Alexa von Tobel
Founder & Managing Partner
Alexa founded Inspired Capital because she deeply understood the unique challenges of the founder journey. Before Inspired, she dropped out of Harvard Business School to launch LearnVest, one of the first fintech companies aimed at making a financial planning software accessible to millions. Discouraged by the capital partners available in NYC at the time, Alexa promised herself she would one day become the kind of investor she wished had existed. In 2015, LearnVest was acquired for nearly $400 million, marking one of the decade’s largest fintech acquisitions. Alexa went on to establish herself as an industry authority and New York Times bestselling author, with three books on financial planning.
Alexa remains deeply committed to being the kind of capital partner she admires. Left to her own devices, she would spend every waking moment building businesses, obsessively focused on solving the biggest and most complex challenges facing our world. At her core, Alexa thrives on problem-solving, collaborating with entrepreneurs of all shapes and sizes, and waking up each day with a renewed sense of purpose—to her core, Inspired.
More About Alexa:
Born in Kentucky and raised in Florida, Alexa attended Harvard College, where she earned an AB in Psychology with Honors. Her career began on Morgan Stanley’s Proprietary Trading Desk, before helping to build Drop.io, an early-stage startup that was later acquired by Facebook.
After LearnVest’s acquisition, Alexa became Northwestern Mutual's first-ever Chief Digital Officer, leading product and technology strategy as the company achieved $30 billion in annual revenue. She later became Chief Innovation Officer, overseeing Northwestern Mutual’s venture arm.
Alexa is a 2016 Henry Crown Fellow and an inaugural member of President Obama’s Ambassadors for Global Entrepreneurship, where she first met her co-founder, Penny Pritzker. Her achievements have earned her numerous accolades, including a Forbes cover, Fortune’s 40 Under 40, Most Powerful Women, Inc. Magazine's 30 Under 30, and the title of World Economic Forum Young Global Leader. She is also the New York Times bestselling author of Financially Fearless, Financially Forward, and Money Matters.
Alexa lives in New York City with her husband, Cliff Ryan, who leads Galvanize Climate Solutions’ venture and growth strategy, one of the world’s leading climate tech funds. Together, they are raising three children.
What Founders Say
Alexa is a spark plug—dynamic, driven, and deeply invested in your success. She inspires belief in your potential, asks tough questions that get to the heart of the matter, and helps you chart a clear path toward impactful solutions. Whether you need a brainstorming session or an emotional support session, Alexa is there with unwavering support, energy, and insight. One of her most remarkable qualities is her responsiveness to feedback and her eagerness to collaborate, always striving to work with you in the most effective and meaningful way.
"Alexa has been a true thought partner on our company strategy and opened so many doors for us. She's connected us with opportunities that have made a real difference in our growth, and the introductions she’s made have been invaluable in taking ShopMy to the next level."
"I’ve known Alexa for well over a decade now, and she has been alongside us through many chapters of our growth at Finix. What stands out is her deep understanding of our vision and her relentless dedication to making it a reality. She brings the best qualities of entrepreneurship—like grit and adaptability—to her role as an investor and thought partner."
