Tiptree : Overview-May 2024

Company Overview

May 2024

Disclaimers

LIMITATIONS ON THE USE OF INFORMATION

This presentation has been prepared by Tiptree Inc. and its consolidated subsidiaries ("Tiptree", "the Company" or "we") solely for informational purposes, and not for the purpose of updating any information or forecast with respect to Tiptree, its subsidiaries or any of its affiliates or any other purpose. Tiptree reports a non-controlling interest in certain operating subsidiaries that are not wholly owned. Unless otherwise noted, all information is of Tiptree on a consolidated basis before non-controlling interest. Neither Tiptree nor any of its affiliates 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. These materials and any related oral statements are not all-inclusive and shall not be construed as legal, tax, investment or any other advice. You should consult your own counsel, accountant or business advisors. 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. All information is as of March 31, 2024 unless otherwise noted.

SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS AND PROJECTIONS

This document contains "forward-looking statements" which involve risks, uncertainties and contingencies, many of which are beyond Tiptree'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," "confident," or similar expressions are intended to identify forward-looking statements. Such forward-looking statements include, but are not limited to, statements about Tiptree'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 the company's control, are difficult to predict and could cause actual results to differ materially from those expressed or forecast in the forward-looking statements. 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 Tiptree's Annual Report on Form 10-K, and as described in the Tiptree's 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 the forward-looking statements. Other unknown or unpredictable factors also could affect the forward-looking statements provided. Consequently, actual performance could be materially different from the results described or anticipated by the forward-looking statements. Given these uncertainties, one should not place undue reliance on these forward-looking statements. Except as required by the federal securities laws, Tiptree Inc. undertakes no obligation to update any forward-looking statements.

In light of the risks and uncertainties inherent in all projections, the inclusion of forward-looking statements and projections in this presentation should not be considered as a representation by us or any other person that our objectives or plans will be achieved. Numerous factors, including those described in Tiptree's Annual Report on Form 10‐K or in Tiptree's other filings with the SEC, could cause our actual results to differ materially from those expressed or implied in 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. Tiptree Inc. believes the data from third-party sources to be reliable based upon 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

This document does not constitute an offer or invitation for the sale or purchase of securities or to engage in any other transaction with Tiptree, 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, financial measures derived from consolidated financial data are sometimes used but not presented in the financial statements prepared in accordance with U.S. generally accepted accounting principles (GAAP). Certain of these data are considered "non-GAAP financial measures" under the SEC rules. These non-GAAP financial measures supplement GAAP disclosures and should not be considered 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.

1

Tiptree Overview

($ in millions)

Our Approach

Focus on		Value
	Oriented
Profitable
	Investment
Growth
	Approach
Patient Capital		Think Like
	Owners
Partner		(33% insider

ownership1)

Specialty

Fee-based

Financials,

Insurance

Services

Real Assets

Capital allocation and investment management

1◼ Long-term focus on total shareholder return while generating consistent earnings

2◼ Strong track record of returning capital to shareholders

3◼ Diversified capital allocation strategy with Fortegra as our largest operating business

Metrics2

$514mm equity	$1.3Bn investment
$127mm Adj. Net Income2	portfolio
Consistent, profitable	High-quality
underwriting	investment portfolio
Stable, predictable	Active management
loss exposures	of reinsurance
Substantial fee-based	Diversified sources
revenues	of earnings

$123mm equity

Investments in

operating companies

Select opportunistic

investments

Invest for

total return

Combines specialty insurance with investment management to drive attractive risk-adjusted returns

1	As of April 29, 2024.	2
2	Operating metrics represent Q1'24 last twelve months (LTM). Adjusted net income is presented before the impacts of non-controlling interests See appendix for reconciliation of non-GAAP measures.

17 Years of Value Creation

($ in millions)

Tiptree formed as a permanent capital vehicle (June 2007)

2007

Tiptree publicly

listed on NASDAQ (TIPT) (July 2013)

Shareholder Total Return (as of March 31, 2024)

	Tiptree	Russell	S&P
	2000	500
1 Year	20.0%	19.7%	29.9%
3 Year	27.5%	(0.1)%	11.5%
5 Year	24.1%	8.1%	15.0%
From Jun'071	10.0%	7.3%	9.9%

• $97 million of share repurchases since 2014
• $52 million of common dividends paid to shareholders

Strategy

• Experienced management team focused on insurance, asset management, specialty finance, infrastructure and real assets
• Invest in businesses that meet the following criteria:
• • Strong and experienced management teams
  • Attractive and stable cash returns
  • Scalable business models with upside potential

1 Based upon a starting point of Tiptree's founding in 2007 and book value per share of $5.36. Cumulative dividends paid from 2007 to March 31, 2024, total $3.10 per share.

3

Track Record of Realized IRRs in Excess of 20%

($ in millions)

					Invested		Realized
	Realized		Current		Capital	Investments1	IRR%2
Insurance &					$63		$150		23%
Insurance Services

Asset	$176	$306	30%
Management
(including credit investments)	+ Cash and U.S. Government Securities

Infrastructure &	$408	$485	9%

Real Assets

Specialty	$71		$148		23%
Finance

	$718	$1,089	22%
1	Realized Investment represents total realized proceeds including cash distributions and cash or marketable securities received upon realization event.		4
2	IRR% presented gross before corporate taxes and corporate expenses. IRR represents the internal rate of return on invested capital based on the realized proceeds of cash or marketable securities and including the

timing of contributions and distributions. Tiptree's IRR% calculation reflects the impact of asset specific leverage and may differ from those used by others. Past performance is not indicative of future results.

