Exihibit 99.1

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

Company to Host Conference Call at 4:30 PM ET Today

WALTHAM, Mass., May 14, 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 third quarter ended March 31, 2021.

Fiscal 2021 Third Quarter Highlights

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

Consolidated:

Operating Companies:

Investment Management (“IM”):

Management Commentary

"Overall, we see positive momentum in all aspects of our business,” stated Peter A. Reed, Chief Executive Officer. “During the quarter, DME resumed its acquisition program and announced the AMPM acquisition, which strengthens DME’s presence in the Midwest and provides future organic growth potential through an expanded patient base and cross selling opportunities. We also anticipate the acquisition will drive margin improvement through operational efficiencies and other benefits of added scale. DME is beginning

to see signs of business recovery from the pandemic impacts as the country continues moving toward a full economic reopening. We are optimistic about the resumption of organic growth at DME and also the potential for future acquisitions.”

“Investment Management had a productive quarter in positioning GECC for further growth, and activity picked up mid-quarter with momentum accelerating through to quarter-end. We were pleased to simplify our balance sheet and corporate structure through previously announced transactions at one of our investment management subsidiaries, GECC GP Corp., resulting in a greater share of investment management profits for GEG. We anticipate further simplifying our balance sheet and corporate structure in the future. We are optimistic IM’s financial results will continue to improve and we see a robust pipeline of opportunities at GECC, particularly in the specialty finance sector. To that end, GECC recently entered into a $25 million revolving credit facility that will enhance its ability to participate in such opportunities.”

Alignment of Interest

A distinct attribute of Great Elm is the particularly strong alignment of interest shared among shareholders and the employees, directors, and other insiders of Great Elm. As of March 31, 2021, employees and directors (including funds under their management) of Great Elm collectively own or manage 7.4 million shares, or approximately 28%, of Great Elm’s outstanding shares.

Discussion of Financial Results for the Quarter ended March 31, 2021

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

Durable Medical Equipment

During the three months ended March 31, 2021, Great Elm’s DME operations recognized $13.1 million in total revenue, compared to $14.1 million during the same period last year. The decrease in revenues was due to the continued suppressed referral pipeline for new equipment set-ups and increased revenue reserve constraints, partially offset by organic growth in resupply sales and one month of contributions from the AMPM acquisition. The demand for sleep studies continues to be soft due to the ongoing impact from the COVID-19 pandemic, and referrals for new equipment set-ups declined as they are generally driven by in-house or external sleep studies.

Great Elm’s DME operations reported net loss of $5.1 million for the fiscal 2021 third quarter compared to net loss of $1.4 million in the prior-year period. Net loss was primarily impacted by a $4.8 million charge related to a fair value adjustment recorded in connection with the preferred stock issued to a subsidiary (Forest Investments, Inc.), with an offsetting impact to General Corporate and eliminated in consolidation.

Adjusted EBITDA, a non-GAAP measure, was $3.4 million in the fiscal 2021 third quarter, compared to $2.5 million in the prior-year period. The increase is primarily related to $2.3 million in Employee Retention Credits claimed during the quarter under the enhanced CARES Act, significantly offsetting operating expenses.

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Investment Management

During the three months ended March 31, 2021, Great Elm’s Investment Management business recognized total investment management revenue of $0.7 million, compared to $0.8 million during the same period in the prior year. Revenue was slightly lower due to decreases in the average assets on which such fees are calculated as a result of the impact of COVID-19 on the portfolio.

Great Elm recognized a net loss of $0.3 million compared to net income of $0.5 million during the same period in the prior year. Adjusted EBITDA was $16 thousand in the fiscal 2021 third quarter, compared to $0.3 million during the same period in the prior year. Adjusted EBITDA was impacted primarily by an increase in allocated payroll costs and consulting fees. We invested $10 million in Great Elm SPAC Opportunity Fund (GESOF) to help seed this vehicle, which we hope will contribute to increased assets under management for the investment management business and help drive additional fee revenue.

Real Estate

During the three months ended March 31, 2021, Great Elm’s real estate business recognized $1.3 million in rental revenue, $73 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, $67 thousand in net income and Adjusted EBITDA of $1.2 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 Myers, Florida.

General Corporate

During the three months ended March 31, 2021, Great Elm’s general corporate segment recognized $0.2 million in revenue compared to $34 thousand in revenue during the same period in the prior year. Revenue increased slightly as a result of increased management fees earned from DME, along with management fees earned with Forest Investments, Inc.

Great Elm recognized $2.4 million in net income vs. net loss of $11.2 million during the same period in the prior year. The difference in net income was driven primarily by substantial net unrealized losses on Great Elm’s investment in GECC during the third quarter in 2020 compared to the net unrealized losses recognized during the third quarter in 2021. Dividend income was higher in the third quarter of 2021 due to a larger investment in GECC following stock distributions received and the Company’s participation in the GECC rights offering in October 2020. Additionally, General Corporate recognized a $4.8 million benefit related to a fair value adjustment recorded in connection with the preferred stock issued to a subsidiary (Forest Investments, Inc.), with an offsetting impact to DME and eliminated in consolidation.

Great Elm recognized $(1.0) million in Adjusted EBITDA compared to Adjusted EBITDA of $(1.4) million during the prior year period. Great Elm made significant progress on reducing its corporate overhead, driven by lower audit fees due to a change in auditors in the prior fiscal year. The Company also entered into a shared services arrangement with DME, which further reduced corporate overhead by $0.1 million.  Great Elm intends to continue to focus on reducing its corporate overhead.

