Exhibit 99.1

TIPTREE REPORTS Q1 2020 RESULTS


•	Revenues of $129.7 million, a decrease of $54.2 million or 29.5% from the prior year period, primarily driven by net unrealized losses of $83.9 million on investments impacted by market disruptions in Q1 2020.


•	Excluding net unrealized losses, revenues were up 18.7% and Operating EBITDA⁽¹⁾of $15.8 million increased 25.4% from the prior year period, primarily driven by improved performance in Tiptree Insurance.


•	Book value per share of $9.73 as of March 31, 2020, a decrease of 15.2% (including dividends), driven by the unrealized mark-to-market losses on our investment in Invesque and other securities in our insurance investment portfolio.


•	Declared a dividend of $0.04 per share to stockholders of record on May 18, 2020 with a payment date of May 25, 2020.

New York, New York - May 7, 2020 - Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), a holding company that combines specialty insurance operations with investment management, today announced its financial results for the three months ended March 31, 2020.



($ in millions, except per share information)	Three Months Ended March 31,
GAAP:	2020			2019
Total revenues	$	129.7		$	183.9
Net income (loss) attributable to common stockholders	$	(60.0	)	$	3.9
Diluted earnings per share	$	(1.74	)	$	0.11
Cash dividends paid per common share	$	0.040		$	—

Non-GAAP: ⁽¹⁾
Operating EBITDA	$	15.8		$	12.6
Adjusted EBITDA	$	(70.9	)	$	14.6
Book value per share	$	9.73		$	11.12

(1) For further information relating to the Company’s Operating EBITDA, Adjusted EBITDA and Book value per share, including a reconciliation to GAAP financials, see “—Non-GAAP Reconciliations” below.

Earnings Conference Call

Tiptree will host a conference call on Thursday, May 8, 2020 at 9:00 a.m. Eastern Time to discuss its Q1 2020 financial results. A copy of our investor presentation, to be used during the conference call, as well as this press release, will be available in the Investor Relations section of the Company’s website, located at www.tiptreeinc.com.

The conference call will be available via live or archived webcast at http://www.investors.tiptreeinc.com. To listen to a live broadcast, go to the site at least 15 minutes prior to the scheduled start time in order to register, download and install any necessary audio software. To participate in the telephone conference call, please dial 1-877-407-4018 (domestic) or 1-201-689-8471 (international). Please dial in at least five minutes prior to the start time.

A replay of the call will be available from Friday, May 8, 2020 at 1:00 p.m. Eastern Time, until midnight Eastern on Friday, May 15, 2020. To listen to the replay, please dial 1-844-512-2921 (domestic) or 1-412-317-6671 (international), Passcode: 13701122.

Financial Overview

Overall:


•	Book value per share of $9.73 as of March 31, 2020, a decrease of 15.2% (including dividends), driven by the unrealized mark-to-market losses on our investment in Invesque and other securities in our insurance investment portfolio.

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•	In February 2020, we refinanced our existing facility with Fortress, extending the maturity to February 2025, and increasing the principal amount to $125 million.


•	Cash and cash equivalents of $108.8 million as of March 31, 2020, of which $84.0 million resides outside our statutory insurance subsidiaries.


•	We purchased and retired 583,131 shares of our common stock for $3.9 million.

Tiptree Insurance:


•	Gross written premiums were $276.8 million, up 39.5% from the prior year period, driven by growth in all product lines. Net written premiums were $132.5 million, up 9.5%, driven by growth in warranty and specialty programs.


•	Pre-tax loss in Tiptree Insurance was $27.1 million, driven primarily by unrealized mark-to-market losses of $33.6 million on equities, loans, and other securities held at fair value, as the markets reflected concerns over the impact of the shut-down of the economy caused by social distancing and other mitigation efforts as a result of COVID-19.


•	Tiptree Insurance Operating EBITDA was $14.3 million, up $0.6 million, reflecting the growth in premiums above.


•	In January 2020, we acquired Smart AutoCare, a vehicle warranty solutions provider in the United States. The transaction valued the business at $160 million of enterprise value, representing a multiple of 8.3x modified cash EBITDA.

Tiptree Capital:


•	The pretax loss in Tiptree Capital was $46.3 million, primarily driven by the unrealized mark-to-market loss of $48.5 million on our investment in Invesque. Operating EBITDA grew year over year, driven by the inclusion of a full quarter of operations for all five vessels in our maritime transportation business.


•	In April 2020, Invesque announced they were suspending their dividend to conserve liquidity until the impact of COVID-19 on their occupancy and operations is better known.

Consolidated Results of Operations

Revenues

For the three months ended March 31, 2020, revenues were $129.7 million, which decreased $54.2 million, or 29.5%. The decrease was primarily driven by net unrealized losses of $83.9 million on Invesque, other equity holdings, loans at fair value and other securities impacted by market disruptions due to the COVID-19 pandemic in the first quarter of 2020. Excluding net unrealized losses, revenues were up 18.7%, primarily driven by improved performance in Tiptree Insurance. Earned premiums and service and administrative fees were $165.0 million for the three months ended March 31, 2020, up $20.1 million, or 13.9%, driven by growth in net written premiums and warranty service contracts. The combination of unearned premiums and deferred revenues on the balance sheet grew by $368.7 million, or 55.5%, from March 31, 2019 to March 31, 2020 as a result of increased written premiums, primarily in credit protection and warranty programs, in addition to the acquisition of Smart AutoCare which contributed $158.4 million of growth in deferred revenues.

The table below provides a break down between net realized and unrealized gains and losses from Invesque and from other securities which impacted our consolidated results on a pre-tax basis. Many of our investments are carried at fair value and marked to market through unrealized gains and losses. As a result, we expect our earnings relating to these investments to be relatively volatile between periods, which is highlighted by the recent market declines caused by uncertainly regarding the impact of COVID-19 and oversupply in the oil markets. Our fixed income securities are primarily marked to market through accumulated other comprehensive income (AOCI) in stockholders’ equity and do not impact net realized and unrealized gains and losses until they are sold.



($ in millions)	Three Months Ended March 31,
	2020			2019
Net realized and unrealized gains (losses)⁽¹⁾	$	(25.2	)	$	1.5
Net realized and unrealized gains (losses) - Invesque	$	(58.7	)	$	2.5

____________________________

⁽¹⁾ Excludes Invesque, Mortgage realized and unrealized gains and losses and NPLs.

