Exhibit 99.1

Great Elm Group, Inc. Reports FISCAL 2021 second quarter financial resulTs

Company to Host Quarterly Conference Call at 8:30 AM ET Today

WALTHAM, Mass., February 16, 2021 -- Great Elm Group, Inc. (“we,” “us,” “our,” “GEG,” or “Great Elm”) (NASDAQ: GEG), a diversified holding company, today announced financial results for its fiscal 2021 second quarter ended December 31, 2020.

Fiscal 2021 Second Quarter Highlights

(all comparisons versus the prior-year period unless otherwise noted)

Operating Companies:

Investment Management (“IM”):

Corporate Structure Reorganization and Strategic Financing Transaction

Management Commentary

"This was a significant quarter for Great Elm, in that we achieved our strategic goals of providing the DME and Investment Management businesses with the financial capacity to pursue their respective growth opportunities,” Peter A. Reed, Chief Executive Officer, stated. “The financing transaction with JPM is important for our DME business, as it immediately lowers DME’s cost of capital, in addition to creating greater leverage capacity at DME to pursue organic and M&A growth. DME was able to grow revenue during the quarter despite the continued negative impact of COVID-19 on its business. Profitability was depressed during the quarter primarily as a result of legacy revenue reserve issues as well as increased operating costs due to the pandemic. Our team remains focused on improving profitability and resuming a more active acquisition program. In our Investment Management business, we were successful in raising $31.7 million in a rights offering at GECC in October 2020. This business is now well capitalized to pursue attractive opportunities to grow its portfolio and our team is actively focused on such efforts.”

Alignment of Interest

A distinct attribute of Great Elm is the particularly strong alignment of interest shared among shareholders and the employees, its directors, and other insiders of Great Elm. As of December 31, 2020, employees and directors of Great Elm and Great Elm Capital Management, Inc. (“GECM”) collectively own or manage 7.1 million shares, or approximately 27% of Great Elm’s outstanding shares.

Discussion of Financial Results for the Quarter ended December 31, 2020

Great Elm has three operating segments: Durable Medical Equipment, Investment Management, Real Estate with general corporate representing unallocated costs and activity to arrive at consolidated operations.

Durable Medical Equipment

During the three months ended December 31, 2020, Great Elm’s DME operations recognized $14.5 million in total revenue, compared to $14.4 million during the same period last year. While revenue was higher by $1.1 million year-over-year, this increase was offset by higher revenue reserves of $1.0 million during the quarter. The increase in revenue was driven primarily by organic growth in CPAP resupply sales year-over-year, offset by lower sleep studies revenue and lower rental revenues for new equipment set-ups. The demand for sleep studies continues to be softened by the ongoing COVID-19 pandemic, and referrals for new equipment set-ups have declined as they are generally driven by in-house or external sleep studies.

Great Elm’s DME operations reported net loss of $2.9 million for the fiscal 2021 second quarter compared to net loss of $0.7 million in the prior-year period. Adjusted EBITDA, a non-GAAP measure, was $1.9 million in the fiscal 2021 second quarter, compared to $3.5 million in the prior-year period. Adjusted EBITDA was lower due primarily to the higher revenue reserves of $1.0 million discussed above, $0.3 million from the reallocation of GEG corporate personnel to DME and $0.2 million increase in operating expenses related to COVID-19. Additionally, operating expenses were higher compared to the year ago period due to additional expenses incurred to enhance the platform and scalability of the business, and also a reduction in sleep study services, which tend to generate higher margin as compared to equipment sales.

-2-

Investment Management

During the three months ended December 31, 2020, Great Elm’s Investment Management business recognized total investment management revenue of $0.8 million, compared to $0.9 million during the same period in the prior year. Revenue was slightly lower due to reduced assets under management in our managed portfolios as compared to pre-pandemic levels.

Great Elm recognized a net loss of $0.3 million compared to net income of $5 thousand during the same period in the prior year. Adjusted EBITDA was $41 thousand in the fiscal 2021 second quarter, compared to $0.3 million during the same period in the prior year. Adjusted EBITDA was impacted by additional staffing costs as this segment intends to continue to focus on attractive acquisition opportunities, particularly in the specialty finance sector which has generated results that have exceeded internal expectations.

