Navigating Entrepreneurship: Lessons from Investopedia

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. _____________________________________________________ TIME STAMPS: 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