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Alexa von Tobel founded LearnVest in 2008 and later sold it to Northwestern Mutual for hundreds of millions of dollars. Her journey from a Harvard dropout to a leading fintech investor offers real lessons on conviction and timing.
Alexa von Tobel’s Early Career
Alexa von Tobel grew up in Jacksonville, Florida, before attending Harvard College. She later enrolled in Harvard Business School in 2008. However, she dropped out at age 25 during the worst recession in decades. She moved to New York City with just a business plan and her own savings.
Building LearnVest From Scratch
She hired her first employee while working out of a Starbucks. Then, in 2009, she officially launched LearnVest. The platform aimed to make financial planning simple and accessible for everyone. Additionally, it matched users with certified planners to create affordable financial plans.
Despite launching during a financial crisis, the company grew steadily. Alexa von Tobel raised nearly $75 million in venture capital from investors like Accel Partners. As a result, LearnVest became one of the most talked-about fintech startups of its time.
The Northwestern Mutual Acquisition
In May 2015, Northwestern Mutual acquired LearnVest in a landmark deal. This became one of the biggest fintech acquisitions of the decade. Furthermore, von Tobel joined the company as its first-ever Chief Digital Officer. She later served as Chief Innovation Officer, overseeing the firm’s venture arm.
Launching Inspired Capital
In 2019, she founded Inspired Capital, a venture capital firm. Today, she serves as Managing Partner, investing in early-stage founders. Meanwhile, she has authored three New York Times bestselling books on finance and entrepreneurship.
Recognition and Life Today
Fortune named her to its 40 Under 40 list, and Inc. included her in its 30 Under 30. She was also an inaugural member of the Presidential Ambassadors for Global Entrepreneurship. Today, she hosts the podcast “American Ambition” and lives in New York City with her husband and three children.