Net Income (Loss) Attributable to Common Stockholders

For the three months ended March 31, 2020, net loss available to common stockholders was $60.0 million, a decrease of $63.9 million. The decrease was primarily driven by the same factors that impacted revenues.

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Non-GAAP

Management uses Operating EBITDA, Adjusted EBITDA and book value per share as measurements of operating performance which are non-GAAP measures. Management believes the use of Operating EBITDA and Adjusted EBITDA provides supplemental information useful to investors as they are frequently used by the financial community to analyze financial performance, and to analyze a company’s ability to service its debt and to facilitate comparison among companies. Management uses Operating EBITDA as part of its capital allocation process and to assess comparative returns on invested capital amongst our businesses and investments. Adjusted EBITDA is also used in determining incentive compensation for the Company’s executive officers. Operating EBITDA and Adjusted EBITDA are not measurements of financial performance or liquidity under GAAP and should not be considered as an alternative or substitute for GAAP net income. Management believes the use of book value per share provides supplemental information useful to investors as it is frequently used by the financial community to analyze company growth on a relative per share basis.

Operating EBITDA for the three months ended March 31, 2020 was $15.8 million, an increase of $3.2 million, or 25.4%. For the three months ended March 31, 2020, the key drivers of the increase were driven by improved performance in Tiptree Insurance.

Total stockholders’ equity was $344.4 million as of March 31, 2020 compared to $394.6 million as of March 31, 2019. The decrease was primarily driven by the net loss in the period, dividends paid, and net share repurchases. Over the past twelve months, Tiptree returned $10.7 million to shareholders through share repurchases and dividends paid. Book value per share for the period ended March 31, 2020 was $9.73, an decrease from book value per share of $11.12 as of March 31, 2019. The key drivers of the period-over-period impact were losses per share and dividends paid of $0.16 per share. The decrease was partially offset by the purchase of 0.6 million shares at an average 41% discount to book value.

Results by Segment

We classify our business into one reportable segment, Tiptree Insurance, with the remainder of our non-insurance operations aggregated into Tiptree Capital. Corporate activities include holding company interest expense, corporate employee compensation and benefits, and other expenses, including, but not limited to, public company expenses. The following table presents the components of total pre-tax income.

Pre-tax Income



($ in millions)	Three Months Ended March 31,
	2020			2019
Tiptree Insurance	$	(27.1	)	$	8.1
Tiptree Capital	(46.3		)	5.9
Corporate	(8.4		)	(8.9		)
Pre-tax income (loss)	$	(81.8	)	$	5.1

Operating EBITDA - Non-GAAP⁽¹⁾

The following tables present the components of Operating EBITDA.



($ in millions)	Three Months Ended March 31,
	2020			2019
Tiptree Insurance	$	14.3		$	13.7
Tiptree Capital	6.1			4.7
Corporate	(4.6		)	(5.8		)
Operating EBITDA⁽¹⁾	$	15.8		$	12.6


(1)	For further information relating to the Company’s Operating EBITDA, including a reconciliation to pre-tax income, see “—Non-GAAP Reconciliations.”

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About Tiptree

Tiptree Inc. (NASDAQ: TIPT) is a holding company that allocates capital across a broad spectrum of businesses, assets and other investments. Our principal operating business, Tiptree Insurance, along with its subsidiaries, is a leading provider of specialty insurance, warranty products and related administration services. We also allocate capital to a diverse group of select investments that we refer to as Tiptree Capital. For more information, please visit www.tiptreeinc.com.

Forward-Looking Statements

This release contains “forward-looking statements” which involve risks, uncertainties and contingencies, many of which are beyond the Company’s control, which may cause actual results, performance, or achievements to differ materially from anticipated results, performance, or achievements. All statements contained in this release 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,” or similar expressions are intended to identify forward-looking statements. Such forward-looking statements include, but are not limited to, statements about the Company’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 the Company’s Annual Report on Form 10-K, and as described in the Company’s other filings with the Securities and Exchange Commission. 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.

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Tiptree Inc.

Condensed Consolidated Balance Sheet

($ in thousands, except share data)



	As of
	March 31, 2020		December 31, 2019
Assets:
Investments:
Available for sale securities, at fair value, net of allowance for credit losses	$	333,703	$	335,192
Loans, at fair value	79,177		108,894
Equity securities	129,022		155,378
Other investments	182,877		137,472
Total investments	724,779		736,936
Cash and cash equivalents	108,785		133,117
Restricted cash	45,416		11,473
Notes and accounts receivable, net	322,793		286,968
Reinsurance receivables	581,717		539,833
Deferred acquisition costs	176,821		166,493
Goodwill	163,623		99,147
Intangible assets, net	139,429		47,974
Other assets	74,346		68,510
Assets held for sale	84,963		107,835
Total assets	$	2,422,672	$	2,198,286

Liabilities and Stockholders’ Equity
Liabilities:
Debt, net	$	433,136	$	374,454
Unearned premiums	728,519		754,993
Policy liabilities and unpaid claims	195,464		144,384
Deferred revenue	304,622		94,601
Reinsurance payable	147,513		143,869
Other liabilities and accrued expenses	189,174		172,140
Liabilities held for sale	79,908		102,430
Total liabilities	$	2,078,336	$	1,786,871

Stockholders’ Equity:
Preferred stock: $0.001 par value, 100,000,000 shares authorized, none issued or outstanding	$	—	$	—
Common stock: $0.001 par value, 200,000,000 shares authorized, 34,302,131 and 34,562,553 shares issued and outstanding, respectively	34		35
Additional paid-in capital	323,064		326,140
Accumulated other comprehensive income (loss), net of tax	2,030		1,698
Retained earnings	8,725		70,189
Total Tiptree Inc. stockholders’ equity	333,853		398,062
Non-controlling interests	10,483		13,353
Total stockholders’ equity	344,336		411,415
Total liabilities and stockholders’ equity	$	2,422,672	$	2,198,286

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Tiptree Inc.

