Slides
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QUARTERLY OVERVIEW September 30, 2025
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Legal Disclaimer This presentation may include forward-looking statements. These forward-looking statements may involve known and unknown risks, uncertainties and other factors that may cause our actual results, levels of activity, performance or achievements to be materially different from any future results, levels of activity, performance or achievements expressed or implied by such forward-looking statements. Such factors include, but are not limited to: (1) changes in the economy and the capital markets, including stock price volatility, inflation, elevated interest rates, tariffs and trade wars and risks of recession; (2) risks associated with negotiation and consummation of pending and future transactions; (3) the loss of one or more of our executive officers, in particular David Gladstone or David Dullum; (4) changes in our investment objectives and strategy; (5) availability, terms (including the possibility of interest rate volatility) and deployment of capital; (6) changes in our industry, interest rates, exchange rates, or the general economy, including inflation; (7) our business prospects and the prospects of our portfolio companies; (8) the degree and nature of our competition; (9) changes in governmental regulation, tax rates and similar matters; (10) our ability to exit investments in a timely manner; (11) our ability to maintain our qualification as a regulated investment company and as a business development company; and (12) those factors listed under the caption “Risk Factors” in our Form 10-K, Form 10-Q, registration statements and related prospectus supplements, and other documents we may file with the Securities and Exchange Commission (“SEC”) from time to time. We caution readers not to place undue reliance on any such forward-looking statements. Actual results could differ materially from those anticipated in our forward-looking statements and future results could differ materially from historical performance. We have based forward-looking statements on information available to us on the date of this presentation. Except as required by the federal securities laws, we undertake no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events or otherwise, after the date of this presentation. Although we undertake no obligation to revise or update any forward-looking statements, whether as a result of new information, future events or otherwise, you are advised to consult any additional disclosures that we may make directly to you or through reports that we have filed or in the future may file with the SEC, including subsequent annual reports on Form 10-K, quarterly reports on Form 10-Q and current reports on Form 8-K. Past or Present Performance Disclaimer: This presentation includes information regarding our past or present performance. Please note, past or present performance is not a guarantee of future performance or future results. We undertake no obligation to update the information contained herein to reflect subsequently occurring events or circumstances, except as required by applicable securities laws and regulations. 2
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QUARTERLY UPDATE Company Overview and Objectives Investment Strategy & Value Creation Current Portfolio, Successful Exits & Market Update Financial Highlights, Shareholder Value & Capital Structure Table of Contents 33
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WHO WE ARE – OVERVIEW & OBJECTIVES 4 Quarterly Presentation
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Gladstone Investment | Who We Are WHO WE ARE – OVERVIEW & OBJECTIVES 5 • Externally managed by an SEC-registered investment adviser, Gladstone Management Corporation, and administrator with over 70 professionals and $4.0+ billion in AUM across four publicly traded funds and one interval fund • Nine investment professionals, a CFO, a Controller and a senior accountant dedicated exclusively to Gladstone Investment Corporation • Proven investment track record across multiple economic cycles EXPERIENCED MANAGEMENT TEAM WITH PROVEN TRACK RECORD 1 All information in this presentation is as of 9/30/2025, except as noted. 2 Subsequent to 9/30/2025, GAIN completed an offering of 6.875% Notes due 2028 with an aggregate principal amount of $60.0 million. 