Biggest changeWe have until October 15, 2024 to file our U.S. federal income tax return for the year ended December 31, 2023. 76 The following table reflects the cash distributions, including distributions reinvested, if any, per share that we have paid on our common stock since the beginning of the 2021 fiscal year through 2023: Date Declared Record Date Payment Date Total Distributions GAAP Net Investment Income Distributions in Excess of/ (Less than) GAAP Net Investment Income (1) Fiscal 2023 August 3, 2023 December 15, 2023 December 29, 2023 $ 0.035 $ N/A $ — August 3, 2023 November 16, 2023 November 30, 2023 0.035 N/A — August 3, 2023 October 17, 2023 October 31, 2023 0.035 N/A — Total (Fourth Quarter 2023) 0.105 0.13 (0.03 ) August 3, 2023 (5) September 15, 2023 September 29, 2023 $ 0.120 $ N/A $ — April 25, 2023 September 15, 2023 September 29, 2023 0.035 N/A — April 25, 2023 August 17, 2023 August 31, 2023 0.035 N/A — April 25, 2023 July 17, 2023 July 31, 2023 0.035 N/A — Total (Third Quarter 2023) 0.225 0.11 0.12 March 16, 2023 June 16, 2023 June 30, 2023 $ 0.035 $ N/A $ — March 16, 2023 May 17, 2023 May 31, 2023 0.035 N/A — March 16, 2023 April 14, 2023 April 28, 2023 0.035 N/A — Total (Second Quarter 2023) 0.105 0.13 (0.03 ) October 20, 2022 March 17, 2023 March 31, 2023 $ 0.035 $ N/A $ — October 20, 2022 February 14, 2023 February 28, 2023 0.035 N/A — October 20, 2022 January 17, 2023 January 31, 2023 0.035 N/A — Total (First Quarter 2023) 0.105 0.13 (0.03 ) Total (2023) $ 0.540 (1) $ 0.51 (4) $ 0.03 (4) Fiscal 2022 July 21, 2022 December 16, 2022 December 30, 2022 $ 0.035 $ N/A $ — July 21, 2022 November 16, 2022 November 30, 2022 0.035 N/A — July 21, 2022 October 17, 2022 October 31, 2022 0.035 N/A — Total (Fourth Quarter 2022) 0.105 0.13 (0.03 ) April 21, 2022 September 16, 2022 September 30, 2022 $ 0.035 $ N/A $ — April 21, 2022 August 17, 2022 August 31, 2022 0.035 N/A — April 21, 2022 July 15, 2022 July 29, 2022 0.035 N/A — Total (Third Quarter 2022) 0.105 0.11 (0.01 ) March 1, 2022 June 16, 2022 June 30, 2022 $ 0.035 $ N/A $ — March 1, 2022 May 17, 2022 May 31, 2022 0.035 N/A — March 1, 2022 April 15, 2022 April 29, 2022 0.035 N/A — Total (Second Quarter 2022) 0.105 0.09 0.02 October 22, 2021 March 17, 2022 March 31, 2022 $ 0.035 $ N/A $ — October 22, 2021 February 14, 2022 February 28, 2022 0.035 N/A — October 22, 2021 January 17, 2022 January 31, 2022 0.035 N/A — Total (First Quarter 2022) 0.105 0.09 0.02 Total (2022) $ 0.420 (2) $ 0.42 $ — Fiscal 2021 July 22, 2021 December 17, 2021 December 31, 2021 $ 0.035 $ N/A $ — July 22, 2021 November 16, 2021 November 30, 2021 0.035 N/A — July 22, 2021 October 15, 2021 October 29, 2021 0.035 N/A — Total (Fourth Quarter 2021) 0.105 0.09 0.02 April 22, 2021 September 16, 2021 September 30, 2021 $ 0.035 $ N/A $ — April 22, 2021 August 17, 2021 August 31, 2021 0.035 N/A — April 22, 2021 July 16, 2021 July 30, 2021 0.035 N/A — Total (Third Quarter 2021) 0.105 0.08 0.02 February 23, 2021 June 16, 2021 June 30, 2021 $ 0.035 $ N/A $ — February 23, 2021 May 14, 2021 May 28, 2021 0.035 N/A — February 23, 2021 April 16, 2021 April 30, 2021 0.035 N/A — Total (Second Quarter 2021) 0.105 0.06 0.05 October 22, 2020 March 17, 2021 March 31, 2021 $ 0.035 $ N/A $ — October 22, 2020 February 12, 2021 February 26, 2021 0.035 N/A — October 22, 2020 January 15, 2021 January 29, 2021 0.035 N/A — Total (First Quarter 2021) 0.105 0.10 — Total (2021) $ 0.420 (3) $ 0.32 (4) $ 0.10 (4) 77 ____________ (1) The tax characterization of cash distributions for the year ended December 31, 2023 will not be known until the tax return for such year is finalized.
Biggest changeWe have until October 15, 2025 to file our U.S. federal income tax return for the year ended December 31, 2024. 75 The following table reflects the cash distributions, including distributions reinvested, if any, per share that we have paid on our common stock since the beginning of the 2022 fiscal year through 2024: Date Declared Record Date Payment Date Total Distributions GAAP net investment income Distributions in excess of/ (less than) GAAP net investment income (1) Fiscal 2024 (1) August 8, 2024 December 17, 2024 December 31, 2024 $ 0.035 $ N/A $ — August 8, 2024 November 15, 2024 November 29, 2024 0.035 N/A — August 8, 2024 October 17, 2024 October 31, 2024 0.035 N/A — Total (Fourth Quarter 2024) 0.105 0.09 0.02 April 25, 2024 September 16, 2024 September 30, 2024 0.035 N/A $ — April 25, 2024 August 16, 2024 August 30, 2024 0.035 N/A — April 25, 2024 July 17, 2024 July 31, 2024 0.035 N/A — Total (Third Quarter 2024) 0.105 0.10 0.01 March 14, 2024 June 14, 2024 June 28, 2024 0.035 N/A — March 14, 2024 May 17, 2024 May 31, 2024 0.035 N/A — March 14, 2024 April 16, 2024 April 30, 2024 0.035 N/A — Total (Second Quarter 2024) 0.105 0.13 (0.02 ) November 2, 2023 March 15, 2024 March 29, 2024 0.035 N/A — November 2, 2023 February 15, 2024 February 29, 2024 0.035 N/A — November 2, 2023 January 17, 2024 January 31, 2024 0.035 N/A — Total (First Quarter 2024) 0.105 0.11 (0.01 ) Total (2024) $ 0.420 (1) $ 0.42 (4) $ 0.00 (4) Fiscal 2023 August 3, 2023 December 15, 2023 December 29, 2023 $ 0.035 $ N/A $ — August 3, 2023 November 16, 2023 November 30, 2023 0.035 N/A — August 3, 2023 October 17, 2023 October 31, 2023 0.035 N/A — Total (Fourth Quarter 2023) 0.105 0.13 (0.03 ) August 3, 2023 (5) September 15, 2023 September 29, 2023 $ 0.120 $ N/A $ — April 25, 2023 September 15, 2023 September 29, 2023 0.035 N/A — April 25, 2023 August 17, 2023 August 31, 2023 0.035 N/A — April 25, 2023 July 17, 2023 July 31, 2023 0.035 N/A — Total (Third Quarter 2023) 0.225 0.11 0.12 March 16, 2023 June 16, 2023 June 30, 2023 $ 0.035 $ N/A $ — March 16, 2023 May 17, 2023 May 31, 2023 0.035 N/A — March 16, 2023 April 14, 2023 April 28, 2023 0.035 N/A — Total (Second Quarter 2023) 0.105 0.13 (0.03 ) October 20, 2022 March 17, 2023 March 31, 2023 $ 0.035 $ N/A $ — October 20, 2022 February 14, 2023 February 28, 2023 0.035 N/A — October 20, 2022 January 17, 2023 January 31, 2023 0.035 N/A — Total (First Quarter 2023) 0.105 0.13 (0.03 ) Total (2023) $ 0.540 $ 0.51 (2)(4) $ 0.03 (2) Fiscal 2022 July 21, 2022 December 16, 2022 December 30, 2022 $ 0.035 $ N/A $ — July 21, 2022 November 16, 2022 November 30, 2022 0.035 N/A — July 21, 2022 October 17, 2022 October 31, 2022 0.035 N/A — Total (Fourth Quarter 2022) 0.105 0.13 (0.03 ) April 21, 2022 September 16, 2022 September 30, 2022 $ 0.035 $ N/A $ — April 21, 2022 August 17, 2022 August 31, 2022 0.035 N/A — April 21, 2022 July 15, 2022 July 29, 2022 0.035 N/A — Total (Third Quarter 2022) 0.105 0.11 (0.01 ) March 1, 2022 June 16, 2022 June 30, 2022 $ 0.035 $ N/A $ — March 1, 2022 May 17, 2022 May 31, 2022 0.035 N/A — March 1, 2022 April 15, 2022 April 29, 2022 0.035 N/A — Total (Second Quarter 2022) 0.105 0.09 0.02 76 Date Declared Record Date Payment Date Total Distributions GAAP net investment income Distributions in excess of/ (less than) GAAP net investment income (1) October 22, 2021 March 17, 2022 March 31, 2022 $ 0.035 $ N/A $ — October 22, 2021 February 14, 2022 February 28, 2022 0.035 N/A — October 22, 2021 January 17, 2022 January 31, 2022 0.035 N/A — Total (First Quarter 2022) 0.105 0.09 0.02 Total (2022) $ 0.420 (3) $ 0.42 $ — ____________ (1) The tax characterization of cash distributions for the year ended December 31, 2024 will not be known until the tax return for such year is finalized.
