436: I Exited My Company for $250M, Here’s The Mistakes I Won’t Repeat Again with Ankur Nagpal

Ever wondered what it’s really like to build a business in your twenties, ride the rollercoaster of entrepreneurship, and come out the other side? In this episode, Natalie sits down with Teachable founder Ankur Nagpal to spill all the tea on the evolution of online education and the booming creator economy.

Together, they take a trip down memory lane, sharing the highs and lows of startup life (spoiler: it’s not always pretty). Ankur also dives into the juicy details of navigating market saturation, using AI to shake up course creation, what happens to your identity after a big business exit, and how he really spends his money after the $250M buy out.

If you’re obsessed with entrepreneurship, creating impact, or staying ahead of the trends in online learning, this episode is packed with value— plus, you’ll learn what his second venture is, why he couldn’t just “live the travel life” + what he’s doing differently in business this time around.

TIMESTAMPS

00:00The Journey Begins: From Teachable to New Ventures

03:13The Evolution of Online Courses and the Creator Economy

05:51Navigating Identity and Growth in Entrepreneurship

08:53The Decision to Sell: Reflections on Success and Freedom

11:49Financial Freedom: The Shift After Selling Teachable

14:53Building Again: Lessons from the First Venture

17:58Hiring and Team Dynamics: The Balancing Act

21:00The Challenges of Industry and Team Management

24:03Personal Finance for Business Owners: Key Insights

27:09The Importance of Mindset in Business Ownership

30:12Maximizing Financial Benefits: Tax Strategies for Entrepreneurs

32:53The Psychology of Spending: Balancing Wealth and Humility

35:54The Impact of Upbringing on Mindset

39:08Understanding Financial Management for Business Owners

43:47The Importance of Recurring Revenue

46:53Navigating the Challenges of Building a Fintech Company

49:57Marketing Strategies and Audience Engagement

52:17Getting Started with Financial Tools

54:37Balancing Personal Life and Work

01:06:04Redefining Success Beyond Money

RESOURCES + LINKS

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