Real Estate

During the three months ended December 31, 2020, Great Elm’s real estate business recognized $1.3 million in rental revenue, $71 thousand in net income and Adjusted EBITDA of $1.1 million. During the same period last year, Great Elm recognized $1.3 million in rental revenue, $60 thousand in net income and Adjusted EBITDA of $1.1 million.

Our revenues, costs and expenses have generally remained consistent year over year, as real estate rental revenue consists of rents received from the two Class A office buildings in Fort Meyers, Florida. Great Elm continues to manage the Fort Myers investment to monetize significant net operating loss carryforwards.

General Corporate

During the three months ended December 31, 2020, Great Elm recognized $45 thousand in revenue compared to $57 thousand in revenue during the same period in the prior year. Revenue increased slightly as a result of increased management fees earned from DME.

Great Elm recognized $2.2 million in net income vs. net loss of $1.4 million during the same period in the prior year.  The increase in net income was driven primarily by net unrealized gains on Great Elm’s investment in GECC and higher dividend income due to a larger investment in GECC following stock distributions received and our participation in the GECC rights offering in October 2020. Great Elm recognized $(0.9) million in Adjusted EBITDA compared to Adjusted EBITDA of $(1.6) million during the prior year period. Great Elm made significant progress on reducing its corporate overhead, driven largely by a reduction in audit cost and the reallocation of certain personnel expenses to DME.  Great Elm intends to continue to focus on reducing its corporate overhead.

-3-

Fiscal 2021 Second Quarter Conference Call & Webcast Information

When:Tuesday, February 16, 2021, 8:30 a.m. Eastern Time (ET)

About Great Elm Group, Inc.

Great Elm Group, Inc. (NASDAQ: GEG) is a publicly-traded holding company that is building a business across two operating verticals: investment management and operating companies. Great Elm Group, Inc.’s website can be found at www.greatelmgroup.com.

Safe Harbor Statement under the Private Securities Litigation Reform Act of 1995

Statements in this press release that are “forward-looking” statements, including statements regarding revenue, Adjusted EBITDA, expected growth, profitability, acquisition opportunities and outlook involve risks and uncertainties that may individually or collectively impact the matters described herein. Investors are cautioned not to place undue reliance on any such forward-looking statements, which speak only as of the date they are made and represent Great Elm’s assumptions and expectations in light of currently available information.  These statements involve risks, variables and uncertainties, and Great Elm’s actual performance results may differ from those projected, and any such differences may be material. For information on certain factors that could cause actual events or results to differ materially from Great Elm’s expectations, please see Great Elm’s filings with the SEC, including its most recent annual report on Form 10-K and subsequent reports on Forms 10-Q and 8-K. Additional information relating to Great Elm’s financial position and results of operations is also contained in Great Elm’s annual and quarterly reports filed with the SEC and available for download at its website www.greatelmgroup.com or at the SEC website www.sec.gov.

Non-GAAP Financial Measures

The SEC has adopted rules to regulate the use in filings with the SEC, and in public disclosures, of financial measures that are not in accordance with US GAAP, such as adjusted earnings before interest, taxes, depreciation and amortization (“Adjusted EBITDA”). Adjusted EBITDA is derived from methodologies other than in accordance with US GAAP. Great Elm believes that Adjusted EBITDA is an important measure for investors to use in evaluating Great Elm’s businesses. In addition, Great Elm’s management reviews Adjusted EBITDA as they evaluate acquisition opportunities.

-4-

Adjusted EBITDA has limitations as an analytical tool, and you should not consider it either in isolation from, or as a substitute for, analyzing Great Elm’s results as reported under US GAAP. Non-GAAP financial measures reported by Great Elm may not be comparable to similarly titled amounts reported by other companies.

Set forth below is a reconciliation of Adjusted EBITDA to the most directly comparable US GAAP financial measure, net income.

Media & Investor Contact:

Investor Relations

+1 (617) 375-3006

[email protected]

Jeehae Linford

The Equity Group Inc.

+1 (212) 836-9615

[email protected]

-5-

Great Elm Group, Inc.

Condensed Consolidated Balance Sheets (Unaudited)

Dollar amounts in thousands (except per share data)

-6-

-7-

Great Elm Group, Inc.