The quantitative inputs and data points that determine which method to utilize to value any given investment include, but are not limited to: • Bid/offer prices; • Depth, which is defined as the number of securities firms that make a market in a respective corporate syndicated loan and contribute data on the corporate syndicated loan to market data providers; • Liquidity score, which is a metric to help market participants ascertain their ability to exit a position within a given time frame and near a prevailing indicative price, which provides a benchmark of liquidity risk; • Financial performance of the underlying portfolio company; • Recent business developments; • Covenant compliance; and • Recent transactions. 80 In instances where secondary market data is limited, we may engage a third -party valuation firm to independently determine an estimate of fair value.
The quantitative inputs and data points that determine which method to utilize to value any given investment include, but are not limited to: • Bid/offer prices; • Depth, which is defined as the number of securities firms that make a market in a respective corporate syndicated loan and contribute data on the corporate syndicated loan to market data providers; • Liquidity score, which is a metric to help market participants ascertain their ability to exit a position within a given time frame and near a prevailing indicative price, which provides a benchmark of liquidity risk; • Financial performance of the underlying portfolio company; • Recent business developments; • Covenant compliance; and • Recent transactions. 79 In instances where secondary market data is limited, we may engage a third -party valuation firm to independently determine an estimate of fair value.
That expense (or the reversal of such an expense) related to that hypothetical liquidation of the portfolio (and assuming no other changes in realized or unrealized gains and losses) would only become payable to our investment adviser in the event of a complete liquidation of our portfolio as of period end and the termination of the Investment Advisory Agreement on such date.
That expense (or the reversal of such an expense) related to that hypothetical liquidation of the portfolio (and assuming no other changes in realized or unrealized gains and losses) would only become payable to our investment adviser in the event of a complete liquidation of our portfolio 71 as of period end and the termination of the Investment Advisory Agreement on such date.
Under the Investment Advisory Agreement, we have agreed to pay Oxford Square Management an annual Base Fee calculated on gross assets, and an incentive fee based upon our performance. Under the Administration Agreement, we have agreed to pay or reimburse Oxford Funds, as administrator, for certain expenses incurred in operating the Company.
Under the Investment Advisory Agreement, we have agreed to pay Oxford Square Management an annual Base Fee calculated on gross assets, 64 and an incentive fee based upon our performance. Under the Administration Agreement, we have agreed to pay or reimburse Oxford Funds, as administrator, for certain expenses incurred in operating the Company.
The following analysis of our financial condition and results of operations should be read in conjunction with our financial statements and the related notes thereto contained elsewhere in this Form 10 -K . 65 OVERVIEW Our investment objective is to maximize our portfolio’s total return.
The following analysis of our financial condition and results of operations should be read in conjunction with our financial statements and the related notes thereto contained elsewhere in this Form 10 -K . OVERVIEW Our investment objective is to maximize our portfolio’s total return.
Our critical accounting estimates, including those relating to the valuation of our investment portfolio, are described below. Actual results could materially differ from those estimates. The critical accounting estimates should be read in conjunction with our risk factors as disclosed in “Item 1A.
Our critical accounting 78 estimates, including those relating to the valuation of our investment portfolio, are described below. Actual results could materially differ from those estimates. The critical accounting estimates should be read in conjunction with our risk factors as disclosed in “Item 1A.
Oxford Square Management, Oxford Lane Management, Oxford Park Management and Oxford Gate Management are subject to a written policy with respect to the allocation of investment opportunities among the Company, Oxford Lane Capital Corp., Oxford Park Income Fund, Inc., Oxford Bridge II, LLC and the Oxford 78 Gate Funds.
Oxford Square Management, Oxford Lane Management, Oxford Park Management and Oxford Gate Management are subject to a written policy with respect to the allocation of investment opportunities among the Company, Oxford Lane Capital Corp., Oxford Park Income Fund, Inc., Oxford Bridge II, LLC and the Oxford Gate Funds.
The fair value of the 6.50% Unsecured Notes, 6.25% Unsecured Notes and 5.50% Unsecured Notes are based upon the closing price on the last day of the period. The 6.50% Unsecured Notes, 6.25% Unsecured Notes and 5.50% Unsecured Notes are listed on the NASDAQ Global Select Market (trading symbol “OXSQL”,“OXSQZ” and “OXSQG”, respectively).
The fair value of the 6.25% Unsecured Notes and 5.50% Unsecured Notes are based upon the closing price on the last day of the period. The 6.25% Unsecured Notes and 5.50% Unsecured Notes are listed on the NASDAQ Global Select Market (trading symbol “OXSQZ” and “OXSQG”, respectively).
We consider the attributes of current market conditions on an on -going basis and have determined that due to the general illiquidity of the market for our investment portfolio, whereby little or no market data exists, substantially all of our fair valued investments are measured based upon Level 3 inputs as of December 31, 2023 and December 31, 2022.
We consider the attributes of current market conditions on an on -going basis and have determined that due to the general illiquidity of the market for our investment portfolio, whereby little or no market data exists, substantially all of our fair valued investments are measured based upon Level 3 inputs as of December 31, 2024 and December 31, 2023.
Oxford Square Management or the Valuation Committee may request an additional analysis by a third -party firm to assist in the valuation process of CLO investment vehicles. All information is presented to our Board for its determination of fair value of these investments. Recently Issued Accounting Standards See “Note 16.
Oxford Square Management or the Valuation Committee may request an additional analysis by a third -party firm to assist in the valuation process of CLO investment vehicles. All information is presented to our Board for its determination of fair value of these investments. Recently Issued Accounting Standards See “Note 17.
The actual amounts and sources of the amounts for tax reporting purposes will depend upon the Company’s investment performance and may be subject to change based on tax regulations. (2) Cash distributions for the year ended December 31, 2022 represented 100% net investment income and therefore there was no tax return of capital.
The actual amounts and sources of the amounts for tax reporting purposes will depend upon the Company’s investment performance and may be subject to change based on tax regulations. (2) Cash distributions for the year ended December 31, 2023 represented 100% net investment income and therefore there was no tax return of capital.
The weighted average annualized yield was computed using the effective interest rates as of December 31, 2023, including accretion of OID and excluding any debt investments on non -accrual status. There can be no assurance that the weighted average annualized yield will remain at its current level.
The weighted average annualized yield was computed using the effective interest rates as of December 31, 2024, including accretion of OID and excluding any debt investments on non -accrual status. There can be no assurance that the weighted average annualized yield will remain at its current level.
(2) Totals may not sum due to rounding. The following tables present the top ten industries (based upon Moody’s industry classifications) of the aggregate holdings of the CLOs included in our portfolio, based on par value, as of December 31, 2023 and December 31, 2022.
(2) Totals may not sum due to rounding. The following tables present the top ten industries (based upon Moody’s industry classifications) of the aggregate holdings of the CLOs included in our portfolio, based on par value, as of December 31, 2024 and December 31, 2023.
For the year ended December 31, 2023, the net increase in net assets resulting from net investment income per common share was $0.51 (basic and diluted), compared to $0.42 (basic and diluted) for the year ended December 31, 2022, based on the weighted average common shares outstanding for the respective periods.
For the year ended December 31, 2024, the net increase in net assets resulting from net investment income per common share was $0.42 (basic and diluted), compared to $0.51 (basic and diluted) for the year ended December 31, 2023, based on the weighted average common shares outstanding for the respective periods.
(3) Cash distributions for the year ended December 31, 2021 represented 100% net investment income and therefore there was no tax return of capital. (4) Totals may not sum due to rounding. (5) Special distribution.
