Senior Secured Notes in an aggregate principal amount of $250 million. In July 2019, we issued Convertible Senior Notes in an aggregate principal amount of $172.5 million. We carry the Senior Secured Notes and Convertible Senior Notes at face value. Since the Senior Secured Notes and Convertible Senior Notes bear interest at a fixed rate, we have no financial statement risk associated with changes in interest rates. However, the fair value of the Convertible Senior Notes changes when the market price of our stock fluctuates, or interest rates change. Our remaining debt ~~instruments bear interest at fixed rates and are not subject to interest rate volatility.~~instrument is a revolving credit facility which has no borrowing outstanding.

Item 4. Controls and Procedures

We have carried out an evaluation under the supervision, and with the participation of, our management including our Chief Executive Officer (“CEO”), Chief Financial Officer (“CFO”), and Chief Accounting Officer (“CAO”), of the effectiveness of the design and operation of our disclosure controls and procedures (as defined in Rules 13a-15(e) and 15d-15(e) under the Exchange Act of 1934, as amended (the “Act”)) as of June 30, ~~2022~~2023. Based upon the evaluation, our CEO, CFO, and CAO concluded our disclosure controls and procedures are not effective as of such date solely due to ~~the~~ material ~~weakness~~weaknesses in internal controls over financial reporting that ~~was~~were disclosed in our Annual Report on Form 10-K for the fiscal year ended December 31, ~~2021.~~

There have been no changes in the Company’s internal control over financial reporting during the fiscal quarter ended June 30, 2022 which have materially affected, or are reasonably likely to materially affect, the Company’s internal control over financial reporting.2022.

As previously described in Part II, Item 9A of our Annual Report on Form 10-K for the fiscal year ended December 31, 2022,

during our evaluation of the effectiveness of our internal control over financial reporting as of December 31, 2022, we ~~began implementing a remediation plan~~concluded that our internal control over financial reporting was not effective solely due to the existence of the following material weaknesses: we did not design and maintain effective internal controls related to our information technology general controls (“ITGCs”) in the areas of user access and program change-management over certain information technology (“IT”) systems that support the Company’s financial reporting processes. Our business process controls (automated and manual) that are dependent on the affected ITGCs were also deemed ineffective because they could have been adversely impacted. We also did not appropriately design and operate controls associated with the risk assessment component of the internal control framework, specifically as it relates to identifying risks around segregation of duties within the financial reporting function, and the identification of all risks relating to the financial statements and controls that would address such risks. This impacts business process controls (automated and manual) throughout financial reporting and the ~~material weakness mentioned above.~~ business transaction cycles.

The material ~~weakness~~weaknesses did not result in any identified misstatements to the financial statements, and there were no changes to previously released financial results. The material weaknesses will not be considered remediated until the applicable controls operate for a sufficient period of time, and management has concluded through testing that these controls are operating effectively. ~~We expect that the remediation of this material weakness will be completed by the end of~~

During the fiscal ~~year 2022.~~quarter ended June 30, 2023, we continued to make progress on our remediation plans to address the material weaknesses in the Company’s internal control over financial reporting. These remediation efforts include hiring additional experienced accounting and internal control specialists and external consultants. In addition, the Company is in process of redesigning key controls for both business processes and information technology controls along with implementing a new enterprise resource planning system.

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PART II—OTHER INFORMATION

Item 1. Legal Proceedings

For a description of our material pending legal proceedings, please see Contingencies in Note 1514 to the Notes to the Consolidated Financial Statements in Part I, Item 1 of this Quarterly Report.

On October 9, 2020, a purported stockholder of the Company, Paul-Emile Berteau (the “Plaintiff”), filed a complaint in the Delaware Court of Chancery (the “Court”) relating to the merger of Standard Diversified, Inc. (“SDI”) with a TPB subsidiary pursuant to the Agreement and Plan of Merger and Reorganization, dated as of April 7, 2020, by and among TPB, SDI and Merger Sub (the “Action”). The complaint purports to assert two derivative counts for breach of fiduciary duty on TPB’s behalf and against the TPB Board of Directors and certain SDI affiliates (collectively, the “Defendants”). The complaint also purports to assert a direct claim against TPB and its Board of Directors based on allegations that TPB’s Amended and Restated Bylaws are inconsistent with TPB’s certificate of incorporation. On October 26, 2020, the TPB Board of Directors adopted Amendment No. 1 to TPB’s Amended and Restated Bylaws, which amended the challenged section of the bylaws. On June 30, 2021, the Court granted in part and denied in part the Defendants’ motions to dismiss. Among other things, the Court dismissed TPB director H.C. Charles Diao as a defendant in the action and dismissed the third count of the Plaintiff’s complaint as moot.

