TIPT · Financials(fire, marine & casualty insurance) · 10 years of annual accounts filed with the SEC · latest fiscal year ended 2025-12-31
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Tiptree Inc. reported revenue of $488,000 in fiscal 2025, after shrinking 42.9% a year over the previous 9 years. Its operating margin narrowed from 93.4% in 2016 to -9574.6%, and it earned -9.1% on its invested capital in the latest year. Of the $1.5 billion its operations generated over 10 years, 16.0% went to acquisitions and 6.7% to buybacks. On the accounting screens, it passes 3 of 8 Piotroski tests and its Altman Z'' of 0.12 is in the distress zone; 2 of the six cross-checks between its statements fire.
Revenue, fiscal 2025488,000-42.9% a year over 9 years
Operating margin-9574.6%gross margin —
Return on invested capital-9.1%-3.1% on average over 5 years
Free cash flow after stock pay156.9M32146.7% of revenue
Net debt ÷ EBITDA-0.9×net debt 41.3M
Piotroski F-score3/8tests of improvement passed
Is it growing?
Revenue and the operating income it turns into. Growth that does not reach operating income is growth bought with margin.
RevenueOperating income
-100M0100M200M300M400M
2016Revenue 75.1MOperating income 70.2M
2017Revenue 66.2MOperating income 22.2M
2018Revenue 76.8MOperating income 7.2M
2019Revenue 89.0MOperating income 56.2M
2020Revenue 163.6MOperating income -6.3M
2021Revenue 258.6MOperating income 103.0M
2022Revenue 300.2MOperating income 84.3M
2023Revenue 341.4MOperating income -43.5M
2024Revenue 341.5MOperating income -40.3M
2025Revenue 488,000Operating income -46.7M
2016201720182019202020212022202320242025
Compound growth a year
3 yrs
5 yrs
9 yrs
Revenue
-88.2%
-68.7%
-42.9%
Net income
—
—
+3.6%
Free cash flow per share
-29.4%
+2.6%
—
Dividend per share
+3.3%
+8.0%
—
Shares
+1.9%
+2.1%
—
Falling shares are buybacks: each remaining share owns more of the company.
Does it earn more than its capital costs?
Margins say how much of each sale is kept; return on invested capital says how much the business earns on the money it needs to operate. Growth only creates value when that return is above the cost of the capital.
Needs a cost of capital, which comes from the valuation below.
Return on equity
6.9%
Return on assets
0.5%
Asset turnover
0.00×
Is the profit cash, and where does the cash go?
Net income is an accounting opinion; free cash flow is what was left in the bank after investing. Stock-based pay does not leave the bank — shareholders pay it through dilution — so it is shown taken off as well.
Net incomeFree cash flowAfter stock-based pay
-200M0200M400M600M
2016Net income 25.3MFree cash flow 35.2MAfter stock-based pay 32.4M
2017Net income 3.6MFree cash flow 45.2MAfter stock-based pay 38.3M
2018Net income 23.9MFree cash flow 54.0MAfter stock-based pay 47.3M
2019Net income 18.4MFree cash flow 15.2MAfter stock-based pay 8.9M
2020Net income -29.2MFree cash flow 133.5MAfter stock-based pay 125.4M
2021Net income 38.1MFree cash flow 201.6MAfter stock-based pay 190.4M
2022Net income -8.3MFree cash flow 452.3MAfter stock-based pay 442.6M
2023Net income 14.0MFree cash flow 67.4MAfter stock-based pay 61.1M
2024Net income 53.4MFree cash flow 240.7MAfter stock-based pay 232.0M
2025Net income 34.9MFree cash flow 168.2MAfter stock-based pay 156.9M
2016201720182019202020212022202320242025
Where 10 years of operating cash went, 2016–2025
1.5B generated by the business. Each band is its share of that total.
Reinvested in the business 3%39.8M
Acquisitions 16%232.9M
Dividends 5%70.5M
Share buybacks 7%98.0M
Kept, or used to pay down debt 70%1.0B
Over the same years it paid 77.8M in stock. 20.2M of the buybacks went beyond offsetting that dilution.
Per share
Earnings per shareFree cash flow per shareDividend per share
-$5$0$5$10$15
2016
2017
2018Earnings per share $0.69Free cash flow per share $1.55Dividend per share $0.14
2019Earnings per share $0.53Free cash flow per share $0.44Dividend per share $0.16
2020Earnings per share $-0.86Free cash flow per share $3.94Dividend per share $0.16
2021Earnings per share $1.13Free cash flow per share $5.98Dividend per share $0.16
2022Earnings per share $-0.23Free cash flow per share $12.73Dividend per share $0.22
2023Earnings per share $0.38Free cash flow per share $1.84Dividend per share $0.20
2024Earnings per share $1.45Free cash flow per share $6.53Dividend per share $0.50
2025Earnings per share $0.93Free cash flow per share $4.48Dividend per share $0.24
2016201720182019202020212022202320242025
Shares outstanding
Diluted shares
33M34M35M36M37M38M
2016
2017
2018Diluted shares 34.7M
2019Diluted shares 34.6M
2020Diluted shares 33.9M
2021Diluted shares 33.7M
2022Diluted shares 35.5M
2023Diluted shares 36.7M
2024Diluted shares 36.9M
2025Diluted shares 37.6M
2016201720182019202020212022202320242025
Debt and liquidity
Debt is not bad in itself; debt the business cannot service in a bad year is. Net debt is debt minus cash, and below zero the company holds more cash than it owes.
