Medley Management Inc. (NYSE: MDLY)Investor Presentation

Quarter ended June 30, 2018

2

Important Notice to InvestorsThis presentation contains “forward looking statements” within the meaning of Section 21E of the Securities Exchange Act of 1934, as amended, that are subject to risks

and uncertainties. Actual outcomes and results could differ materially from those suggested by this presentation due to the impact of many factors beyond the control of

Medley Management Inc., including those listed in the "Risk Factors" section of our Annual Report on Form 10-K for the fiscal year ended December 31, 2017 and our

other filings with the Securities and Exchange Commission (“SEC”). Any such forward-looking statements are made pursuant to the safe harbor provisions available under

applicable securities laws and Medley Management Inc. assumes no obligation to update or revise any such forward-looking statements except as required by law.

Certain information discussed in this presentation (including information relating to portfolio companies) was derived from third party sources and has not been

independently verified and, accordingly, the Company makes no representation or warranty in respect of this information.

The following slides contain summaries of certain financial and statistical information about Medley Management Inc. The information contained in this presentation is

summary information that is intended to be considered in the context of our SEC filings and other public announcements that we may make, by press release or

otherwise, from time to time. In addition, information related to past performance, while helpful as an evaluative tool, is not necessarily indicative of future results, the

achievement of which cannot be assured. You should not view the past performance of Medley Management Inc., or information about the market, as indicative of Medley

Management Inc.’s future results. This presentation does not constitute an offer to sell or the solicitation of an offer to buy any securities of Medley Management Inc.

This presentation includes certain non-GAAP financial measures, including Core Net Income, Core EBITDA, Core Net Income Per Share, Pre-Tax Core Net Income per

Share, Pre-Tax Core Net Income Margin, Core Net Income Margin and Pro-Forma Weighted Average Shares Outstanding. These measures should be considered only as

supplemental to, and not as superior to, financial measures prepared in accordance with U.S. GAAP.

Please refer to the financial performance section of this presentation for a reconciliation of the non-GAAP financial measures included in this presentation to the most

directly comparable financial measures prepared in accordance with U.S. GAAP.

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Table of Contents

1. Overview 4

2. Market Opportunity 9

3. Investment Process 12

4. Financials 14

5. Appendix 18

OVERVIEW

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• Diversified credit manager offering yield solutions for institutional and retail investors• $5.0B of assets under management (“AUM”) and $3.0B of fee-earning assets under management

(“FEAUM”)• Success in developing innovative new products and accessing multiple distribution channels

65%13%

1%

21%Permanent

9+ Years

6-9 Years

3-6 Years

Company Overview

Note: Metrics in billions of USD. Due to rounding figures may not sum. 1. As of June 30, 2018.

Total AUM Fee Earning AUM(1)

5

$1.3$1.8

$2.3

$3.7

$4.8$5.3 $5.2 $5.0

2011 2012 2013 2014 2015 2016 2017 2Q18

Permanent Capital Institutional Capital

Liquid Income Securities

Structured Credit

Corporate Credit

Direct Lending

Tactical Opportunities

• Public, yield-driven investments including trust preferred, BDCs, residential and commercial mortgage REITs and yield oriented equity and equity-linked products

• Flagship product delivering capital solutions to private, middle market companies

• National direct origination franchise

• Medley leads origination, underwriting and credit management

• Primarily focused on syndicated middle market corporate credit

• Typically larger borrowers than direct lending

• Focus on preferred and structured equity

• Leverages direct lending and institutional deal sourcing capabilities

• Private equity type risk-reward profile

• Investing in CLO equity issued by top tier managers

• Secondary markets investing in CLO equity and related securities

• Capability to sponsor and issue Medley-branded CLOs

Investment Capabilities

6

• Broad distribution through public and private channels • Permanent capital, long-dated funds and managed accounts not subject to traditional outflows

Diversified AUM Across Multiple Funds

SierraTotal

ReturnFund

MEDLEY(NYSE: MDLY)

Public Vehicles

Medley Capital

Corporation(NYSE: MCC)

Long-Dated Funds andSeparately Managed Accounts

Senior Loan Fund

MedleyOpportunity

Funds

SeparatelyManagedAccounts

Institutional Capital

Medley Credit

OpportunityFund

SierraIncome

Corporation

SeniorLoan Fund

TacticalOpportunities

7

Portfolio Summary

8

Note: Portfolio summary represents total committed amounts as of 6/30/2018 and represents assets in all investment vehicles including TRS and SLS assets. In addition, non-U.S. investments comprise approximately 1% of Medley’s overall investment portfolio.

