259 Sieva Kozinsky on The Path from early failures to Enduring Ventures: lessons on fear, focus, and the long game

Behind the Brilliance

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15d ago 1:37:37

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THE SHOW In this episode of Behind the Brilliance, 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 extends beyond building businesses to explore a useful philosophy for building a life you’ll still be proud of twenty years from now.

Behind his Brilliance: His mother and grandmother

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

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