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

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

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

05:51 Navigating Identity and Growth in Entrepreneurship

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

11:49 Financial Freedom: The Shift After Selling Teachable

14:53 Building Again: Lessons from the First Venture

17:58 Hiring and Team Dynamics: The Balancing Act

21:00 The Challenges of Industry and Team Management

24:03 Personal Finance for Business Owners: Key Insights

27:09 The Importance of Mindset in Business Ownership

30:12 Maximizing Financial Benefits: Tax Strategies for Entrepreneurs

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

35:54 The Impact of Upbringing on Mindset

39:08 Understanding Financial Management for Business Owners

43:47 The Importance of Recurring Revenue

46:53 Navigating the Challenges of Building a Fintech Company

49:57 Marketing Strategies and Audience Engagement

52:17 Getting Started with Financial Tools

54:37 Balancing Personal Life and Work

01:06:04 Redefining Success Beyond Money

RESOURCES + LINKS

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• Ankur Nagpal: @ankurna