Net debt
-400M-200M0200M400M600M
2016Net debt 505.1M
2017Net debt 235.4M
2018Net debt 268.1M
2019Net debt 241.3M
2020Net debt 229.3M
2021Net debt 217.6M
2022Net debt -278.7M
2023Net debt -66.3M
2024Net debt -19.4M
2025Net debt 41.3M
2016201720182019202020212022202320242025
Net debt ÷ EBITDA
-0.9×
Interest coverage
— operating income ÷ interest
Current ratio
1.88 current assets ÷ current liabilities
Cash conversion cycle
—
Three classic screens of the accounts
Each asks a different question of the same statements — is it improving, does it look like a company heading for distress, do the accounts resemble ones that were manipulated. None is a verdict; each shows what moves it.
Piotroski F-score
Is the business improving? Nine yes-or-no tests, this year against last.
3of 8 tests passed
✓ProfitableReturn on assets above zeropassed
✓Cash from operationsOperating cash flow above zeropassed
✕Profitability improvedReturn on assets higher than a year beforefailed
✓Profit backed by cashOperating cash flow above net income (low accruals)passed
✕Less long-term debtLong-term debt as a share of assets fellfailed
✕More liquidCurrent ratio higher than a year beforefailed
✕No new sharesShare count did not growfailed
–Better gross marginGross margin higher than a year before — not reportedno data
✕Sells more per assetAsset turnover higher than a year beforefailed
Where it misleads: it measures change, not level. An excellent business that stood still for a year scores low; a poor one recovering from a disaster scores high.
Altman Z''-score
Does the balance sheet look like those of companies that went bankrupt?
0.12distress zone
1.12.6
Working capital ÷ assets 0.00 × 6.56+0.02
Retained earnings ÷ assets 0.02 × 3.26+0.06
Operating income ÷ assets -0.01 × 6.72-0.05
Equity ÷ liabilities 0.08 × 1.05+0.09
Where it misleads: buybacks. A company that returns so much cash that its equity turns small or negative sinks the last two ratios without being anywhere near bankruptcy. Banks and insurers do not fit the model at all.
Beneish M-score
Do the accounts resemble those of companies that manipulated their earnings?
The accounts lack too many of the lines it needs.
Where the statements disagree
Cross-checks between the income statement, the balance sheet and the cash flow for the latest year, each with the benign reading and the worrying one.
Capital spending (0M) is well below depreciation (1M).
Benign
Mature assets, or a business that has become less capital-intensive.
Worrying
Under-investing: today's profit is being held up by consuming tomorrow's capacity.
The effective tax rate is -12.8%.
Benign
A favourable geographic mix, or legitimate tax credits.
Worrying
Not sustainable; projecting it forward inflates the valuation.
What is it worth, under which assumptions?
A company is worth the cash it will generate, brought back to today. This model projects revenue with growth that fades over the years, applies a free cash flow margin, and discounts the result at the cost of capital. Every assumption says where it came from, and all of them can be changed.
With a free cash flow margin at or below zero in year ten, the business never generates cash for its owners and a DCF says nothing useful. Set a positive margin for year ten to see what it would take.
What it has filed lately
The last twelve months at the SEC, most important first: annual and quarterly reports, events, large holders and insiders.
Every Form 4 filed in the last twelve months, read line by line: 6 filings by 4 people. Open-market purchases and sales are counted apart from awards, option exercises and shares withheld for taxes.
Bought on the open market$78,9583 purchase(s) by 2 insider(s)
Sold on the open market—none in the period
Under pre-arranged plans—of the sales followed a 10b5-1 plan set months earlier
A Form 4 says what happened, when, how many shares and at what price. It does not say why: a sale can be diversification, a tax bill or a plan fixed months earlier, and an award is pay, not a purchase. Nothing here is a reason to buy or sell anything.
Which large funds report holding it
From the Form 13F of the 28 institutions followed on this site, as of the end of their last reported quarter. A 13F is filed up to 45 days later and shows only long positions in US-listed shares.
Accounts from the company's own SEC filings; lines some companies do not report are shown as a dash rather than estimated. The risk-free rate is the 10-year US Treasury yield. A DCF is a way of making assumptions explicit, not a forecast: it states what the company would be worth if the assumptions held. The scores are screens that point where to look, not verdicts. Nothing here is a recommendation to buy or sell.
