Alexa von Tobel

From Founder to Investor

Inspired Capital

Alexa von Tobel

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What You'll Learn

  • Her entrepreneurial spirit was ignited early in her childhood, culminating in the creation of Learnvest.
  • How the passion for building has led her to venture capital with Inspired Capital
  • Writing a children’s book on financial literacy that underlines her lifelong commitment to educating people on managing their finances.
  • The evolution of Learnvest from a content site centered on women and finance to a comprehensive financial planning platform.

We Been Drankin'


Episode Details

About the Guest(s):

Alexa von Tobel is a highly-driven founder and financial expert best known for her pioneering work in the financial technology sector. She’s the founder and former CEO of Learnvest, a personal finance company that was acquired by Northwestern Mutual. Alexa’s relentless pursuit to make financial understanding accessible has led her to author several books, including “Financially Fearless” and a kid’s book, “Rebel Girls: Money Matters.” Her latest endeavor, Inspired Capital, finds her on the venture capital scene, investing in other innovative founders with big ideas.

Episode Summary:

In this insightful episode of Story in a Bottle, host Dan Maccarone engages with Alexa von Tobel over several glasses of Chardonnay. Alexa dives into her journey from art-fencing entrepreneur as a child to revolutionizing personal finance with Learnvest. The conversation provides a raw look at the trials and tribulations of standing up a disruptive fintech startup and the road leading to its eventual acquisition.

Alexa also discusses the inception of her venture fund, Inspired Capital, which focuses on early-stage, generalist investments. From discussing the success and mindset required to back transformative ventures to understanding the intricates of raising a venture fund, the episode is a treasure trove of experiences. With marriage-like mergers and the significance of education in finance, Alexa outlines a life dedicated to impact.

Notable Quotes:

  • “Learnvest, I really love investing my core. I am somebody who is really thoughtful about how do we make great financial decisions.”
  • “I think social media is the one that’s, like, a third rail for us. And so there’s this great professor at NYU, Jonathan Hate, who’s talking all about the impacts, like, the data-driven impacts.”
  • “It’s New York City. And so I love to think, know, New York City is an underdog. We’re in so many ways a capital of the.”
  • “I became a certified financial planner. I was like, if I’m going to do this, I got to do it right.”


  • Alexa von Tobel’s book: “Financially Fearless”
  • Her book focussed on tech and finance: “Financially Forward”
  • Kid’s book on financial literacy: “Rebel Girls: Money Matters”

Tune in to the full episode to hear the complete narrative of Alexa von Tobel’s entrepreneurial journey and her insightful views on investing and finance. Be sure to catch more episodes from Story in a Bottle for compelling conversations with leading voices in tech, media, and entertainment.


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