Continuing to Build Value

($ in millions)

Adjusted Net Income1

$69.9

$50.9

LTM LTM

Q1'23 Q1'24

Adj ROAE%1

13.3%

16.9%

LTM		Transaction	Peer
Adj. NI		Multiple	Multiples

$127 million1	13.5x2	12x - 32x6
48% year-over-year	70% diluted	(Median 18x)
growth	ownership3

Book value

$151 million4

100% ownership

Total Diluted Shares

38.1 million5

1	See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income and Adjusted return on average equity (annualized). Fortegra Adjusted Net Income is presented before the impacts of non-controlling interests.
2	Based on Warburg Pincus valuation trailing multiple of 13.5x adjusted net income at deal signing in September 2021.
3	Tiptree's 70.4% as converted ownership as of Q1'24 (including impact of employee stock awards at Fortegra) assuming valuation at 13.5x trailing adjusted net income.
4	Includes Tiptree Inc. stockholders' equity of Mortgage, Tiptree Capital - Other and Corporate, excluding the deferred tax liability relating to Tiptree's investment in Fortegra.	5
5	Diluted shares as of March 31, 2024, represents basic outstanding shares of 36,781,281 plus dilutive shares of 1,350,723 which includes unvested Tiptree RSUs and outstanding Tiptree options (assumed to be exercised cashless).
6	Peer multiples include AFG, AIZ, KNSL, MKL, PLMR, RLI, SKWD, WRB and represent share price as of 4/26/2024 over trailing twelve months normalized EPS as of 12/31/2023. Source: S&P Capital IQ.

Specialty Insurance Overview

Fortegra Overview

($ in millions)

• Established, growing, specialty insurer that focuses on niche insurance & capital-light fee business.
• Long standing track record of disciplined and stable underwriting results, generating highly consistent and attractive returns.

91%	29% Q1'24 LTM	$514mm
5-year Average	Adjusted	Q1'24 GAAP
Combined Ratio	ROAE2	Equity
A- A.M. Best &	95%+	25 years
5-year Agent	Average Mgmt.
KBRA Ratings
Persistency Rate	Experience

• Underwrite and administer niche or midmarket specialty risks utilizing agent distribution model.
• Opportunistic allocation of capital through combining insurance underwriting and fee-based revenues.
• Scalable technology & deep industry expertise provide the foundation to be a global market leader in specialty insurance.

Growth in GWPPE¹

					$2,748	$2,790
			$1,936	$2,263
$939	$1,090	$1,430
2018	2019	2020	2021	2022	2023	Q1'24
						LTM

Differentiated approach has led to robust growth, consistent profitability & high cash flows

1	Gross written premium & premium equivalents.	7
2	Adjusted return on average equity (annualized) is presented before non-controlling interests.

Underwriting & Fees Support Consistent & Sustainable Growth

Key Highlights

✓ Diversified and complementary business mix focused on

underserved specialty insurance markets

Lines of Business

Q1'24 LTM

GWPPE(1)

$2.8Bn

E&S

✓	Agent-centric distribution model leveraging independent &
	retail agent networks while maintaining economic alignment
✓	Complementary mix of underwriting & fee revenue leads to
	more stable earnings

Insurance

30%

Admitted

Insurance

57%

Services

13%

Diversified Revenue Sources

Service and

administrative

fees 24%

Earned

premiums, net

71%

Other revenue(2) 5%

1 Gross written premiums & premium equivalents.).

2 Includes ceding commissions, net investment income & other revenue, excluding net realized & unrealized gains (losses).

		Personal
		Insurance
		(14%)
Professional	General	Personal
Liability	Services
Liability	13%
9%
(13%)
12%	Auto
		Consumer
		Warranty	Other
		11%
		Services
Contractual			2%
Liability			Europe
14%			5%
	Property and
Commercial	Short-tail
22%	Alternative Risks
Insurance
(73%)			12%

8

Highly Profitable and Growing

($ in millions)

Total Revenues by Revenue Stream

Earned Premiums, Net

Service & Administrative Fees

Other Income(1)

						$1,597	$1,700
						76
						73
					$1,269	396	414
					44
				$986	321
				40
		$628	$703	261
	$556	38				1,210
$490	26	23	187			1,128
106
23	102				905
95
			686
372	428	499	478
2017	2018	2019	2020	2021	2022	2023	Q1'24
							LTM

Combined Ratio

92%

92%

92%

91%

90%

90%

90%

90%

Adjusted Net Income²

							$127
						$116
					$84
				$67
			$43
$26	$31	$33
2017	2018	2019	2020	2021	2022	2023	Q1'24
							LTM

Adjusted ROAE2

11%

12%

12%

15%

22%

26%

29%

29%

1	Includes ceding commissions, net investment income, & other revenues, excludes net realized & unrealized gains (losses).	9
2	See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income (before non-controlling interests) and Adjusted return on average equity (annualized).