(3) Cash distributions for the year ended December 31, 2022 represented 100% net investment income and therefore there was no tax return of capital. (4) Totals may not sum due to rounding. (5) Special distribution.
Risk Factors.” See Note 2 to our financial statements for the year ended December 31, 2023 for more information on our critical accounting policies. 79 Investment Valuation We fair value our investment portfolio in accordance with the provisions of ASC 820, Fair Value Measurement and Disclosure (“ASC 820”) and Rule 2a -5 under the 1940 Act.
Risk Factors.” See Note 2 to our financial statements for the year ended December 31, 2024 for more information on our critical accounting policies. Investment Valuation We fair value our investment portfolio in accordance with the provisions of ASC 820, Fair Value Measurement and Disclosure (“ASC 820”) and Rule 2a -5 under the 1940 Act.
Equity securities are not graded. As of December 31, 2023 and 2022 our portfolio had a weighted average grade of 2.3 and 2.2, respectively, based upon the fair value of the debt investments in the portfolio.
Equity securities are not graded. As of December 31, 2024 and 2023 our portfolio had a weighted average grade of 2.3 and 2.3, respectively, based upon the fair value of the debt investments in the portfolio.
For the years ended December 31, 2023 and 2022, no accrual was required as a result of the impact of accumulated net unrealized depreciation and net realized losses on our portfolio.
For the years ended December 31, 2024 and 2023, no accrual was required as a result of the impact of accumulated net unrealized depreciation and net realized losses on our portfolio.
The final determination of the source of all distributions in 2023 will be made after year -end and the amounts represented may be materially different from the amounts disclosed in the final Form 1099 -DIV notice.
The final determination of the source of all distributions in 2024 will be made after year -end and the amounts represented may be materially different from the amounts disclosed in the final Form 1099 -DIV notice.
Contractual obligations (in millions) Principal Amount Payments Due by Period Less than 1 year 1 – 3 years 3 – 5 years More than 5 years Long-term debt obligations: 6.25% Unsecured Notes $ 44.8 $ — $ 44.8 $ — $ — 5.50% Unsecured Notes 80.5 — — 80.5 — $ 125.3 $ — $ 44.8 $ 80.5 $ — Share Issuance and Repurchase Programs On August 22, 2023, we entered into Amendment No. 1 to that certain Equity Distribution Agreement dated August 1, 2019 with Ladenburg Thalmann & Co. through which we may offer for sale, from time to time, up to $150.0 million of our common stock through an At -the-Market (“ATM”) offering.
Contractual obligations (in millions) Principal Amount Payments Due by Period Less than 1 year 1 – 3 years 3 – 5 years More than 5 years Long-term debt obligations: 6.25% Unsecured Notes $ 44.8 $ — $ 44.8 $ — $ — 5.50% Unsecured Notes 80.5 — — 80.5 — $ 125.3 $ — $ 44.8 $ 80.5 $ — Share Issuance and Repurchase Programs On August 22, 2023, we entered into Amendment No. 1 to the Equity Distribution Agreement dated August 1, 2019 with Ladenburg Thalmann & Co. through which we may offer for sale, from time to time, up to $150.0 million of our common stock through an ATM offering.
For the year ended December 31, 2023, the amounts and sources of distributions reported are only estimates and are not being provided for U.S. tax reporting purposes.
For the year ended December 31, 2024, the amounts and sources of distributions reported are only estimates and are not being provided for U.S. tax reporting purposes.
The number and amount of investments included in Grade 3, 4 or 5 may fluctuate from year to year. 70 RESULTS OF OPERATIONS Set forth below is a comparison of our results of operations for the years ended December 31, 2023 and 2022.
The number and amount of investments included in Grade 3, 4 or 5 may fluctuate from year to year. RESULTS OF OPERATIONS Set forth below is a comparison of our results of operations for the years ended December 31, 2024 and 2023.
In addition, we receive principal repayments of some of our investments prior to their scheduled maturity date. The frequency or volume of these repayments may fluctuate significantly from period to period. For the years ended December 31, 2023 and December 31, 2022, we had loan principal repayments of approximately $15.8 million and approximately $50.0 million, respectively.
In addition, we receive principal repayments of some of our investments prior to their scheduled maturity date. The frequency or volume of these repayments may fluctuate significantly from period to period. For the years ended December 31, 2024 and December 31, 2023, we had loan principal repayments of approximately $75.0 million and approximately $15.8 million, respectively.
Borrowings In accordance with the 1940 Act, with certain limited exceptions, we are only allowed to borrow amounts such that our asset coverage, as defined in the 1940 Act, is at least 150% immediately after such borrowing. As of December 31, 2023, our asset coverage for borrowed amounts was approximately 219%.
Borrowings In accordance with the 1940 Act, with certain limited exceptions, we are only allowed to borrow amounts such that our asset coverage, as defined in the 1940 Act, is at least 150% immediately after such borrowing. As of December 31, 2024, our asset coverage for borrowed amounts was approximately 227%.
Rubin serves as the Chief Financial Officer, Treasurer and Corporate Secretary of Oxford Park Income Fund, Inc. and Chief Financial Officer and Treasurer of Oxford Park Management, and Mr. Cummins serves as the Chief Compliance Officer of Oxford Park Income Fund, Inc. and Oxford Park Management.
Rubin serves as the Chief Financial Officer, Treasurer and Corporate Secretary of Oxford Park Income Fund, Inc. and Chief Financial Officer and Treasurer of Oxford Park Management, and Mr.
Our primary focus is to seek an attractive risk -adjusted total return by investing primarily in corporate debt securities and in CLOs, which are structured finance investments that own corporate debt securities.
Our primary focus is to seek an attractive risk -adjusted total return by investing primarily in corporate debt securities and, to a lesser extent, in CLOs, which are structured finance investments that own corporate debt securities.
For information regarding results of operations for the year ended December 31, 2021, refer to Part II Item 7 in our Form 10 -K for the year ended December 31, 2022, as filed with the SEC on March 23, 2023, which is incorporated by reference herein.
For information regarding results of operations for the year ended December 31, 2022, refer to Part II Item 7 in our Form 10 -K for the year ended December 31, 2023 , as filed with the SEC on March 19, 2024, which is incorporated by reference herein.
The aggregate accrued interest which remained payable as of December 31, 2023 and 2022, was approximately $1.2 million.
The aggregate accrued interest which remained payable as of December 31, 2024 and 2023, was approximately $1.2 million.
Compensation expense was approximately $825,000 for the year ended December 31, 2023, compared to approximately $916,000 for the year ended December 31, 2022, reflecting the allocation of compensation expenses for the services of our Chief Financial Officer, accounting personnel, and other administrative support staff. As of December 31, 2023, there was no compensation expense payable.
Compensation expense was approximately $747,000 for the year ended December 31, 2024, compared to approximately $825,000 for the year ended December 31, 2023, reflecting the allocation of compensation expenses for the services of our Chief Financial Officer, accounting personnel, and other administrative support staff. As of December 31, 2024 and 2023, there was no compensation expense payable.
This includes net unrealized appreciation of approximately $15.3 million resulting from reductions to the cost value of our CLO equity investments representing the difference between distributions received, or entitled to be received, on our investments held in CLO equity subordinated notes and fee notes, of approximately $32.0 million and the effective yield interest income recognized on our CLO equity subordinated notes and the amortized cost adjusted income on our CLO equity fee notes of approximately $16.7 million.
This includes net unrealized appreciation of approximately $13.0 million resulting from reductions to the cost value of our CLO equity investments representing the difference between distributions received, or entitled to be received, on our investments held in CLO equity subordinated notes and fee notes, of approximately $28.4 million and the effective yield interest income recognized on our CLO equity subordinated notes and the amortized cost adjusted income on our CLO equity fee notes of approximately $15.3 million.
Top Ten Industries December 31, 2023 High tech industries 11.3 % Healthcare & pharmaceuticals 10.1 % Banking, finance, insurance & real estate 9.9 % Business services 9.4 % Media: broadcasting & subscription 5.6 % Telecommunications 4.9 % Hotels, gaming & leisure 4.4 % Chemicals, plastics & rubber 3.9 % Beverage, food & tobacco 3.7 % Construction & building 3.5 % Total 66.7 % Top Ten Industries December 31, 2022 High tech industries 10.1 % Healthcare & pharmaceuticals 9.8 % Banking, finance, insurance & real estate 9.6 % Business services 8.8 % Media: broadcasting & subscription 5.0 % Telecommunications 4.8 % Hotels, gaming & leisure 4.7 % Chemicals, plastics & rubber 4.5 % Beverage, food & tobacco 3.7 % Construction & building 3.6 % Total 64.6 % 69 PORTFOLIO GRADING We have adopted a credit grading system to monitor the quality of our debt investment portfolio.