14%

12%

8%

8%

7%6%5%

4%

4%

4%

3%

3%

3%

3%2%

2%2%

10%Services: BusinessHealthcare & PharmaceuticalsConstruction & BuildingBanking, Finance, Insurance & Real EstateHigh Tech IndustriesHotels, Gaming & LeisureMulti-Sector HoldingsServices: ConsumerEnergy: Oil & gasAerospace & DefenseAutomotiveWholesaleContainers, Packaging and GlassMedia: Advertising, Printing & PublishingCapital EquipmentChemicals, Plastics & RubberBeverage & FoodOther

83%

17%

Floating

Fixed

77%

9%

5%

9%

First Lien

Second Lien

Unsecured

Equity

23.8%

25%

12%

18% 31%

Industry Breakout

13%

Investment Type Breakout

Medley Investments by Geography

Floating vs. Fixed Rate

MARKET OPPORTUNITY

9

7%

13%

24%

0%

10%

20%

30%

40%

Traditional Managers Alternative Managers MDLY

AUM CAGR Since 2010(1)

$-

$5

$10

$15

$20

$25

2008 2015 2020E

Alternative Investments

$5T$8T

$23T

8% CAGR

24% CAGR

• Market leading growth in AUM driven by:

- Increasing demand for yield in low rate environment

- Increasing demand by investors for senior secured and floating rate exposure

• Growth in alternatives continues to outpace that of traditional asset managers

- Increased allocation from both retail and institutional investors

- Retail investors significantly underweight exposure to alternatives

Increasing Demand for Alternatives

Note: Metrics in trillions of USD.1. Traditional managers include: BEN, BLK, IVZ, JNS, OMAM, and TROW. Alternative managers include APO, BX, CG, KKR, OAK, and OZM. Medley selected the traditional and

alternative manager groups based on subjective factors. There may be other managers not mentioned.2. Based on BCG, Global Asset Management 2016.

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Growth in Alternatives(2)

Large and Growing Market in Private CreditBank Consolidation(1)(2)

$16.8

$9.2$6.7

$4.9$3.6 $2.7 $2.5 $2.2

UnitedStates

China USMiddleMarket

Japan Germany France UK Brazil

• Traditional lenders to the middle market have changed in recent years

- Consolidation of the banking system

- Regulatory headwinds for banks and CLO managers

• The middle market remains a large opportunity

- 20 years ago banks represented over 70%

- Today banks represent 10%

• US middle market would rank as the 3rd largest global economy

• Private credit has emerged as an important asset class for all investors

- Retail

- Insurance companies

- Pension funds

- Endowments

1. Federal Deposit Insurance Corporation, represents number of commercial banking institutions insured by the FDIC as of 3/31/2018.2. S&P LCD’s Leveraged Lending Review – Q1’18.3. International Monetary Fund, World Economic Outlook Database, June 2014. Metrics in trillions of USD.

11

Top GDPs(3)

0%

10%

20%

30%

40%

50%

60%

70%

80%

4,000

5,000

6,000

7,000

8,000

9,000

10,000

11,000 U.S. FDIC Insured Commercial Banks¹

Bank Participation in Levered Loan Market (%)²

INVESTMENT PROCESS

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• Downside protection – focused on capital preservation• Three step underwriting process • Multiple touch points and evaluations• Disciplined Investment Committee process

Origination

Underwriting

Asset and PortfolioManagement

• Nationwide platform• Targeted middle market sectors

Origination1

Underwriting

• Multi-step approval process• Documentation process• 3rd party resources• Approve 1-3% of opportunities• Medley has invested in over

400 borrowers(1)

2

• Best-in-class technology and systems

• Frequent interaction with borrowers

• Credit monitoring and reporting

Asset and Portfolio Management3

1

2

3

Integrated Investing Processes

13

1. Since inception through 6/30/2018.

FINANCIALS

14

Consolidated Income Statements

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1. Core Net Income reflects standalone net income attributable to the controlling and non-controlling interests in Medley LLC adjusted to exclude reimbursable expenses associated with the launch of funds, certain one-time severance costs and stock-based compensation associated with restricted stock units that were granted in connection with our initial public offering (“IPO”), as well as other non-core items and, in 2018, unrealized losses related to our investment in shares of MCC. Please refer to the reconciliation of net income attributed to controlling and non-controlling interests in Medley LLC to Core Net Income on the following page.

2. Core Net Income Per Share reflects an adjustment for federal, state and local corporate income taxes. Please refer to the calculation of Core Net Income Per Share on the following page.

3. Core Net Income Margin equals Core Net Income Per Share divided by total revenue per share.4. The calculation of Pro-Forma Weighted Average Shares Outstanding assumes the conversion by the pre-IPO holders of up to 24,639,302 Medley LLC units for 24,639,302

shares of Class A common stock at the beginning of each period presented, as well as the vesting of the weighted average number of restricted stock units.