Condensed Consolidated Statements of Operations

($ in thousands, except share data)



	Three Months Ended March 31,
	2020			2019
Revenues:
Earned premiums, net	$	121,321		$	118,973
Service and administrative fees	43,724			25,895
Ceding commissions	6,525			2,504
Net investment income	3,488			4,301
Net realized and unrealized gains (losses)	(62,441		)	20,111
Other revenue	17,054			12,119
Total revenues	129,671			183,903
Expenses:
Policy and contract benefits	60,876			40,841
Commission expense	70,401			74,903
Employee compensation and benefits	38,501			29,153
Interest expense	7,551			6,920
Depreciation and amortization	3,863			3,094
Other expenses	30,230			23,837
Total expenses	211,422			178,748
Income (loss) before taxes	(81,751		)	5,155
Less: provision (benefit) for income taxes	(21,181		)	854
Net income (loss) before non-controlling interests	(60,570		)	4,301
Less: net income (loss) attributable to non-controlling interests	(563		)	376
Net income (loss) attributable to common stockholders	$	(60,007	)	$	3,925

Net income (loss) per common share:
Basic earnings per share	$	(1.74	)	$	0.11
Diluted earnings per share	$	(1.74	)	$	0.11

Weighted average number of common shares:
Basic	34,566,330			34,673,054
Diluted	34,566,330			34,673,054

Dividends declared per common share	$	0.04		$	0.04

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Tiptree Inc.

Non-GAAP Reconciliations (Unaudited)

Non-GAAP Financial Measures — Adjusted EBITDA and Operating EBITDA

The Company defines Adjusted EBITDA as GAAP net income of the Company adjusted to add (i) corporate interest expense, consolidated income taxes and consolidated depreciation and amortization expense, (ii) adjust for the effect of purchase accounting, (iii) adjust for non-cash fair value adjustments, and (iv) any significant non-recurring expenses. Operating EBITDA represents Adjusted EBITDA plus stock based compensation expense, less realized and unrealized gains and losses and less third party non-controlling interests. Operating EBITDA and Adjusted EBITDA are not measurements of financial performance or liquidity under GAAP and should not be considered as an alternative or substitute for GAAP net income.



($ in millions)	Three Months Ended March 31,
	2020			2019
Net income (loss) attributable to common stockholders	$	(60.0	)	$	3.9
Add: net (loss) income attributable to non-controlling interests	(0.6		)	0.4
Income (loss)	$	(60.6	)	$	4.3
Corporate debt related interest expense⁽¹⁾	5.3			5.0
Consolidated income tax expense (benefit)	(21.2		)	0.9
Depreciation and amortization expense⁽²⁾	3.8			3.0
Non-cash fair value adjustments⁽³⁾	(0.8		)	(0.6		)
Non-recurring expenses⁽⁴⁾	2.6			2.0
Adjusted EBITDA	$	(70.9	)	$	14.6
Add: Stock based compensation expense	1.7			1.4
Add: Vessel depreciation, net of capital expenditures	1.1			0.6
Less: Realized and unrealized gains (losses)⁽⁵⁾	(83.9		)	4.0
Operating EBITDA	$	15.8		$	12.6

_______________________________



(1)	Corporate debt interest expense includes interest expense from secured corporate credit agreements, junior subordinated notes and preferred trust securities. Interest expense associated with asset-specific debt in Tiptree Insurance and Tiptree Capital is not added-back for Adjusted EBITDA and Operating EBITDA.
(2)	Represents total depreciation and amortization expense less purchase accounting amortization related adjustments at our insurance companies. Following the purchase accounting adjustments, current period expenses associated with deferred costs were more favorably stated and current period income associated with deferred revenues were less favorably stated. Thus, the purchase accounting effect related to our insurance companies increased EBITDA above what the historical basis of accounting would have generated.
(3)	For our maritime transportation operations, depreciation and amortization is deducted as a reduction in the value of the vessel.
(4)	Acquisition, start-up and disposition costs, including debt extinguishment, legal, taxes, banker fees and other costs.
(5)	Adjustment excludes Mortgage realized and unrealized gains and losses - Performing and NPLs, as those are recurring in nature and align with those business models.

Non-GAAP Financial Measures — Adjusted EBITDA and Operating EBITDA

The tables below present Adjusted EBITDA and Operating EBITDA by business component.



	Three Months Ended March 31, 2020
($ in millions)	Tiptree Insurance			Tiptree Capital			Corporate Expenses			Total
Pre-tax income (loss)	$	(27.1	)	$	(46.3	)	$	(8.4	)	$	(81.8	)
Adjustments:
Corporate debt related interest expense⁽¹⁾	3.3			—			2.0			5.3
Depreciation and amortization expense ⁽²⁾	2.2			1.4			0.2			3.8
Non-cash fair value adjustments⁽³⁾	—			(0.8		)	—			(0.8		)
Non-recurring expenses⁽⁴⁾	2.2			—			0.4			2.6
Adjusted EBITDA	$	(19.4	)	$	(45.7	)	$	(5.8	)	$	(70.9	)
Add: Stock based compensation expense	0.3			0.2			1.2			1.7
Add: Vessel depreciation, net of capital expenditures	—			1.1			—			1.1
Less: Realized and unrealized gains (losses)⁽⁵⁾	(33.4		)	(50.5		)	—			(83.9		)
Operating EBITDA	$	14.3		$	6.1		$	(4.6	)	$	15.8

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	Three Months Ended March 31, 2019
($ in millions)	Tiptree Insurance		Tiptree Capital			Corporate Expenses			Total
Pre-tax income (loss)	$	8.1	$	5.9		$	(8.9	)	$	5.1
Adjustments:
Corporate debt related interest expense⁽¹⁾	3.4		—			1.6			5.0
Depreciation and amortization expense⁽²⁾	2.2		0.8			0.1			3.1
Non-cash fair value adjustments⁽³⁾	—		(0.6		)	—			(0.6		)
Non-recurring expenses⁽⁴⁾	1.3		—			0.7			2.0
Adjusted EBITDA	$	15.0	$	6.1		$	(6.5	)	$	14.6
Add: Stock based compensation expense	0.6		0.1			0.7			1.4
Add: Vessel depreciation, net of capital expenditures	—		0.6			—			0.6
Less: Realized and unrealized gains (losses)⁽⁵⁾	1.9		2.1			—			4.0
Operating EBITDA	$	13.7	$	4.7		$	(5.8	)	$	12.6

_______________________________

The footnotes below correspond to the tables above, under “—Adjusted EBITDA and Operating EBITDA - Non-GAAP”



(1)	Corporate debt interest expense includes interest expense from secured corporate credit agreements, junior subordinated notes and preferred trust securities. Interest expense associated with asset-specific debt in Tiptree Insurance and Tiptree Capital is not added-back for Adjusted EBITDA and Operating EBITDA.
(2)	Represents total depreciation and amortization expense less purchase accounting amortization related adjustments at our insurance companies. Following the purchase accounting adjustments, current period expenses associated with deferred costs were more favorably stated and current period income associated with deferred revenues were less favorably stated. Thus, the purchase accounting effect related to our insurance companies increased EBITDA above what the historical basis of accounting would have generated.
(3)	For our maritime transportation operations, depreciation and amortization is deducted as a reduction in the value of the vessel.
(4)	Acquisition, start-up and disposition costs, including debt extinguishment, legal, taxes, banker fees and other costs.
(5)	Adjustment excludes Mortgage realized and unrealized gains and losses - Performing and NPLs, as those are recurring in nature and align with those business models.