Top Ten Industries December 31, 2024 High tech industries 12.0 % Healthcare & pharmaceuticals 10.3 % Banking, finance, insurance & real estate 10.1 % Business services 9.7 % Hotels, gaming & leisure 4.9 % Media: broadcasting & subscription 4.2 % Construction & building 4.1 % Chemicals, plastics & rubber 4.0 % Telecommunications 3.9 % Consumer services 3.5 % Total 66.7 % Top Ten Industries December 31, 2023 High tech industries 11.3 % Healthcare & pharmaceuticals 10.1 % Banking, finance, insurance & real estate 9.9 % Business services 9.4 % Media: broadcasting & subscription 5.6 % Telecommunications 4.9 % Hotels, gaming & leisure 4.4 % Chemicals, plastics & rubber 3.9 % Beverage, food & tobacco 3.7 % Construction & building 3.5 % Total 66.7 % 68 PORTFOLIO GRADING We have adopted a credit grading system to monitor the quality of our debt investment portfolio.
For the year ended December 31, 2023, the net increase in net assets resulting from operations per common share was $0.32 (basic and diluted), compared to a net decrease in net assets per common share of $1.72 (basic and diluted) for the year ended December 31, 2022, based on the weighted average common shares outstanding for the respective periods.
For the year ended December 31, 2024, the net increase in net assets resulting from operations per common share was $0.09 (basic and diluted), compared to a net increase in net assets per common share of $0.32 (basic and diluted) for the year ended December 31, 2023, based on the weighted average common shares outstanding for the respective periods.
As of December 31, 2022, our asset coverage for borrowed amounts was approximately 171%. The following are our outstanding principal amounts, carrying values and fair values of our borrowings as of December 31, 2023 and December 31, 2022.
As of December 31, 2023, our asset coverage for borrowed amounts was approximately 219%. The following are our outstanding principal amounts, carrying values and fair values of our borrowings as of December 31, 2024 and December 31, 2023.
At December 31, 2023 and 2022, our debt investment portfolio was graded as follows: ($ in millions) December 31, 2023 Grade Summary Description Principal Value Percentage of Debt Portfolio Portfolio at Fair Value Percentage of Debt Portfolio 1 Company is ahead of expectations and/or outperforming financial covenant requirements of the specific tranche and such trend is expected to continue. $ — — % $ — — % 2 Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 175.5 60.4 % 134.5 74.9 % 3 Closer monitoring is required.
At December 31, 2024 and 2023, our debt investment portfolio was graded as follows: ($ in millions) December 31, 2024 Grade Summary Description Principal Value Percentage of Debt Portfolio Portfolio at Fair Value Percentage of Debt Portfolio 1 Company is ahead of expectations and/or outperforming financial covenant requirements of the specific tranche and such trend is expected to continue. $ — — % $ — — % 2 Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 117.5 58.2 % 112.2 74.5 % 3 Closer monitoring is required.
The Base Fee which remained payable to Oxford Square Management as of December 31, 2023 and 2022 was approximately $1.0 million and $1.3 million, respectively.
The Base Fee which remained payable to Oxford Square Management as of December 31, 2024 and 2023 was approximately $1.2 million and $1.0 million, respectively.
Qualifying assets must represent at least 70% of the Company’s total assets at the time of acquisition of any additional non -qualifying assets. As of December 31, 2023 and 2022, we held qualifying assets that represented 70.6% and 70.1%, respectively, of the total assets.
Qualifying assets must represent at least 70% of the Company’s total assets at the time of acquisition of any additional non -qualifying assets. As of December 31, 2024 and 2023, we held qualifying assets that represented 63.8% and 70.6%, respectively, of the total assets.
The aggregate accrued interest which remained payable as of December 31, 2023 and 2022 was approximately $1.2 million. The Base Fee decreased by approximately $1.3 million in 2023 compared to 2022 due to lower average adjusted gross assets in 2023.
The aggregate accrued interest on existing debt which remained payable as of December 31, 2024 and 2023 was approximately $1.2 million. The Base Fee decreased by approximately $0.3 million in 2024 compared to 2023 due to lower average adjusted gross assets in 2024.
The following table indicates the quarterly portfolio investment activity for the years ended December 31, 2023 and 2022: ($ in millions) Purchases of Investments Repayments of Principal Sales of Investments Reductions to CLO Equity Cost (1) Quarter ended December 31, 2023 $ 3.5 $ 0.8 $ 3.7 $ 2.8 September 30, 2023 — 14.2 1.9 5.1 June 30, 2023 — 0.4 13.9 4.4 March 31, 2023 8.2 0.3 — 3.0 Total (2) $ 11.7 $ 15.8 $ 19.6 $ 15.3 December 31, 2022 $ 6.1 $ 0.2 $ — $ 2.3 September 30, 2022 3.9 11.0 1.8 3.9 June 30, 2022 26.9 0.2 9.5 6.4 March 31, 2022 47.4 38.6 3.4 7.8 Total (2) $ 84.2 $ 50.0 $ 14.6 $ 20.4 ____________ (1) Represents reductions to CLO equity cost value (representing distributions received, or entitled to be received, in excess of effective yield interest income and amortized cost adjusted CLO fee note income).
The following table indicates the quarterly portfolio investment activity for the years ended December 31, 2024 and 2023: ($ in millions) Purchases of Investments Repayments of Principal Sales of Investments Reductions to CLO Equity Cost (1) Quarter ended December 31, 2024 $ 25.1 $ 15.0 $ 7.0 $ 3.3 September 30, 2024 47.7 27.9 — 2.5 June 30, 2024 27.3 14.3 3.4 6.3 March 31, 2024 12.1 17.9 1.4 0.8 Total (2) $ 112.2 $ 75.0 $ 11.8 $ 13.0 December 31, 2023 $ 3.5 $ 0.8 $ 3.7 $ 2.8 September 30, 2023 — 14.2 1.9 5.1 June 30, 2023 — 0.4 13.9 4.4 March 31, 2023 8.2 0.3 — 3.0 Total (2) $ 11.7 $ 15.8 $ 19.6 $ 15.3 ____________ (1) Represents reductions to CLO equity cost value (representing distributions received, or entitled to be received, in excess of effective yield interest income and amortized cost adjusted CLO fee note income).
(f/k/a Aspect Software, Inc.) (3.2 ) Dodge Data & Analytics, LLC (3.3 ) ConvergeOne Holdings, Inc. (3.5 ) Careismatic Brands, Inc.
(f/k/a Aspect Software, Inc.) (3.2 ) Dodge Data & Analytics, LLC (3.3 ) ConvergeOne Holdings, Inc.
As of ($ in millions) December 31, 2023 December 31, 2022 Principal Amount Carrying Value Fair Value Principal Amount Carrying Value Fair Value 6.50% Unsecured Notes $ — $ — $ — $ 64.4 $ 64.0 $ 63.4 6.25% Unsecured Notes 44.8 44.2 42.9 44.8 44.0 42.6 5.50% Unsecured Notes 80.5 78.7 72.5 80.5 78.3 70.0 Total (1) $ 125.3 $ 123.0 $ 115.4 $ 189.7 $ 186.3 $ 176.0 ____________ (1) Totals may not sum due to rounding. 75 The weighted average stated interest rate and weighted average maturity on all our debt outstanding as of December 31, 2023 were 5.77% and 3.8 years, respectively, and as of December 31, 2022 were 6.02% and 3.6 years, respectively.
($ in millions) As of December 31, 2024 December 31, 2023 Principal Amount Carrying Value Fair Value Principal Amount Carrying Value Fair Value 6.25% Unsecured Notes $ 44.8 $ 44.5 $ 44.4 $ 44.8 $ 44.2 $ 42.9 5.50% Unsecured Notes 80.5 79.1 74.7 80.5 78.7 72.5 Total (1) $ 125.3 $ 123.6 $ 119.1 $ 125.3 $ 123.0 $ 115.4 ____________ (1) Totals may not sum due to rounding. 74 The weighted average stated interest rate and weighted average maturity on all our debt outstanding as of December 31, 2024 were 5.77% and 2.8 years, respectively, and as of December 31, 2023 were 5.77% and 3.8 years, respectively.
