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Gladstone Alternative Income Fund

1301 Pennsylvania Avenue, N.W.

Washington, D.C. 20004

Erin M. Lett

United States

To Call Writer Directly:

Facsimile:

+1 202 389 3353

+1 202 389 5000

+1 202 389 5200

erin.lett@kirkland.com

www.kirkland.com

August 28, 2024

 By EDGAR

 United States
Securities and Exchange Commission

 Division of Investment Management

100 F Street, N.E.

 Washington, D.C. 20549

Attn: Aaron Brodsky

Re:
 Gladstone Alternative Income Fund

 
 Registration Statement on Form N-2

 
 File Nos. 333-280771 and
811-23983

 Dear Ladies and Gentlemen:

On behalf of Gladstone Alternative Income Fund, a Delaware statutory trust (the “Fund”), we hereby respond to the comments raised by the staff
(the “Staff”) of the Securities and Exchange Commission (the “Commission”) regarding the Fund’s Registration Statement on Form N-2, filed on July 12, 2024 (the
“Registration Statement”), in a letter dated August 9, 2024 from Aaron Brodsky of the Staff and to William J. Tuttle of Kirkland & Ellis LLP, outside counsel to the Fund. For your convenience, the Staff’s comments
are included in this letter, with each comment followed by the Fund’s response. Except as provided in this letter, terms used in this letter have the meanings given to them in the Registration Statement. Concurrently herewith, the Fund is
filing Pre-Effective Amendment No.1 (the “Amendment”) to the Registration Statement which responds to certain of the Staff’s comments.

PROSPECTUS

 Cover Page

1.
 Under the “Investment Risks” heading on the cover page, please also disclose the following risks
in bold:

(a)
 The Fund’s shares will not be listed on an exchange and it is not anticipated that a secondary market
will develop. Thus, an investment in the Fund may not be suitable for investors who may need the money they invest in a specified timeframe.

Austin Bay Area Beijing Boston Brussels Chicago Dallas Hong Kong Houston London Los
Angeles Miami Munich New York Paris Riyadh Salt Lake City Shanghai

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(b)
 An investor in Class A Shares, if offered, will pay a sales load of up to [_]% and offering expenses of
up to [_]% on the amounts it invests. If you pay the maximum aggregate [__]% for sales load and offering expenses, you must experience a total return on your net investment of [__]% in order to recover these expenses.

Response: The Fund respectfully notes that the requested disclosure in Comment 1(a) is covered by the existing risk disclosure on the cover page of the
Registration Statement. The Fund has revised the cover in the Amendment consistent with Comment 1(b).

2.
 Please remove the discussion in footnote 5 of the offering table regarding the Expense Support and
Conditional Reimbursement Agreement given that it may impede investor understanding of the proceeds to the Fund. See Item 1.

Response: The Fund has revised its disclosure in the Amendment consistent with this comment.

Prospectus Summary

3.
 Please consider deleting duplicative disclosure on page 1 from either the discussion under the “The
Fund” or “The Offering” regarding the potential offering of additional share classes.

 Response: The Fund has
revised its disclosure in the Amendment consistent with this comment.

4.
 In the third paragraph under the “The Offering” subheading on page 1, please delete the following
language and conform to the requirements under rule 23c-3: “We reserve the right to reject a purchase order for any reason.”

Response: The Fund respectfully submits that the referenced disclosure is regarding the purchase of Shares by investors, not with respect to the
Fund’s repurchase of Shares from investors whether pursuant to Rule 23c-3 or otherwise. The Fund has revised its disclosure in the Amendment to clarify this point.

5.
 Please supplementally explain if the Fund will invest through any entity which it primarily controls, and
which entity primarily engages in investment activities in securities or other assets. We may have further comments.

Response: The Fund does not currently intend to invest through any entity which it primarily controls and which primarily engages in investment
activities in securities or other assets, other than wholly owned subsidiaries.

 Summary of Fund Expenses

6.
 In footnote 6 on page 11, please clarify that “other expenses” are based on estimated amounts for
the current fiscal year.

 Response: The Fund has revised its disclosure in the Amendment consistent with this comment.

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7.
 Please discuss in your response letter the Fund’s method for accounting for organizational and offering
costs. Please include appropriate U.S. GAAP citations that support the accounting treatment.