Non-GAAP Financial Measures — Book value per share

Management believes the use of this financial measure provides supplemental information useful to investors as book value is frequently used by the financial community to analyze company growth on a relative per share basis. The following table provides a reconciliation between total stockholders’ equity and total shares outstanding, net of treasury shares.



($ in millions, except per share information)	As of March 31,
	2020		2019
Total stockholders’ equity	$	344.4	$	394.6
Less: Non-controlling interests	10.5		11.0
Total stockholders’ equity, net of non-controlling interests	$	333.9	$	383.6

Total common shares outstanding	34.3		34.5

Book value per share	$	9.73	$	11.12

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Exhibit 99.2 NASDAQ: TIPT Investor Presentation - First Quarter 2020 May 2020 Financial information for the three months ended March 31, 2020

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," 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

Overview & Financial Highlights

Overview Financial Results First quarter 2020 highlights Revenue Overall þ 3 $129.7 million Year-to-date total return of (15.2)% , driven by unrealized mark-to-market losses reflecting the market disruptions caused by COVID-19 þ (29.5)% vs. prior Operating EBITDA of $15.8 million, up 25% driven by growth in insurance business and improved returns in Tiptree Capital year þ Refinanced our existing facility with Fortress (Feb'20), extending the maturity and increasing the principal amount to $125 million þ Cash and cash equivalents of $108.8 million as of March 31, 2020, of which $84.0 million resides outside our statutory insurance companies Net loss1 million $(60.6) Tiptree Insurance vs. prior year income of $4.3 þ million Gross written premiums of $277 million, up 40%, with net written premiums of $133 million, up 10%, driven by growth in warranty and specialty programs þ 2 Expect warranty sales growth to slow in Q2'20 as certain auto dealers and retail partners are impacted by the economic shut-down and Operating EBITDA social distancing measures þ $15.8 million Combined ratio of 93.3%, consistent with prior years þ 25.4% vs. prior year Acquired Smart AutoCare (Jan'20), a vehicle warranty solutions provider in the U.S. Book Value Tiptree Capital per share2 þ Operating EBITDA grew year over year, with a full quarter of shipping operations and steady performance from our mortgage business $9.73 þ In April'20, Invesque suspended its dividend to conserve liquidity until the impact of COVID-19 on its operations is better known (15.5)% vs. 12/31/19 1 Net income before non-controlling interests which Includes continuing and discontinued operations. 2 For a reconciliation of Non-GAAP metrics Operating EBITDA and book value per share to GAAP financials, see the Appendix. 3 Defined as cumulative dividends paid of $0.04 per share plus book value per share as of March 31, 2020 3

Financial Results ($ in millions, except per share information) Consolidated financial metrics Key drivers Q1'19 Q1'20 V% Highlights: • Revenues up 18.7%, excluding investment gains and losses, driven by Total Revenues $183.9 $129.7 (29.5)% improvement in Insurance top-line results (including Smart Auto acquisition) Net income (loss) before NCI $4.3 $(60.6) (1,509.3)% • Stable growth in insurance underwriting income & Operating EBITDA Diluted EPS $0.11 $(1.74) (1,681.8)% • Full quarter of results from our 5 vessels Operating EBITDA1 $12.6 $15.8 25.4 % Challenges: Adjusted EBITDA1 $14.6 $(70.9) (585.6)% • Earnings volatility from unrealized mark to market on our Invesque common Total shares outstanding 34.5 34.3 (0.6)% shares and other securities held at fair value 1 Book Value per share $ 11.12 $ 9.73 (12.5)% • Invesque dividend suspension will reduce Operating EBITDA beginning in Q2'20 Q1'20 Operating EBITDA to Pre-tax Income Bridge $15.8 Q1'20 $ (58.7) Invesque mark-to-market loss $ (23.2) Equities (non-Invesque) & other losses $ (2.0) Mark-to-market loss on MSR portfolio $(83.9) $(3.8) $(5.3) $(1.7) $(2.9) $(81.8) Operating Unrealized & Depreciation & Corporate Stock Based Transaction Costs & Total Pre-tax EBITDA Realized Gains2 Amortization Interest Expense Compensation Debt Extinguishment Losses expense 1 See the appendix for a reconciliation of Non-GAAP metrics including Operating EBITDA, Adjusted EBITDA and Book Value per share. 2 Excludes Mortgage realized and unrealized gains and losses - Performing and NPLs. 4

Capital Allocation ($ in millions, except per share information) Q1'20 financials by component Q1'20 Last Twelve Month Highlights Tiptree Total Operating Operating EBITDA of $66.9m, up 14.2% from Q1 2019 1,2 1 Equity Capital EBITDA • Return on average total capital (ROATC%) of 9.7% Business Lines Q1'20 Q1'20 Q1'20 LTM Tiptree Insurance: 13.2% ROATC% Tiptree Insurance $268.1 $531.4 $64.0 • Growth in insurance underwriting income and fee revenue - Underwriting $49.9 Reduced by $51.1m of acquisition • Continued growth in unearned premiums and deferred revenue - Investments purchase price amortization $14.1 (an indicator of future revenues) (or $1.49 per share after-tax) Tiptree Capital: 13.4% ROATC% Tiptree Capital $149.0 $149.0 $24.2 • $2.5m of dividends received from Invesque • Positive contributions from all investments Corporate $(83.2) $41.8 $(21.3) - Corporate expenses $(15.7) Recent transactions - Q1'20 - Corporate incentive comp expense $(5.6) • Acquired Smart AutoCare - Enterprise valuation of $160m, representing a multiple of 8.3x adjusted cash EBITDA Total Tiptree $333.9 $722.2 $66.9 - Corporate interest expense2 $(20.0) • Increased corporate debt facility to $125m - Total shares outstanding 34.3 1 See the appendix for a reconciliation of Non-GAAP metrics including Total Capital and Operating EBITDA. 2 Total Capital adds-back $208m Corporate Debt ($13.3m interest expense over LTM) and $55.1m accumulated amortization and acquisition costs (net of tax) in Tiptree Insurance and $125m Corporate Debt in Corporate ($6.7m interest expense over LTM). 5

