What if life insurance actually gave you life? In the 48th episode of Bald Ambition, host Mookie Spitz sits down with Craig Du Bruyn, serial entrepreneur and founder of Kaleido Life, a company re-engineering the very foundations of the 150-year-old life insurance industry.
Craig shares his personal and professional journey from early battles convincing architects to abandon drafting tables for CAD systems, to the heartbreaking loss of a business partner that sparked his deep dive into how life insurance really works. That search uncovered a system stuck in the past, built on archaic models and impersonal actuarial tables.
Kaleido Life’s radical vision is to flip the model on its head: using AI, biometrics, psychometrics, and behavioral modeling to create a 360° wellness matrix—a dynamic profile that determines not just your premiums, but how much of your death benefit you can access while you’re alive. Instead of paying premiums for decades only to benefit your heirs, Kaleido lets you “inherit from your future self,” unlocking up to 25% of your policy upfront to fund the things that matter most—whether that’s health, family, or just living fully now.
The conversation dives deep into:
- The pain points of disruption—why people cling to the old way even when better tech exists.
- Death insurance vs. life insurance—and why Craig insists on reframing the entire lexicon.
- Gamification of wellness—how lifestyle improvements can literally increase your liquidity.
- Transparency and trust—giving customers direct access to the very data that determines their benefits.
- Regulatory realities—navigating the red tape as Kaleido gears up for its official 2026 launch.
Mookie brings his trademark mix of humor and sharp questioning, pressing on skepticism, teasing about spoiled heirs, and cutting to the heart of the matter: can Kaleido turn an archaic, impersonal industry into a living, personalized partnership? Craig's answers will intrigue you.
The Guest
Craig Du Bruyn doesn’t fit the mold—and never tried to. He’s built and led companies through market upheaval, regulatory gridlock, and cultural landmines. What most call chaos, Craig calls Tuesday.
As CEO and Co-Founder of Kaleido Life, he’s reimagining life insurance as living capital—helping people inherit from their future selves using AI, behavioral science, and a radically human approach to financial empowerment. It’s bold. It’s regulated. It’s working—and it’s just getting started.
Craig’s journey has taken him from solo motorbike expeditions across Africa and the Himalayas to boardrooms more dangerous than the jungle. He’s raised millions, rebuilt companies from collapse, and endured more due diligence than most auditors could stomach. Along the way, he’s built a life he loves—with his family at the center and a deep, unwavering commitment to giving back.
His Company
Kaleido Life is the third financial rail—beyond cash or credit. We let people inherit from their future selves, unlocking up to 25% of their life insurance upfront with no debt, no interest, and no waiting. With trillions trapped in legacy systems, Kaleido is liberating wealth for the living and igniting a movement to redefine what money means for humanity.
Learn More
https://www.linkedin.com/in/craig-du-bruyn/
https://www.linkedin.com/company/kaleidolife
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