Alexa is the co-founder and managing partner of Inspired Capital.
Prior to Inspired Capital, Alexa founded LearnVest in 2008 with the goal of helping people make progress on their money. After raising nearly $75 million in venture capital, LearnVest was acquired by Northwestern Mutual in May 2015 in one of the biggest fintech acquisitions of the decade. Following the acquisition, von Tobel joined the management team of Northwestern Mutual as the company’s first-ever Chief Digital Officer. She later assumed the role of Chief Innovation Officer through which she oversaw Northwestern Mutual’s venture arm.
Alexa, who holds a Certified Financial Planner™ designation, is the New York Times-Bestselling Author of Financially Fearless and Financially Forward. She is also the host of The Founders Project with Alexa von Tobel, a weekly podcast with Inc. that highlights top entrepreneurs.
I have been obsessed with entrepreneurship for as long as I can remember. I founded LearnVest in New York in 2009 and scaled the company through an acquisition by Northwestern Mutual in 2015. On the side, I found myself helping early-stage founders and angel investing and realized it’s what I loved doing most. I started Inspired Capital to build the kind of firm I wish existed in my earliest days as a founder.
We look at the obvious - market size, strong underlying technology, early traction. But beyond that, I care deeply about the founding team’s 1) Long-term vision. It often takes at least a decade to build something successful. 2) Grit. I look for founders for whom stress wakes them up and creates maniacal focus, and 3) Salesmanship. Founders must constantly be in sales mode—to customers, top talent, and investors.
We are all-in with our founders. As founders and operators, we bring deep empathy to all we do. We know that success is hard-fought, and we’ve experienced the sleepless nights ourselves. We work best with those who are equally scrappy and hard-working. We look for founders who view us as a strategic partner—we want to be their first phone call not just for the good news, but in moments of stress too.
You’re evaluating us, too. Partnering with a VC is like a marriage. You’re signing on for a long-term relationship, and you’re often building that trust and rapport quickly through an intense investment process. Don’t be afraid to ask questions and test out what it would be like to work through challenges together, as we’ll do regularly post-investment.
My mom always said, love what you do, and you’ll never work a day in your life. I believe the opposite: love what you do, and you’ll work 24/7 with no boundaries. At Inspired, I am on a mission to build a standout firm that is here for the long haul, and I care about getting there through hard work, integrity, empathy, inclusivity, and humility. Those are the values that guide me personally, the whole team at Inspired, and represent what we look for in the founders we back.
I could not be more bullish on NYC tech. I’ve seen the startup ecosystem scale tremendously over the past decade, and I expect that growth to continue. New York is home to massive sectors like finance and media, and the talent pool in our own backyard is incredibly powerful and experienced. We back companies across the country, and many of our founders view our New York home base as a distinct advantage.
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