Tiptree Insurance - Financial Performance Highlights ($ in millions) Financial metrics Q1'20 Highlights & Outlook Q1'19 Q1'20 V% 1 Continuing to expand through product offerings and onboarding new clients, Gross Written Premiums $198.4 $276.8 39.5 % with a focus on growth and stable profitability Revenue $154.6 $143.3 (7.3)% • $1,033m of unearned premiums and deferred revenue, representing 55.5% Pre-tax income (loss) $8.1 $(27.1) (434.6)% year-over-year growth ($158m from Smart AutoCare acquisition) 1 Net portfolio income (loss) $9.1 $(29.7) (426.4)% • Net written premiums grew by $11.5m, or 9.5% driven by growth in Combined ratio1 93.5% 93.3% (0.2)% warranty and specialty programs Total Capital1 $465.2 $531.4 14.2 % • Consistent profitability with combined ratio of 93.3% Unearned premiums & Deferred $664.4 $1,033.1 55.5 % revenue • Expect to see slowing sales growth and claims in Q2 in response to reduced economic activity, particularly in brick/mortar auto & retail warranty programs Insurance products 2 Produced stable underwriting results Operating Net Written Underwriting • Underwriting margin of $42.1m, up 29.5%, driven by strong performance EBITDA1 Premiums Margin1 in all product lines $14.3 $132.5 $42.1 $13.7 $121.0 Services/other • Continued investment in strategic growth initiatives, including premium finance 19.2 Specialty 2.7 3.2 9.2 3.9 Specialty Investments $32.5 4.1 22.8 Warranty 31.5 2.5 Warranty 2.0 14.6 8.5 3 Net portfolio loss of $29.7m, a reduction of $38.9m from prior year period Insurance 11.1 Credit Credit underwriting 9.6 89.0 81.8 • Decrease driven by realized and unrealized losses of $33.2m, versus gains of protection 20.9 protection & fees 19.5 $5.2m in the prior year 2018 2019 2018 2019 2018 2019 1 See the appendix for a reconciliation of Non-GAAP measures underwriting margin, combined ratio, Operating EBITDA and Investment Net portfolio income to GAAP financials. 7

Insurance Investment Portfolio ($ in millions) $529.0 19.3 Investment approach 1.8 31.3 $462.4 Other investments We manage our investment portfolio to achieve a balance of: 8.9 9.9 63.6 27.0 Real Estate • Short-term liquidity to cover claims obligations $399.7 6.3 16.7 19.3 16.8 71.6 Equities • Enhanced risk-adjusted returns through selective alternative investments 53.7 34.3 with a focus on longer-term higher yielding assets Corporate bonds 61.1 90.0 Loans2 13% Total Fixed Income: $407m (AA) 3 1% 5% 29.1 Cash & cash equivalents Cash & Equivalents — $19m Government & Agency — $181m Fixed income ETFs 11% 333.7 Fixed income ETFs — $54m 283.9 Available for sale Securities 45% AAA — $50m 212.8 13% AA — $54m A — $47m 12% BBB & below — $2m Q1'18 Q1'19 Q1'20 Financials1 Financial highlights $4.2 $4.3 $3.5 Net investment income 0.2 0.2 — Other income • Net investments grew $67m, or 14.4% from Q1'19, driven by growth in 5.1 0.2 (17.0) Realized gains net written premiums and the acquisition of Smart AutoCare (8.5) 1.9 (16.6) Unrealized gains (losses) (1.8) 3.1 0.4 Unrealized gains (losses) on AFS securities • $19m of cash and cash equivalents available to invest (1.2) (0.6) — Interest expense $(2.0) $9.1 $(29.7) Net Portfolio Income • Unrealized and realized losses of $26.1m on equities in Q1'20 compared 4 (2.1)% 2.0% (5.6)% Total Return % to gains of $1.8m in Q1'19 ($10.2m related to Invesque) $(5.5) $1.8 $(26.1) Equity realized & unrealized gains (losses) 1 See the appendix for a reconciliation of Non-GAAP measures Net Investments and Net Portfolio Income to GAAP financials. 2 Net of non-recourse asset based financing for 2018 period. 3 Cash and cash equivalents, plus restricted cash, net of due to/due from brokers[, cash pledged for securities sold but not purchased,] and borrowings under the revolving line of credit. See appendix for reconciliation to GAAP financials. 4 Total Return % represents the ratio of annualized net investment income, realized and unrealized gains (losses) (including on AFS securities which is included in AOCI) less investment portfolio interest expense to the average of the prior five quarters Net Investments. 8

Tiptree Capital - Financial Performance Highlights ($ in millions) Invested Capital1 Q1'20 Highlights & Outlook Seniors Housing (Invesque): $175.9 • Full quarter of dividends received from Invesque of $2.5m $151.4 29.7 $149.0 • Impacts from market conditions relating to COVID-19 Specialty finance & ◦ $48.5m of negative marks on common shares in Tiptree Capital 29.1 45.5 Other ◦ Invesque recently announced suspension of dividends to preserve liquidity and strengthen balance sheet 97.5 45.1 Seniors Housing (Invesque/Care)2 105.9 Maritime transportation Maritime transportation: 74.8 • Improvements driven by increased investment and full quarter of 48.7 operations on vessels purchased in 2019 • Improved demand in tanker sector driven by over-supply of oil globally, Q1'18 Q1'19 Q1'20 partially offset by dampening performance in dry-bulk sector 1 Return on Invested Capital Specialty finance/other: • Mortgage Operating EBITDA driven by strong origination volumes Pre-tax income Operating EBITDA • Mortgage pre-tax income impacted by $2.0m of mark to market losses Q1'19 Q1'20 Q1'19 Q1'20 on MSR portfolio Senior living (Invesque)2 4.6 (46.0) 2.5 2.5 Maritime transportation 0.5 1.2 1.1 2.5 Specialty finance/other 0.8 (1.5) 1.1 1.1 Total $5.9 $(46.3) $4.7 $6.1 1 See the appendix for a reconciliation of Operating EBITDA and Invested Capital to GAAP financials. 2 16.6m of Invesque common shares, 2.9m shares held in the insurance company investment portfolio. On balance sheet at fair value - $53.2 million, $44.0 million in Tiptree Capital. 10

