This story is part of CNBC Make It's The Moment series, where highly successful people reveal the critical moment that changed the trajectory of their lives and careers, discussing what drove them to make the leap into the unknown.
In 2008, with the Great Recession just beginning, 24-year-old Alexa von Tobel walked into the admissions office at Harvard Business School and declared her plan to take a formal leave of absence so she could launch a business.
The seeds of her idea for LearnVest, a New York-based online financial advisory firm, were planted at age 14, when her father passed away. She watched her nurse practitioner mother assume control of the family's finances, and decided the world needed more personal finance tools intended for average people.
In 2007, while working as a Morgan Stanley analyst, von Tobel started working on a 75-page business plan. A year later, she entered Harvard Business School, assuming she'd need training and connections to launch a successful startup.
But when the financial crisis struck, her gut told her that people needed personal finance help right away. Leaving school to launch LearnVest was "the most formidable big swing in my life that I took," von Tobel, now 39, tells CNBC Make It.
Her friends questioned her sanity: "I think you're ruining your career, and you have this amazing trajectory," she recalls one of her best friends telling her. On her flight to New York, she cried from fear. She had no clue how to start a business, and the city wasn't teeming with entrepreneurial funding at the time, she says.
Yet within a year, she raised more than $1 million from venture capital and angel investors. She credits her detailed business plan, and her conviction that she could tap into an underserved market of people who urgently needed help.
Von Tobel grew LearnVest to 1.5 million users before selling her company to Northwestern Mutual for a reported $375 million in 2015. Today, she manages Inspired Capital, a New York-based venture fund she co-founded in 2019 to invest in early-stage startups.
Here, she discusses the challenges and fears of dropping out to launch her startup, how to know when risks are worth taking and the psychology that helped her avoid the regret of inaction.
CNBC Make It: What was it about watching your mother take over your family's finances that inspired you to launch LearnVest?
Von Tobel: It wasn't that she necessarily struggled with finances. It was more that she hadn't managed them [before]. It was an eye-opening moment: Where are they? What do I do?
It left a really big imprint on me. For the rest of my life, I wanted to manage our finances, be very equipped at it and learn about them.
Fast forward: I went to Harvard and Harvard Business School, and I remember being taken aback that there was zero education about the wallet and our finances. I was like, "This is just absolutely absurd, [it's] this critical life habit that impacts the entire planet."
That idea was burned into my bones as something to figure out.
Why take a huge risk as the economy was crashing down, instead of finishing out business school?
I was in this extremely cozy, safe cocoon with a clear life plan. Something deep in my instincts knew that I had to get out of the safe, well-trodden bubble.
I took my formal leave of absence, flew to New York to [start] up the company and cried the entire flight. I said to myself: "What the heck did I just do?"
At the exact same time, I had this deep instinct that when the world zigs, you have to zag. It was so clear that this was the time America needed [a tool like LearnVest] the most.
So, the next day, I said, "Well, I'm here, so it's time to go." And I just got going.
What were your biggest fears in that moment?
For me, it was the fear of: I don't even know how to do this.
Now, there's a playbook. You [type] "I want to start a company" online and here's the deck, here's who to talk to. None of that was clear. There wasn't a path. And I was doing it in a city, New York, where there wasn't a clear capital set — which is precisely why I've now built this [venture capital] fund, Inspired Capital.
I sat on a couch in my apartment, and that was our office for a year. I was using all of my own savings. At the time, I always joked: "This is the amount I can spend. After that, I'm Cinderella and the dress is gone, the carriage is gone."
But the scarier thing for me was not living the authentic life that I was meant to live, and it just didn't look like what everybody else was doing.
How do you recognize a window of opportunity, while also reckoning with what could go wrong if you seize it?
I felt like I had to do a lot of work to be lucky, see the window and know when it was time.
I had written a 75-page business plan. I talked to, literally, hundreds of people, anyone who would talk to me, about their wallet and how they felt about it. The answer was: Nobody felt good.
The market opportunity, in my mind, was screaming ahead of me. I say I jumped out of the plane, but I had two parachutes and a map of where to land. It was very much a thoughtful, calculated risk.
It was a very big risk, don't get me wrong. I assumed I would fail, and I was comfortable with that. But at least I would have left it on the field.
Where do you think you'd be today if you hadn't taken that risk at that time?
I think I probably would have ended up doing similar things, but the timeline would've been delayed, or I might have missed the opportunity altogether.
Maybe it would be more successful. Maybe it would be less successful. I don't know.
I worked in the happiness lab at Harvard, and one of the things I learned is that if you ask 90-year-olds, or people in the last chapter of their life, what they would have changed, they never regret something they did. You always regret the thing you didn't do.
So I had a moment where I was like, "90-year-old Alexa is going to absolutely regret it if I don't have the guts to go do this."
This interview has been edited and condensed for clarity.
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