RECENT DEVELOPMENTS The following distributions payable to stockholders are shown below: Date Declared Record Dates Payable Dates Per Share Distribution Amount Declared November 2, 2023 January 17, 2024 January 31, 2024 $ 0.035 November 2, 2023 February 15, 2024 February 29, 2024 $ 0.035 November 2, 2023 March 15, 2024 March 29, 2024 $ 0.035 March 14, 2024 April 16, 2024 April 30, 2024 $ 0.035 March 14, 2024 May 17, 2024 May 31, 2024 $ 0.035 March 14, 2024 June 14, 2024 June 28, 2024 $ 0.035
RECENT DEVELOPMENTS The following distributions payable to stockholders are shown below: Date Declared Record Dates Payable Dates Per Share Distribution Amount Declared October 31, 2024 January 17, 2025 January 31, 2025 $0.035 October 31, 2024 February 14, 2025 February 28, 2025 $0.035 October 31, 2024 March 17, 2025 March 31, 2025 $0.035 February 27, 2025 April 16, 2025 April 30, 2025 $0.035 February 27, 2025 May 16, 2025 May 30, 2025 $0.035 February 27, 2025 June 16, 2025 June 30, 2025 $0.035
The following table shows the fair value of our portfolio of investments by asset class as of December 31, 2023 and 2022: December 31, 2023 December 31, 2022 ($ in millions) Investments at Fair Value Percentage of Total Portfolio Investments at Fair Value Percentage of Total Portfolio Senior Secured Notes $ 179.5 67.2 % $ 211.4 67.2 % CLO Equity 82.2 30.8 % 98.9 31.4 % Equity and Other Investments 5.3 2.0 % 4.3 1.4 % Total (1) $ 266.9 100.0 % $ 314.7 100.0 % ____________ (1) Totals may not sum due to rounding.
The following table shows the fair value of our portfolio of investments by asset class as of December 31, 2024 and 2023: ($ in millions) December 31, 2024 December 31, 2023 Investments at Fair Value Percentage of Total Portfolio Investments at Fair Value Percentage of Total Portfolio Senior Secured Notes $ 150.7 57.8 % $ 179.5 67.2 % CLO Equity 104.6 40.1 % 82.2 30.8 % Equity and Other Investments 5.6 2.1 % 5.3 2.0 % Total (1) $ 260.9 100.0 % $ 266.9 100.0 % ____________ (1) Totals may not sum due to rounding.
LIQUIDITY AND CAPITAL RESOURCES During the year ended December 31, 2023, cash and cash equivalents decreased from approximately $9.0 million at the beginning of the period to approximately $5.7 million at the end of the period.
LIQUIDITY AND CAPITAL RESOURCES During the year ended December 31, 2024, cash and cash equivalents increased from approximately $5.7 million at the beginning of the period to approximately $34.9 million at the end of the period.
Full repayment of the outstanding amount of OXSQ’s cost basis is expected for the specific tranche. — — % — — % 5 Full repayment of the outstanding amount of OXSQ’s cost basis is not expected for the specific tranche and the investment is placed on non-accrual status 42.9 14.8 % 1.7 1.0 % Total $ 290.7 100.0 % $ 179.5 100.0 % ($ in millions) December 31, 2022 Grade Summary Description Principal Value Percentage of Debt Portfolio Portfolio at Fair Value Percentage of Debt Portfolio 1 Company is ahead of expectations and/or outperforming financial covenant requirements of the specific tranche and such trend is expected to continue. $ — — % $ — — % 2 Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 230.1 74.9 % 180.0 85.1 % 3 Closer monitoring is required.
Full repayment of the outstanding amount of OXSQ’s cost basis is expected for the specific tranche. — — % — — % 5 Full repayment of the outstanding amount of OXSQ’s cost basis is not expected for the specific tranche and the investment is placed on non-accrual status 2.5 1.2 % 0.5 0.3 % Total $ 202.0 100.0 % $ 150.7 100.0 % ($ in millions) December 31, 2023 Grade Summary Description Principal Value Percentage of Debt Portfolio Portfolio at Fair Value Percentage of Debt Portfolio 1 Company is ahead of expectations and/or outperforming financial covenant requirements of the specific tranche and such trend is expected to continue. $ — — % $ — — % 2 Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 175.5 60.4 % 134.5 74.9 % 3 Closer monitoring is required.
Related Party Transactions” in the notes to our financial statements. 72 The expense attributable to the capital gains incentive fee, as reported under GAAP, is calculated as if the Company’s entire portfolio had been liquidated at period end, and therefore is calculated on the basis of net realized and unrealized gains and losses at the end of each period.
The expense attributable to the capital gains incentive fee, as reported under GAAP, is calculated as if the Company’s entire portfolio had been liquidated at period end, and therefore is calculated on the basis of net realized and unrealized gains and losses at the end of each period.
Net cash provided by operating activities for the year ended December 31, 2023, consisting primarily of the items described in “— Results of Operations,” was approximately $65.7 million, largely reflecting repayments of principal of approximately $15.8 million, proceeds from the sale of investments of approximately $19.6 million and reductions to CLO equity cost value of approximately $15.3 million, partially offset by purchases of new investments of approximately $11.7 million.
Net cash provided by operating activities for the year ended December 31, 2024, consisting primarily of the items described in “— Results of Operations,” was approximately $25.7 million, largely reflecting repayments of principal of approximately $75.0 million, proceeds from the sale of investments of approximately $11.8 million and reductions to CLO equity cost value of approximately $13.0 million, partially offset by purchases of new investments of approximately $100.2 million.
Net Increase/Decrease in Net Assets Resulting from Operations Net increase in net assets resulting from operations for the year ended December 31, 2023 was approximately $17.2 million, compared to a net decrease of $85.6 million for year ended December 31, 2022.
Net Increase in Net Assets Resulting from Operations Net increase in net assets resulting from operations for the year ended December 31, 2024 was approximately $5.9 million, compared to a net increase of $17.2 million for year ended December 31, 2023.
During the year ended December 31, 2022, we purchased approximately $84.2 million in portfolio investments, including additional investments of approximately $58.9 million in existing portfolio companies and approximately $25.3 million in new portfolio companies. In certain instances, we receive payments based on scheduled amortization of the outstanding balances.
During the year ended December 31, 2023, we purchased approximately $11.7 million in portfolio investments, including additional investments of approximately $3.5 million in existing portfolio companies and approximately $8.2 million in new portfolio companies. In certain instances, we receive payments based on scheduled amortization of the outstanding balances.
The decrease in the value of investments during the year ended December 31, 2023 was due primarily to repayments of principal of approximately $15.8 million and sales of securities totaling approximately $19.6 million, partially offset by a net change in unrealized appreciation on our investment portfolio of approximately $7.1 million (which incorporates reductions to CLO equity cost value of $15.3 million) and purchases of investments of approximately $11.7 million.
The decrease in the value of investments during the year ended December 31, 2024 was due primarily to repayments of principal of approximately $75.0 million, sales of securities totaling approximately $11.8 million, and realized losses of approximately $96.2 million, partially offset by a net change in unrealized appreciation on our investment portfolio of approximately $75.7 million (which incorporates reductions to CLO equity cost value of $13.0 million) and purchases of investments of approximately $112.2 million.
A reconciliation of the investment portfolio for the years ended December 31, 2023 and 2022 follows: ($ in millions) December 31, 2023 December 31, 2022 Beginning investment portfolio $ 314.7 $ 420.8 Portfolio investments acquired 11.7 84.2 Debt repayments (15.8 ) (50.0 ) Sales of securities (19.6 ) (14.6 ) Reductions to CLO equity cost value (1) (15.3 ) (20.4 ) Accretion of discounts on investments 1.1 0.9 Net change in unrealized appreciation/(depreciation) on investments 7.1 (105.9 ) Net realized losses on investments (17.1 ) (0.3 ) Ending investment portfolio (2) $ 266.9 $ 314.7 ____________ (1) For the year ended December 31, 2023, the reductions to CLO equity cost value of approximately $15.3 million represented the distributions received, or entitled to be received, on our investments held in CLO equity subordinated and income notes of approximately $32.0 million, plus the amortization of cost on our CLO fee notes of approximately $123,000, less the effective yield interest income recognized on our CLO equity subordinated and income notes of approximately $16.8 million.