Condensed Consolidated Statements of Operations (Unaudited)

Dollar amounts in thousands (except per share data)

-8-

-9-

-10-

Great Elm Group, Inc. Conference Call Presentation Fiscal Second Quarter Ended December 31, 2020 February 16, 2021 NASDAQ: GEG Exhibit 99.2

Disclaimer 2 Statements in this press release that are “forward-looking” statements, including statements regarding expected growth, profitability, acquisition opportunities and outlook involve risks and uncertainties that may individually or collectively impact the matters described herein. Investors are cautioned not to place undue reliance on any such forward-looking statements, which speak only as of the date they are made and represent Great Elm’s assumptions and expectations in light of currently available information. These statements involve risks, variables and uncertainties, and Great Elm’s actual performance results may differ from those projected, and any such differences may be material. Among the key factors that could cause actual results to differ materially from those projected in the forward-looking statements are risks associated with the economic impact of the COVID-19 pandemic on Great Elm’s businesses, including DME as well as GECC and its portfolio investments. For information on certain factors that could cause actual events or results to differ materially from Great Elm’s expectations, please see Great Elm’s filings with the SEC, including its most recent annual report on Form 10-K and subsequent reports on Forms 10-Q and 8-K. Additional information relating to Great Elm’s financial position and results of operations is also contained in Great Elm’s annual and quarterly reports filed with the SEC and available for download at its website www.greatelmgroup.com or at the SEC website www.sec.gov. Non-GAAP Financial Measures The SEC has adopted rules to regulate the use in filings with the SEC, and in public disclosures, of financial measures that are not in accordance with US GAAP, such as adjusted earnings before interest, taxes, depreciation and amortization (“Adjusted EBITDA”) and free cash flow. See the Appendix for important information regarding the use of non-GAAP financial measures and reconciliations of non-GAAP measures to their most directly comparable GAAP measures. This presentation does not constitute an offer of any securities for sale.

Corporate Reorganization and Financing Transaction Overview On December 29, 2020, we completed a reorganization of our corporate structure and executed a financing transaction with J.P. Morgan Broker-Dealer Holdings (“JPM”), wherein JPM invested a total of $37.7 million Great Elm Capital Group, Inc. (“GEC”) changed its name to Forest Investments, Inc. (“Forest”) and became a subsidiary of a new parent holding company, Great Elm Group, Inc. (“Great Elm” or “GEG”) Common shares of GEC automatically converted into common shares of Great Elm Group, and began trading on NASDAQ under a new ticker “GEG”; GEC stock was delisted and deregistered JPM Financing Details JPM purchased Preferred Shares and common equity of Forest Forest issued to JPM $35 million of 9.0% Preferred Shares maturing 2027 JPM also purchased 20% of the common equity of Forest for $2.7 million Proceeds were used to refinance DME’s existing term loan of approximately $24.8 million and provide growth capital; DME also distributed approximately $2.3 million to GEG inclusive of fees and expenses Distributions and Ownership Forest distributed to GEG its common ownership of the DME business, its ownership of the Investment Management business, its GECC shares and its cash, and retained ownership of the Real Estate business and a preferred interest in the DME business Forest also retained its U.S. Federal NOLs, which were unaffected and remain usable across the Great Elm platform 3

Organization: Structure 4 Great Elm Group, Inc. (“Great Elm” or “GEG”) (NASDAQ: GEG) Great Elm Capital Management, Inc. (“GECM”) Investment advisor to GECC Great Elm Capital Corp (“GECC”) (NASDAQ: GECC) Publicly traded BDC Great Elm Durable Medical Equipment (“DME”) Business Forest Investments, Inc. (“Forest”) fka Great Elm Capital Group, Inc. (formerly NASDAQ: GEC) Real Estate Business 80% Holds ~23.6% shares 100% 80.1% 80.1% Former owners 19.9% Former owners 19.9% JPM 20% Note: Chart is designed to be illustrative following the JPM financing transaction and does not include all entities comprising Great Elm Group, Inc’s corporate structure.