 Response: The
Fund’s method for accounting for organizational and offering costs is consistent with FASB ASC 720-15-25-1, FASB ASC 946-20-25-6 and
946-20-35-5. Organizational costs consist of costs incurred to establish the Fund and enable it legally to do business,
and such costs are expensed as incurred. Offering costs include registration fees, legal fees regarding the preparation of the Registration Statement and initial registration statement and auditing the initial seed capital statement of assets
and liabilities. Offering costs are accounted for as deferred costs until operations begin and thereafter will be amortized to expense over 12 months on a straight-line basis.

In addition, as Fund will be reimbursed by the Adviser as set forth in the Expense Support and Conditional Reimbursement Agreement, any reimbursement received
by the Fund will be reflected on the statement of operations as a separate line item and netted with the Fund’s total expenses. Because the Adviser has the ability to recoup any of the amounts that are waived and/or reimbursed to the Fund
(subject to the terms of the e Expense Support and Conditional Reimbursement Agreement), and because the amounts do not meet the criteria to record a liability in accordance with ASC 946-20-25-4, the notes to the financial statements will include
disclosure detailing the expiration of the recoupment period and the corresponding amount that the Fund may have to reimburse to the Adviser.

8.
 Please remove the contents of footnote 7 on page 11 from the fee table footnote, and instead include the
discussion later in the filing where the Expense Support and Conditional Reimbursement Agreement is discussed in detail. There, please also disclose:

(a)
 the period for which the expense reimbursement arrangement is expected to continue, including the expected
termination date;

(b)
 that the expense reimbursement agreement can only be terminated by the board, and under what circumstances;

(c)
 that recoupment is limited to 3 years from the date such amount was initially reimbursed; and

(d)
 that the Fund may only make repayments to Gladstone Management Corporation, the adviser
(“Adviser”) if such repayment does not cause the Fund’s expense ratio (after the repayment is taken into account) to exceed both: (1) the expense cap in place at the time such amounts were waived; and (2) the Fund’s
current expense cap (if any).

 Response: The Fund acknowledges the Staff’s comment and respectfully notes that the
information requested by Comments 8(a) and (b) is disclosed in the Registration Statement under “Management of the Fund—Expense Support and Conditional Reimbursement Agreement”. With respect to Comments 8(c) and (d) above,
the Fund has revised its disclosure in the Amendment consistent with this comment.

 The Fund has retained the footnote to the fee table information, as
the Fund thinks it is useful to investors to know whether any waivers or reimbursements are reflected in the table.

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 Use of Proceeds

9.
 Disclosure in the second sentence under the “Use of Proceeds” heading indicates that the Fund
anticipates that it will invest net proceeds within six months. Please disclose the reasons why it is expected to take up to six months to invest proceeds in accordance with the Fund’s objective and strategies.

Response: The Fund has revised its disclosure in the Amendment consistent with this comment.

Investment Objectives, Strategies, and Principal Risks; Investment Strategies

10.
 Disclosure on page 13 under the “Direct Lending” subheading references “sustainability of the
business’ free cash flow.” Please briefly clarify how this sustainability is measured and/or evaluated.

 Response:
The Fund has revised its disclosure in the Amendment consistent with this comment.

11.
 Disclosure on page 13 under the “Broadly Syndicated Loans” subheading states that broadly
syndicated loans are typically “relatively liquid and readily tradable.” Please briefly clarify how this is measured and/or assessed.

Response: The Fund has revised its disclosure in the Amendment consistent with this comment.

12.
 Please supplementally explain if the Fund will invest more than 15% of its assets in hedge funds and private
equity issuers that rely on 3(c)(1) and 3(c)(7) of the 1940 Act. We may have further comments.

 Response: The Fund
supplementally confirms to the Staff that it will not invest more than 15% of its assets in hedge funds and private equity issuers that rely on 3(c)(1) and 3(c)(7) of the 1940 Act.

Investment Process; Prospective Portfolio Company Characteristics

13.
 Disclosure under the “Strong Competitive Position in an Industry” subheading on page 15 states
that the Fund will invest in companies with “strong market positions” that are “well-positioned to capitalize on growth opportunities.” Please disclose how the Fund is defining “strong market positions” and
“well-positioned to capitalize on growth opportunities.”

 Response: The Fund has revised its disclosure in the
Amendment consistent with this comment.

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14.
 Under the “Properties Important to Tenant Operations” subheading on page 16, please provide an
example and/or clarify what it means for a property to be “essential or important to the ongoing operations of the tenant or prospective tenant.”

