Cash flow generation remains highly erratic, evidenced by the OCF/NI ratio swinging from 21.09 in 2025Q3 to a negative 0.59 in 2026Q1.
| Metric | TTM | Dec'25 | Dec'24 | Dec'23 | Dec'22 | Dec'21 | Dec'20 | Dec'19 | Dec'18 | Dec'17 | Dec'16 | Dec'15 | Dec'14 | Dec'13 | Dec'12 | Dec'11 | Dec'10 | Dec'09 | Dec'08 | Dec'07 |
|---|
| Cash from Operations | 193.2M | 168.22M | 240.76M | 71.45M | 463.07M | 204.32M | 140.17M | 23.74M | 57.72M | 46.92M | 36.64M | -6.29M | 91.05M | -18.39M | 626K | 7.83M | 1.44M | 6.65M | 13.03M | 11.87M |
| Operating CF Margin % | - | 34470.9% | 11.79% | 4.33% | 33.13% | 17.02% | 17.3% | 3.1% | 9.22% | 8.09% | 7.24% | -1.6% | 113.37% | -77.44% | 0.92% | 54.09% | 4.23% | 33.26% | 58.53% | 91.91% |
| Operating CF Growth % | 105.65% | -30.13% | 236.95% | -84.57% | 126.65% | 45.76% | 490.38% | -58.87% | 23.03% | 28.04% | 683.02% | -106.9% | 595.2% | -3037.06% | -92.01% | 443.54% | -78.35% | -48.93% | 9.75% | - |
| Net Income | 43.54M | 34.93M | 87.67M | 40M | 3.56M | 44.05M | -25.23M | 20.12M | 29.88M | 5.23M | 32.34M | 8.8M | 4.58M | 16.42M | -510K | 16.53M | 3.75M | -2.83M | -30.81M | -1.56M |
| Depreciation & Amortization | 706K | 191K | 21.65M | 23.47M | 22.97M | 24.44M | 17.58M | 13.57M | 12.6M | 29.99M | 28.54M | 45.12M | 10.87M | 6.52M | 3.97M | 3.61M | 69.54K | 3.42M | 1.55M | 725K |
| Stock-Based Compensation | 3.59M | 11.34M | 17.72M | 8.28M | 9.71M | 11.13M | 8.12M | 6.36M | 6.66M | 6.56M | 2.58M | 2.36M | 748K | 2.56M | 259K | 56K | 13.94M | 2.27M | 1.21M | 0 |
| Deferred Taxes | -13.57M | -6.58M | 31.14M | 37.02M | 47.55M | 17.73M | 10.73M | 6.82M | 4.01M | -11.25M | 6.45M | -19.55M | -249K | 2.23M | -86K | -12.86M | -22.24M | 12.17M | 12.6M | 0 |
| Other Non-Cash Items | 582.71M | 125.65M | 935.51M | -24.84M | 2.34B | 3.79B | 3.1B | 1.96B | 1.51B | 1.61B | 1.74B | 1.1B | 98.16M | -40.72M | 142K | -1.52M | 5.89M | -6.61M | 28.11M | 4.55M |
| Working Capital Changes | -452.44M | 2.68M | -852.94M | -12.47M | -1.96B | -3.68B | -2.98B | -1.99B | -1.5B | -1.6B | -1.78B | -1.14B | -31.32M | -5.4M | -3.15M | 2.01M | 24.66K | -1.77M | 358K | 8.15M |
| Change in Receivables | -246.54M | 0 | -149.94M | 0 | -295.25M | -152.83M | -116.84M | -119.48M | -67.38M | -53.26M | -35.19M | -102.96M | 0 | 0 | 0 | 0 | 68.01K | 0 | 0 | -3.14M |
| Change in Inventory | 0 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Change in Payables | 108.79M | 0 | -100.52M | 238.5M | 39.53M | 40.91M | 53.72M | 26.27M | 27.04M | 19.97M | 4.75M | 48.01M | 0 | 0 | -279M | 600M | -102.08K | 0 | 0 | 7.21M |
| Cash from Investing | -201.72M | -202.03M | -322.99M | -244.67M | 9.51M | -273.76M | -123.49M | -8.33M | -109.11M | 205.68M | -319.99M | -215.12M | -494.17M | -689.18M | 356K | 29.28M | -513.8K | 135.97M | -67.92M | -227.32M |
| Capital Expenditures | 1.12M | 0 | -4.03M | -14.03M | -10.73M | -2.76M | -6.69M | -8.52M | -3.75M | -2.89M | -7.16M | -5.66M | -245K | -13K | -29K | -260K | -289.54K | 0 | 0 | -204.27M |
| CapEx % of Revenue | 0.11% | - | 0.2% | 0.85% | 0.77% | 0.23% | 0.83% | 1.11% | 0.6% | 0.5% | 1.41% | 1.44% | 0.31% | 0.05% | 0.04% | 1.8% | 0.85% | - | - | 1581.54% |
