Here Is How Alexa von Tobel Raised $75 Million


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Learnvest founder Alexa von Tobel was in the hot seat at last week’s StartupGrind, and it’s amazing what you can learn from a 90-year-old. Ok, that might need a bit of an explanation:

While in school, the Harvard grad and HBS dropout worked in the Happiness Lab.

“We took 90 year olds and asked them what they regretted, looking back. They never regretted anything they did. Just what they didn’t do,” she said. “Like, that girl they didn’t ask out in high school.”

Which is when she realized that money won’t make you happy, but if your finances aren’t in order, it can really stress you out.

That was it. She was going to start a company addressing the financial services needs of people who couldn’t ordinarily afford a financial planner.

2008 was not the best time to drop out of grad school and start a company, but then, as many a successful entrepreneur will tell you, the best of times to start a company is in the worst of times. So von Tobel wrote her business plan and forged ahead.

“It was terrifying,” she said. “But when I’m 90 and looking back, I thought, ‘will I regret not doing this?’ It’s a clear decision, once you put it through that filter.”

She also had what she called her Cinderella Pumpkin Fund, which was nine months worth of emergency savings – enough to fund the start-up for exactly nine months. If after that time the company hadn’t made any progress, that would be her ‘Cinderella moment,’ and she would go back to business school.


“Having a financial plan is critical when you’re starting a business,” advised the former financial planner. “Not having one is really dangerous.”

So she wrote a 75-page business plan.

If you do the math, that’s a page for every million the company has raised, to date.

“Don’t do that, either,” she warned, referring to the inordinately lengthy plan. Instead, she advised having a strategy and taking calculated risks. “Milestone-setting is important.”

Not getting a paycheck was also terrifying, she confessed, but building a product that would help people sort out their finances and build a financial plan, step by step was important to her. Having come from a family of doctors, doing something that improved people’s lives was where her passions lay.

She dropped out of business school on December 18, 2008 and raised her first round of funding ($5 million) in June.

Like the product itself, von Tobel is very step-by-step oriented.

“Be clear. Get your first team members, raise money, build the software,” she suggested. “I was client #1, starting from my own needs. I was 23 and couldn’t pay thousands of dollars for a financial plan – necessity is the mother of invention.”

No one ever made (financial planning) accessible to people outside of the 1%,” said the New York Times best-selling author (Financially Fearless. A CERTIFIED FINANCIAL PLANNER™). “That’s a big product vision. But it’s rewarding, because it’s disruptive – and disruptive is hard work. But I love consumer products and making things accessible.

She compared the financial services industry prior to Learnvest to the healthcare system.

“It’s wealth care. Only wealthy people get to see doctors. If people can access Learnvest and get a handle on their finances, that’s what gets me out of bed in the morning.”

Startup founders sometimes forget that, once the money’s in the bank, that’s when the real work begins.

“When you’re building a startup, your job changes every six months”, she warned. “I was builder, marketer, hirer, firer, project manager, product manager…”

Whatever it takes, and it’s never a straight line to where one needs to go in the startup world.

“When everyone else zigs, you zag,” she suggested.

And no regrets about leaving Boston to launch her company here in New York.

“I abandoned everything and moved in with my boyfriend (whom she has since married). New York is the best place to start a company. There’s a community here. There was no General Assembly, no WeWork, no New York Tech Meetup in Boston. There was no ecosystem. Working alone in an apartment, it’s hard to get your energy up. It’s hard to do it alone. That’s why I feel strongly about giving back.”

Fresh off raising her latest round ($28 million), a whirlwind national book tour (“don’t do that in winter,” she advised, and especially not during the polar vortex), and a new focus on talent acquisition and sales, what’s her latest best advice to the room?

“Take it one day at a time and bring 120% every day,” she said.  “Crush it!”

About the author: AlleyWatch

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