COVER

COVER

June 2019 Investor Presentation Standard Diversified Inc. owns and operates subsidiaries in a variety of industries, including other tobacco products, outdoor advertising and insurance. SAFE HARBOR This presentation contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995, Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended. Certain statements contained in this presentation, including those that express a belief, expectation or intention, as well as those that are not statements of historical fact, are forward-looking statements within the meaning of the federal securities laws and as such are based upon the current beliefs of Standard Diversified Inc.(we, us, our, SDI, or the Company) as to the outcome and timing of future events. There can be no assurance that the expectations, conclusions or beliefs expressed in any forward-looking statements will in fact occur. Examples of forward looking statements in this presentation include, but are not limited to, statements regarding: (i) the earnings impact of our investments; (ii) improvements in our new business production; (iii) future M&A activity; (iv) global brand recognition; (v) the leveraging of internal resources across divisions; (vi) our ability to stay in front of improvements in technology; (vii) growth drivers and expected levels of our organic growth; (viii) our management team; (ix) our balance sheet; and (x) our return to shareholders. Forward-looking statements are generally identifiable by use of forward-looking terminology such as may, will, should, potential, intend expect, seek, anticipate, estimate, believe, could, project, predict, hypothetical, continue, future or other similar words or expressions. All forward-looking statements included in this presentation are based upon information available to the Company on the date hereof and the Company is under no duty to update any of the forwardlooking statements after the date of this presentation to conform these statements to actual results. The forward-looking statements involve a number of significant risks and uncertainties. Factors that could have a material adverse effect on the Companys operations and future prospects are set forth in the Companys Annual Report on Form 10-K for the fiscal year ended December 31, 2018, including the sections entitled Risk Factors contained therein. The factors set forth in the Risk Factors section and otherwise described in the Companys filings with SEC could cause the Companys actual results to differ significantly from those contained in any forward-looking statement contained in this presentation. The Company does not guarantee that the assumptions underlying such forward-looking statements are free from errors. Should one or more of these risks or uncertainties occur, or should underlying assumptions prove incorrect, the Companys business, financial condition, liquidity, cash flows and results could differ materially from those expressed in any forward-looking statement. While forward-looking statements reflect our good faith beliefs, they are not guarantees of future performance. Any forward-looking statement speaks only as of the date on which it is made. New risks and uncertainties arise over time, and it is not possible for us to predict the occurrence of those matters or the manner in which they may affect us. We disclaim any obligation to publicly update or revise any forward-looking statement to reflect changes in underlying assumptions or factors, of new information, data or methods, future events or other changes. Use caution in relying on past forward-looking statements, which

were based on results and trends at the time they were made, to anticipate future results or trends. 2 Standard Diversified Inc. (SDI or the Company) AT A GLANCE A publicly-listed, diversified holding company Experienced management team focused on investing in quality operating businesses run by high-caliber executive teams Create and maximize long-term value for shareholders Public platform in which to pursue opportunistic M&A Selected Financial Information as of December 31, 2018 Ticker (NYSE) SDI Shares Outstanding 16,814,696*

Cash and cash equivalents $21.2 Million Market Cap $363.2 Million** Total Assets $425.6 Million * The total is comprised of Class A and Class B shares of common stock outstanding as of March 31, 2019, which includes shares owned by affiliates ** The Market Cap is calculated utilizing the SDI stock price as of the close of market on May 31, 2019 3 Standard General Entity Shareholders Other Shareholders (~ 85% ownership) (~ 15% ownership - includes directors/officers ownership) ORGANIZATION AL STRUCTURE STANDARD DIVERSIFIED INC.

