Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder

My guest today is Cory Janssen, co-founder of Investopedia. 

Cory sold the business 17 years ago, but what came next was far from the smooth ride he or anyone might have expected. He spent years in painful trial and error, half-heartedly starting new ventures while avoiding real work, experimenting with professional investing and retirement. None of it satisfied his deeper need for the sense of purpose he felt while building Investopedia. 

Everything changed when Cory went back to building and working. But this time it felt different. 

His focus shifted toward unselfish, larger impact goals. His new non-monetary motivation gave him powerful drive and a clear sense of direction and alignment. 

Today, Cory finally feels deeply fulfilled, energised and joyful. 

There is so much to learn from Cory's story and we are so lucky he agreed to share it openly. It's rare, raw and packed with specific practical insights for anyone navigating the complexities of post-exit life.
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00:00:00 Introduction
00:01:40 Guest Introduction: Cory Janssen’s Story
00:04:00 Founding Investopedia: The Early Days
00:10:55 Deciding to Sell Investopedia
00:22:15 Regret After Selling: Financial and Emotional Impact
00:35:10 Working for the Acquirer: Lessons Learned
00:46:50 Negotiating the Sale Process: Tips for Founders
00:56:20 Post-Exit Struggles: Managing Wealth and Purpose
01:07:10 Challenges of Professional Investing
01:15:30 Rediscovering Passion for Building: Transitioning to AI
01:26:15 Balancing Parenthood and Entrepreneurship
01:37:30 Raising Kids with Wealth: Avoiding Entitlement
01:40:00 Closing Reflections and Key Takeaways