Refer to the table below, which reconciles the investment portfolio for the year ended December 31, 2024 and the year ended December 31, 2023. 65 A reconciliation of the investment portfolio for the years ended December 31, 2024 and 2023 follows: ($ in millions) December 31, 2024 December 31, 2023 Beginning investment portfolio $ 266.9 $ 314.7 Portfolio investments acquired 112.2 11.7 Debt repayments (75.0 ) (15.8 ) Sales of securities (11.8 ) (19.6 ) Reductions to CLO equity cost value (1) (13.0 ) (15.3 ) Accretion of discounts on investments 1.7 1.1 PIK income 0.5 — Net change in unrealized appreciation/(depreciation) on investments 75.7 7.1 Net realized losses on investments (96.2 ) (17.1 ) Ending investment portfolio (2) $ 260.9 $ 266.9 ____________ (1) For the year ended December 31, 2024, the reductions to CLO equity cost value of approximately $13.0 million represented the distributions received, or entitled to be received, on our investments held in CLO equity subordinated and income notes of approximately $28.4 million, plus the amortization of cost on our CLO fee notes of approximately $71,000, less the effective yield interest income recognized on our CLO equity subordinated and income notes of approximately $15.4 million.
We sold a total of 2,695,388 shares of common stock pursuant to the ATM offering during the year ended December 31, 2023. The total amount of capital raised net of underwriting fees and offering costs was approximately $8.1 million during the year ended December 31, 2023.
We sold a total of 10,132,282 shares of common stock pursuant to the ATM offering during the year ended December 31, 2024. The total amount of capital raised net of underwriting fees and offering costs was approximately $29.2 million during the year ended December 31, 2024.
For the year ended December 31, 2022, the reductions to CLO equity cost value of approximately $20.4 million represented the distributions received, or entitled to be received, on our investments held in CLO equity subordinated and income notes of approximately $37.3 million, plus the amortization of cost on our CLO fee notes of approximately $128,000, less the effective yield interest income recognized on our CLO equity subordinated and income notes of approximately $17.1 million.
For the year ended December 31, 2023, the reductions to CLO equity cost value of approximately $15.3 million represented the distributions received, or entitled to be received, on our investments held in CLO equity subordinated and income notes of approximately $32.0 million, plus the amortization of cost on our CLO fee notes of approximately $123,000, less the effective yield interest income recognized on our CLO equity subordinated and income notes of approximately $16.8 million.
The change was primary the result of higher investment income, partially offset by an increase in operating expenses, as discussed above.
The change was primary the result of lower operating expenses, partially offset by a decrease in investment income, as discussed above.
No additional non -qualifying assets were acquired during the periods, if any, when qualifying assets were less than 70% of the total assets. 68 The following table shows our portfolio of investments by industry at fair value, in millions, as of December 31, 2023 and 2022: December 31, 2023 December 31, 2022 Investments at Fair Value Percentage of Fair Value Investments at Fair Value Percentage of Fair Value ($ in millions) ($ in millions) Structured finance (1) $ 82.2 30.8 % $ 98.9 31.4 % Software 66.0 24.7 % 69.0 21.9 % Business services 43.0 16.1 % 53.4 17.0 % Healthcare 28.4 10.7 % 33.6 10.7 % Telecommunication services 20.9 7.8 % 22.2 7.0 % Diversified insurance 13.9 5.2 % 14.7 4.7 % Utilities 7.2 2.7 % 6.8 2.2 % IT consulting 5.3 2.0 % 4.3 1.4 % Plastics manufacturing — — % 11.7 3.7 % Total (2) $ 266.9 100.0 % $ 314.7 100.0 % ____________ (1) Reflects our equity investments in CLOs as of December 31, 2023 and December 31, 2022, respectively.
No additional non -qualifying assets were acquired during the periods, if any, when qualifying assets were less than 70% of the total assets. 67 The following table shows our portfolio of investments by industry at fair value, in millions, as of December 31, 2024 and 2023: December 31, 2024 December 31, 2023 Investments at Fair Value Percentage of Fair Value Investments at Fair Value Percentage of Fair Value ($ in millions) ($ in millions) Structured finance (1) $ 104.6 40.2 % $ 82.2 30.8 % Business services 45.5 17.4 % 43.0 16.1 % Software 42.0 16.1 % 66.0 24.7 % Healthcare 18.9 7.2 % 28.4 10.7 % Industrials 16.0 6.1 % — — % Food and Beverage 10.0 3.8 % — — % Telecommunication Services 7.2 2.8 % 20.9 7.8 % Aerospace and Defense 6.0 2.3 % — — % Materials 6.0 2.3 % — — % IT Consulting 4.6 1.8 % 5.3 2.0 % Diversified Insurance — — % 13.9 5.2 % Utilities — — % 7.2 2.7 % Total (2) $ 260.9 100.0 % $ 266.9 100.0 % ____________ (1) Reflects our equity investments in CLOs as of December 31, 2024 and December 31, 2023, respectively.
(2) Totals may not sum due to rounding. During the year ended December 31, 2023, we purchased approximately $11.7 million in portfolio investments, including additional investments of approximately $3.5 million in existing portfolio companies and approximately $8.2 million in new portfolio companies.
(2) Totals may not sum due to rounding. During the year ended December 31, 2024, we purchased approximately $112.2 million in portfolio investments, including additional investments of approximately $31.0 million in existing portfolio companies and approximately $81.2 million in new portfolio companies.
There was no Net Investment Income Incentive Fee for the year ended December 31, 2022, primarily as a result of the Net Investment Income Incentive Fee being reduced as the result of the Total Return Requirement.
There was no Net Investment Income Incentive Fee for the year ended December 31, 2024, primarily as a result of the Net Investment Income Incentive Fee being reduced as the result of the Total Return Requirement. Net Investment Income Incentive Fees for the year ended December 31, 2023 were approximately $3.7 million.
The increase in 2023 is attributable primarily to higher Net Investment Income Incentive Fees and excise tax, partially offset by lower interest expense and Base Fee. Interest expense decreased by approximately $1.5 million in 2023 compared to 2022. The decrease in 2023 was due to the full paydown of the 6.50% Unsecured Notes.
The decrease in 2024 is attributable primarily to lower Net Investment Income Incentive Fees, excise tax, and interest expense. Interest expense decreased by approximately $3.0 million in 2024 compared to 2023. The decrease in 2024 was due to the full paydown of the 6.50% Unsecured Notes throughout 2023.
Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 48.9 15.9 % 31.3 14.8 % 4 A loss of interest income has occurred or is expected to occur and, in most cases, the investment is placed on non-accrual status.
Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 82.0 40.6 % 38.0 25.2 % 4 A loss of interest income has occurred or is expected to occur and, in most cases, the investment is placed on non-accrual status.
For the year ended December 31, 2022, our net change in unrealized depreciation was approximately $105.9 million, composed of approximately $3.8 million in gross unrealized appreciation, approximately $109.0 million in gross unrealized depreciation and approximately $0.7 million relating to the reversal of prior period net unrealized depreciation as investment gains and losses were realized.
For the year ended December 31, 2024, our net change in unrealized appreciation was approximately $75.7 million, comprised of approximately $7.1 million in gross unrealized appreciation, approximately $17.1 million in gross unrealized depreciation and approximately $85.7 million relating to the reversal of prior period net unrealized depreciation as investment gains and losses were realized.
We expect that our investment portfolio will be diversified among a large number of investments with few investments, if any, exceeding 5.0% of the total portfolio. As of December 31, 2023, our debt investments had stated interest rates of between 9.22% and 16.00% and maturity dates of between 0 and 74 months.
We expect that our investment portfolio will be diversified among a large number of investments with few investments, if any, exceeding 5.0% of the total portfolio. As of December 31, 2024, our debt investments (excluding debt investments on non -accrual status) had stated interest rates of between 7.61% and 13.13% and maturity dates of between 3 and 82 months.
(f/k/a AIS Intermediate, LLC) 0.7 Net all others 1.3 Total repayments $ 15.8 67 Portfolio activity also reflects sales of securities in the amounts of approximately $19.6 million and approximately $14.6 million for the years ended December 31, 2023 and 2022, respectively.
(f/k/a ScribeAmerica, LLC) 0.2 Net all others 0.5 Total repayments $ 75.0 66 Portfolio activity also reflects sales of securities in the amounts of approximately $11.8 million and approximately $19.6 million for the years ended December 31, 2024 and 2023 respectively.
In addition, our total portfolio had a weighted average annualized yield on debt investments of approximately 13.30%.
In addition, our total portfolio had a weighted average annualized yield on debt investments of approximately 15.76% as of December 31, 2024.
These statements are not guarantees of future performance and are subject to risks, uncertainties, and other factors, some of which are beyond our control and difficult to predict and could cause actual results to differ materially from those expressed or forecasted in the forward -looking statements, including without limitation: • an economic downturn could impair our portfolio companies’ and CLO investments’ ability to continue to operate, which could lead to the loss of some or all of our investments in such portfolio companies and CLO investments; • a contraction of available credit and/or an inability to access the equity markets could impair our lending and investment activities; • interest rate volatility could adversely affect our results, particularly because we use leverage as part of our investment strategy; • the elevated levels of inflation and its impact on our investment activities and the industries in which we invest; • currency fluctuations could adversely affect the results of our investments in foreign companies, particularly to the extent that we receive payments denominated in foreign currency rather than U.S. dollars; • the impact of information technology system failures, data security breaches, data privacy compliance, network disruptions and cybersecurity attacks; and • the risks, uncertainties and other factors we identify in Item 1A.