Our Business Operating Segments Operating Companies Investment Management Real Estate Office property located in Fort Myers, FL Fully leased, triple-net basis through March 2030 Limited equity capital deployed, and building equity value over time with no additional capital necessary Monetizes significant NOLs Great Elm Capital Management, Inc. (“GECM”) SEC Registered Investment Advisor Investment Advisor to Great Elm Capital Corp. (Nasdaq: GECC), a publicly-traded business development company Three IMAs with a leading institutional investor Manager of the Great Elm Opportunities Fund, a fund structured for a series of co-investment opportunities Manager of future funds, co-investments and separately managed accounts Great Elm Durable Medical Equipment (“DME”) Business Distributor of respiratory care equipment (CPAP, ventilators, oxygen) and sleep study services Services a large and growing segment of the population who suffer from sleep disorders Aging population, rising obesity rates and the prevalence of smoking are causative factors Operates in AK, AZ, KS, IA, NE, OR, WA 337 employees

Driving Shareholder Value 6 Business Segment Strategy Operating Companies Investment Management Real Estate Target undercapitalized small and mid-sized companies where we can partner with management to accelerate earnings and cash flow growth Focus on growing Great Elm DME, Inc. both organically and via an expansion strategy that targets existing and adjacent markets Focus on driving asset growth in GECC Increase AUM via new fund launches, SMAs and co-investments and leverage the existing team and infrastructure to generate incremental free cash flow Seek to enhance the value of our existing Fort Myers property through property improvement and lease modification Seek other opportunities like the Fort Myers transaction that utilize modest equity capital and monetize significant NOLs

Strong Shareholder Alignment 7 Employee Share Ownership Significant Alignment of Interest Director Share Ownership Employees of GEG/Great Elm Capital Management, Inc. (“GECM”) collectively own approximately 1.9 million shares of GEG, representing approximately 7% of GEG’s outstanding shares1 The directors of GEG beneficially own approximately 5.2 million shares of GEG in the aggregate, representing approximately 20% of GEG’s outstanding shares When combined, insider ownership totals approximately 27% of the outstanding shares We believe this level of insider ownership results in a significant and long-term alignment of interest between the shareholders and the insiders of GEG (1) This includes restricted shares that are subject to both performance and service vesting and is based on the share count pro forma for the vesting of said restricted shares. Strong Shareholder Alignment Employee Share Ownership Significant Alignment of Interest Employees of GEG/Great Elm Capital Management, Inc. (“GECM”) collectively own approximately 1.9 million shares of GEG, representing approximately 7% of GEG’s outstanding shares1 The directors of GEG beneficially own approximately 5.2 million shares of GEG in the aggregate, representing approximately 20% of GEG’s outstanding shares When combined, insider ownership totals approximately 27% of the outstanding shares We believe this level of insider ownership results in a significant and long-term alignment of interest between the shareholders and the insiders of GEG

8 Consolidated Summary Financials: Q2 FY 2021 (1) Prior year non-GAAP adjustments have been updated to conform to current year presentation by removing adjustments associated with the adoption of ASC 606 Contracts with Customers. (2) Please refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix.

In fiscal 2Q21, Great Elm DME, Inc. (“DME”) generated $14.5 million of revenue, $2.9 million of net loss and $1.9 million of adjusted EBITDA1 The PAP supplies category continued to experience robust growth, with softness in sleep studies revenue and PAP rental Operating expenses increased year-over-year due to the reallocation of compensation from Great Elm Group due to greater resources required at DME and increased costs attributable to cope with the effects of COVID-19 COVID-19 continued to negatively impact physician referrals and new order volumes in most segments New PAP patient setups declined 17.0% year over year, but improved 5.2% from previous quarter Referrals for sleep studies remain down 15% year over year, but showing signs of stabilization JPM Financing Transaction Proceeds from the JPM financing were used to repay the $24.8 million term loan, immediately lowering our cost of capital We have the ability to incur senior debt to fund acquisition opportunities Acquisitions Having completed significant investments into the platform, DME management is fully focused on executing on additional acquisition opportunities. (1) Please refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix Operating Companies: Stable results at DME and recapitalization 9

Operating Companies: DME Segment Financial Detail (1) Please also refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 10