The Defendants and the Company deny that any of them has committed or threatened to commit any violations of law, breaches of duty or other wrongdoing arising out of or related to any of the conduct, statements, acts or omissions alleged by Plaintiff, and maintain that their conduct was at all times proper, in the best interests of the Company and its stockholders, and in compliance with applicable law. Nevertheless, following a mediation in November 2022, the Defendants agreed to settle with the Plaintiff, because doing so will eliminate the distraction, burden, expense, risks and potential delay of further litigation involving the asserted claims. The parties entered into a Stipulation and Agreement of Compromise, Settlement and Release, dated and filed with the Court on June 27, 2023 (together with the exhibits thereto, the “Settlement Stipulation”). The Settlement Stipulation includes as an exhibit thereto a Notice of Pendency of Settlement of Action (the “Notice”). On July 12, 2023, the Court approved the form of the Notice. The material terms of the proposed settlement of the Action are summarized in the Notice and include, without limitation, that the Defendants’ insurers will pay or cause to be paid an aggregate of $5,000,000 into an escrow account (the “Settlement Payment”) in exchange for a release of all claims. The Court has scheduled a hearing on the proposed settlement for November 9, 2023, at 3:15 p.m. at the Leonard L. Williams Justice Center, 500 North King Street, Wilmington, Delaware 19801 to consider whether the terms of the settlement are fair, reasonable, and adequate and whether to approve Plaintiff’s counsel’s request for attorneys’ fees. Also, as described in the Notice, Plaintiff intends to seek an award of attorneys’ fees and expenses related to Plaintiff’s counsel of up to $1,000,000 and an additional mootness fee of up to $500,000 in connection with the third count of the complaint. Any fee awarded to Plaintiff’s counsel will be paid out of the Settlement Payment and the remaining funds will be paid to the Company. The proposed settlement is subject to, and conditioned on approval by the Court, and no assurances can be given that such Court approval will be obtained. The impact to the Company is not expected to be material.

A copy of the Notice is attached hereto as Exhibit 99.1, and a copy of the Settlement Stipulation, including the Notice, will be available on the Company’s website at https://www.turningpointbrands.com/investor-relations/resources/notice-of-proposed-settlement/default.aspx. The foregoing description of the terms and provisions of the proposed settlement as set forth in the Notice is a summary only, does not purport to be complete, and is qualified in its entirety by reference to the full text of the Settlement Stipulation, which text is incorporated herein by reference. Interested parties are encouraged to read the entire text of the Settlement Stipulation and the Notice carefully for further information. Information on our website is not incorporated by reference into this Quarterly Report on Form 10-Q.

See ‘Risk Factors—We may become subject to significant product liability litigation’ within our ~~2021~~2022 Annual Report on Form 10-K for additional details.

Item 1A. Risk Factors

In addition to the other information set forth in this report, carefully consider the factors discussed in the ‘Risk Factors’ section contained in our ~~2021~~2022 Annual Report on Form 10-K. There have been no material changes to the Risk Factors set forth in the ~~2021~~2022 Annual Report on Form 10-K.

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Item 2. Unregistered Sales of Equity Securities and Use of Proceeds

On February 25, 2020, the Company’s Board of Directors approved a $50.0 million share repurchase program, which is intended for opportunistic execution based upon a variety of factors including market dynamics. On October 25, 2021, the Board of Directors increased the approved share repurchase program by $30.7 million bringing the authority at the time back to ~~$50~~$50.0 million (including approximately $19.3 million available for repurchases under the Board’s previous authorization). On February 24, 2022, the Board of Directors increased the approved share repurchase program by $24.6 million bringing total authority at that time to ~~$50~~$50.0 million. This share repurchase program has no expiration date and is subject to the ongoing discretion of the ~~Board.~~Board of Directors. All repurchases to date under our stock repurchase programs have been made through open market transactions, but in the future, we may also purchase shares through privately negotiated transactions or 10b5-1 repurchase plans.

The following table includes information regarding purchases of our common stock made by us during the quarter ended June 30, ~~2022~~2023 in connection with the repurchase program described ~~above:~~above.

Period	Total Number of Shares Purchased ⁽¹⁾		Average Price Paid per Share		Total Number of Shares Purchased as Part of Publicly Announced Plans or Programs		Maximum Number (or Approximate Dollar Value) of Shares that May Yet Be Purchased Under the Plans or Programs		Total Number of Shares Purchased ⁽¹⁾		Average Price Paid per Share		Total Number of Shares Purchased as Part of Publicly Announced Plans or Programs		Maximum Number (or Approximate Dollar Value) of Shares that May Yet Be Purchased Under the Plans or Programs
April 1 to April 30		74,071	$	31.88		74,071	$	43,439,027		4,431	$	23.65		-	$	27,197,886
May 1 to May 31		90,721	$	29.05		83,002	$	41,045,250		-	$	-		-	$	27,197,886
June 1 to June 30		144,589	$	27.95		144,589	$	37,003,987		-	$	-		-	$	27,197,886
Total		309,381				301,662				4,431				-

⁽¹⁾ The total number of shares purchased includes ~~(a) shares purchased under the February 2020 share repurchase program (which totaled 74,071 shares in April, 83,002 in May and 144,589 shares in June) and (b)~~ shares withheld by the Company in an amount equal to the statutory withholding taxes for holders who vested in stock-based awards (which totaled ~~7,719~~4,431 shares in ~~May)~~April). Shares withheld by the Company to cover statutory withholdings taxes are repurchased pursuant to the applicable plan and not the authorization under the share repurchase program.