3 Subsequent to 9/30/2025, GAIN announced it will redeem 100%, or $74.8 million, of its outstanding 8.00% Notes due 2028 on 12/16/2025. In connection with this redemption, the 2028 Notes will be delisted from the Nasdaq. • Nasdaq symbol “GAIN” | market cap of $547 million o $2.2+ billion invested since 2005 IPO o $1.1+ billion in total assets at fair value • 2026 Notes listed on Nasdaq under “GAINN” with 5.00% interest rate • 2028 Notes listed on Nasdaq under “GAINZ” with 4.875% interest rate • 2028 Notes listed on Nasdaq under “GAINL” with 8.00% interest rate(3) • 2030 Notes listed on Nasdaq under “GAINI” with 7.875% interest rate SIGNIFICANT CAPITAL RAISED AND DEPLOYED (2) 5 GLADSTONE INVESTMENT BACKGROUND (1) • Founded in 2005 with the purpose of investing in debt and equity securities of established lower middle market U.S. businesses • GAIN holds investments in 28 portfolio companies with an aggregate fair value of $1.1B+ • Since inception, invested in 65 buyout companies • Exited 33 portfolio companies acquired under buyout strategy generating significant realized gains and other income upon exit
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Differentiated buyout structure • Primary equity investor – lead sponsor in majority of prospective transactions, often partnering with existing management teams • Differentiated approach – turnkey provider of the equity & secured debt in change of control buyouts o Typically provides most, if not all, of the debt capital along with a majority of the equity capital o Target mix of total invested dollars per transaction is 75% debt & 25% equity (at cost) o Traditional BDCs typically have equity exposure of 5% - 10% • Turnkey approach greatly increases certainty and speed of closing, providing business owners and intermediaries with confidence in GAIN’s ability to execute a buyout transaction Dedicated lower middle market focus on niche market leaders • Target lower middle market companies (EBITDA of $4 - $15 million) domiciled in the United States • Focused on businesses with leading market positions, positive cash flow generation, and strong management teams • Industry agnostic with investments in manufacturing, business/consumer services, and consumer products Gladstone Investment | Overview WHO WE ARE – OVERVIEW & OBJECTIVES GAIN is differentiated from other BDCs through its buyout investment strategy. 6
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Evergreen fund structure creates alignment with management • Investment decisions not guided by fundraising or end-of-fund deadlines unlike a traditional buy-out fund • Provides portfolio company boards and management teams with flexibility in terms of strategy and timing • Allows all stakeholders to focus on sustainable, long-term value creation Active portfolio management • Active leadership on portfolio company boards to drive alignment and accountability with management teams • Leverage knowledge, experience and leadership from past deals and current portfolio to identify revenue and cost opportunities • Current portfolio is diversified across 28 companies, 20 states and Canada, and 16 industries 1 1 All information in this presentation is as of 9/30/2025, except as noted. Gladstone Investment | Overview WHO WE ARE – OVERVIEW & OBJECTIVES GAIN is differentiated from other BDCs through its buyout investment strategy. 7
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8 Gladstone Investment | Overview WHO WE ARE – OVERVIEW & OBJECTIVES 1 All data as of 9/30/2025 slides 26-27 for detail. 2 GAIN’s fiscal year commences on April 1st and ends on March 31st. 3 Assumes a full year of the $0.08 per share regular monthly distributions, including amounts not yet paid and/or declared in November 2025 through March 2026 and the $0.54 per share supplemental distribution paid during FY26. Investment structure creates attractive risk-reward profile • Senior secured debt provides downside protection, along with the upside potential of GAIN’s equity investments • No third-party sponsor risk as GAIN is the sponsor • Greater ability to influence decision making or changes to drive shareholder value, due to GAIN’s significant economic ownership position in its portfolio companies Outperformance and outsized upside potential compared to industry peers 1 • Excellent historical