On this page of StockholderLetter.com we present the latest annual shareholder letter from TIPTREE INC. — ticker symbol TIPT. Reading current and past TIPT letters to shareholders can bring important insights into the investment thesis.
2023 1
Annual percentage change in share price of Tiptree Inc. vs. equity indices as of 12/31/23*: 1 Year 3 Year 5 Year 10 Year From Inception (June 2007) *Including dividends Tiptree 38.4% 58.5% 29.8% 11.1% 10.6% Russell 2000 16.9% 2.2% 10.0% 7.2% 7.1% S&P 500 26.3% 10.0% 15.7% 12.0% 9.4% To Our Fellow Shareholders: 2023 was a year of strong performance for Tiptree. Our businesses continued to build upon their history of growth and profitability, producing an 18% increase in revenues to $1.6 billion for the year, and an adjusted return on equity of 15.2%. Tiptree s share price appreciation and dividends produced a total return of 38.4% for the year, compared to 16.9% for the Russell 2000 and 26.3% for the S&P 500. We are proud of our 2023 results, yet we keep a greater focus on long-term performance, and like to compare our results to other investment strategies. With this in mind, Tiptree s performance over three, five, and ten years (and since inception) are worth noting in the chart above. We are also pleased to have increased our quarterly dividend by 20% to $0.06 per share, payable to shareholders of record as of March 11, 2024. The Fortegra Group, our specialty insurance business under the leadership of CEO Rick Kahlbaugh, achieved record results for the year, with premium and premium equivalent growth of 21%, and an adjusted return on equity of 29%. Although the recent market environment was unconducive for a public offering, we firmly believe Fortegra is strategically positioned to maintain a trajectory of consistent topline growth and sustained underwriting profitability over the long-term. Tiptree Capital, our subsidiary through which we invest opportunistically in a broad range of assets and businesses, finished the year with a book value of $178 million consisting primarily of 1) cash, 2) our mortgage origination and servicing business, Reliance First Capital, and 3) a liquid investment portfolio. At Reliance, led by CEO Hugh Miller, origination volumes remained muted given the interest rate environment, although the income and sustained market value of our retained servicing book allowed the business to remain stable for the year; this performance contrasts significantly with the havoc taking place in the mortgage industry writ large. Given Reliance s proven nimbleness, we maintain a positive outlook for the business. We see greater potential for future profit as mortgage rates stabilize, in addition to the increased potential of finding bolt-on acquisitions. We are always looking for new investment opportunities, with the objective of generating attractive allweather , absolute returns. Having no set holding period and no risk of redemption of our capital gives us a distinct advantage, as we are able to take a long-term view on our outlook for returns. 1
Looking ahead, we see significant opportunities to expand our businesses and remain confident in the long-term outlook for the company. 2023 was a year of strong performance, with our businesses continuing their history of growth and profitability. Once again, we credit these results to the experience and expertise of Tiptree s team of professionals and those of our related companies. We begin 2024 well positioned financially, and we could not be more excited about Tiptree s future. We welcome any and all questions from our shareholders and look forward to speaking with you. With best regards, Michael Barnes Executive Chairman Jonathan Ilany Chief Executive Officer 2
 • shareholder letter icon 3/18/2024 Letter Continued (Full PDF)
 • stockholder letter icon 3/8/2023 TIPT Stockholder Letter
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TIPT Shareholder/Stockholder Letter Transcript:

2023
1

Annual percentage change in share price of Tiptree Inc. vs. equity indices as of 12/31/23*:
1 Year
3 Year
5 Year
10 Year
From Inception (June 2007)
*Including dividends
Tiptree
38.4%
58.5%
29.8%
11.1%
10.6%
Russell 2000
16.9%
2.2%
10.0%
7.2%
7.1%
S&P 500
26.3%
10.0%
15.7%
12.0%
9.4%
To Our Fellow Shareholders:
2023 was a year of strong performance for Tiptree. Our businesses continued to build upon their
history of growth and profitability, producing an 18% increase in revenues to $1.6 billion for the year,
and an adjusted return on equity of 15.2%. Tiptree   s share price appreciation and dividends produced a
total return of 38.4% for the year, compared to 16.9% for the Russell 2000 and 26.3% for the S&P 500.
We are proud of our 2023 results, yet we keep a greater focus on long-term performance, and like to
compare our results to other investment strategies. With this in mind, Tiptree   s performance over
three, five, and ten years (and since inception) are worth noting in the chart above. We are also pleased
to have increased our quarterly dividend by 20% to $0.06 per share, payable to shareholders of record
as of March 11, 2024.
The Fortegra Group, our specialty insurance business under the leadership of CEO Rick Kahlbaugh,
achieved record results for the year, with premium and premium equivalent growth of 21%, and an
adjusted return on equity of 29%. Although the recent market environment was unconducive for a public
offering, we firmly believe Fortegra is strategically positioned to maintain a trajectory of consistent topline growth and sustained underwriting profitability over the long-term.
Tiptree Capital, our subsidiary through which we invest opportunistically in a broad range of assets and
businesses, finished the year with a book value of $178 million consisting primarily of 1) cash, 2) our
mortgage origination and servicing business, Reliance First Capital, and 3) a liquid investment portfolio.
At Reliance, led by CEO Hugh Miller, origination volumes remained muted given the interest rate
environment, although the income and sustained market value of our retained servicing book allowed the
business to remain stable for the year; this performance contrasts significantly with the havoc taking
place in the mortgage industry writ large. Given Reliance   s proven nimbleness, we maintain a positive
outlook for the business. We see greater potential for future profit as mortgage rates stabilize, in addition
to the increased potential of finding bolt-on acquisitions.
We are always looking for new investment opportunities, with the objective of generating attractive    allweather   , absolute returns. Having no set holding period and no risk of redemption of our capital gives us
a distinct advantage, as we are able to take a long-term view on our outlook for returns.
1

Looking ahead, we see significant opportunities to expand our businesses and remain confident in the
long-term outlook for the company. 2023 was a year of strong performance, with our businesses
continuing their history of growth and profitability. Once again, we credit these results to the
experience and expertise of Tiptree   s team of professionals and those of our related companies. We
begin 2024 well positioned financially, and we could not be more excited about Tiptree   s future.
We welcome any and all questions from our shareholders and look forward to speaking with you.
With best regards,
Michael Barnes
Executive Chairman
Jonathan Ilany
Chief Executive Officer
2



shareholder letter icon 3/18/2024 Letter Continued (Full PDF)
 

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