| Acquisitions | 0 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Investments | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Other Investing | -253.94M | -195.86M | -6.48M | -15.02M | -28.01M | -12.42M | -17.52M | -18.63M | 15.61M | 203.4M | -145.81M | 16.82M | -589.06M | -546.62M | 299K | 29.54B | 0 | 98.04M | 0 | 46.46M |
| Cash from Financing | -33.85M | 11.48M | 6.29M | 113.41M | -115.19M | 73.73M | 31.75M | 36.93M | -2M | -194.41M | 276.95M | 243.66M | 506.83M | 739.56M | -6.86M | 10.16M | -1.42M | -51.91M | 71.38M | 230.76M |
| Debt Issued (Net) | 0 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Equity Issued (Net) | 2.69M | -6.6M | 0 | 0 | 180.19M | -8.14M | -13.89M | -9.09M | -14.11M | -7.3M | -43.75M | -3.98M | -39K | 3.74M | -72K | 0 | -1.36M | -4K | -8.33M | 210.16M |
| Dividends Paid | -7.46M | -9.07M | -24.82M | -13.73M | -7.78M | -5.41M | -5.57M | -5.5M | -4.78M | -3.5M | -3.19M | -3.31M | -370K | -366K | -5.57M | -4.12M | 0 | -13.78M | -14.28M | -3.57M |
| Share Repurchases | -5M | 0 | 0 | 0 | -1.73M | -8.14M | -13.89M | -9.09M | -14.11M | -7.3M | -43.75M | -3.98M | -39K | -2K | -72K | 0 | -1.36M | -4K | -8.33M | 0 |
| Other Financing | -32.55M | -44.03M | 501K | -16.27M | 13.18M | -3.65M | -6.71M | -4.11M | 1.77M | -224.64M | 195.94M | -1.06M | 486.3M | 519.85M | -100.94M | -264K | 2.1K | 0 | -1.01M | -826K |
| Net Change in Cash | -50.37M | 11.35M | -76.3M | -58.29M | 355.57M | -5.07M | 43.55M | 45.21M | -56.25M | 47.66M | -6.39M | 16.41M | -67.57M | 31.99M | -5.88M | 47.27M | -494.51K | 90.71M | 16.48M | 15.32M |
| Free Cash Flow | 194.32M | 168.22M | 236.72M | 57.42M | 452.35M | 201.55M | 133.47M | 15.22M | 53.98M | 44.03M | 29.48M | -11.95M | 90.8M | -18.4M | 597K | 7.57M | 1.15M | 6.65M | 13.03M | -192.4M |
| FCF Margin % | 18.5% | 34470.9% | 11.59% | 3.48% | 32.36% | 16.79% | 16.47% | 1.99% | 8.62% | 7.59% | 5.82% | -3.05% | 113.06% | -77.49% | 0.88% | 52.29% | 3.38% | 33.26% | 58.53% | -1489.63% |
| FCF Growth % | 38.44% | -28.94% | 312.25% | -87.31% | 124.43% | 51% | 776.8% | -71.8% | 22.58% | 49.34% | 346.79% | -113.16% | 593.52% | -3181.91% | -92.11% | 557.68% | -82.7% | -48.93% | 106.77% | - |
| FCF per Share | 5.14 | 4.48 | 6.24 | 1.53 | 12.73 | 5.98 | 3.94 | 0.44 | 1.55 | 1.18 | 0.93 | -0.36 | 5.41 | -1.79 | 0.06 | 0.73 | 0.11 | 0.22 | 0.41 | -6.15 |
| FCF Conversion (FCF/Net Income) | 4.46x | 4.82x | 4.51x | 5.12x | -55.97x | 5.36x | -4.81x | 1.29x | 2.41x | 13.02x | 1.45x | -1.09x | -53.24x | -1.77x | 0.05x | 0.47x | 0.38x | -2.35x | -0.42x | -7.62x |
| Interest Paid | 0 | 26.33M | 28.71M | 0 | 29.44M | 36.88M | 29.54M | 26.22M | 0 | 34.11M | 27.16M | 55.08M | 65.1M | 43.43M | 16.91M | 0 | 0 | 0 | 0 | 0 |
| Taxes Paid | 0 | 53.47M | 15.29M | 0 | 2.26M | 2.08M | 1.07M | 3.3M | 0 | 5.05M | 6.18M | 38.74M | 5.17M | 7.72M | 1.29M | 0 | 0 | 0 | 0 | 0 |
Deconsolidation obscures cash visibility
As reported in recent financial statements, Tiptree's OCF/NI ratio has exhibited extreme volatility, swinging from a high of 21.09 in 2025Q3 to a negative 0.59 in 2026Q1, indicating that net income is currently a poor proxy for the company's underlying cash-generating capacity.
