From Harvard Dropout to VC Powerhouse: How to Bet on Yourself with Alexa von Tobel

Ambition 2.0

Girlboss

Entrepreneurship, Careers, Business

4.4 • 1.9K Ratings

🗓️ 6 January 2026

⏱️ 42 minutes

🔗️ Recording | iTunes | RSS

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Summary

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. Sustainable ambition comes from doing what you love + what you’re excellent at, then turning the intensity toward your whole life. 00:00 Intro 02:46 Reclaiming ambition as a positive force 04:11 The LearnVest origin story and dropping out during the economic downturn of 2008 07:53 Raising $75M and the difference between capital vs. “world-class” capital 15:24 What founders get wrong in pitches (and what great answers sound like) 24:20 Identity beyond titles, exits, and the founder doom spiral 33:54 Speed round: The one quality she looks for before investing in founders (and the one that’s a major red flag) GUEST LINKS IG: https://www.instagram.com/alexavontobel/?hl=en Listen to her podcast here: https://www.inspiredcapital.com/content/podcasts Learn more about Inspired Capital: https://www.inspiredcapital.com FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss Amanda Goetz: https://www.instagram.com/theamandagoetz/ https://girlboss.com/pages/ambition-2-0-podcast SIGN UP Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/ For all other Girlboss links: https://linkin.bio/girlboss/ ABOUT AMBITION 2.0Powered by Girlboss, Ambition 2.0 is a podcast where we’ll be exploring what it really means to “have it all” in work, family, identity, and self… and if it’s actually worth it. Each week, you'll hear from hardworking women who’ve walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

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0:00.0	They took people at the end of their lives that were in their 90s and said, what would you change? No one ever changes anything you do. And all of us make mistakes and we're not perfect and we've gotten things wrong. And on your deathbed, you don't think about those things. What you think about is the swing that you didn't take. The thing that you didn't fix. It's the didn't. It's the I didn't have the courage. And so I always joked the 90-year-old Alexis sits on my shoulder.
0:23.4	She's extremely tough. you didn't fix. It's the didn't. I didn't have the courage. And so I always joke the 90-year-old
0:22.3	Alexis sits on my shoulder. She's extremely tough. She's very clear. She is like, is this going to be
0:28.2	something I would regret? And if the answer is yes, then I have to go do it. And it really is that simple.
0:33.7	But dropping out a business school to go start learn best was it was the clearest I'd been in my life at that point.
0:51.8	Welcome to Ambition 2.0, the new podcast by Girl Boss, where we're going to really dive into what it costs and takes to have it all, work, life, family, and self.
1:01.7	I'm Amanda Gets, your host. I'm a two-time founder, four-time CMO, mom of three, and author of the new book, Toxic Grit, How to Have It All, and actually love what you have.
1:11.0	I have been watching our guests today build since I was a first time founder in 2009,
1:17.5	watching her take up so much space, raising over $75 million in VC Capital.
1:24.1	She is the founder of LearnVest, which she scaled and exited to Northwestern Mutual.
1:30.3	She now leads a venture fund backing the next generation of founders.
1:33.3	She knows what it takes to build across multiple startup cycles to shift from founder to investor and to hold space for ambitions that evolve over time.
1:42.3	She is also the host of her new podcast, Inspired, and founder and
1:46.2	managing partner at Inspired Capital. Everyone, please welcome Alexa Von Tovel. Good morning. Good morning.
1:52.3	I'm so happy to be here. I'm so excited. Truly, like, I know I was saying this to you before we started,
1:57.3	but you were one of those people for me that I was like, in 2009, I hadn't
2:04.3	seen a lot of women just coming in and being like, I'm taking up space, raising capital,
2:11.7	just like everyone else. I'm the best founder. It doesn't matter that I'm a woman. I'm going to
2:15.9	show up and be the best. And so I'm so excited to talk to you today. I'm, first time, like, giggling because I'm like, basically you're like, you were coming in hot, Alexa. No, but we needed that energy in 2009. So I loved it. Okay. So we asked everybody the same question to kick off. What does ambition mean to you today and how has it evolved over time for you?
2:37.2	It's such a great question. And it's something that over, as you mentioned, I'm on now season seven of my podcast and we simply just transitioned to calling it inspired, which is my goal and sort of purpose in this world.
2:53.5	I've thought a lot about the word ambition, and I think the word ambition is really important,
2:57.3	which is, in general, the word ambition has had kind of a bad tone, or at least in like my own
	...

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