Entrepreneur Chat
LearnVest & Inspired Capital's Alexa von TobelIn 2008, as the economy collapsed, Alexa Von Tobel took a leave of absence from Harvard Business School to start LearnVest, an online financial planning startup. Her goal was to empower women financially, especially during unstable financial times.
Seven years later she sold her company to Northwestern Mutual for over $300 million, and eventually became the bank’s chief innovation officer. She’s also authored two books on teaching both women and men how to take control of their personal finances.
Von Tobel, who recently welcomed her third child, is now switching from founder to backer. She's partnered with former U.S. Secretary of Commerce Penny Pritzker to create a new, early-stage venture fund called Inspired Capital. The duo is reportedly raising $200 million to invest in startups, which would make it one of the largest funds headed by women.
We sat down with Von Tobel to hear more about her journey and the risks she took along the way.
Alexa von Tobel in the Earl crew-neck cable sweater and Darcy skirt
Q&A
That entrepreneurs are rockstars. I think society has glorified this concept of being a founder. Behind the scenes it’s not nearly as glamorous. It’s a ton of hard work, sleepless nights and scary moments. It can be deeply rewarding and fun at times, but being a founder is incredibly hard.
That it was going to fail. I felt like I went into Learnvest knowing that it could fail, and that the majority of startups don’t make it. I think it was important to be committed to the entrepreneurial journey and knowing it would be a long term bet. Lots of founders want quick wins, but slow and steady wins the race and building a business can take 10 years or more.
It’s so hard to name just one! If I had to pick, two of my business partners at Inspired Capital are incredible entrepreneurs—Penny Pritzker and Lucy Grayson Deland. Penny is an amazing founder who has given me great advice. Lucy, who is the co-founder of Paperless Post, have been friends since we both started our respective startups and we would call each other multiple times a week for support. That’s how our fund, Inspired Capital, came together. We wanted to build a fund that really understands and supports founders and the entrepreneurial journey!
President Obama. He’s changed the trajectory of our country’s history.
I was raising money for Learnvest and we thought we were getting a term sheet from an investor I was really excited to work with. I was working through the night, and exhausted myself preparing for the pitch. In the end, the investor decided not to invest in Learnvest.
I learned pretty early as a founder that if you let rejections sting too deeply then you don’t have the energy to get to the next one.
Keep on going. I also think that if 20-year-old Alexa saw 36-year-old Alexa, she’d be proud of me. I’ve stayed true to my values and always do things I believe in.
Remember to enjoy the “moments” every day. For example, my daughter wrote my name down for the first time ever and it was an amazing feeling. This morning, she came into my room at 6:45 AM in a full super-woman costume. My husband and I just turned to each other and started to laugh.
Lots of founders want quick wins, but slow and steady wins the race and building a business can take 10 years or more.
I unplug by devouring design magazines. It’s very healing for me to look at well-designed and organized homes and spaces.
Do your homework. Know more about the subject you are pitching than anyone else in the room. And practice.
Honing my digital shopping. Every Sunday night, I take ten minutes and I order groceries, birthday presents, household items, basically everything the house needs for the week.
My style is optimistic and energetic. My go to is a dress and booties, or jeans, a simple shirt and a great blazer. And heels, always heels.