Tiptree Inc. Third Quarter 2021 Overview

Investor Presentation - Third Quarter 2021

November 2021

Financial Information for the three and nine months ended September 30, 2021

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.

SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

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 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 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 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 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

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, 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"). Certain of these data are considered "non-GAAP financial measures" under the SEC rules. These non-GAAP financial measures supplement our 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

Year-to-Date Highlights

($ in millions, except per share information)

Revenue

$881.0 million

59.3% vs. prior year

Overall

• Adjusted net income2 of $47.0 million, with a 16.2% adj ROAE2, driven by improvement in insurance, mortgage and shipping operations.
• On October 12, 2021, announced a $200 million investment in Fortegra from Warburg Pincus, which upon closing will result in an approximate 24% ownership of Fortegra on an as converted basis.

Net income1

$38.6 million

vs. prior year net loss

of $43.4 million

Adjusted Net Income2

$47.0million

33.4% vs. prior year

Book Value

per share2,3

$11.37

11.3% vs. 9/30/20

Insurance

• $1.7 billion of gross written premiums and premium equivalents (GWPPE)4, 44% increase from PY driven by all product lines.
• Combined ratio of 91.0% improved from 92.1% in PY driven by the continued scalability of Fortegra's technology and shared service platform, which improved the expense ratio, while the underwriting ratio remained stable.
• Adjusted net income of $46.4 million, up 56% from PY driven by revenue growth and improved combined ratio.
• Annualized Adjusted ROAE of 20.9%.

Tiptree Capital

• Mortgage Adjusted net income of $15.5 million and Adjusted ROAE of 33.3% as volumes and margins remain strong
• Shipping Adjusted net income improved to $8.1 million from $1.5 million in PY due to increased dry-bulk rates

1	Net income (loss) attributable to common stockholders.
2	For a reconciliation of Non-GAAP metrics Adjusted net income, adjusted return on average equity and book value per share to GAAP financials, see the Appendix.
3	Year-over-year total return defined as cumulative dividends paid of $0.16 per share plus book value per share as of September 30, 2021.	2
4	Gross written premium and premium equivalents are the base used to calculate the service fee income for non-insurance products. This base includes the amount charged to end consumers for a warranty or a car club membership.

Financial Results

($ in millions, except per share information)

	Q3'20		Q3'21		Q3'20		Q3'21
			YTD		YTD
Total Revenues	$224.0	$286.6	$552.9	$881.0
Net income (loss)	$12.8	$2.0	$(43.4)	$38.6
Diluted EPS	$0.35	$0.06	$(1.27)	$1.11
Adjusted net income1	$17.8	$20.7	$35.2	$47.0
Adjusted ROAE1	20.1%	20.5%	12.2%	16.2%
Total shares outstanding				33.6	33.9
Book Value per share1				$10.36	$11.37

Key Highlights - Q3'21

Revenuesup 31%, excluding the impact of investment gains/losses, and net income decreased by $10.8mm to $2.0mm

• Continued growth in Fortegra's earned premiums, service and administration fees and investment income
• Mortgage origination volumes and margins remain strong
• Increase in dry-bulk charter rates
• Offset by mark-to-market losses related to our investment in Invesque and other equities

Adjusted Net Income by business

		$20.7				$47.0	Tiptree Capital	Adj net incomeof $20.7mm, increased by 16% versus prior year
					$8.1	• Growth in Fortegra's revenues and improved combined ratio
	$17.8				$35.2	- Other
	$5.5			$15.5		• Improved operating performance in Tiptree Capital
	$0.5			$3.6	Mortgage
	$4.0
		$16.9	$19.5			• Partially offset by increased performance-based incentive compensation
$7.8	$11.9
	$7.3
$0.5
		$2.2		$46.4
$1.9		$19.5				Insurance
		$25.3	$29.8
$11.8	$12.1
								BVPSof $11.37 increased by 11.3% over prior year driven by net income
			$(17.9)	$(17.7)		Corporate
			$(23.0)	• Decrease of $0.22 from Q2'21 driven by exchange of dilutive securities
$(6.4)	$(6.7)	$(8.3)
Q3'19	Q3'20	Q3'21		Q3'19	Q3'20	Q3'21
				YTD	YTD	YTD

3

1 For a reconciliation of Non-GAAP metrics Adjusted net income, adjusted return on average equity and book value per share to GAAP financials, see the Appendix.

Tiptree Snapshot

($ in millions)

Adjusted Net Income1

$63.2

$45.9

	Q3'20 LTM	Q3'21 LTM
Shares	33.6	33.9
outstanding
Adj ROAE%	11.9%	16.5%

				Tiptree Sum of the Parts
					PF SOTP Value	Value/TIPT share
					$644 million2	$19.00
					(Transaction multiple)

$175 million

$5.16

(Book value ex. NCI)

Holding Company	$68 million2	$2.00
	(Book value)
	$887 million	$26.16

1) See the appendix for a reconciliation of Non-GAAP measures including Operating EBITDA	4
2)	Estimated Based on Warburg Pincus valuation multiple of 13.5x Adj. Net Income, multiplied LTM Adjusted Net Income of $60.0 million, multiplied by Tiptree's 79.5% ownership pro-forma as of closing date.
3)	Pro-forma Q3'21 Tiptree holdco book equity of $(72) million plus $140 million of transaction proceeds that will be used to extinguish $110 million of Fortress debt, assumed from Tiptree, and $30 million to repay notes to Tiptree, used for general corporate purposes.