NYSE: SDI Turning Point Brands, Inc. Standard Outdoor LLC Standard Outdoor Southeast I LLC Standard Outdoor Southeast II LLC NYSE: TPB (~50.3% ownership) Standard Outdoor Southwest LLC Pillar General Inc. Interboro Holdings, Inc. Interboro Management Maidstone Insurance Company AIM Insurance Agency (New York State domiciled insurance company) All ownership percentages are 100% unless otherwise noted

4 Value to the Company INVESTMEN T THESIS Established operating business in the expanding Other Tobacco Products market with a strong executive management team Current size and scale facilitates substantial growth Value to the SDI Investor The Company owns a 50.3% of Turning Point Brands, Inc. a NYSElisted company (TPB) The Companys stock provides an alternative opportunity to participate in TPBs growth TPB is a dividend-paying stock PILLAR GENERAL Free cash flow generating business model Uncorrelated risk profile in the out-ofhome advertising space Maidstone Insurance Co, a P&C carrier licensed in 23 states and the District of Columbia that carries brand recognition in the New York market Potential for long-term capital growth

with a focus on BOTH underwriting and active asset investing 5 LONG TERM VIEW Develop a platform to facilitate long-term value creation Focus on acquisitions of sustainable cash flow generating businesses with top-quality management teams Drive growth across the portfolio with appropriate capital allocation Diverse Portfolio of Scalable Businesses Cash Flow Generating Businesses with Strong Managemen t Teams LongTerm Value Creation 6 Objective

UNIQUE VALUE PROPOSITI ON Approach to Acquisitions Offer solutions to companies with management teams that: Have successfully implemented their business plan Want to continue building upon their historical profits and growth Have identifiable, untapped business potential Seek the flexibility and liquidity of public markets Company Target Size: $40 - $400 million Enterprise Value Industry agnostic, with a focus on: Situations with social issues Distressed opportunities Scalable businesses Legacy holdings of PE/Asset Managers Generational businesses 7 CORPORAT E TIMELINE 2013 Management exits operating businesses and company converts to a publicly-traded shell

2015 Greg Baxter nominated to Board of Directors 2016 In February, Greg Baxter named Chairman of the Board of Directors; The largest shareholder proposes the contribution and exchange of a controlling interest in Turning Point Brands (TPB) 2017 In June, Company closes on the TPB acquisition and emerges from shell company status In July, Company closes on acquisition of billboard assets from Metro Outdoor Advertising 2018 In January, Company closes on acquisition of Maidstone

Insurance Company; Bradford Tobin named as General Counsel In January and February, Company closes on two significant acquisition of billboard assets In April, Company listed on the NYSE American exchange under the ticker symbol SDI 8 EXECUTIVE LEADERSHI P TEAM Greg Baxter Bradford Tobin Interim Chief Executive Officer, Executive Chairman of the Board General Counsel and Secretary Mr. Baxter has served as a director on the Board of the Company since October 2015 and Executive Chairman since June 2017, and has over 40 years of financial and operational experience. Mr. Baxter has also served as a director of Turning Point Brands (NYSE: TPB and its predecessor), since April 2006. Mr. Baxter has held senior level

positions at Diaz & Altschul Capital Management, SG Cowen, and Rothschild Inc. Mr. Baxter holds a Bachelor of Arts from the University of Victoria in Canada and a Master of Business Administration from the Ivey Business School in London. Mr. Tobin joined the Company as the General Counsel in January 2018 with over 10 years of legal and operational experience. Immediately prior to joining the Company, Mr. Tobin served as the General Counsel and Senior Vice President of General Wireless Operations Inc. dba RadioShack where he steered operations and the legal team through two bankruptcies. Preceding this role, Mr. Tobin served on the distressed debt team at Silver Point Capital, LP. Mr. Tobin holds a Juris Doctor from St. Johns University, School of Law in New York and a B.S. in Economics from the University of Wisconsin-Madison. 9 OPERATING SUBSIDIARIES SUBSIDIARI ES: A GROWTH PLATFORM PILLAR

GENERAL Turning Point Brands, Inc. is a leading U.S. provider of Other Tobacco Products Through its three focus brands Stokers in Smokeless Products, Zig-Zag in Smoking Products and the VaporBeast distribution engine in NewGen Products TPB generates solid cash flow which it uses to finance acquisitions, increase brand support and strengthen its capital structure Standard Outdoor is a full-service outdoor advertising company. Standard Outdoor recently closed on acquisitions of billboard assets located near Austin, TX and in Northern Alabama Standard Outdoor is a wholly-owned subsidiary of the Company Pillar General is an insurance holding company, which recently acquired Maidstone Insurance, a New York domiciled seller of auto and personal lines of property and casualty insurance. Pillar General is a wholly-owned subsidiary of the Company TPB does not sell cigarettes