performance compared to industry peers in total return and return of equity (“ROE”) over the past five and ten years • GAIN’s 5- and 10-year total return is 168% and 437% vs. industry peers of 106% and 148% • GAIN’s 5- and 10-year average ROE is 16% and 14% vs. industry peers of 12% and 9% Strong and growing distributions • Consistently raised regular monthly distributions to shareholders, as a result of growing debt portfolio, and has never missed a monthly distribution since its IPO in 2005 • GAIN’s equity ownership provides further upside to shareholders through prospective capital gains from successful exits, which supports supplemental distributions, including the $0.54 per share distribution paid in FY26 • Since inception through FY252, average buyout exit cash-on-cash equity return of 4.0x • Dividend yield of 10.72% as of November 7, 20253 Delivering to investors consistent and increasing distributions
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• GAIN’s equity ownership provides further upside potential to shareholders through prospective capital gains and other income from successful exits which support supplemental distributions from time to time. • Since inception, GAIN has generated $424.4 million of net realized gains and dividends on the exit of the equity portion of buyout portfolio companies, representing 4.0x cash on cash return. Upside Potential Driven by Focus on Equity Securities Approximately 39% of GAIN’s portfolio, at fair value, is comprised of equity securities (typically preferred equity with common equity participation) 1 At fair value as of 9/30/2025. 9 WHO WE ARE – OVERVIEW & OBJECTIVES 39% 8% 53% Meaningful Equity Component in GAIN Portfolio1 Preferred & Common Equity Secured Second Lien Debt Secured First Lien Debt
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$153.3 $225.7 $286.5 $314.4 $466.1 $487.7 $501.6 $599.1 $624.2 $565.9 $633.8 $714.4 $753.5 $920.5 $974.3 $- $100.0 $200.0 $300.0 $400.0 $500.0 $600.0 $700.0 $800.0 $900.0 $1,000.0 $1,100.0 $1,200.0 FY11 FY12 FY13 FY14 FY15 FY16 FY17 FY18 FY19 FY20 FY21 FY22 FY23 FY24 FY25 Q2 FY26 1st Lien 2nd Lien Preferred & Common Equity Growing Portfolio WHO WE ARE – OVERVIEW & OBJECTIVES From 4/1/2010 to 9/30/2025, we have: • Made investments in 52 new companies of approximately $1.7 billion 1 • Exited 33 companies for a return of proceeds of $1.1 billion 1,2 Total investments, at fair value ($MM) 1 Excludes line of credit commitments. 2 Includes return of capital, realized gains and dividends received from initial investment date through exit, net of losses on debt/equity and cost balances written-off or restructured. 3 As of 9/30/2025. 10 3 $1,130.9
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$0.48 $0.59 $0.60 $0.66 $0.72 $0.75 $0.75 $0.77 $0.81 $0.82 $0.84 $0.87 $0.93 $0.96 $0.96 $0.96 $0.03 $0.05 $0.05 $0.12 $0.12 $0.21 $0.09 $0.30 $0.48 $1.24 $0.70 $0.54 $- $0.50 $1.00 $1.50 $2.00 $2.50 FY 2011 FY 2012 FY 2013 FY 2014 FY 2015 FY 2016 FY 2017 FY 2018 FY 2019 FY 2020 FY 2021 FY 2022 FY 2023 FY 2024 FY 2025 FY 2026 Regular Distribution Supplemental Distribution 11 • From inception through 9/30/25, GAIN has paid 243 consecutive monthly distributions to common shareholders • GAIN’s regular annual distribution run-rate has increased 100% from $0.48 per common share in FY11 to $0.96 per common share for FY26, most recently increased in October 2022 • In addition to regular distributions, GAIN has a history of paying supplemental distributions to common shareholders, consist ing of realized capital gains from portfolio company exits WHO WE ARE – OVERVIEW & OBJECTIVES History of Strong Monthly and Supplemental Distributions $0.48 $0.62 $0.60 $0.71 $0.77 $0.75 $0.75 $0.89 $0.93 $1.03 $0.93 $1.17 $1.41 $2.20 Distributions per common share ($) $1.66 1 Assumes a full year of the $0.08 per share regular monthly distributions, including amounts not yet paid and/or declared in November 2025 through March 2026. $1.50 1
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INVESTMENT STRATEGY & VALUE CREATION 12 Quarterly Presentation