11 Investment Management: A Scalable, High Margin Business AUM Growth High Margins Scalable Model Free Cash Flow AUM GROWTH Grow GECC’s AUM through the issuance of additional debt and equity, supplemented by accretive acquisitions of other BDCs, resulting in an increase in fee revenue Grow the Investment Management business by leveraging the existing team to launch additional vehicles HIGH MARGINS Given the largely fixed cost nature of the Investment Management business, we expect adjusted EBITDA margins to increase as our AUM increases and the business scales SCALABLE MODEL Investment team and infrastructure in place to support growth in AUM and new investment vehicles FREE CASH FLOW Growth in AUM in the Investment Management business coupled with its high margins and scalable business model could result in operating leverage and, thus, the potential for growth in adjusted EBITDA and free cash flow

Investment Management: A Focus on Opportunity In fiscal 2Q21, Investment Management generated $0.8 million of revenue, $0.3 million of net loss and $41 thousand of adjusted EBITDA1 Revenue and profitability were stable We are seeking to capitalize upon our successful investments in the specialty finance sector GECC’s investment in Prestige Capital has exceeded internal expectations GECC has an attractive pipeline of potential investments in the specialty finance sector On October 1, 2020, GECC closed a successful non-transferable rights offering in order to capitalize upon this attractive pipeline, raising $31.7 million in gross proceeds This was an important step in our plan to increase AUM at GECM Increasing GECM’s AUM should increase our revenue, earnings and cash flow We created a new fund to invest in SPAC transactions We believe this asset class has the potential to deliver attractive risk-adjusted and highly asymmetric returns given their cash-in-trust structure coupled with our prudent investing and underwriting process Invested $3 million into new fund as of the current quarter, with an additional $5 million invested subsequent to quarter end (1) Please refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 12

Investment Management: Segment Financial Detail (1) Please also refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 13

14 Real Estate: Overview Limited Equity Capital Deployed High Level of Non-Recourse Leverage Monetization of Significant NOLs Generates stable, consistent cash flows Our current Real Estate investment is attractive for the following reasons:

Real Estate: Fort Myers – Organic Equity Growth Assuming a constant property value of $61.2 million, GEG’s equity value grows as cash flows from the rental stream are utilized to amortize debt over the lease term GEG builds significant equity value1 over time without any additional capital deployment (1) Equity value is equal to the property value at acquisition minus the face value of the debt on a given date. 15

Real Estate: Segment Financial Detail (1) Please also refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 16

General Corporate: Segment Financial Detail (1) Please also refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 17

Financial Review: 2Q21 Consolidating Balance Sheets (Unaudited) 18 (1) Intercompany balances, including intercompany borrowings and GEG investments in subsidiaries. All intercompany balances eliminate in consolidation.

Financial Review: 2Q21 Consolidating Income Statement (Unaudited) (1) Please refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 19

Appendix 20

Appendix: Non-GAAP Reconciliation 21 (1) Prior year non-GAAP adjustments have been updated to conform to current year presentation by removing adjustments associated with the adoption of ASC 606 Contracts with Customers. (2) Transaction and integration related costs include costs to acquire and integrate acquired businesses. This also represents change in contingent consideration liability since the initial valuation at the acquisition date.

Appendix: Non-GAAP Reconciliation (Continued) 22 (1) Prior year non-GAAP adjustments have been updated to conform to current year presentation by removing adjustments associated with the adoption of ASC 606 Contracts with Customers. (2) Transaction and integration related costs include costs to acquire and integrate acquired businesses. This also represents change in contingent consideration liability since the initial valuation at the acquisition date.

23 Appendix: Non-GAAP Reconciliation (Continued) (1) Prior year non-GAAP adjustments have been updated to conform to current year presentation by removing adjustments associated with the adoption of ASC 606 Contracts with Customers. (2) Transaction and integration related costs include costs to acquire and integrate acquired businesses. This also represents change in contingent consideration liability since the initial valuation at the acquisition date.

24 Appendix: Non-GAAP Reconciliation (Continued) (1) Prior year non-GAAP adjustments have been updated to conform to current year presentation by removing adjustments associated with the adoption of ASC 606 Contracts with Customers. (2) Transaction and integration related costs include costs to acquire and integrate acquired businesses. This also represents change in contingent consideration liability since the initial valuation at the acquisition date.

Appendix: Contact Information Investor Relations 800 South Street, Suite 230 Waltham, MA 02453 Phone: +1 (617) 375-3006 [email protected] Jeehae Linford The Equity Group Inc. +1 (212) 836-9615 [email protected] 25