The Company owns 50.3% of the outstanding common stock of TPB at March 31, 2019 11 TURNING POINT BRANDS Turning Point Brands For the year ended December 31, 2018: $332.7 million of net sales (up 16.4% from prior year) $142.6 million of gross profit (up 14.1% from prior year) $64.6 million of Adjusted EBITDA* (up 7.6% from prior year) * This is a non-GAAP figure. Reconciliation to the most comparable GAAP measure, as well as related disclosure, can be found in the Appendix 12 DISTRIBUTION SYSTEM AT A

GLANCE: BRINGING IT ALL TOGETHER Consolidated distribution into Kentucky with integrated systems. 1-2 days across the US at low rates SALES FORCE & ROBUST ECOMMERCE ENGINE Trusted relationships with independent retail world and eCommerce engine gets products into consumers hands SOURCING TEAM Sourcing teams in China and across North American farm networks gives best-in-class products World-Class Go-To Market Strategy HANDS-ON MANAGEMENT Management team is hands-on with product development and go-to market strategies REGULATORY

STRENGTH Significant experience navigating federal, state, and local regulations. Tobacco expertise translates into alternative markets. Key advantage to startup CBD/alternative companies. FINANCIAL STRENGTH Strong balance sheet with capital flexibility for acquisitions and working capital investments 13 ANNUAL FINANCIAL PERFORMA ($NCE in millions) Net Sales Year Ended December 31, 2018 Year Ended December 31, 2017 $332.7 $285.8 +16.4

% Adjusted EBITDA* $64.6 $60.0 +7.6% Net Income $25.3 $20.2 +25.1 % * This is a non-GAAP figure. Reconciliation to the most comparable GAAP measure, as well as related disclosure, can be found in the Appendix 14 QUARTERLY FINANCIAL PERFORMA ($ in millions) NCE Net Sales Q1 2019 Q1 2018 $91.6

$73.9 +23.9% Adjusted EBITDA* $16.1 $13.7 +17.3% Net Income $6.6 $3.0 +116.4% * This is a non-GAAP figure. Reconciliation to the most comparable GAAP measure, as well as related disclosure, can be found in the Appendix 15 60 $49.23 May 31, 2019 POST - IPO MARKET PERFORMA NCE 50

40 30 IPO $10.00 May 11, 2016 20 10 0 4 1 9 6 4 0 9 5 3 9 5 4 0 0 9 5 4 0 8 5 3 9 8 4 3 9 5 4 0 8 4 2 9 7 5 4 0 9 5 4 0 8 5 4 0 9 5 3 0 8 4 2 8 7 4 4 3 9 8 4 0 9 5 4 51 53 54 56 58 60 61 63 65 66 68 70 72 74 75 77 79 81 82 84 86 87 89 91 93 94 96 98 00 01 03 05 06 08 10 12 14 15 17 19 21 22 24 26 28 29 31 33 35 36 38 40 41 43 45 47 49 50 52 54 56 57 59 61 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 43 16 STANDARD OUTDOOR A wholly-owned subsidiary of the Company Standard Outdoor is committed to expansion in the out-of-home advertising space through acquisition and organic growth in local markets across the country 17 Standard Outdoor owns and

operates approximately 400 billboard faces located across Alabama, Florida, Georgia and Texas, as follows: AT A GLANCE Location # of Faces Texas 14 Alabama 192 Florida 40 Georgia 162 Market Opportunity With technological advances driving demand, the out-of-home advertising space continues to expand The Company believes there is an attractive opportunity in this industry, which consists of three large nationwide players, a few medium-sized regional companies and hundreds of independent sign owners

18 Market Approach GROWTH STRATEGY Acquire high-quality outdoor advertising assets with upside potential from strategic sales efforts Aggressively pursue growth through tuck-in acquisitions, new site development and digital conversion Establish regional operation hubs for managing assets Focus on markets dominated by local ad sales and establish relationships through direct market participation in these communities 19 PILLAR GENERAL AT A GLANCE PILLAR GENERAL