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Investment Focus • Target stable lower middle market companies with EBITDA of $4 – $15 million • Investment size (debt & equity) generally up to $75 million (typically 75% debt & 25% equity) • Lead or co-lead prospective transactions • Focused on cash-flow positive businesses with proven competitive advantages and strong management teams • Sector agnostic with focus and experience in manufacturing, business services/distribution, and consumer products Investment Structures • Preferred equity is typically participating with a stated dividend of around 8% • Secured 1st or 2nd lien term debt with current interest rates in the low- to mid-teens, generally with a success fee due upon a change of control and 5-year term without amortization • Revolver may be provided with the expectation of refinancing shortly after close • Portfolio company management option pool typically of 10% Investment Focus and Process INVESTMENT STRATEGY & VALUE CREATION Driving performance with a focused and diligent approach to investment selections. 13
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Deal Sourcing • Source opportunities from investment banks, M&A advisory firms, and industry executives • Regionally focused sourcing strategy, spearheaded by senior members of the investment team • Debt & equity from single investor provides competitive advantage by improving the certainty of close and decreasing deal complexity Due Diligence • Typical due diligence period of 45 to 60 days after executing letter of intent • Thorough multi-disciplinary approach – blending internal industry experience, onsite visits and management assessments, supplemented with third party quality of earnings reports, industry studies, management assessments, and customary legal and insurance investigations Investment Focus and Process INVESTMENT STRATEGY & VALUE CREATION Driving performance with a focused and diligent approach to investment selections. 14
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GAIN takes a long-term approach with a strategy to deploy debt & equity designed to streamline post-close value creation. CERTAINTY AND SPEED TO CLOSE No third-party capital required to close transactions, as GAIN provides substantially all the debt & equity. 1 INVESTMENT HORIZON Long-term investment horizon as a publicly-traded fund, GAIN has no fund life constraints. 2 BOARD PARTICIPATION GAIN participates on boards of its portfolio companies and regularly engages with management. 3 VALUE CREATION Streamlined post-close value creation, as GAIN is the primary third-party term debt & equity investor. 4 15 INVESTMENT STRATEGY & VALUE CREATION Risk Management and Value Creation
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EXPERIENCED GOVERNANCE STRUCTURE STRATEGIC PLANNING ADD-ON AND PLATFORM STRATEGIES SALES AND OPERATIONAL INITIATIVES GAIN helps to establish an effective board governance structure at the onset of each investment. • Enables GAIN to help influence company strategy • GAIN supports board members with relevant value-added industry expertise • GAIN works alongside the board of directors to replace and enhance management when needed At the outset of its investment, GAIN, along with company management, develop a strategic plan. • Builds buy-in with management on what we plan to do and when • Creates a framework for alignment and accountability at the Board level When appropriate, GAIN develops add-on and platform strategies to build value. • GAIN has executed three roll-up strategies as well as 10 add-on acquisitions since FY19 Proactive interaction with company management to drive long term value creation. • Leverage knowledge and experience from past deals to identify revenue and cost opportunities • Significant experience in professionalizing sales management, investing in personnel and equipment, and negotiating costs 16 Equity ownership allows GAIN to effect change with its investments. Value Creation Across the Portfolio INVESTMENT STRATEGY & VALUE CREATION
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17 CURRENT PORTFOLIO, SUCCESSFUL EXITS & MARKET UPDATE Quarterly Presentation
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MANUFACTURING BUSINESS/CONSUMER SERVICES CONSUMER PRODUCTS Portfolio is Broad and Diversified1 18 CURRENT PORTFOLIO, SUCCESSFUL EXITS & MARKET UPDATE 1 Portfolio companies as of 9/30/2025. Excludes Gladstone Alternative Income Fund.
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Geographic Diversification1 19 CURRENT PORTFOLIO, SUCCESSFUL EXITS & MARKET UPDATE 1 Portfolio companies as of 9/30/2025. Excludes Gladstone Alternative Income Fund.
