Ryan Specialty Holdings, Inc. (RYAN)

Price$37.89Cached quoteAs of 2026-09-27 05:48 UTC

AI: Overvalued

Price checkStrong growth is already priced in, leaving too little protection against slower earnings or weaker margins.

Using 2025 adjusted diluted earnings of $1.96 per share, then replacing first-half 2025 with first-half 2026, gives about $2.13 of trailing adjusted earnings. Adjusted earnings remove acquisition, restructuring, and other special costs. The market therefore values Ryan at about 20 times those earnings. On the supplied cash-flow history, trailing free cash flow—cash left after running and investing in the business—is roughly $555 million, only about a 5% yield on the fully converted equity value. With slower organic growth and high debt, that premium offers little value-investor margin of safety.

Big pictureRevenue and cash generation have compounded strongly, but recent cash conversion has become less dependable.

The supplied SEC history shows revenue rising from $1.02 billion in 2020 to $2.99 billion in 2025, while operating cash flow climbed from $135 million to $644 million. Capital spending is very low, so most operating cash can become free cash flow. However, 2025 net income fell to $63 million from $95 million even as operating income rose, and trailing operating cash flow through June 2026 slipped to roughly $559 million. The business remains cash-generative, but recent conversion is less smooth than the long-term trend suggests.

Business strengthRyan's specialty franchise is valuable, but acquisition-driven leverage limits the balance sheet's safety cushion.

Ryan earns recurring brokerage and underwriting-management fees without directly bearing most insurance claims, helping revenue compound through specialty-market growth and acquisitions. The balance sheet is the main weakness: June 2026 debt was $3.63 billion against only $140 million of cash, leaving about $3.49 billion of net debt. That equals roughly 3.4 times trailing company-adjusted operating profit before interest and certain noncash or special costs, or about 4.6 times the supplied reported version. Goodwill of $3.22 billion also dwarfs $509 million of stockholders' equity.

What could change the storyBetter organic growth and cost savings could justify the premium, while property weakness could break the case.

The bull case needs Ryan to keep winning specialty business while Empower delivers $80 million of savings by 2029 after $160 million of charges. The bear case is visible: second-quarter organic growth—growth excluding acquisitions and currency effects—slowed to 6.7%, property revenue declined moderately, and management guides 2026 organic growth to mid-single digits while adjusted profit margin falls 0.5 to 1.0 percentage point. Ryan spent $300 million on first-half buybacks as the fully converted average share count fell from 279.4 million to 270.1 million, but debt rose $282 million from year-end. The current multiple requires growth to stay resilient.

AI: News

Second-quarter growth slowedSecond-quarter growth stayed positive, but softer property demand and weaker margin guidance reduced confidence in near-term acceleration.

On July 30, Ryan reported second-quarter revenue of $916.6 million, up 7.2%, with organic growth of 6.7%. Adjusted earnings, which remove certain acquisition, restructuring, and other special costs, rose to $0.74 per diluted share, while the related profit margin slipped to 35.7% from 36.1%. Management maintained mid-single-digit organic growth guidance and forecast that margin to fall 0.5 to 1.0 percentage point for 2026. The next session opened sharply higher but closed only about 0.2% above the release-day close, indicating a mixed reaction.

Buyback authorization expandedRyan expanded its buyback after repurchasing shares well below the later market level, improving per-share economics.

On May 26, Ryan announced a $300 million increase to its repurchase authorization, bringing the program to $600 million. By May 22 it had already spent $260 million during the quarter and exhausted the original authorization. The June filing later showed 8.1 million May shares bought at an average of $31.98, materially below the later observed market level. That can improve value per remaining share if intrinsic value exceeds the repurchase cost. Shares closed about 1.1% lower on May 26, but timing alone cannot attribute the move to the announcement.

Pricing concerns triggered downgradeGoldman Sachs downgraded Ryan as softer insurance pricing threatened the growth acceleration investors had expected.

On June 8, Goldman Sachs downgraded Ryan to Neutral from Buy and cut its price target to $35 from $42. The firm cited prolonged softening in commercial property and casualty insurance pricing, which could keep organic growth, margins, and earnings below market expectations. The shares closed about 2.8% lower that day. The timing is consistent with the downgrade affecting sentiment, but it does not prove the analyst action alone caused the move.