Pillar General is SDIs insurance holding company subsidiary On January 2, 2018, the Company acquired Interboro Holdings, Inc., the parent of Maidstone Insurance Company, an automobile and personal property and casualty insurance company Maidstone is licensed to write automobile and/or personal property and casualty insurance in 23 states and the District of Columbia Licensed States 20 PILLAR GENERAL Market Approach GROWTH STRATEGY Focus on four primary lines of business: homeowners, automobile, workers compensation and general liability

Utilize local independent agents that control substantial small to mid-sized insurance markets Develop niche policyholders residential and commercial programs to target small-sized Unique Strategy Accumulate safe risk on both sides of the balance sheet risk that can be underwritten with a margin of safety and has the potential to generate long-term capital appreciation Generate higher asset returns, supported by the leveraged and stable balance sheet of an insurance company, resulting in a lower cost of capital 21

APPENDIX Sum of the Parts Analysis* (in 000s except percentages) Market Cap 25.9 % Disco unt to ENA V ENA V Debt ($23,984) Inputs for Sum of the Parts Analysis $540... $510... $480... $450... as of March 31, 2019, unless otherwise noted Turning Point Brands (TPB) Shares Owned by SDI 9,842,373 TPB Per Share Price (as of May 31, 2019) $49.23

SDI Shares Outstanding** 16,814,696 SDI Class A Common Stock Per Share Price (as of May 31, 2019) $21.60 $420... Sum of the Parts Analysis except where indicated, all amounts as of March 31, 2019; in 000s except per share data $390... Total $360... $330... $300... $484,540 $270... $240... $210... 363197 $180... $150... $120... $90 $60 $2,915 $18,292 $8,209 $30

$0 Per Share Cash and cash equivalents $8,209 $0.49 Investment in Standard Outdoor 18,292 1.09 2,915 0.17 Market value of Turning Point Brands shares (as of May 31, 2019) 484,540 28.82 Total Assets 513,956 30.57 Debt (23,984)

(1.42) Estimated Net Asset Value (ENAV) 489,972 $29.15 Investment in Pillar General SDI Share Price Premium/(Discount) to ENAV (SDI Share Price as of May 31, 2019) (25.9%) * The estimated net value of assets and liabilities has been determined based on the information and methods described herein and is not intended to, and does not constitute, an appraisal or estimate of value based on any other method. The estimated net value of Company assets and liabilities described herein is not necessarily indicative of the value that could be realized upon a liquidity or sale event (if any). The methods used herein include the use of per share market prices for our subsidiaries whose common stock is publicly traded, but these prices are not necessarily reflective of the actual value that we would receive if we were to sell or liquidate those investments. We have used book value determined in accordance with GAAP for purposes of preparing our balance sheet to estimate the value of our assets for which there is no trading market. These book value determinations are not necessarily reflective of the value that we would receive if we were to sell or liquidate those investments. As a result, you are cautioned not to place undue reliance on the estimated net valuations set forth herein and carefully consider alternatives to the assumptions and methods described above. Actual results and value that may be available to our stockholders may differ significantly from those presented herein. This information is subject to change without notice and should not be relied upon for any purpose. Neither the Company nor any of its affiliates or subsidiaries makes any representation or warranty, express or implied, as to the accuracy or completeness of the information contained herein and no such party shall have any liability for such information. In furnishing this information and making any oral statements, neither the Company nor any of its affiliates or subsidiaries undertakes any obligation to provide the recipient with access to any additional information or to update or correct such information. The information herein or in any oral statements are prepared as of the date hereof or as of such earlier dates as presented herein; neither the delivery of this document nor any other oral statements regarding the affairs of the Company, its affiliates or subsidiaries shall create any implication that the information contained herein or the affairs of the Company, its affiliates or subsidiaries have not changed since the date hereof or after the dates presented herein (as applicable); that such information is correct as of any time subsequent to its date; or that such information is an indication regarding the valuation of the Company, of its affiliates or subsidiaries ** The total is comprised of Class A and Class B shares of common stock outstanding as of May 1, 2019, which includes shares owned by affiliates 2 23

Annual Reconciliation 24 Quarterly Reconciliation 25 CONTACT INFORMATION Investor Relations: The Equity Group Inc. Adam Prior Senior Vice President [email protected] 212-836-9606

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