Shifting from Founder to Investor

In this episode of Ambition 2.0, host Amanda Goetz sits down with Alexa von Tobel—the founder of LearnVest (where she raised $75M and successfully sold it to Northwestern Mutual) and current founder and managing partner of Inspired Capital—to unpack the resilient mindset that has shaped her successful career, from founder to venture-capital veteran.Alexa dropped out of Harvard Business School and poured her life savings into LearnVest, a multimillion-dollar business idea—despite warnings from nearly everyone around her that she was making a big mistake. She did it in the middle of the 2008 economic recession, no less.

Alexa shares why her 90-year-old self (and the fear of regret) fuels her to take big risks, the qualities she looks for when investing in a founder, and practical tips for pitching your business to VCs for the first time. She also shares an unpopular truth: if you’re becoming an entrepreneur for the status or the “quick money,” it’s going to be a rough ride. There’s only one reason why you should start your own business: because you can’t do any other job.

Key takeaways

• Regret is usually about the swings you didn’t take—not the mistakes you made.

• Raising capital gets easier when you combine mission + proof + obsessive category insight.

• Feedback is a competitive edge (and ego is the fastest way to lose it).

• Entrepreneurship shouldn’t be “cool”—it should be inevitable for the person doing it.

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