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Fiscal 2021 Third Quarter Conference Call & Webcast Information

When:Friday, May 14, 2021, 4:30 p.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.

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

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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]

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Great Elm Group, Inc.

Condensed Consolidated Balance Sheets (Unaudited)

Dollar amounts in thousands (except per share data)

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Great Elm Group, Inc.

Condensed Consolidated Statements of Operations (Unaudited)

Dollar amounts in thousands (except per share data)

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Great Elm Group, Inc. Conference Call Presentation Fiscal Third Quarter Ended March 31, 2021 May 14, 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. 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.

Notable Highlights – Third Quarter Fiscal 2021 Overall, we see positive momentum in all aspects of our business DME is beginning to see signs of business recovery following pandemic impacts DME acquisition program resumed this quarter, and optimistic for future acquisition opportunities On March 1, 2021, Great Elm DME closed the acquisition of Advanced Medical DME, LLC and PM Sleep Lab, LLC (“AMPM”), providers of sleep testing, PAP, and other respiratory products and services Small tuck-in acquisition supports growth strategy through expansion and leverage of existing operating footprint; AMPM has 9 locations throughout Kansas and Missouri Meaningfully increased the patient base by 2,500+ active patients; potential operating efficiencies and other added scale benefits Investment Management had a productive quarter in positioning GECC for further growth GECC reported a significant increase in NAV per share during the period, largely due to unrealized gains as a result of positive developments at portfolio companies during the quarter GECC entered into a new three-year $25 million revolving credit facility for greater flexibility and to support future investments Simplified balance sheet and corporate structure at subsidiary, GECC GP Corp., resulting in a greater share of investment profits for GEG Fully implemented Great Elm SPAC Opportunity Fund (GESOF) in order to increase AUM and drive additional fee revenue; $10 million invested at quarter-end to help seed this new vehicle 3

4 Consolidated Summary Financials: Q3 FY 2021 (1) Please refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix.

AMPM Acquisition On March 1, 2021 closed the acquisition of Advanced Medical DME, LLC and PM Sleep Lab, LLC (“AMPM”), providers of sleep testing, PAP, and other respiratory products and services in 9 locations throughout Kansas and Missouri, for purchase consideration of $1.1 million Increased the patient base by 2,500+ active patients to provide full range of respiratory equipment and PAP resupply, and the opportunity to introduce ventilator and oxygen services and gain additional referral opportunities in the acquired markets Potential operating efficiencies and procurement savings through better pricing and volumes In fiscal 3Q21, Great Elm DME, Inc. (“DME”) generated $13.1 million of revenue, $5.1 million of net loss and $3.4 million of adjusted EBITDA1 Revenues overall decreased due to continued suppressed referral pipeline for new equipment set-ups and increased revenue reserve requirements; partially offset by organic growth in resupply sales and one month of contributions from the AMPM acquisition Operating expenses decreased due to Employee Retention Credits received in the quarter and lower cost of rental equipment in line with reduced rental revenue Physician referrals and new order volumes continued to be negatively impacted by COVID-19 New PAP patient setups declined 12.7% year over year, but has stabilized Referrals for sleep studies down 15% y-o-y, but increased 8% from prior quarter to current quarter (1) Please refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix Operating Companies: DME closes AMPM Acquisition 5

Operating Companies: DME Financial Detail (1) Please also refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 6

7 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: Solid Progress and Momentum Increasing In fiscal 3Q21, Investment Management generated $0.7 million of revenue, $0.3 million of net loss and $16 thousand of adjusted EBITDA1 Revenue and profitability were stable and reflect the decreases in average assets on which management fees are calculated as a result of the impact of COVID-19 on the portfolio Deployment accelerated throughout the quarter, ending solidly with $44 million in new investments (excluding SPACs) NAV per share increased driven by unrealized gains as a result of positive developments at several portfolio companies Great Elm SPAC Opportunity Fund, LLC (GESOF) successfully implemented Fully implemented Great Elm SPAC Opportunity Fund (GESOF) in order to increase AUM and drive additional fee revenue; $10 million invested at quarter-end to help seed new vehicle Simplified balance sheet and corporate structure at subsidiary, GECC GP Corp., resulting in a greater share of investment profits for GEG Subsequent to quarter-end, GECC entered into a new $25 million revolving credit facility with City National Bank for greater flexibility and to support future investments Three-year facility at LIBOR rate plus 3.50% (1) Please refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 8

Investment Management: Segment Financial Detail (1) Please also refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 9

10 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. 11

Real Estate: Segment Financial Detail (1) Please also refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 12

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

Financial Review: 3Q21 Consolidating Balance Sheets (Unaudited) 14 (1) Intercompany balances, including intercompany borrowings and GEC investments in subsidiaries. All intercompany balances eliminate in consolidation.

Financial Review: 3Q21 Consolidating Income Statement (Unaudited) (1) Please refer to the disclaimers on slide 2 and the Adjusted EBITDA reconciliation tables in the Appendix 15

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, MO, NE, OR, WA 362 employees

Driving Shareholder Value 17 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 18 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 collectively own approximately 2.0 million shares of GEG, representing approximately 8% of GEG’s outstanding shares1 The directors of GEG beneficially own approximately 5.4 million shares of GEG in the aggregate, representing approximately 20% of GEG’s outstanding shares When combined, insider ownership totals approximately 28% 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

Appendix 19

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 20

Organization: Structure 21 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.

Appendix: Non-GAAP Reconciliation 22 (1) 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) 23 (1) 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) 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.

25 Appendix: Non-GAAP Reconciliation (Continued) (1) 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] 26