Gladstone Investment : Investor Day Presentation September 20, 2023

GLADSTONE INVESTMENT

Investor Day Presentation

September 20, 2023

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, rising interest rates and risks of recessions; (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, David Dullum, or Terry Lee Brubaker; (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, regulation, 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.

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Investor Day Presentation Agenda

1. Who We Are - Overview and Objectives

1. Portfolio & Investment Strategy

1. Financial Highlights, Shareholder Value & Capital Structure IV. Outlook

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Investor Day Presentation

I. Who We Are - Overview and Objectives

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Gladstone Investment | Who We Are (1)

The Gladstone Companies were founded in 2001 and are comprised of two publicly traded BDCs and two publicly traded REITs.

Gladstone Capital	Gladstone Investment
2001	2005
Gladstone Commercial	Gladstone Land
2003	2013

Significant capital raised and deployed

• Nasdaq symbol "GAIN" | market cap of $438 million
• • $1.6+ billion invested since 2005 IPO
  • $847 million in total assets at fair value
• 2026 Notes listed on Nasdaq under the symbol "GAINN," with an interest rate of 5.00%
• 2028 Notes listed on Nasdaq under the symbol "GAINZ," with an interest rate of 4.875%
• 2028 Notes listed on Nasdaq under the symbol "GAINL," with an interest rate of 8.00%

Experienced management team with proven track record

• Externally managed by an SEC-registered investment adviser, Gladstone Management Corporation, and administrator with over 70 professionals
• Nine investment professionals, and a CFO and Controller dedicated exclusively to Gladstone Investment Corporation
• Proven investment track record across multiple economic cycles

(1) All information in this presentation is as of 6/30/2023, except as noted.

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