Outlook ($ in millions) 1 Operating EBITDA Q1'20 Highlights ü Year-to-date returns negatively impacted by mark-to-market losses from broader market $15.8 conditions $12.6 ü Steady underlying operational performance in Q1'20 ü Continued execution on growth initiatives in our insurance operations ü Acquired Smart AutoCare and refinanced existing facility with Fortress Q1'19 Q1'20 Looking ahead BVPS & Dividends Paid1 1• Continue growth in insurance – Growth in written premiums while maintaining underwriting standards Dividends $ - paid $0.040 $11.12 – Expect softening in Q2'20 in certain sectors related to economic impacts of social distancing $9.73 Book value 2 Maintain focus on liquidity and business execution while navigating current market conditions per share 3• Focus on growing and improving long-term, net investment income Q1'19 Q1'20 1 See the appendix for a reconciliation of Book value per share and Operating EBITDA to GAAP financials. 11

Appendix

Non-GAAP Reconciliations Operating EBITDA and Adjusted EBITDA Management uses Operating EBITDA, Adjusted EBITDA and book value per share as measurements of operating performance which are non-GAAP measures. Management believes the use of Operating EBITDA and Adjusted EBITDA provides supplemental information useful to investors as it is frequently used by the financial community to analyze financial performance, and to analyze a company’s ability to service its debt and to facilitate comparison among companies. Management uses Operating EBITDA as part of its capital allocation process and to assess comparative returns on invested capital amongst our businesses and investments. Adjusted EBITDA is also used in determining incentive compensation for the Company’s executive officers. The Company defines EBITDA as GAAP net income of the Company adjusted to add consolidated interest expense, consolidated income taxes and consolidated depreciation and amortization expense as presented in its financial statements. Adjusted EBITDA represents EBITDA adjusted to (i) subtract interest expense on asset-specific debt incurred in the ordinary course of its subsidiaries’ business operations, (ii) adjust for the effect of purchase accounting, (iii) adjust for certain non-cash fair value adjustments, and (iv) any significant non-recurring expenses. Operating EBITDA represents Adjusted EBITDA plus stock based compensation expense, less realized and unrealized gains and losses and less third party non-controlling interests. Operating EBITDA and Adjusted EBITDA are not measurements of financial performance or liquidity under GAAP and should not be considered as an alternative or substitute for GAAP net income. Book value per share Management believes the use of book value per share provides supplemental information useful to investors as it is frequently used by the financial community to analyze company growth on a relative per share basis. Invested Capital and Total Capital Management evaluates the return on Invested Capital and Total Capital, which are non-GAAP financial measures, when making capital investment decisions. Invested Capital represents its total equity investment, including any re-investment of earnings, and acquisition costs, net of tax. Total Capital represents Invested Capital plus Corporate Debt. Management believes the use of these financial measures provide supplemental information useful to investors as they are frequently used by the financial community to analyze how the Company has allocated capital over-time and provide a basis for determining the return on capital to shareholders. Management uses both of these measures when making capital investment decisions, including reinvesting cash, and evaluating the relative performance of its businesses and investments. Insurance - Underwriting Margin We generally limit the underwriting risk we assume through the use of both reinsurance (e.g., quota share and excess of loss) and retrospective commission agreements with our partners (e.g., commissions paid adjust based on the actual underlying losses incurred), which manage and mitigate our risk. Period-over-period comparisons of revenues are often impacted by the PORCs and clients’ choice as to whether to retain risk, specifically with respect to the relationship between service and administration expenses and ceding commissions, both components of revenue, and the offsetting policy and contract benefits and commissions paid to our partners and reinsurers. Generally, when losses are incurred, the risk which is retained by our partners and reinsurers is reflected in a reduction in commissions paid. In order to better explain to investors the net financial impact of the risk retained by the Company of the insurance contracts written and the impact on profitability, we use the Non-GAAP metric - Underwriting Margin. Insurance - Combined Ratio Expressed as a percentage, the combined ratio represents the relationship of policy and contract benefits, commission expense (net of ceding commissions), employee compensation and benefits, and other expenses to net earned premiums, service and administrative fees, and other income. Investors use this ratio to evaluate our ability to profitably underwrite the risks we assume over time and manage our operating costs. As such, we believe that presenting underwriting margin and the combined ratio provides useful information to investors and aligns more closely to how management measures the underwriting performance of the business. Insurance Investment Portfolio - Net Investments and Net Portfolio Income In managing our investment portfolio we analyze net investments and net portfolio income, which are non-GAAP measures. Our presentation of net investments equals total investments plus cash and cash equivalents minus asset based financing of investments. Our presentation of net portfolio income equals net investment income plus realized and unrealized gains and losses and minus interest expense associated with asset based financing of investments. Net investments and net portfolio income are used to calculate average annualized yield, which management uses to analyze the profitability of our investment portfolio. Management believes this information is useful since it allows investors to evaluate the performance of our investment portfolio based on the capital at risk and on a non-consolidated basis. Our calculation of net investments and net portfolio income may differ from similarly titled non-GAAP financial measures used by other companies. Net investments and net portfolio income are not measures of financial performance or liquidity under GAAP and should not be considered a substitute for total investments or net investment income. 13

Non-GAAP Reconciliations - Adjusted and Operating EBITDA ($ in millions) Three Months Ended March 31, (1) Corporate debt interest expense includes interest expense from secured corporate credit agreements, junior subordinated notes and preferred trust securities. Interest expense associated with asset-specific debt in Tiptree 2020 2019 Insurance and Tiptree Capital is not added-back for Adjusted EBITDA and Operating EBITDA. Net income (loss) attributable to common stockholders $ (60.0) $ 3.9 (2) Represents total depreciation and amortization expense less purchase accounting amortization related adjustments at Add: net (loss) income attributable to non-controlling interests (0.6) 0.4 our insurance companies. Following the purchase accounting adjustments, current period expenses associated with Income (loss) $ (60.6) $ 4.3 deferred costs were more favorably stated and current period income associated with deferred revenues were less (1) favorably stated. Thus, the purchase accounting effect related to our insurance companies increased EBITDA above Corporate debt related interest expense 5.3 5.0 what the historical basis of accounting would have generated. Consolidated income tax expense (benefit) (21.2) 0.9 (3) For our maritime transportation operations, depreciation and amortization is deducted as a reduction in the value of Depreciation and amortization expense(2) 3.8 3.0 the vessel. Non-cash fair value adjustments(3) (0.8) (0.6) (4) Acquisition, start-up and disposition costs, including debt extinguishment, legal, taxes, banker fees and other costs. Non-recurring expenses(4) 2.6 2.0 (5) Adjustment excludes Mortgage realized and unrealized gains and losses - Performing and NPLs, as those are recurring in nature and align with those business models. Adjusted EBITDA $ (70.9) $ 14.6 (6) Add: Stock based compensation expense 1.7 1.4 Removes the Operating EBITDA associated with third party non-controlling interests. Does not remove the non- controlling interests related to employee based shares. Add: Vessel depreciation, net of capital expenditures 1.1 0.6 Less: Realized and unrealized gains (losses)(5) (83.9) 4.0 Less: Third party non-controlling interests(6) — — Operating EBITDA $ 15.8 $ 12.6 Total Adjusted EBITDA $ (70.9) $ 14.6 Total Operating EBITDA $ 15.8 $ 12.6 14

