What if you’ve been playing the wealth game on hard mode without knowing it? In this episode, Wesley Sierk breaks down the secret financial infrastructure used by the ultra-wealthy to protect profits, minimize tax exposure, and reduce liability—captive insurance.You'll learn:
Why most entrepreneurs overpay for risk—and how to fix it
How captive insurance works to turn expenses into assets
Red flags in the financial advisory world (and how to think independently)
Why mainstream wealth strategies often serve the system, not you
This is a behind-the-curtain conversation for business owners who are ready to take control, think strategically, and play the wealth game differently.
Guest Bio
Entrepreneur | Risk Strategist | Wealth Architect
Wesley Sierk isn’t your typical insurance guy—he’s a serial entrepreneur who thrives at the intersection of risk, reward, and reinvention. With nearly three decades of experience advising closely held businesses, he’s best known as the Managing Director of Risk Management Advisors, where he builds customized captive insurance companies to help entrepreneurs protect and multiply their wealth. He began the company with his partner Jarid Beck and one assistant. They have grown the captive management company to the fifth largest in the world.
But that’s just one chapter in a much bigger story.
Wes is also the founder of 33 Medical Inc., a medical device company developing breakthrough solutions for degenerative disc disease, and an owner in Capitalogix, an AI-powered hedge fund that's redefining how high-net-worth investors approach the markets. Through self-improving algorithms they have been able to deliver consistent returns that dwarf the S&P500 with the volatility of government bonds.
As if that weren’t enough, Wes is also the creative force behind Caliwood Pictures—a boutique film production company blending entrepreneurial storytelling with cinematic impact. Whether it’s producing thought-provoking films or developing passion projects, Caliwood reflects Wes’s belief that great stories—like great businesses—are built with intention and clarity of vision.
What ties it all together? A deep belief in rational self-interest, strategic thinking, and helping business owners reclaim control—of their risks, their money, and their future.
He’s authored two books for entrepreneurs and the affluent—Taken Captive and You Can Make It, But Can You Keep It?—and is one of the few professionals worldwide to earn the prestigious Associate in Captive Insurance (ACI) designation.
Whether he’s working with elite athletes, entertainers, homebuilders, manufacturers, or family offices, Wes brings a mindset of intelligent design and execution. He regularly collaborates with CPAs, attorneys, and financial advisors to create structures that endure.
Outside of work, Wes is a devoted husband and father, an amateur chef, and an advocate for high-performance living—which often includes hiking with his family and two massive dogs or teeing up a round of golf.
https://www.instagram.com/wesleysierk/
https://www.youtube.com/c/RiskManagementAdvisors
Resources & Mentions
Come Up for Air: How Teams Can Leverage Systems and Tools to Stop Drowning in Work
The Last Rodeo film
You Can Make It But Can You Keep It? By Wes Sierk