Tiptree : 2023 KBW Insurance Conference

KBW Insurance Conference

Legal Disclaimers

BASIS OF PRESENTATION AND LIMITATIONS ON THE USE OF INFORMATION - The Fortegra Group, Inc. ("Fortegra") reports a non-controlling interest in certain operating subsidiaries that are not wholly owned. Unless otherwise noted, all information is of Fortegra on a consolidated basis before non-controlling interest. Neither Fortegra nor any of its affiliates makes any representation or warranty, express or implied, as to the accuracy or completeness of the information contained herein, or any other written or oral communication transmitted or made available to any recipient or its affiliates or representatives. The Company and its affiliates or representatives expressly disclaim to the fullest extent permitted by law any and all liability based, in whole or in part, on the presentation or any information contained herein or any other written or oral communication transmitted or made available to any recipient or its affiliates or

representatives, including, without limitation, with respect to errors therein or omissions therefrom. This presentation is for informational purposes and reference only pursuant to your request and is not intended to be, and must not be, taken as the basis for a decision with respect to any possible transaction. These materials and any related oral statements do not purport to contain all of the information that may be required to evaluate all of the factors that would be relevant

to your consideration of any potential transaction and shall not be construed as legal, tax, investment or any other advice. You should consult your own counsel, accountant or business advisors and should conduct your own investigation and analysis. Performance information is historical and is not indicative of, nor does it guarantee future results. There can be no assurance that similar performance may be experienced in the future. No securities commission or securities regulatory authority in the United States or any other jurisdiction has in any way passed upon the accuracy or adequacy of this presentation.​

SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS - This document contains "forward-looking statements" which involve risks, uncertainties and contingencies, many of which are beyond Fortegra's control, which may cause actual results, performance, or achievements to differ materially from anticipated results, performance, or achievements. All statements contained herein that are not clearly historical in nature are forward-looking, and the words "anticipate," "believe," " estimate," " expect," "intend," "may," "might," " plan," "project," "should," " target," "will," " view," the negative of these terms, and similar expressions are intended to identify forward-looking statements, although not all forward-looking statements contain these identifying words. Such forward-looking statements include, but are not limited to, statements about Fortegra's plans, objectives, expectations and intentions. The forward-looking statements are not guarantees of future performance and are subject to risks, uncertainties and other factors, many of which are beyond our control, are difficult to predict and could cause actual results to differ materially from those expressed or forecast in the forward-looking statements. Our actual results could differ materially from those anticipated in these forward-looking statements as a result of various factors, including, but not limited to those described in the section entitled "Risk Factors" in disclosure regarding Fortegra in the periodic Form 10-Qs and Form 10-Ks filed by Tiptree Inc., and as described by Tiptree Inc. in other filings with the SEC. Readers are cautioned not to place undue reliance on these forward-looking statements, which speak only as to the date of this release. The factors described therein are not necessarily all of the important factors that could cause actual results or developments to differ materially from those expressed in any of our forward-looking statements. Other unknown or unpredictable factors also could affect our forward-looking statements. Consequently, our actual performance could be materially different from the results described or anticipated by our forward-looking statements. Given these uncertainties, you should not place undue reliance on these forward-looking statements. Except as Tiptree is required by the federal securities laws, we undertake no obligation to update any forward-looking statements.​

MARKET AND INDUSTRY DATA - Certain market data and industry data used in this presentation were obtained from reports of governmental agencies and industry publications and surveys. We believe the data from third-party sources to be reliable based upon our management's knowledge of the industry, but have not independently verified such data and as such, make no guarantees as to its accuracy, completeness or timeliness.

NOT AN OFFER OR A SOLICIATION - Neither Fortegra nor its shareholders are currently making any offer to sell, or soliciting any offer to buy, securities of Fortegra, and cannot accept any orders for securities at this time. This document also does not constitute an offer or invitation to engage in any transaction with Fortegra, its subsidiaries or its affiliates. The information in this document is not targeted at the residents of any particular country or jurisdiction and is not intended for distribution to, or use by, any person in any jurisdiction or country where such distribution or use would be contrary to local law or regulation.

NON-GAAP MEASURES - In this document, we sometimes use financial measures derived from consolidated financial data but not presented in our financial statements prepared in accordance with U.S. generally accepted accounting principles ("GAAP"), and these financial measures may exclude items that are significant in understanding and assessing Fortegra's financial results. Certain of these data, including, but not limited to adjusted net income and adjusted return on average equity are considered "non-GAAP financial measures" under the SEC rules. These non-GAAP financial measures supplement our GAAP disclosures, are subject to inherent limitations, and should not be considered in isolation or as an alternative to the GAAP measure. Management's reasons for using these non-GAAP financial measures and the reconciliations to their most directly comparable GAAP financial measures are posted in the Appendix. You should be aware that the Company's presentation of these measures may not be comparable to similarly-titled measures used by other companies.

TRADEMARKS - This presentation may include trademarks, service marks, trade names and copyrights of other companies, which are the property of their respective owners. Solely for convenience, some of the trademarks, service marks, trade names and copyrights referred to in this presentation may be listed without the TM, SM, (C), (R) or TM symbols, but Fortegra will assert, to the fullest extent under applicable law, the right of the applicable owners, if any, to these trademarks, service marks, trade names and copyrights.​

By leveraging insurance to manage uncertainty and risk, both businesses and individuals are empowered to seize bold opportunities in a rapidly evolving world.

A Specialty Insurer Focused on Consistency

CONSISTENT

Growth

Our deep market expertise and strategic approach to program business fuels sustainable growth.

26% CAGR

GWPPE(1)

CONSISTENT

Risk Management

We combine disciplined, quality

underwriting with aligned partner interests to enhance program performance.

91% Avg

Combined Ratio(1)

CONSISTENT

Profitability

Investments in systems, technology and talent strengthen the scalability of our operational framework.

29% CAGR

Adj Net Income(2)

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1. 2018-Q2'23 TTM
2. 2018-Q2'23 TTM. See appendix for reconciliation of Non-GAAP measures, including Adjusted Net Income.

Strategic Evolution Into A Global Specialty Insurer

Add fee revenue	Broadly	Expanded to	Expanded to	Program footprint
through motor club	licensed P&C	include	include	expands to
and premium finance	companies	warranty lines	specialty lines	Europe

1978 - 2010

Monoline

Credit Insurer

2011 - 2012

Multiline

Insurer

2013 - 2018

Multiline

Specialty Insurer

2019 - 2023+

Global Specialty

Insurer

Life of the	Summit Partner	Fortegra	Acquired by	$1.0B+	Warburg Pincus	$2.0B+	$3.0B+
South founded	investment	IPO	Tiptree	GWPPE(1)	investment	GWPPE(1)	GWPPE(1)
1978	2007	2010	2014	2018	2021	2021	2023

Since 2005, Fortegra grew from $242M(2) of GWPPE to over $3.0B(3) while maintaining underwriting profitability.

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1. Gross Written Premium and Premium Equivalents
2. Gross Written Premium and Premium Equivalents - YTD as of December 31, 2005
3. Gross Written Premium and Premium Equivalents - TTM as of June 30, 2023