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Deal Sourcing • GAIN primarily targets two sets of intermediaries to obtain deal flow: o Investment Banks and M&A Advisory Firms – generally through a bidding process that targets a likely set of buyers with experience or a “thesis” in the relevant industry/category. o Independent Sponsors – generally value add individuals that source proprietary transactions. Deal Flow • Over the last few quarters deal flow has gradually increased across most industries as sellers and buyers have adapted to the current macroeconomic environment. • Companies operating in fragmented industries with some level of perceived recession proof recurring/repeatable revenue continue to receive significant attention. Opportunities • GAIN expects the recent pickup in deal flow to result in more actionable new deal opportunities, including add-ons for our existing portfolio. • Although it is a competitive market and valuation expectations remain elevated, the current environment has been impacted by tariffs and economic uncertainty in the near term. • Given the recent market dislocation, investment bankers increasingly value speed and certainly to close, which aligns well with GAIN’s one- stop-shop capital solution providing both the debt and equity necessary to close a transaction. • Increasing importance, particularly from owner founders, to partner with investors that have the ability to be patient; traditional private- equity is increasingly targeting shorter hold periods and recent market dislocation limits investment timeline flexibility. 20 Buyout Market Update CURRENT PORTFOLIO, SUCCESSFUL EXITS & MARKET UPDATE Increased deal flow leading to more actionable opportunities
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21 FINANCIAL HIGHLIGHTS, SHAREHOLDER VALUE & CAPITAL STRUCTURE Quarterly Presentation
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• Continuous growth in overall NAV since FY 2011, driven by diligent growth and value creation in investment portfolio • Significant NAV per share growth to $13.53 at 9/30/2025 from $9.00 at 3/31/2011 22 Continuous NAV Growth Since FY 2011 FINANCIAL HIGHLIGHTS, SHAREHOLDER VALUE & CAPITAL STRUCTURE $- $200.0 $400.0 $600.0 $800.0 $1,000.0 $1,200.0 FY 2011 FY 2012 FY 2013 FY 2014 FY 2015 FY 2016 FY 2017 FY 2018 FY 2019 FY 2020 FY 2021 FY 2022 FY 2023 FY 2024 FY 2025 Q2 FY 2026 Investment Portfolio, at Fair Value Net Asset Value $MM
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$15.7 $19.6 $24.8 $30.5 $36.7 $46.4 $46.1 $48.8 $49.6 $49.6 $47.2 $59.6 $60.3 $81.8 $83.4 $44.0 $10.3 $1.7 $5.7 $5.8 $5.0 $4.6 $5.7 $9.6 $10.0 $12.4 $9.5 $12.9 $21.3 $5.5 $10.1 $4.5 $- $10.0 $20.0 $30.0 $40.0 $50.0 $60.0 $70.0 $80.0 $90.0 $100.0 FY 2011 FY 2012 FY 2013 FY 2014 FY 2015 FY 2016 FY 2017 FY 2018 FY 2019 FY 2020 FY 2021 FY 2022 FY 2023 FY 2024 FY 2025 Q2 FY 2026 Interest Income Dividend & Success Fee Income $26.1 $21.2 $30.5 $36.3 $41.6 $51.0 $51.9 $58.4 $59.7 $61.9 $56.6 $72.6 $81.5 $87.3 $93.4 0.0% 2.0% 4.0% 6.0% 8.0% 10.0% 12.0% 14.0% 16.0% $MM • Significant growth in Investment Income since FY 2011, driven by growth in investment portfolio, increased yields and other inco me. • Other income is comprised of dividends on preferred investments and success fees from our portfolio companies. 1 Annualized weighted-average yield on our interest-bearing investment portfolio. 23 Investment Income Growth Since FY 2011 FINANCIAL HIGHLIGHTS, SHAREHOLDER VALUE & CAPITAL STRUCTURE Weighted-Average Yield1 $48.5