Non-GAAP Reconciliations - Adjusted and Operating EBITDA For the Three Months Ended March 31, 2020 Three Months Ended March 31, 2019 (1) Corporate debt interest expense includes interest expense Specialty Tiptree Corporate Specialty Tiptree Corporate ($ in millions) Insurance Capital Expenses Total Insurance Capital Expenses Total from secured corporate credit agreements, junior subordinated notes and preferred trust securities. Interest Pre-tax income (loss) $ (27.1) $ (46.3) $ (8.4) $ (81.8) $ 8.1 $ 5.9 $ (8.9) $ 5.1 expense associated with asset-specific debt in Tiptree Adjustments: Insurance and Tiptree Capital is not added-back for Adjusted EBITDA and Operating EBITDA. Corporate debt related interest expense(1) 3.3 — 2.0 5.3 3.4 — 1.6 5.0 (2) (2) Represents total depreciation and amortization expense less Depreciation and amortization expense 2.2 1.4 0.2 3.8 2.2 0.8 0.1 3.1 purchase accounting amortization related adjustments at our Non-cash fair value adjustments(3) — (0.8) — (0.8) — (0.6) — (0.6) insurance companies. Following the purchase accounting (4) adjustments, current period expenses associated with Non-recurring expenses 2.2 — 0.4 2.6 1.3 — 0.7 2.0 deferred costs were more favorably stated and current period Adjusted EBITDA $ (19.4) $ (45.7) $ (5.8) $ (70.9) $ 15.0 $ 6.1 $ (6.5) $ 14.6 income associated with deferred revenues were less favorably Add: Stock based compensation expense 0.3 0.2 1.2 1.7 0.6 0.1 0.7 1.4 stated. Thus, the purchase accounting effect related to our insurance companies increased EBITDA above what the Add: Vessel depreciation, net of capital expenditures — 1.1 — 1.1 — 0.6 — 0.6 historical basis of accounting would have generated. (5) Less: Realized and unrealized gains (losses) (33.4) (50.5) — (83.9) 1.9 2.1 — 4.0 (3) For our maritime transportation operations, depreciation and Operating EBITDA $ 14.3 $ 6.1 $ (4.6) $ 15.8 $ 13.7 $ 4.7 $ (5.8) $ 12.6 amortization is deducted as a reduction in the value of the vessel. (4) Acquisition, start-up and disposition costs, including debt extinguishment, legal, taxes, banker fees and other costs. (5) Adjustment excludes Mortgage realized and unrealized gains and losses - Performing and NPLs, as those are recurring in Trailing Twelve Months Ended March 31, 2020 nature and align with those business models. Specialty Tiptree Corporate (6) Removes the Operating EBITDA associated with third party ($ in millions) Insurance Capital Expenses Total non-controlling interests. Does not remove the non- Pre-tax income (loss) $ 5.8 $ (31.2) $ (32.4) $ (57.8) controlling interests related to employee based shares. Adjustments: Corporate debt related interest expense(1) 13.3 — 6.7 20.0 Depreciation and amortization expense (2) 8.6 4.4 0.8 13.8 Non-cash fair value adjustments(3) — (3.3) — (3.3) Non-recurring expenses(4) 4.6 0.2 — 4.8 Adjusted EBITDA $ 32.3 $ (29.9) $ (24.9) $ (22.5) Add: Stock based compensation expense 2.9 0.3 3.6 6.8 Add: Vessel depreciation, net of capital expenditures — 3.4 — 3.4 Less: Realized and unrealized gains (losses)(5) (28.8) (50.5) — (79.3) Less: Third party non-controlling interests(6) — 0.1 — 0.1 Operating EBITDA $ 64.0 $ 24.2 $ (21.3) $ 66.9 15

