NYAIR Episode 35
Save on Insurance, Taxes, & Be More Profitable: Captive Insurance Companies Decoded for Fund Managers
How can alternative fund managers and enterprises use captive insurance to optimize risk, taxes, and profitability—legally? In this essential NY-AIR episode, industry expert Wesley Sierk (Risk Management Advisors) shares high-level strategies with moderator Robert Akeson (formerly COO, Mirae Asset Securities USA) that can save millions for financial professionals, private funds, family offices, and large enterprises navigating today’s regulatory minefields.
Featured Guests
Wesley Sierk
President & Lead Strategist, Risk Management Advisors
A nationally recognized authority in captive insurance design and management, Wesley Sierk serves as President and Lead Strategist for Risk Management Advisors. With nearly three decades in the field, he has partnered with top-tier businesses, family offices, and financial professionals to structure innovative captive solutions that maximize tax efficiency and risk control. Wesley holds the rare ACI designation, is a Chartered Financial Consultant (ChFC), and is the author of “Taken Captive: The Secret to Capturing Your Piece of America’s Multi-Billion Dollar Insurance Industry” and “You Can Make It, But Can You Keep It?”. He is a frequent speaker at industry events and trusted advisor for strategic business risk, executive compensation, and asset protection.
Robert Akeson
Managing Director Investment Banking at Riverside Management Group
Robert Akeson is a veteran executive with deep expertise in brokerage, prime brokerage, agency execution, and financial technology. As former COO and Co-Head of Prime Brokerage at Mirae Asset Securities (USA), he built best-in-class solutions for hedge funds and institutional investors, and is widely regarded as an innovation leader across capital markets. Now Managing Director at Riverside Management Group, Robert guides fintechs, asset managers, and professional investor platforms, while drawing on years of speaking and teaching at New York’s top financial forums.
Key Insights From This Episode
Captive Insurance as a Legal Tax and Risk Strategy
Captives enable companies—including hedge funds and private equity—to shift risk premiums into a wholly owned insurance company, unlocking legal tax deferral and operational control usually reserved for giant carriers.
Why More Funds Are Forming Captives
Professional liability, regulatory gap coverage, and creative asset protection are driving alternative investment firms to adopt captive insurance, sidestepping market rate hikes and tightening coverage.
Profit and Flexibility: The Numbers That Convince CEOs
Firms paying seven figures in premiums can recapture profits inside their captive, invest reserves for growth, and control payouts with full regulatory legitimacy—turning insurance from a sunk cost to a capital asset.
Multi-Jurisdictional Setup: Pitfalls and Opportunities
Not all captives are created equal; Sierk walks through how to select the right state/domicile, balance regulatory oversight with tax goals, and futureproof captive structures against legislative change.
When and Why Captives Are the Right Fit
From minimum premium thresholds to scaling strategies, this episode details real-world criteria for when an organization should consider self-insuring and how to drive maximum value beyond traditional plans.
Exit Strategies and Optimal Structures
Wesley details how companies can unlock retained earnings upon sale or succession, deploy dividends strategically, and even consolidate insurance management for multi-entity family offices.
Access the Full Conversation
Don’t miss the complete episode audio and exclusive insights deck. Hedge fund managers, CFOs, private equity professionals, and ambitious entrepreneurs—discover game-changing risk, tax, and profit tools that mainstream insurers won’t tell you about.
Soundbites Worth Saving
“If you’re paying millions to an insurer, why not pay your own insurance company—and keep the profit, tax deferred?”
— Wesley Sierk
“If you’re paying millions to an insurer, why not pay your own insurance company—and keep the profit, tax deferred?”
— Wesley Sierk
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