The persistent divergence between net income and operating cash flow suggests that non-cash accounting adjustments and the deconsolidation of Fortegra are significantly distorting the quality of earnings. Investors should monitor whether this gap narrows as the new holding company structure stabilizes, as current figures appear to reflect accounting artifacts rather than operational cash conversion.
Based on the provided quarterly data, Tiptree's free cash flow trajectory has been highly erratic, shifting from a peak of $133.4 million in 2025Q3 to a negative $8.3 million in 2026Q1, reflecting the lumpy nature of cash flows in a post-deconsolidation environment.
The lack of a consistent FCF trend suggests that the company's cash flow profile is currently driven by episodic events rather than recurring operational performance. This volatility warrants further investigation into whether the holding company can maintain positive cash flow without the direct consolidation of its primary insurance subsidiary's premium inflows.
According to historical cash flow data, Tiptree has experienced massive working capital outflows, including a $280.1 million drain in 2025Q2, which suggests that the company's cash position is highly sensitive to the timing of insurance-related settlements and internal capital movements between the parent and its subsidiaries.
These significant working capital fluctuations appear to be the primary driver of the company's erratic operating cash flow, rather than changes in core business profitability. Analysts should interpret these swings as evidence of the complex liquidity management required within a deconsolidated holding company structure.
As indicated by recent filings, Tiptree has utilized $5.0 million for share repurchases in 2026Q1 despite negative operating cash flow, suggesting a management preference for returning capital to shareholders even when internal cash generation is temporarily pressured by the ongoing corporate restructuring.
The decision to prioritize buybacks and dividends while operating cash flow is negative may indicate management's confidence in the liquidity provided by the Fortegra stake sale. However, investors should monitor whether this capital deployment strategy remains sustainable if the holding company's cash reserves are not replenished by consistent dividend distributions from its underlying assets.
Quick answers to the most common questions about buying TIPT stock.
Tiptree Inc. (TIPT) generated $168.2M in net cash from operating activities in 2025. This reflects the cash generated directly from core business operations.
Tiptree Inc. (TIPT) generated $168.2M in free cash flow in 2025. Free cash flow is the cash left over after capital expenditures, which can be used to pay dividends, repurchase shares, or pay down debt.
Tiptree Inc. (TIPT) spent $0.0M on capital expenditures in 2025. CapEx represents the cash invested in physical assets like property, plant, and equipment to maintain or grow the business.
In 2025, Tiptree Inc. (TIPT) returned $9.1M to shareholders via cash dividends. This shows the company's commitment to returning capital to its equity investors.