Response: The Fund has revised its disclosure in the Amendment consistent with this comment.

Investment Process; Investment Structure

15.
 Under the second bullet point under the “Investment Structure” subheading on page 17, disclosure
states that the Adviser will seek to limit downside risk, including by “seeking collateral or superior positions in the portfolio company’s capital structure…” Please clarify what the Fund means by “superior positions”
in this context.

 Response: The Fund has revised its disclosure in the Amendment by substituting “senior” for
“superior”.

 Ongoing Management of Investments and Portfolio Company Relationships

16.
 Disclosure on page 17 states that the Adviser will typically work collaboratively with the portfolio
company’s management to identify and incorporate best resources and practices that help the Fund achieve its projected investment performance. Please reconcile this statement with disclosure on page 29, which states that the Fund generally will
not be involved in the day-to-day operations and decision making of portfolio companies, and will remain subject to the risk that a portfolio company may make business
decisions with which the Fund disagrees.

 Response: The Fund has revised its disclosure in the Amendment to remove any
inconsistency between the two sections.

 Principal Risks of the Fund

17.
 The Fund’s fundamental policy states that the Fund will not invest more than 25% of its total assets in
the securities of issuers in any particular industry. However, disclosure in the second-to-last paragraph on page 32 states that the portfolio is expected to be
concentrated in a limited number of companies and industries, that the Fund does “not have fixed guidelines for industry concentration,” and that the Fund’s investments “could potentially be concentrated in relatively few
industries.” Please reconcile and revise accordingly.

 Response: The Fund respectfully submits that it is not the
Fund’s intention or strategy to focus on any specific industry. However, the Fund’s investment strategy includes direct lending as a principal strategy, and direct lending requires significant time and resources to diligence and negotiate
each investment. As a result, the Fund expects that its portfolio may contain fewer investments (and thus investments in fewer industries) than a comparably sized fund that exclusively invests in broadly-syndicated loans or other investments
purchased on the secondary market, as such investments are less time and resource demanding and such a fund can efficiently make more investments of a smaller size. As a general matter, the Fund does not intend to invest more than 25% of its total
asset in securities of issuers in any particular industry. To avoid confusion, the Fund has revised its disclosure throughout the Amendment to avoid using the word “concentrated” when describing the Fund’s expected portfolio.

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18.
 Disclosure in the last paragraph on page 32 states that the Fund will not employ an industry or sector
focus. Please reconcile this with the disclosure in the previous paragraph that the Fund is expected to be concentrated in a limited number of companies and industries.

Response: As noted in response to Comment #17, it is not the Fund’s intention or strategy to focus on any specific industry or sector. However,
the Fund’s investment strategy includes direct lending as a principal strategy, and direct lending requires significant time and resources to diligence and negotiate each investment. As a result, the Fund expects that its portfolio may contain
fewer investments than a comparably sized fund that exclusively invests in broadly-syndicated loans or other investments purchased on the secondary market, as such investments are less time and resource demanding and a fund can efficiently make more
investments of a smaller size. Given the above, the Fund believes its existing disclosure to be accurate and provides investors with the information necessary to assess the Fund’s strategy and risks.

19.
 If the Fund intends to incur debt to finance a share repurchase, please disclose the maximum amount of debt
that may be incurred for that purpose, the restrictions imposed by the Investment Company Act and by rule 23c-3 on leverage, the attendant risks of leveraging, and the extent to which the financing costs of
borrowing may be borne by shareholders who do not tender.

 Response: The Fund supplementally informs that Staff that it does
not currently intend to incur debt to finance share repurchases.

20.
 Disclosure on page 35 under the “We are subject to risks related to corporate social
responsibility” subheading states that “The SEC has adopted rules that require additional disclosures about ESG investment practices by investment advisers and certain funds.” Please delete this language, or explain which rules the
language is referencing.

 Response: The Fund has revised the language in the Amendment to clarify that only the rules
relating to climate risk disclosures have been adopted to date, but that other ESG related rules have been proposed and such or similar rules may be adopted in the future.

Management of the Fund

21.
 Given that the Fund may invest in foreign securities, please provide a basis to assess the expertise and
experience of the Adviser with respect to foreign investments.

 Response: The Fund respectfully notes, as disclosed in the
Registration Statement, that the “direct lending” portion of the Fund’s investment strategy will focus on investments in U.S. businesses. However, the Fund has retained flexibility