Item 3. Defaults Upon Senior Securities

Not applicable.

Item 4. Mine Safety Disclosures

Not applicable.

Item 5. Other Information

None

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Item 6. Exhibits

Exhibit No.	Description

10.1	Amendment No 1. Dated as of May 10, 2023, to the Credit Agreement, dated as of February 11, 2021, by and among Turning Point Brands, Inc., the obligors party thereto, Barclays Bank PLC, as administrative agent, and the lenders party thereto (incorporated herein by reference to Exhibit 10.1 of Turning Point Brand, Inc’s Current Report on Form 8-K filed with the Commission on May 16, 2023 (File No. 001-37763) *

31.1	Rule 13a-14(a)/15d-14(a) Certification of ~~Yavor Efremov.~~Graham Purdy.*

31.2	Rule 13a-14(a)/15d-14(a) Certification of Luis Reformina.*

31.3	Rule 13a-14(a)/15d-14(a) Certification of Brian Wigginton.*

32.1	Section 1350 Certifications pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.*

99.1	Notice of Pendency of Settlement of Action *

101	XBRL (eXtensible Business Reporting Language). The following materials from Turning Point Brands, Inc.’s Quarterly Report on Form 10-Q for the quarter ended June 30, ~~2022,~~2023, filed on ~~July 27, 2022,~~August 2, 2023, formatted in Inline XBRL (iXBRL): (i) consolidated balance sheets, (ii) consolidated statements of income, (iii) consolidated statements of comprehensive income, (iv) consolidated statements of cash flows, and (v) the notes to consolidated financial statements.*

104	Cover Page Interactive Data File (formatted in iXBRL and included in Exhibit 101).*

*	Filed or furnished herewith

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~~Signatures~~Signatures

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized.

	TURNING POINT BRANDS, INC.

		By: /s/ ~~Yavor Efremov~~	Graham Purdy
		Name: ~~Yavor Efremov~~	Graham Purdy

Title: President and Chief Executive Officer


		By: /s/ Luis Reformina
		Name: Luis Reformina

Title: Chief Financial Officer


		By: /s/ Brian Wigginton
		Name: Brian Wigginton

		Title: Chief Accounting Officer

Date: ~~July 27, 2022~~August 2, 2023

Delaware		20-0709285
(State or other jurisdiction of Incorporation or organization)		(I.R.S. Employer Identification No.)

5201 Interchange Way, Louisville, KY		40229
(Address of principal executive offices)		(Zip Code)

Title of each class	Trading Symbol(s)	Name of each exchange on which registered
Common Stock, $0.01 par value	TPB	New York Stock Exchange

Large accelerated filer	☐	Accelerated filer	☑
Non-accelerated filer	☐	Smaller reporting company	☐
Emerging growth company	☐

	As of June 30, 2022									As of December 31, 2021
	Cost		Gross Unrealized Gains		Gross Unrealized Losses			Estimated Fair Value		Cost		Gross Unrealized Gains		Gross Unrealized Losses			Estimated Fair Value
Cash and cash equivalents	$	2,035	$	0	$	0		$	2,035	$	12,155	$	0	$	0		$	12,155
U.S. Governmental agency obligations (unrealized position < 12 months)		21,090		0		(1,772	)		19,318		19,918		4		(357	)		19,565
U.S. Governmental agency obligations (unrealized position > 12 months)		8,948		0		(1,077	)		7,871		0		0		0			0
	$	32,073	$	0	$	(2,849	)	$	29,224	$	32,073	$	4	$	(357	)	$	31,720

Total consideration transferred	$	3,462
Adjustments to consideration transferred:
Cash acquired		(43	)
Accrued consideration		472
Adjusted consideration transferred		3,891
Assets acquired:
Working capital (primarily AR and inventory)		1,334
Fixed assets and Other long term assets		27
Net assets acquired	$	1,361

Goodwill	$	2,530

	As of June 30,
	2022			2021
Weighted-average remaining lease term - operating leases	6.36 years			7.0 years
Weighted-average discount rate - operating leases		4.87	%		4.93	%

	June 30, 2022
2022	$	1,851
2023		3,632
2024		2,501
2025		2,187
2026		2,101
Years thereafter		5,344
Total lease payments	$	17,616
Less: Imputed interest		2,614
Present value of lease liabilities	$	15,002