THE SHOW
Entrepreneur and investor Sieva Kozinsky joins the show to share his journey from first-generation immigrant beginnings to co-founding Enduring Ventures, a holding company that acquires and grows businesses for the long game. Sieva opens up about the fear that fueled his early ventures, the lessons learned from failed startups and pivots, and why fundraising can sometimes blind founders to what really matters.
We dive deep into the psychology of selling a company, the art of negotiation with founders, and how legacy is built (or destroyed) in the years after an exit. Sieva also reflects on emotional discipline, meditation, and why surrounding yourself with the right five people may be the single most important factor in your growth. This conversation isn’t just about building businesses—it’s about building a life you’ll still be proud of twenty years from now.
Behind His Brilliance: Turning fear into fuel and building for legacy instead of ego
THE GUEST
SIEVA KOZINSKY | FOUNDER, ENDURING VENTURES
Sieva Kozinsky is an entrepreneur and investor. He’s raised $10M+ in venture capital and scaled his businesses to tens of millions of users (mostly in the US and Canada). Today he is the Co-Founder of Enduring Ventures which buys beautiful businesses and holds them forever.
TOPICS COVERED
- How Sieva’s immigrant upbringing shaped his resilience
- Pivoting from pre-med to entrepreneurship
- The pivotal college class that changed everything
- Why early failures were his best education
- Lessons from building and pivoting StudySoup
- Bootstrapping vs. raising venture capital (and why he regrets fundraising early)
- The psychology of fear as a driver in entrepreneurship
- Emotional discipline: responding instead of reacting
- The role of meditation in business and life
- The dangers of selling to universities (and what that taught him)
- Negotiating with founders who are selling their life’s work
- Why most entrepreneurs misunderstand exits and valuations
- The holding company model and why it’s different from private equity
- How to minimize regret when selling a business
- Finding the right cofounder and what to look for beyond skills
- The importance of discomfort in building a meaningful life
- Why you become the average of the five people closest to you
- Seeking serendipity and building networks through curiosity
THINGS MENTIONED IN THIS EPISODE
- Enduring Ventures
- Sam Walton: Made in America by Sam Walton and John Huey – Sieva’s pick
- The Gambler (Kirk Kerkorian biography) by William Rempel – Sieva’s pick
- Titan by Ron Chernow – Sieva’s pick
- Walter Isaacson’s Steve Jobs – Sieva’s pick
- The Snowball by Alice Schroeder (Warren Buffett & Charlie Munger) – Sieva’s pick
- The Second Mountain by David Brooks
- Summit Series (entrepreneurship gathering)