The forward -looking statements contained in this Annual Report on Form 10 -K involve risks and uncertainties, including statements as to: • our future operating results, including our ability to achieve objectives; • our business prospects and the prospects of our portfolio companies; • the impact of investments that we expect to make; • our contractual arrangements and relationships with third parties; • the dependence of our future success on the general economy and its impact on the industries in which we invest; • the ability of our portfolio companies and CLO investments to achieve their objectives; • the valuation of our investments in portfolio companies and CLOs, particularly those having no liquid trading market; • market conditions and our ability to access alternative debt markets and additional debt and equity capital; • our expected financings and investments; • the adequacy of our cash resources and working capital; • the timing of cash flows, if any, from the operations of our portfolio companies and CLO investments; and • the ability of our investment adviser to locate suitable investments for us and monitor and administer our investments. 63 These statements are not guarantees of future performance and are subject to risks, uncertainties, and other factors, some of which are beyond our control and difficult to predict and could cause actual results to differ materially from those expressed or forecasted in the forward -looking statements, including without limitation: • an economic downturn could impair our portfolio companies’ and CLO investments’ ability to continue to operate, which could lead to the loss of some or all of our investments in such portfolio companies and CLO investments; • a contraction of available credit and/or an inability to access the equity markets could impair our lending and investment activities; • interest rate volatility could adversely affect our results, particularly because we use leverage as part of our investment strategy; • inflation and its impact on our investment activities and the industries in which we invest; • currency fluctuations could adversely affect the results of our investments in foreign companies, particularly to the extent that we receive payments denominated in foreign currency rather than U.S. dollars; • the impact of information technology system failures, data security breaches, data privacy compliance, network disruptions and cybersecurity attacks; and • the risks, uncertainties and other factors we identify in Item 1A.
As a result, certain conflicts of interest may arise with respect to the management of our portfolio by Messrs. Cohen and Rosenthal on the one hand, and the obligations of Messrs. Cohen and Rosenthal to manage Oxford Lane Capital Corp., Oxford Park Income Fund, Inc., Oxford Bridge II, LLC and the Oxford Gate Funds, respectively, on the other hand.
Cummins serves as the Chief Compliance Officer of Oxford Park Income Fund, Inc. and Oxford Park Management. 77 As a result, certain conflicts of interest may arise with respect to the management of our portfolio by Messrs. Cohen and Rosenthal on the one hand, and the obligations of Messrs.
As of December 31, 2022, we had investments in debt securities of, or loans to, 20 portfolio companies, with a fair value of approximately $211.4 million, and CLO equity investments of approximately $98.9 million.
As of December 31, 2023, we had investments in debt securities of, or loans to, 19 portfolio companies, with a fair value of approximately $179.5 million, CLO equity investments of approximately $82.2 million and equity and other investments of approximately $5.3 million.
In addition, our total portfolio had a weighted average yield on debt investments of approximately 13.30% as of December 31, 2023, compared to a weighted average yield on debt investments of 11.85% as of December 31, 2022. 71 Operating Expenses The following table sets forth the components of operating expenses for the years ended December 31, 2023 and 2022: December 31, 2023 December 31, 2022 Interest expense $ 10,825,877 $ 12,354,392 Base Fee 4,613,664 5,903,986 Net Investment Income Incentive Fees 3,705,387 — Professional fees 1,426,098 1,393,116 Excise Tax 1,423,686 252,172 Compensation expense 825,226 915,583 General and administrative 638,350 583,740 Director’s fees 429,500 417,500 Insurance 329,892 378,804 Transfer agent and custodian fees 246,562 231,241 Total operating expenses $ 24,464,242 $ 22,430,534 Total operating expenses for the year ended December 31, 2023 increased by approximately $2.0 million compared to the year ended December 31, 2022.
In addition, our total portfolio had a weighted average yield on debt investments of approximately 15.76% as of December 31, 2024, compared to a weighted average yield on debt investments of 13.30% as of December 31, 2023. 70 Operating Expenses The following table sets forth the components of operating expenses for the years ended December 31, 2024 and 2023: December 31, 2024 December 31, 2023 Interest expense $ 7,847,320 $ 10,825,877 Base Fee 4,310,484 4,613,664 Professional fees 1,537,434 1,426,098 Compensation expense 746,762 825,226 General and administrative 597,883 638,350 Director’s fees 417,500 429,500 Insurance 308,552 329,892 Transfer agent and custodian fees 260,330 246,562 Excise Tax 216,528 1,423,686 Net Investment Income Incentive Fees — 3,705,387 Total operating expenses $ 16,242,793 $ 24,464,242 Total operating expenses for the year ended December 31, 2024 decreased by approximately $8.2 million compared to the year ended December 31, 2023.
The total principal outstanding on income producing debt investments as of December 31, 2023 and December 31, 2022 was approximately $247.7 million and $279.0 million, respectively. As of December 31, 2023, our debt investments had stated interest rates of between 9.22% and 16.00% and maturity dates of between 0 and 74 months.
As of December 31, 2024, our income producing debt investments had stated interest rates of between 7.61% and 13.13% and maturity dates of between 3 and 82 months. As of December 31, 2023, our debt investments had stated interest rates of between 9.22% and 16.00% and maturity dates of between 0 and 74 months.
The change year over year was largely due to approximately $7.1 million of net change in unrealized appreciation recognized in the year ended December 31, 2023, compared to approximately $105.9 million of net change in unrealized depreciation recognized in the year ended December 31, 2022, as discussed above.
The change year over year was largely due to approximately $20.6 million of net realized and unrealized losses for the year ended December 31, 2024, compared to approximately $10.1 million of net realized and unrealized losses for the year ended December 31, 2023, as discussed above.
The components of the net change in unrealized appreciation/(depreciation) during the year ended December 31, 2023 were as follows ($ in millions): Portfolio Company Changes in Unrealized Appreciation/ (Depreciation) Nassau 2019-I Ltd. $ 9.4 Telos CLO 2013-4, Ltd. 4.9 THL Credit Wind River 2012-1 CLO, Ltd. 2.9 Carlyle Global Market Strategies CLO 2021-6, Ltd. 2.7 Global Tel Link Corp. 2.2 Alvaria, Inc.
This includes net unrealized appreciation of approximately $15.3 million resulting from reductions to the cost value of our CLO equity investments representing the difference between distributions received, or entitled to be received, on our investments held in CLO equity subordinated notes and fee notes, of approximately $32.0 million and the effective yield interest income recognized on our CLO equity subordinated notes and the amortized cost adjusted income on our CLO equity fee notes of approximately $16.7 million. 72 The components of the net change in unrealized appreciation/(depreciation) during the year ended December 31, 2023 were as follows ($ in millions): Portfolio Company Changes in Unrealized Appreciation/ (Depreciation) Nassau 2019-I Ltd. $ 9.4 Telos CLO 2013-4, Ltd. 4.9 THL Credit Wind River 2012-1 CLO, Ltd. 2.9 Carlyle Global Market Strategies CLO 2021-6, Ltd. 2.7 Global Tel Link Corp. 2.2 Alvaria, Inc.
As of December 31, 2022, approximately $31,000 in compensation expenses remained payable. General and administrative expenses, which consist primarily of listing fees, office supplies, facilities costs and other miscellaneous expenses, increased by approximately $55,000 for the year ended December 31, 2023 compared to the year ended December 31, 2022.
General and administrative expenses, which consist primarily of listing fees, office supplies, facilities costs and other miscellaneous expenses were approximately $598,000 for the year ended December 31, 2024 and decreased by approximately $40,000 from the year ended December 31, 2023. Office supplies, facilities costs and other expenses are allocated to us under the terms of the Administration Agreement.
We expect that a portion of our investments will be in the Grades 3, 4 or 5 categories from time to time, and, as such, we will be required to work with troubled portfolio companies to improve their business and protect our investment.
Full repayment of the outstanding amount of OXSQ’s cost basis is expected for the specific tranche. — — % — — % 5 Full repayment of the outstanding amount of OXSQ’s cost basis is not expected for the specific tranche and the investment is placed on non-accrual status. 42.9 14.8 % 1.7 1.0 % Total $ 290.7 100.0 % $ 179.5 100.0 % 69 We expect that a portion of our investments will be in the Grades 3, 4 or 5 categories from time to time, and, as such, we will be required to work with troubled portfolio companies to improve their business and protect our investment.