(Dollars in thousands except share and per share amounts)

RevenuesManagement fees $ 11,965 $ 13,201 $ 24,050 $ 27,096 Performance fees — 546 — (1,817)Other revenues and fees 3,038 2,668 5,367 4,988 Investment income (loss):Carried interest 432 28 597 173 Other investment income (284) (9) (467) (10)

Total revenues 15,151 16,434 29,547 30,430 Expenses

Compensation and benefits 7,333 5,705 15,671 11,499 Performance fee compensation (26) 50 (33) (831)General, administrative and other expenses 4,342 2,754 8,851 5,422

Total expenses 11,649 8,509 24,489 16,090 Other income (expense)

Dividend income 960 733 2,389 1,468 Interest expense (2,715) (2,766) (5,396) (6,413)Other income (expenses), net (4,011) 31 (13,766) 1,591

Total other expense, net (5,766) (2,002) (16,773) (3,354)Income (loss) before income taxes (2,264) 5,923 (11,715) 10,986 Provision for income taxes 195 428 385 841

Net income (loss) (2,459) 5,495 (12,100) 10,145

(2,464) 1,304 (6,978) 2,792

$ 5 $ 4,191 $ (5,122) $ 7,353

Core Net Income (1) $ 2,018 $ 4,733 $ 3,275 $ 9,321

Core EBITDA $ 5,351 $ 8,226 $ 10,359 $ 16,146

Core Net Income per share (2) $ 0.05 $ 0.10 $ 0.10 $ 0.19

Core Net Income Margin (3) 10.7% 18.1% 10.2% 19.5%

Pro Forma Weighted Average Shares Outstanding (4)

For the Three Months Ended June 30,

2017

31,028,903

(Unaudited)2018

31,790,112

Less: Net income (loss) attributable to redeemable non-controlling interests and non-controlling interests in consolidated subsidiaries

Net income (loss) attributable to Medley Management Inc. and non-controlling interests in Medley LLC

For the Six Months Ended June 30,

(Unaudited)2018 2017

31,215,945 30,997,006

Consolidated Income Statements (Cont.)

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1. Amounts relate to additional interest expense associated with the acceleration of amortization of debt issuance costs and discount relating to prepayments made on our Term Loan Facility as a result of the refinancing of our indebtedness from the issuance of Senior Unsecured Debt.

2. For the three and six months ended June 30, 2018, other items consists of expenses related to non-core business development activities and other expenses. 3. Represents a per share adjustment for income taxes assuming that all of our pre-tax earnings were subject to federal, state and local corporate income taxes. We assumed an

annualized effective corporate tax rate of 33.0% for 2018 and 43.0% for 2017.

$ 5 $ 4,191 $ (5,122) $ 7,353 Reimbursable fund startup expenses 442 226 1,065 251 IPO date award stock-based compensation 433 318 574 (343)Other non-core items

Unrealized losses on shares of MCC - - 3,543 - Severance expense 338 65 2,224 1,164 Acceleration of debt issuance costs (1) - - - 1,149 Other (2) 1,008 - 1,860 -

Income tax expense on adjustments (208) (67) (869) (253)Core Net Income $ 2,018 $ 4,733 $ 3,275 $ 9,321

Interest expense 2,715 2,766 5,396 5,264 Income taxes 403 495 1,254 1,094 Depreciation and amortization 215 232 434 467

Core EBITDA $ 5,351 $ 8,226 $ 10,359 $ 16,146

The calculation of Core Net Income Per Share is as follows:

$ 2,018 $ 4,733 $ 3,275 $ 9,321 Add: Income taxes 403 495 1,254 1,094

Pre-tax Core Net Income $ 2,421 $ 5,228 $ 4,529 $ 10,415

DenominatorClass A common stock 5,543,802 5,588,978 5.513.719 5,697,483

Conversion of LLC Units to Class A common stock 24,372,591 23,653,333 24,023,329 23,561,400

Restricted stock units and restricted LLC units 1,873,719 1,786,592 1,678,897 1,738,123

Pro-Forma Weighted Average Shares Outstanding 31,790,112 31,028,903 31,215,945 30,997,006

Pre-tax Core Net Income Per Share $ 0.08 $ 0.17 $ 0.15 $ 0.34Less corporate income taxes per share (3) (0.03) (0.07) (0.05) (0.15)Core Net Income Per Share $ 0.05 $ 0.10 $ 0.10 $ 0.19

For the Three Months Ended June 30,

(Unaudited)

2017

2017

2018

For the Three Months Ended June 30,

(Unaudited)

2018

Net income (loss) attributable to Medley Management Inc. and non-controlling interests in Medley LLC

NumeratorCore Net income

(Dollars in thousands except per share amounts)The reconciliation of Net income (loss) attributable to Medley Management Inc. and non-controlling interests in Medley LLC to Core Net Income and Core EBITDA is as follows:

