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

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