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Revenue

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Net income

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Free cash flow

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Total cash / debt

CashTotal debt

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Financial statements

	2025	2024	2023	2022	2021	2020	2019
Revenue	$2.99B	$2.46B	$2.03B	$1.71B	$1.43B	$1.02B	$758.4M
Operating expenses	$2.56B	$2.09B	$1.72B	$1.44B	$1.25B	$859.7M	$664.1M
Operating income	$493.6M	$427.8M	$359.1M	$289.5M	$186.6M	$158.5M	$101.0M
Operating margin	16.48%	17.42%	17.72%	16.91%	13.03%	15.59%	13.32%
EBITDA	$781.1M	$595.4M	$474.9M	$398.8M	$299.1M	$226.1M	$105.8M
EBITDA margin	26.08%	24.25%	23.43%	23.30%	20.89%	22.24%	13.95%
Net income	$63.4M	$94.7M	$61.0M	$61.1M	$65.9M	$68.1M	$64.2M
Net profit margin	2.12%	3.85%	3.01%	3.57%	4.60%	6.70%	8.46%
Basic EPSper basic share	$0.50	$0.78	$0.53	$0.57	—	—	—
Diluted EPSper diluted share	$0.47	$0.71	$0.52	$0.52	—	—	—

Review official source filings ↗

Owners

Reported shareholders

Reference date Jun 30, 2026

≈11.42%of listed shares

RYAN PATRICK G13.87M shares · Jun 5, 2026

View holders

Top 20 reported holders of RYAN
Holder	% owned
RYAN PATRICK G	≈11.42%13.87M shares
BlackRock, Inc.	8.64%10.49M shares
Vulcan Value Partners, LLC	6.52%7.91M shares
T. Rowe Price Investment Management, Inc.	5.46%6.63M shares
Orbis Allan Gray Ltd	5.19%6.31M shares
NEUBERGER BERMAN GROUP LLC	4.59%5.57M shares
VANGUARD PORTFOLIO MANAGEMENT LLC	4.34%5.27M shares
VANGUARD CAPITAL MANAGEMENT LLC	4.30%5.22M shares
FMR LLC	4.22%5.13M shares
STATE STREET CORP	3.05%3.71M shares
Polar Capital Holdings Plc	2.42%2.94M shares
BANK OF MONTREAL /CAN/	2.28%2.77M shares
Stephens Investment Management Group LLC	2.24%2.72M shares
MONTRUSCO BOLTON INVESTMENTS INC.	2.21%2.69M shares
Independent Franchise Partners LLP	2.18%2.65M shares
KAYNE ANDERSON RUDNICK INVESTMENT MANAGEMENT LLC	1.93%2.34M shares
UBS Group AG	1.81%2.2M shares
GEODE CAPITAL MANAGEMENT, LLC	1.75%2.12M shares
MANUFACTURERS LIFE INSURANCE COMPANY, THE	1.66%2.01M shares
MORGAN STANLEY	1.39%1.68M shares

Percentages use 121.43M shares of this listed class outstanding on Jun 30, 2026. ≈ compares the latest reported holding with a share total from a different date; it is not a confirmed current stake.

Gray completes the 100% scale. Reported positions may overlap; holders have different reporting dates.

Source: SEC Form 4 ↗Updated Sep 29, 2026 · Quarterly data

Insider buys & sells

Jul 1, 2024–Jun 30, 2026

Buys16$19.99M disclosed value

Sells (SEC code S)74$418.71M disclosed value

Transaction	Insider	Type	Shares	Price	Value	Owned after
Jun 12, 2026Form 4	Kuczinski Anthony JDirector	BuyClass A Common Stock	500	$35.77	$17.9K	13.1K
Jun 11, 2026Form 4	Kuczinski Anthony JDirector	BuyClass A Common Stock	2.5K	$34.83	$87.1K	12.6K
Jun 10, 2026Form 4	ROGERS JOHN W JRDirector	BuyClass A Common Stock	7.5K	$35.16	$263.7K	117.9K
Jun 5, 2026Form 4	RYAN PATRICK GExecutive Chairman	BuyClass A Common Stock · indirect	120.0K	$32.50	$3.90M	13.82M
Jun 3, 2026Form 4	Hamilton Janice MChief Financial Officer	BuyClass A Common Stock	6.3K	$31.79	$200.3K	14.6K