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Additionally, the Board declared five special dividends of $0.06 per share to be paid quarterly beginning in the second quarter of 2024. These special dividends will provide an additional $0.30 per share in distributions, which will be funded with spillover income accumulated to date. Since inception, we have accumulated $0.42 per share of spillover income through year-end.
Accounting for both the regular and special dividends starting in the second quarter of 2024, shareholders would earn $0.41 per share of total dividends, which equates to a 10.5%7 estimated annualized dividend yield based on fourth quarter NAV per share. We believe this dividend yield profile is competitive with other public BDCs in the market today and also provides OBDE shareholders with clear visibility into expected distributions through the second quarter of 2025.
Additionally, in connection with the listing, the Board approved a repurchase program under which up to $100 million of outstanding common stock may be repurchased in the open market from time to time.
Portfolio
We ended the fourth quarter with total portfolio investments of $3.6 billion, of which 76% are first lien investments. We are pleased to report another quarter of excellent credit performance. Our strong results throughout the year are the outcome of our emphasis on great credit selection and a proactive approach to liability management.
Looking at our borrowers’ results, we saw continued resilience across our portfolio companies throughout 2023. We came into the year appropriately cautious and prepared for a challenging economic environment. Over the last twelve months, our borrowers, on average, delivered low-to-mid single digit growth in both revenue and EBITDA each quarter.
Further, we believe our borrowers are well-positioned coming into 2024. Our largest sectors are software, insurance brokerage, healthcare and business services – all of which serve diversified and durable end markets. Our portfolio is comprised of 153 companies that have a weighted average EBITDA of over $200 million8. We believe this scale provides strategic benefits and operational stability, as many of our borrowers remain market leaders within their sectors.
Looking forward, while rates are expected to decline in the long term, short term rates remain elevated and, as a result, we remain focused on potential portfolio company challenges. We believe interest coverage levels will trough in the first half of 2024 at a level of approximately 1.5x to 1.6x.
Our non-accrual rate remains low at only 0.6% of the portfolio of debt investments at both fair value and cost. Since inception, OBDE’s annual net loss rate is only 0.06%.
We continue to have a small list of borrowers who we believe may see challenges in the months ahead. Our underwriting and portfolio management teams are closely monitoring these situations.
Based on the visibility we have today into the favorable positioning of our borrowers, we expect that the vast majority of our portfolio companies will maintain solid coverage metrics and adequate liquidity through this period. We believe any challenges ultimately will be manageable across our portfolio as a whole.
Overall, our record year in 2023 demonstrates the resilience of our portfolio companies and strength of our underwriting and portfolio management process.
(7) Annualized dividend yield is calculated as follows: annualized total dividends per share of $0.41 divided by fourth quarter 2023 NAV per share of $15.56.
(8) This represents 86.5% of our total debt portfolio based on fair value as of 12/31/23 and excludes certain investments that fall outside of our typical borrower profile.