2018 2017

For the Six Months Ended June 30,

(Unaudited)2018 2017

For the Six Months Ended June 30,

(Unaudited)

Consolidated Balance Sheets

17

(Dollars in thousands)

(unaudited)

Assets Cash and cash equivalents $ 24,862 $ 36,327 Investments, at fair value 44,359 56,632 Management fees receivable 10,325 14,714 Performance fees receivable - 2,987 Other assets 14,635 17,262

Total assets $ 94,181 $ 127,922

Liabilities and Equity Senior unsecured debt, net $ 117,239 $ 116,892 Loans payable, net 9,559 9,233 Accounts payable, accrued expenses and other liabilities 21,461 25,130

Total liabilities 148,259 151,255

Redeemable Non-controlling interests 42,395 53,741

EquityClass A common stock 56 55 Class B common stock - - Additional paid in capital 5,155 2,820 Accumulated other comprehensive loss - (1,301)Accumulated deficit (15,637) (9,545)

Total stockholders' deficit, Medley Management Inc. (10,426) (7,971)Non-controlling interests in consolidated subsidiaries (1,644) (1,702)Non-controlling interests in Medley LLC (84,403) (67,401)

Total deficit (96,473) (77,074)Total liabilities, redeemable non-controlling interests and equity $ 94,181 $ 127,922

2018 2017

As of December 31,

As of June 30,

APPENDIX

18

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Endnotes & DefinitionsDefinitions:

“Assets Under Management” or “AUM” refers to the assets of our funds, which represents the sum of the NAV of such funds, the drawn and undrawn debt (at the fund level, including amounts subject to restrictions) and uncalled committed capital (including commitments to funds that have yet to commence their investment periods).

“Core Earnings Before Interest, Income Taxes, Depreciation and Amortization (Core EBITDA)” is calculated as Core Net Income before interest expense, income taxes, depreciation and amortization.

“Core Net Income” is calculated by adjusting net income attributable to Medley Management Inc. and net income attributable to non-controlling interests in Medley LLC to exclude reimbursable expenses associated with the launch of funds, amortization of stock-based compensation expense associated with grants of restricted stock units at the time of our IPO, other non-core items and the income tax impact of these adjustments.

“Core Net Income Margin” equals Core Net Income Per Share divided by total revenue per share.

“Core Net Income Per Share” is Core Net Income adjusted for corporate income taxes assuming that all of our pre-tax earnings are subject to federal, state and local corporate income taxes, divided by Pro-Forma Weighted Average Shares Outstanding (as defined above). In determining corporate income taxes we used an annual effective corporate tax rate of 33% for 2018, and 43% for 2017.

“Fee Earning Assets Under Management” refers to the assets under management on which we directly earn base management fees.

“Pre-Tax Core Net Income” is calculated as Core Net Income excluding the impact of income taxes.

“Pre-Tax Core Net Income Margin” equals Pre-Tax Core Net Income Per Share divided by total revenue per share.

“Pre-Tax Core Net Income Per Share” is calculated as Pre-Tax Core Net Income divided by Pro-Forma Weighted Average Shares Outstanding.

“Pro-Forma Weighted Average Shares Outstanding” assumes the conversion by the pre-IPO holders of up to 24,639,302 Medley LLC units for 24,639,302 shares of Class A common stock at the beginning of each period presented, as well as the vesting of the weighted average number of restricted stock units.

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Corporate InformationBoard of Directors

BROOK TAUBE Co-Chairman

SETH TAUBECo-Chairman

JEFF TONKEL Director

JAMES G. EATONIndependent Director

JEFFREY T. LEEDSIndependent Director

GUY ROUNSAVILLE, JR.Independent Director

Corporate Officers

BROOK TAUBE Co-Chief Executive Officer

SETH TAUBE Co-Chief Executive Officer

JEFF TONKELPresident

RICHARD T. ALLORTO, JR.Chief Financial Officer

JOHN FREDERICKSGeneral Counsel & Secretary

Research Coverage

COMPASS POINTCasey Alexander – (646) 452-7083

CREDIT SUISSECraig Siegenthaler - (212) 325-3104

Corporate Headquarters

280 Park Avenue, 6th Floor EastNew York, NY 10017(212) 759-0777

Investor Relations

SAM ANDERSONHead of Capital Markets & Risk Management(212) 759-0777

Corporate Counsel

LOWENSTEIN SANDLER LLPNew York, NY

Independent Registered Public Accounting Firm

RSM US, LLPNew York, NY

Securities Listing

NYSE: MDLY (Common Stock)MDLQ (Senior Notes Due 2024)MDLX (Senior Notes Due 2026)

Transfer Agent

AMERICAN STOCK TRANSFER & TRUST COMPANY, LLC(888) 777-0324

Media Contact

TENEO(212) 498-9197