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Successful Realizations Enhance Shareholder Value $ in ‘000s History of exits generating significant capital gains. GAIN’s target investment mix of 75% debt and 25% equity provides potential for high returns through consistent current yield and capital appreciation at exit. Since inception, total equity proceeds returned through successful exits of $565.0 million, inclusive of $424.4 million of ne t realized gains and dividends. 1 As of 9/30/2025. 2 Some capital may have been returned/restructured/written-off prior to ultimate exit. 3 Excludes line of credit commitments. 4 Includes all equity proceeds on exit (return of capital, realized gains, and dividends); does not include debt repayments or gains/losses on debt. 5 FY 2023 includes $3,735 and prior FY’s include $3,890 in equity returned prior to exit. 6 Includes all buyout exits from inception in 2005 through 3/31/2022 and other non-material buyout exits. INVESTED CAPITAL2 EQUITY RETURN AT EXIT EXITS IN FISCAL YEAR1 TOTAL DEBT3 EQUITY EQUITY PROCEEDS4 COC FY 2025 $ 117,419 $ 104,600 $ 12,819 $ 75,982 5.9x FY 2024 76,295 62,400 13,895 50,454 3.6x FY 2023 64,625 56,000 8,6255 10,378 2.1x Exits in prior FYs/others6 493,314 380,314 113,0005 428,172 3.5x TOTAL $ 751,653 $ 603,314 $ 148,339 $ 564,986 4.0x 24 FINANCIAL HIGHLIGHTS, SHAREHOLDER VALUE & CAPITAL STRUCTURE
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SIX MONTHS ENDED FISCAL YEAR ENDED SEPTEMBER 30, 2025 MARCH 31, 2025 MARCH 31, 2024 MARCH 31, 2023 MARCH 31, 2022 Net investment income (NII) $ 13,367 $ 28,095 $ 21,777 $ 37,000 $ 14,990 (+) Capital gains-based incentive fee 4,688 7,445 12,711 (296) 18,286 Adjusted NII2 $ 18,055 $ 35,540 $ 34,488 $ 36,704 $ 33,276 Realized (loss) gain $ (29,938) $ 63,184 $ 30,256 $ 10,753 $ 12,444 Unrealized appreciation (depreciation) $ 53,052 $ (25,960) $ 33,272 $ (12,206) $ 74,882 Weighted-average shares 37,681 36,735 34,467 33,312 33,205 Regular Monthly Distributions per share $ 0.48 $ 0.96 $ 0.96 $ 0.93 $ 0.87 Supplemental Distributions per share 0.54 0.70 1.24 0.48 0.30 Total Distributions per share $ 1.02 $ 1.66 $ 2.20 $ 1.41 $ 1.17 NII/NIL per weighted-average share $ 0.35 $ 0.76 $ 0.63 $ 1.11 $ 0.45 Adjusted NII per weighted-average share2 $ 0.48 $ 0.97 $ 1.00 $ 1.10 $ 1.00 Financial Highlights1 25 FINANCIAL HIGHLIGHTS, SHAREHOLDER VALUE & CAPITAL STRUCTURE 1 Dollar amounts in thousands, except per share amounts. The financial information above is not comprehensive and is without notes, so readers should obtain and carefully review the consolidated financial statements and notes contained therein of GAIN’s Form 10-Q and Form 10-K, as filed with the SEC for the respective periods. 2 Adjusted NII – Non-GAAP Financial Measure: Adjusted net investment income represents net investment income, excluding the capital gains-based incentive fee. The Company uses this non-GAAP financial measure internally in analyzing financial results and believes that this non-GAAP financial measure is useful to investors as an additional tool to evaluate ongoing results and trends for the Company. The Company’s investment advisory agreement provides that a capital gains-based incentive fee is determined and paid annually with respect to realized capital gains (but not unrealized capital gains) to the extent such realized capital gains exceed realized losses and unrealized depreciation on investments for such year. However, under U.S. GAAP, a capital gains-based incentive fee is accrued if realized capital gains and unrealized appreciation of investments exceed realized capital losses and unrealized depreciation of investments. The Company believes that Adjusted net investment income is a useful indicator of operations exclusive of any capital gains-based incentive fee as net investment income does not include realized or unrealized investment activity associated with the capital gains-based incentive fee.
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History of Driving High Shareholder Returns 1 Source: Capital IQ, latest available quarterly data as of 11/10/2025. BDC peer group defined as participants in MVIS US BDC Index as of 11/10/2025. ROE defined as LTM NII +/- real & unrealized gains/losses divided by average NAV. 26 FINANCIAL HIGHLIGHTS, SHAREHOLDER VALUE & CAPITAL STRUCTURE Long-term return on equity outperforming compared to industry peer group.1 19% 14% 16% 14% 9% 10% 12% 9%9% 10% 11% 8% 0% 2% 4% 6% 8% 10% 12% 14% 16% 18% 20% 1 Year 3 Years 5 Years 10 Years Return on Equity 9/30/2025 GAIN Mean BDC Median BDC
