Tiptree [TIPT] vs Ryan Specialty [RYAN] Detailed Stock Comparison

Tiptree Inc.

NASDAQ
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Ryan Specialty Holdings Inc.

NYSE
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TLDR: Quick Comparison Summary

Based on 20 vital metrics comparison: Tiptree Inc. wins in 8 metrics, Ryan Specialty Holdings Inc. wins in 12 metrics, with 0 ties. Ryan Specialty Holdings Inc. appears stronger overall.

View Metrics Details

Vital Metrics Comparison

Metric Tiptree Inc. Ryan Specialty Holdings Inc. Better
P/E Ratio (TTM) 14.14 77.21 Tiptree Inc.
Price-to-Book Ratio 1.27 7.26 Tiptree Inc.
Debt-to-Equity Ratio 10.98 281.55 Tiptree Inc.
PEG Ratio -0.18 -1.70 Tiptree Inc.
EV/EBITDA -19.91 10.09 Ryan Specialty Holdings Inc.
Profit Margin (TTM) 0.00% 2.12% Ryan Specialty Holdings Inc.
Operating Margin (TTM) 902.42% 19.00% Tiptree Inc.
EBITDA Margin (TTM) 902.42% 19.00% Tiptree Inc.
Return on Equity -5.52% 18.21% Ryan Specialty Holdings Inc.
Return on Assets (TTM) -0.48% 3.54% Ryan Specialty Holdings Inc.
Free Cash Flow (TTM) $168.22M $575.71M Ryan Specialty Holdings Inc.
Dividend Yield 1.45% 1.55% Ryan Specialty Holdings Inc.
1-Year Return -17.76% -55.50% Tiptree Inc.
Price-to-Sales Ratio (TTM) -630.30 3.20 Ryan Specialty Holdings Inc.
Enterprise Value $931.49M $8.68B Ryan Specialty Holdings Inc.
EV/Revenue Ratio -904.36 2.90 Ryan Specialty Holdings Inc.
Revenue per Share (TTM) $0 $24 Ryan Specialty Holdings Inc.
Earnings per Share (Diluted) $-1.04 $0.47 Ryan Specialty Holdings Inc.
Beta (Stock Volatility) 1.00 0.71 Ryan Specialty Holdings Inc.
Short % of Float 1.94% 8.68% Tiptree Inc.

Tiptree Inc. vs Ryan Specialty Holdings Inc. Stock Performance Analysis

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TIPT
RYAN

Performance Comparison

Short-term Returns

Stock1D1W1M3M6MYTD
Tiptree Inc.-3.11%1.08%3.81%3.15%-4.84%-1.83%
Ryan Specialty Holdings Inc.-4.43%-0.09%8.90%-19.67%-42.76%-36.18%

Long-term Returns

Stock1Y3Y5Y10Y15Y20Y
Tiptree Inc.-17.76%32.27%80.42%231.64%155.46%35.11%
Ryan Specialty Holdings Inc.-55.50%-23.93%11.40%11.40%11.40%11.40%

Performance & Financial Health Analysis: Tiptree Inc. vs Ryan Specialty Holdings Inc.

MetricTIPTRYAN
Market Information
Market Cap i$649.21M$9.35B
Market Cap CategorySmall capMid cap
10 Day Avg. Volume i194,2911,677,772
90 Day Avg. Volume i257,2371,831,667
Last Close$17.16$30.86
52 Week Range$15.49 - $27.41$29.28 - $72.50
% from 52W High-37.40%-57.43%
All-Time High$27.38 (Sep 25, 2025)$77.16 (Mar 31, 2025)
% from All-Time High-37.33%-60.01%
Growth Metrics
Quarterly Revenue Growth-3.96%0.14%
Quarterly Earnings Growth-0.70%-0.42%
Financial Health
Profit Margin (TTM) i0.00%0.02%
Operating Margin (TTM) i9.02%0.19%
Return on Equity (TTM) i-0.06%0.18%
Debt to Equity (MRQ) i10.98281.55
Cash & Liquidity
Book Value per Share (MRQ)$13.45$5.00
Cash per Share (MRQ)$1.39$1.22
Operating Cash Flow (TTM) i$168.22M$643.67M
Levered Free Cash Flow (TTM) i$-18,469,250$506.21M
Dividends
Last 12-Month Dividend Yield i1.45%1.55%
Last 12-Month Dividend i$0.24$0.61

Valuation & Enterprise Metrics Analysis: Tiptree Inc. vs Ryan Specialty Holdings Inc.