Non-GAAP Reconciliations - BVPS, Invested & Total Capital, Insurance Investment Portfolio ($ in millions, except per share information) As of March 31, Management uses Book value per share, which is a non-GAAP financial measure. Management believes the use of this financial measure 2020 2019 provides supplemental information useful to investors as it is frequently used by the financial community to analyze company growth on Total stockholders’ equity $ 344.4 $ 394.6 a relative per share basis. Tiptree’s book value per share was $9.73 as of March 31, 2020 compared with $11.12 as of March 31, 2019. Total Less: Non-controlling interests 10.5 11.0 stockholders’ equity, net of other non-controlling interests for the Company was $333.9 million as of March 31, 2020, which comprised total stockholders’ equity of $344.4 million adjusted for $10.5 million attributable to non-controlling interest at certain operating subsidiaries Total stockholders’ equity, net of non-controlling interests $ 333.9 $ 383.6 that are not wholly owned by the Company, such as Luxury and management interests in subsidiaries. Total stockholders’ equity, net of Total shares outstanding 34.3 34.5 other non-controlling interests for the Company was $383.6 million as of March 31, 2019, which comprised total stockholders’ equity of $394.6 million adjusted for $11.0 million attributable to non-controlling interest at subsidiaries that are not wholly owned by the Company. Book value per share $ 9.73 $ 11.12 ($ in millions) As of March 31, 2020 2019 Management evaluates the return on Invested Capital and Total Capital, which are non-GAAP financial measures, when making capital Total stockholders’ equity $ 344.4 $ 394.6 investment decisions. Invested capital represents its total cash investment, including any re-investment of earnings, and acquisition costs, net of tax. Total Capital represents Invested Capital plus Corporate Debt. Management believes the use of these financial measures Less: Non-controlling interests 10.5 11.0 provide supplemental information useful to investors as they are frequently used by the financial community to analyze how the Total stockholders’ equity, net of non-controlling interests - other $ 333.9 $ 383.6 Company has allocated capital over-time and provide a basis for determining the return on capital to shareholders. Management uses (1) Plus Insurance accumulated depreciation and amortization, net of tax 51.1 44.8 both of these measures when making capital investment decisions, including reinvesting distributable cash flow, and evaluating the Plus: Acquisition costs 4.0 4.2 relative performance of its businesses and investments. Invested Capital $ 389.0 $ 432.6 (1) As of March 31, 2020, add-back of $74.4 million of accumulated intangible amortization at our insurance companies. On Plus corporate debt(2) 333.2 238.7 as exchanged basis, assumes 35% tax rate on total accumulated amortization before 2018 and 21% post 2018. Total Capital $ 722.2 $ 671.3 (2) Corporate debt consists of Secured Corporate Credit Agreements, plus preferred trust securities. ($ in millions) As of March 31, 2020 2019 2018 Total Investments $ 509.7 $ 401.3 $ 467.2 (1) The insurance investment portfolio consists of insurance premiums written, cash generated from operations, and assets contributed by Investment portfolio debt (48.2) — (96.6) Tiptree. The investment portfolio of our regulated insurance companies, captive reinsurance company and warranty business are subject Securities sold, not yet purchased (32.5) — — to different regulatory considerations, including with respect to types of assets, concentration limits, affiliate transactions and the use of Cash and cash equivalents 78.5 58.7 27.2 leverage. Our investment strategy is designed to achieve attractive risk-adjusted returns across select asset classes, sectors and geographies Restricted cash (2) 33.1 1.0 3.1 while maintaining adequate liquidity to meet our claims payment obligations. (3) Receivable due from brokers — 1.4 2.9 (1) For 2019 and 2020, consists of borrowings under the revolving line of credit at our insurance company. For the 2018 and 2017 Liability due to brokers (3) (11.6) — (4.2) periods, consists of asset-based financing on loans, at fair value including certain credit investments, net of deferred financing costs, Net investments - Non-GAAP $ 529.0 $ 462.4 $ 399.6 see Note 11 - Debt, net for further details. (2) Restricted cash available to invest within certain credit investment funds which are consolidated under GAAP. ($ in millions) For the Three Months Ended March 31, (3) Receivable due from and Liability due to brokers for unsettled trades within certain credit investment funds which are consolidated 2020 2019 2018 under GAAP. Net investment income $ 3.5 $ 4.3 $ 4.2 (4) Average Annualized Yield % represents the ratio of annualized net investment income, other income, realized and unrealized gains (losses) less investment portfolio interest expense to the average of the prior two quarters (five quarters for trailing twelve months) Other income — 0.2 0.2 total investments less investment portfolio debt plus cash. Realized gains (losses) (17.0) 0.2 5.1 Unrealized gains (losses) (16.6) 1.9 (8.5) Unrealized gains (losses) on AFS securities 0.4 3.1 (1.8) Interest expense — (0.6) (1.2) Net portfolio income (loss) $ (29.7) $ 9.1 $ (2.0) Average Annualized Yield % (4) (5.6)% 2.0% (2.1)% 16

Non-GAAP Reconciliations - Insurance Combined Ratio, Underwriting Revenues & Margin ($ in millions) Three Months Ended March 31, The following table provides a reconciliation between underwriting margin and pre-tax income. We generally limit the underwriting risk Revenues: 2020 2019 we assume through the use of both reinsurance (e.g., quota share and excess of loss) and retrospective commission agreements with Net earned premiums $ 121.3 $ 119.0 our partners (e.g., commissions paid adjust based on the actual underlying losses incurred), which manage and mitigate our risk. Period- over-period comparisons of revenues are often impacted by the PORCs and clients’ choice as to whether to retain risk, specifically with Service and administrative fees 43.7 25.9 respect to the relationship between service and administration expenses and ceding commissions, both components of revenue, and the Ceding commissions 6.5 2.5 offsetting policy and contract benefits and commissions paid to our partners and reinsurers. Generally, when losses are incurred, the risk Other income 1.9 0.8 which is retained by our partners and reinsurers is reflected in a reduction in commissions paid. In order to better explain to investors the net financial impact of the risk retained by the Company of the insurance contracts written and the impact on profitability, we use Underwriting revenues - Non-GAAP $ 173.4 $ 148.2 the Non-GAAP metric - Underwriting Margin. Less underwriting expenses: Policy and contract benefits 60.9 40.8 Expressed as a percentage, the combined ratio represents the relationship of policy and contract benefits, commission expense (net of ceding commissions), employee compensation and benefits, and other expenses to net earned premiums, service and administrative Commission expense 70.4 74.9 fees, and other income. Investors use this ratio to evaluate our ability to profitably underwrite the risks we assume over time and manage Underwriting margin - Non-GAAP $ 42.1 $ 32.5 our operating costs. As such, we believe that presenting underwriting margin and the combined ratio provides useful information to Less operating expenses: investors and aligns more closely to how management measures the underwriting performance of the business. Employee compensation and benefits 17.0 12.0 Other expenses (excluding non-recurring expenses) 14.0 11.1 Combined Ratio 93.3% 93.5% Plus investment revenues: Net investment income 3.5 4.3 Net realized and unrealized gains (33.6) 2.1 Less other expenses: Interest expense 3.6 4.1 Non-recurring expenses 2.2 1.2 Depreciation and amortization expense 2.3 2.3 Pre-tax income (loss) $ (27.1) $ 8.2 17



Maryland	001-33549	38-3754322
(State or Other Jurisdiction of Incorporation)	(Commission File Number)	(I.R.S. Employer Identification No.)



299 Park Avenue, 13th Floor New York, New York		10171
(Address of Principal Executive Offices)		(Zip Code)



Title of each class	Trading Symbol(s)	Name of each exchange on which registered
Common Stock, par value $0.001 per share	TIPT	Nasdaq Capital Market




		TIPTREE INC.

Date:	May 7, 2020	By:	/s/ Jonathan Ilany
			Name: Jonathan Ilany
			Title: Chief Executive Officer



¨	Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)



¨	Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)



¨	Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))



Item 7.01	Regulation FD Disclosure.



Item 9.01	Financial Statements and Exhibits.