Related Party Transactions” in the notes to our financial statements. A summary of our significant contractual payment obligations is as follows as of December 31, 2023. Refer to “Note 5. Borrowings” in the notes to our financial statements.
Refer to “— Overview”. We incurred approximately $4.3 million for the Base Fee and approximately $1.7 million for administrative services for the year ended December 31, 2024. Refer to “Note 7. Related Party Transactions” in the notes to our financial statements. A summary of our significant contractual payment obligations is as follows as of December 31, 2024.
(3.7 ) Net all other (43.4 ) Total (1) $ (105.9 ) ____________ (1) Totals may not sum due to rounding. Net Increase in Net Assets Resulting from Net Investment Income Net investment income for the year ended December 31, 2023 was approximately $27.4 million, compared to $20.7 million for the year ended December 31, 2022.
(3.5 ) Careismatic Brands, LLC (6.2 ) Magenta Buyer, LLC (f/k/a McAfee Enterprise) (6.3 ) Net all other 7.5 Total $ 7.1 Net Increase in Net Assets Resulting from Net Investment Income Net investment income for the year ended December 31, 2024 was approximately $26.4 million, compared to $27.4 million for the year ended December 31, 2023.
The tables below summarize the components of interest expense for the years ended December 31, 2023 and 2022: Year Ended December 31, 2023 ($ in thousands) Stated Interest Expense Amortization of Deferred Debt Issuance Costs Loss on Extinguishment Total 6.50% Unsecured Notes $ 2,765.0 $ 215.3 $ 190.4 $ 3,170.6 6.25% Unsecured Notes 2,799.4 233.2 — 3,032.6 5.50% Unsecured Notes 4,427.5 385.5 — 4,813.0 Total $ 9,991.9 $ 834.0 $ 190.4 $ 11,016.2 Year Ended December 31, 2022 ($ in thousands) Stated Interest Expense Amortization of Deferred Debt Issuance Costs Total 6.50% Unsecured Notes $ 4,184.1 $ 324.7 $ 4,508.8 6.25% Unsecured Notes 2,799.4 233.2 3,032.6 5.50% Unsecured Notes 4,427.5 385.5 4,813.0 Total $ 11,411.0 $ 943.4 $ 12,354.4 ____________ (1) Totals may not sum due to rounding.
The tables below summarize the components of interest expense for the years ended December 31, 2024 and 2023: ($ in thousands) Year Ended December 31, 2024 Stated Interest Expense Amortization of Deferred Debt Issuance Costs Loss on Extinguishment Total 6.25% Unsecured Notes $ 2,799.4 $ 233.8 — 3,033.2 5.50% Unsecured Notes 4,427.5 386.6 — 4,814.1 Total $ 7,226.9 $ 620.4 $ — $ 7,847.3 ($ in thousands) Year Ended December 31, 2023 Stated Interest Expense Amortization of Deferred Debt Issuance Costs Loss on Extinguishment Total 6.50% Unsecured Notes $ 2,765.0 $ 215.3 $ 190.4 $ 3,170.6 6.25% Unsecured Notes 2,799.4 233.2 — 3,032.6 5.50% Unsecured Notes 4,427.5 385.5 — 4,813.0 Total $ 9,991.9 $ 834.0 $ 190.4 $ 11,016.2 Distributions In order to qualify for tax treatment as a RIC, we are required, under Subchapter M of the Code, to distribute at least 90% of our ordinary income and realized net short -term capital gains in excess of realized net long -term capital losses to our stockholders on an annual basis.
Investment Income The following table sets forth the components of investment income for the years ended December 31, 2023 and 2022: December 31, 2023 December 31, 2022 Interest Income Stated interest income $ 32,434,732 $ 23,954,078 Original issue discount and market discount income 1,094,874 880,671 Discount income derived from unscheduled remittances at par 62,560 399,566 Total interest income 33,592,166 25,234,315 Income from securitization vehicles and investments 16,796,699 17,093,203 Other income Fee letters 649,260 544,267 Money market fund income and all other fees 786,056 246,327 Total other income 1,435,316 790,594 Total investment income $ 51,824,181 $ 43,118,112 The increase in total investment income of approximately $8.7 million for the year ended December 31, 2023 over the year ended December 31, 2022 was largely due to an increase of stated interest income from our debt investments (approximately $8.5 million) resulting from higher weighted average yields in 2023 compared to 2022.
Investment Income The following table sets forth the components of investment income for the years ended December 31, 2024 and 2023: December 31, 2024 December 31, 2023 Interest Income Stated interest income $ 22,453,772 $ 32,434,732 PIK interest income 462,883 — Original issue discount and market discount income 1,688,134 1,094,874 Discount income derived from unscheduled remittances at par 324,498 62,560 Total interest income 24,929,287 33,592,166 Income from securitization vehicles and investments 15,403,586 16,796,699 Other income Fee letters 661,281 649,260 Money market fund income and all other fees 1,689,051 786,056 Total other income 2,350,332 1,435,316 Total investment income $ 42,683,205 $ 51,824,181 The decrease in total investment income of approximately $9.1 million for the year ended December 31, 2024 from the year ended December 31, 2023 was largely due to a decrease of stated interest income from our debt investments (approximately $10.0 million) resulting from multiple restructurings and refinancings that occurred during the year ended December 31, 2024 and a decrease in floating interest rates.
The repayments during the year ended December 31, 2023 were as follows ($ in millions): Portfolio Company 2023 Repayments OMNIA Partners, Inc. $ 13.8 Affinion Insurance Solutions, Inc.
The repayments during the year ended December 31, 2024 were as follows ($ in millions): Portfolio Company 2024 Repayments Global Tel Link Corp. $ 16.9 Access CIG, LLC 16.9 Viant Medical Holdings, Inc. 14.5 Affinion Insurance Solutions, Inc.
(f/k/a KPEX Holdings, Inc.) $ 12.7 PPM CLO 4, Ltd. 3.7 Nassau 2019-I Ltd. 1.8 Babson CLO Ltd. 2015-I 1.2 Net all others 0.2 Total sales $ 19.6 As of December 31, 2023, we had investments in debt securities of, or loans to, 19 portfolio companies, with a fair value of approximately $179.5 million, and CLO equity investments of approximately $82.2 million.
The sales during the year ended December 31, 2024 were as follows ($ in millions): Portfolio Company 2024 Sales Quest Software, Inc. $ 7.0 Veritas USA, Inc. 3.4 Octagon Investment Partners 49, Ltd. 1.4 Total sales $ 11.8 As of December 31, 2024, we had investments in debt securities of, or loans to, 21 portfolio companies, with a fair value of approximately $150.7 million, CLO equity investments of approximately $104.6 million and equity and other investments of approximately $5.6 million.
Interest payments, if not deferred, are normally payable quarterly with most debt investments having scheduled principal payments on a monthly or quarterly basis.
Interest payments, if not deferred, are normally payable quarterly with most debt investments having scheduled principal payments on a monthly or quarterly basis. When we receive a warrant to purchase stock in a portfolio company, the warrant will typically have a nominal strike price, and will entitle us to purchase a modest percentage of the borrower’s stock.
During the year ended December 31, 2023, net cash used in by financing activities was approximately $69.0 million, reflecting the payment of distributions of approximately $28.6 million and full 74 principal repayment of the 6.50% Unsecured Notes of approximately $64.4 million, partially offset by proceeds from issuance of common stock from our ATM program and rights offering (net of underwriting fees and offering costs) of approximately $24.0 million.
During the year ended December 31, 2024, net cash provided by financing activities was approximately $3.5 million, reflecting the proceeds from issuance of common stock from our ATM program (net of underwriting fees and offering costs) of approximately $29.2 million, partially offset by the payment of distributions of approximately $25.8 million. 73 Contractual Obligations We have certain obligations with respect to the investment advisory and administration services we receive.
When we receive a warrant to purchase stock in a portfolio company, the warrant will typically have a nominal strike price, and will entitle us to purchase a modest percentage of the borrower’s stock. 66 PORTFOLIO COMPOSITION AND INVESTMENT ACTIVITY The total fair value of our investment portfolio was approximately $266.9 million and $314.7 million as of December 31, 2023 and December 31, 2022, respectively.
PORTFOLIO COMPOSITION AND INVESTMENT ACTIVITY The total fair value of our investment portfolio was approximately $260.9 million and $266.9 million as of December 31, 2024 and December 31, 2023, respectively.