Operating cash flow volatility is pronounced, with a $167.4 million outflow in 2026Q1 contrasting sharply with the $353.6 million inflow recorded in 2025Q2, complicating the sustainability of dividend payments.
| Cash from Operations | 619.08M | 643.67M | 514.87M | 477.2M | 335.51M | 273.49M | 135.39M | 149.51M |
| Operating CF Growth % | 82.81% | 25.02% | 7.89% | 42.23% | 22.68% | 102% | -9.44% | - |
| Operating CF / Revenue % | 19.61% | 21.1% | 20.47% | 22.97% | 19.45% | 19.09% | 13.3% | 19.54% |
| Net Income | 131.64M | 214.16M | 229.91M | 194.48M | 163.26M | 56.63M | 70.51M | 63.06M |
| Depreciation & Amortization | 298.38M | 287.51M | 167.63M | 115.84M | 109.29M | 112.68M | 67.5M | 53.1M |
| Stock-Based Compensation | 63.28M | 38.78M | 79M | 69.74M | 77.48M | 67.53M | 10.8M | 8.15M |
| Deferred Taxes | 12.54M | 26.05M | 24.22M | 36.66M | 14.54M | -1.15M | 203K | -800K |
| Other Non-Cash Items | -240.47M | 114.45M | 43.49M | 22.59M | 45.94M | 67.23M | 27.89M | 5.56M |
| Working Capital Changes | 249.47M | -37.28M | -29.38M | 37.9M | -74.99M | -29.44M | -41.51M | 20.44M |
| Cash from Investing | -274.24M | -834.01M | -1.76B | -476.23M | -22.42M | -457.94M | -768.51M | -148M |
| Capital Expenditures | -64.49M | -67.95M | -47M | -29.78M | -15.04M | -9.78M | -12.5M | -7.99M |
| Acquisitions | -190.84M | -746.49M | -1.71B | -446.68M | 0 | -108.88M | -741.46M | -144.4M |
| Purchase of Investments | -16.64M | -16.56M | 0 | 0 | 0 | 0 | 0 | 0 |
| Sale/Maturity of Investments | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Other Investing | -2.27M | -3.01M | 0 | 228K | -7.38M | -339.27M | -14.55M | 4.39M |
| Cash from Financing | -172.44M | 78.12M | 1.17B | -12.61M | 314.76M | 429.28M | 1.13B | 62.27M |
| Dividends Paid | -64.06M | -62.34M | -80.24M | -71.67M | -39.88M | -47.1M | -50.12M | -72.29M |
| Share Repurchases | -41.01M | -3.73M | -27.46M | -8.79M | -7.17M | -967.85M | -52.56M | -3.17M |
| Stock Issued | -164K | 0 | 0 | 0 | 0 | 1.45B | 0 | 0 |
| Debt Issuance (Net) | -3M | 1000K | 1000K | -1000K | 1000K | -1000K | 1000K | 1000K |
| Other Financing | 271.09M | 89.79M | -37.55M | 12.68M | -15.66M | 92.12M | 176.2M | 58.91M |
| Net Change in Cash | 173.02M | -96.33M | -75.53M | -11.05M | 627.72M | 243.96M | 493.54M | 64.05M |
| Exchange Rate Effect | 623K | 15.89M | -1.51M | 584K | -126K | -883K | 1.35M | 265K |
| Cash at Beginning | 1.58B | 1.68B | 1.76B | 1.77B | 1.14B | 895.7M | 402.16M | 338.11M |
| Cash at End | 1.48B | 1.58B | 1.68B | 1.76B | 1.77B | 1.14B | 895.7M | 402.16M |
| Free Cash Flow | 554.59M | 575.71M | 467.87M | 447.43M | 320.47M | 263.71M | 122.89M | 141.52M |
| FCF Growth % | 28.24% | 23.05% | 4.57% | 39.62% | 21.52% | 114.58% | -13.16% | - |
| FCF Margin % | 17.57% | 18.87% | 18.6% | 21.54% | 18.58% | 18.41% | 12.07% | 18.5% |
| FCF per Share | 4.28 | 2.07 | 1.7 | 3.56 | 1.21 | 2.49 | 1.15 | 1.33 |
Acquisition integration and talent costs
As evidenced by the quarterly data, Ryan Specialty exhibits significant volatility in underwriting cash generation, with net cash outflows reaching $167.4 million in 2026Q1, a sharp contrast to the $353.6 million inflow recorded in 2025Q2, highlighting the inherent lumpiness of specialty insurance premium and claim cycles.
The extreme variance in operating cash flow suggests that the firm's cash position is highly sensitive to the timing of large premium settlements and the subsequent remittance of claims. Investors should monitor whether these swings are indicative of seasonal underwriting patterns or a broader instability in the firm's ability to maintain consistent float levels.
According to the provided financial data, the relationship between net income and operating cash flow is highly inconsistent, with OCF/NI ratios fluctuating from -4.12 in 2026Q1 to 32.99 in 2025Q4, suggesting that GAAP earnings provide a limited view of the company's actual cash-generative capacity.
This disconnect implies that non-cash accruals and acquisition-related accounting adjustments significantly distort the firm's reported profitability. The reliance on adjusted metrics appears necessary to reconcile the gap between accounting income and the actual cash flows available for reinvestment or capital return.
Based on reported figures, Ryan Specialty has maintained consistent dividend payments despite periods of negative operating cash flow, such as the $16.8 million dividend distribution in 2026Q1 occurring alongside a $167.4 million cash burn, which warrants further investigation into the source of funding for these shareholder returns.
The persistence of dividend payments during quarters of significant cash outflow suggests that the firm may be utilizing balance sheet liquidity or external financing to support its capital return policy. This strategy may be sustainable in the short term, but it raises questions regarding the long-term durability of payouts if cash generation does not stabilize.
Financial statements indicate that claims payments are highly irregular, with spikes such as the $495.2 million outflow in 2026Q1, which appears to be a primary driver of the firm's recent cash flow volatility and suggests a potential mismatch between premium collection and loss settlement timing.
The magnitude of these claims payments relative to net income suggests that the firm's cash position is vulnerable to sudden, large-scale loss events. This dynamic may force the company to maintain higher levels of liquid assets than would otherwise be required, potentially impacting the efficiency of its capital allocation strategy.
Quick answers to the most common questions about buying RYAN stock.
Ryan Specialty Holdings, Inc. (RYAN) generated $643.7M in net cash from operating activities in 2025. This reflects the cash generated directly from core business operations.
Ryan Specialty Holdings, Inc. (RYAN) generated $575.7M 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.
Ryan Specialty Holdings, Inc. (RYAN) spent $68.0M 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, Ryan Specialty Holdings, Inc. (RYAN) returned $62.3M to shareholders via cash dividends and spent $3.7M on share repurchases. This shows the company's commitment to returning capital to its equity investors.