MetricTIPT (Apr 22, 2026)RYAN (Apr 24, 2026)
Price Ratios
P/E Ratio (TTM) i14.1477.21
Forward P/E iN/A14.15
PEG Ratio i-0.18-1.70
Price to Sales (TTM) i-630.303.20
Price to Book (MRQ) i1.277.26
Market Capitalization
Market Capitalization i$649.21M$9.35B
Enterprise Value i$931.49M$8.68B
Enterprise Value Metrics
Enterprise to Revenue i-904.362.90
Enterprise to EBITDA i-19.9110.09
Risk & Other Metrics
Beta i1.000.71
Book Value per Share (MRQ) i$13.45$5.00

Financial Statements Comparison: Tiptree Inc. vs Ryan Specialty Holdings Inc.

Financial Metrics

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Revenue

Operating Margin

Profit Margin

Long Term Debt

Income Flow Analysis

Financial Statements Comparison

Income Statement

MetricTIPT (2025)RYAN (2025)
Revenue/Sales i-1.03M3.05B
Cost of Goods Sold iN/AN/A
COGS % of Revenue i0.0%0.0%
Gross Profit iN/AN/A
Gross Margin i0.0%0.0%
Research & Development iN/AN/A
Operating Income (EBIT) iN/AN/A
Operating Margin i0.0%0.0%
EBITDA iN/AN/A
EBITDA Margin i0.0%0.0%
Pre-Tax Income i-44.60M293.18M
Pre-Tax Income % of Revenue i4,330.3%9.6%
Income Tax i-5.69M79.03M
Income Tax % of Revenue i552.5%2.6%
Net Income (Profit) i34.93M214.16M
Profit Margin i-3,391.0%7.0%

Balance Sheet & Liquidity Metrics

MetricTIPT (2025)RYAN (2025)
Cash & Equivalents i30.78M158.32M
Total Current Assets iN/AN/A
Total Current Assets % of Revenue i0.0%0.0%
Total Current Liabilities iN/AN/A
Total Current Liabilities % of Revenue i0.0%0.0%
Long-Term Debt i72.60M3.44B
Long-Term Debt % of Revenue i-7,048.7%112.9%
Total Shareholders Equity i752.40M1.25B
Retained Earnings i121.57M120.35M
Retained Earnings % of Revenue i-11,803.3%3.9%
Property, Plant & Equipment iN/AN/A

Cash Flow Statement Comparison

MetricTIPT (2025)RYAN (2025)
Operating Cash Flow i-29.55M351.50M
Operating Cash Flow % of Revenue i2,868.8%11.5%
Capital Expenditures i0N/A
Free Cash Flow i168.22M575.71M
FCF Margin i-16,331.8%18.9%
Debt Repayment i-751,000-1.28B
Common Stock Repurchase iN/A-3.73M

Short Interest & Institutional Ownership Analysis

MetricTIPTRYAN
Shares Short i516,3479.71M
Short Ratio i1.805.49
Short % of Float i1.94%8.68%
Shares Outstanding i37.82M129.60M
Float Shares i23.35M113.81M
% Held by Insiders i38.51%13.80%
% Held by Institutions i44.68%88.15%
% Held by Public i16.81%-1.95%

Dividend Analysis & Yield Comparison: Tiptree Inc. vs Ryan Specialty Holdings Inc.

MetricTIPTRYAN
Last 12-Month Dividend i$0.24$0.61
Last 12-Month Dividend Yield i1.45%1.55%
3-Year Avg Annual Dividend i$0.33$0.35
3-Year Avg Dividend Yield i0.37%0.20%
3-Year Total Dividends i$0.99$1.05
Ex-Dividend DateMar 16, 2026Feb 24, 2026