There’s a point in many a millenial’s young-adult life when they’re startled to realize they know virtually nothing about managing their money. When Alexa von Tobel experienced this phenomenon herself, she set out to democratize financial literacy. Adamant that every family should have access to a financial plan, in 2009 she launched LearnVest, an online personal-finance site originally geared towards women and “the 99 percent.” Six years and millions of users later, she sold the company for $375 million. Today, von Tobel is largely to thank for the ready availability of digital financial-planning and investment tools, a quiet revolution stemming from the young founder’s own sweat equity. Her endurance and leadership are values shared by Rolex, our partner for the video above.
The key irony in von Tobel’s startup story is her then-lack of personal money-management skills—despite working at a big-deal New York financial firm. Von Tobel sets the scene: “It was 2008, and the economy falls apart. The whole world was really scared. For me, I said, this is the exact right time to take a leave of absence and found a company.” At 24, von Tobel dropped out of Harvard Business School to make her vision a reality: LearnVest would be an accessible resource for the average person dealing with credit card shuffling, student debt, retirement-savings questions, and mortgage inexperience.
Working extreme hours, von Tobel constantly traveled cross-country and spent nights and weekends crafting a 75-page business plan. To power through the unending challenges of building the business, she’s said she took a radical head-down approach. “People used to say to me, if you knew what it takes to be successful as an entrepreneur, you would never start,” she says. “Two years in, I was like, yes, this is so true.” After landing in the hospital for exhaustion, the incredibly driven new CEO made a point to care for herself better, understanding that she couldn’t be effective without prioritizing her own well-being.
Active health became a useful mindset for von Tobel. “Being a CEO is not dissimilar to being an athlete,” she says. “You have to train, you have to get people who’ve done it before to come in and criticize you and help you get better. You have to put in the hours [and] the work.” Along with self-care, she believes that leaning into that growth process—especially taking the time to process negative feedback—is critical to being a successful entrepreneur.
By March 2015, von Tobel’s tenacity paid off with an offer from Northwestern Mutual to acquire the company. While handling the Herculean task of managing the sale, she gave birth to a daughter who spent her first days in the ICU. The uncertainty and constant setbacks of entrepreneurship, she says, aren’t for everyone. But the resiliency to take a blow, then get back to work, saw her through. Her other principles for success include mentorship and being vulnerable about what she doesn’t have figured out. Also, she advises: “Trust yourself, trust your instincts if you’ve done the work. There’s a little voice in all of us telling you how to live your life. Listen to that little voice.”
LearnVest, which grew into a resource for all, is currently phasing into its next chapter. Von Tobel is still CEO, as well as chief innovation officer at Northwestern Mutual. An important part of her personal mission now is helping and inspiring other women. She’s also a media-featured financial expert, spokesperson, and bestselling author—proving that no matter what’s next, she’ll just keep going.
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