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50% 150% 250% 350% 450% 550% Sep-15 Sep-17 Sep-19 Sep-21 Sep-23 Sep-25 10-Year Total Return GAIN S&P BDC Index 40% 80% 120% 160% 200% 240% 280% 320% Sep-20 Mar-21 Sep-21 Mar-22 Sep-22 Mar-23 Sep-23 Mar-24 Sep-24 Mar-25 Sep-25 5-Year Total Return GAIN S&P BDC Index History of Driving High Shareholder Returns 1 Total return as of 9/30/2025 inclusive of reinvested dividends. BDC peer group defined as participants in the S&P BDC Index as of 11/10/2025. 27 FINANCIAL HIGHLIGHTS, SHAREHOLDER VALUE & CAPITAL STRUCTURE 5- AND 10-YEAR TOTAL RETURNS OF 168% AND 437% VS. BDC INDUSTRY PEERS OF 106% AND 148% 106% 168% 148% 437% Greater long-term total return compared to BDC peer group.1
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• GAIN maintains a conservative balance sheet with low leverage and available liquidity to support needs of the business. o Asset coverage ratio on senior securities representing indebtedness of 193.2% compared to the required 150%. o Focus on long-term fixed rate financing to match funding needs. • GAIN utilizes common stock offerings to tap into the equity market when prices are accretive. o Since IPO, raised an aggregate $123.5MM of gross proceeds from multiple post-IPO common stock offerings and $99.8MM of gross proceeds using various common stock At-the-Market (“ATM”) programs. o Current $75.0MM ATM program established in May 2024. We have raised aggregate gross proceeds of $41.7MM as of November 4, 2025, with all sales above then-current NAV per share. 28 Capital Structure: Conservative Approach FINANCIAL HIGHLIGHTS, SHAREHOLDER VALUE & CAPITAL STRUCTURE COMPONENTS OF TOTAL DEBT AS OF 9/30/2025 PUBLICLY TRADED NOTES1 • GAINN: $127.9MM of 5.00% 2026 Notes • GAINZ: $134.6MM of 4.875% 2028 Notes • GAINL: $74.8MM of 8.00% 2028 Notes2 • GAINI: $126.5MM of 7.875% 2030 Notes $270MM CREDIT FACILITY • 1-month SOFR + 3.15% spread + 0.10% SOFR adjustment • $172.3MM of availability at 9/30/2025 17% 23% 24% 13% 23% Credit Facility GAINN GAINZ GAINL GAINI 1 Subsequent to 9/30/2025, GAIN completed an offering of 6.875% Notes due 2028 with an aggregate principal amount of $60.0 million. 2 Subsequent to 9/30/2025, GAIN announced it will redeem 100%, or $74.8 million, of its outstanding 8.00% Notes due 2028 on 12/16/2025. In connection with this redemption, the 2028 Notes will be delisted from the Nasdaq.
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29 Continue to Execute on Strategy OUTLOOK Disciplined underwriting and continued portfolio performance allows GAIN to historically outperform peer group. EXECUTE ON BUYOUT STRATEGY • Expand portfolio through attractive investments • Drive portfolio company value creation through active ownership PROVIDE STRONG AND GROWING DISTRIBUTIONS • Maintain and grow regular distribution to shareholders • Continue making supplemental distributions, driven by realized gains on portfolio exits MAXIMIZE SHAREHOLDER VALUE • Focus on ROE and distributions to shareholders • Grow awareness of GAIN’s differentiated investment model
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30 Key Executive Officers Research Coverage Websites Independent Directors David Gladstone Chairman & CEO David Dullum President Taylor Ritchie CFO & Treasurer B. Riley Securities Sean-Paul Adams Clear Street Mickey M. Schleien Janney John Rowan Ladenburg Thalmann Christopher Nolan Lucid Capital Markets Erik Zwick Oppenheimer & Co. Mitchel Penn Gladstone Investment: www.gladstoneinvestment.com Investment Adviser: www.gladstonemanagement.com Information on all Gladstone Funds: www.gladstonecompanies.com www.gladstonedividend.com Michela A. English Katharine C. Gorka John Outland Anthony W. Parker Walter H. Wilkinson, Jr Investor Relations Other Nasdaq Listings Corporate Headquarters Catherine Gerkis Director of Investor Relations 703-287-5893 info@gladstonecompanies.com Corporate Counsel: Kirkland & Ellis LLP Transfer Agent: Computershare Auditors: PricewaterhouseCoopers LLP Common: GAIN 2026 5.00% Notes: GAINN 2028 4.875% Notes: GAINZ 2030 7.875% Notes: GAINI 1521 Westbranch Drive, Ste. 100 McLean, VA 22102 703-287-5800 Corporate Data