Editor's note: We asked noted entrepreneurs to reflect on what they wish they'd known starting out. Alexa von Tobel founded LearnVest in 2009 to make financial planning less expensive and more accessible.
When Alexa von Tobel first started building her business, she concentrated on appealing to women, but its mission quickly broadened. Now, LearnVest is unabashedly trying to provide financial planning to all of America, including those who might not have the resources to be attractive clients for traditional financial planners. By 2015, when LearnVest was acquired by Northwestern Mutual Life for a reported $250 million, von Tobel had earned her CFP certification and raised $72 million. Here, von Tobel takes a look back and talks about the lessons she learned.
What do you wish you knew when you were younger?
It's hard to think about what I wish I knew earlier. There's still so much I need to learn now.
The most important thing so far was something I learned as I was graduating from college. I saw a study of 90-year-olds who were asked what they regretted, and what they would have done differently. The most amazing thing was that none of them regretted anything they had done. They regretted the things they didn't do.
How does that knowledge change the way you work today?
If I know that at the end of my life I'm not going to be mad about some dumb thing that didn't work out, it's easier to forgive myself for the things that go wrong. It's incredibly liberating.
When did you start to really internalize this message?
The 90-year-old Alexa started sitting on my shoulder when I was 23 or 24. When I faltered, she would ask, "Are you going to regret it?" And I would be like, "That's easy. Of course I'm not going to regret it. I'm going to do it." It gave me the ability to command more guts.
I wish I would have learned this earlier. I feel like I'm only learning to live it now.
It's not just the 90-year-olds in the study. I wish I had understood how much, in general, we can learn from older people who've come before us.
Is that something you can do in your role at LearnVest?
Absolutely. I surround myself with people in their 60s and 70s. These are my mentors, and I love to drink in what they're learned. It's maybe one of my favorite things to do. I had lunch with one of my mentors today. I'm half his age. I'm inspired for months after one of these sessions.
When you are 15 or 16 or 17 you are invincible. In your 20s you still feel that way. Now I'm learning things aren't always that simple.
It's similar to the respect and admiration you have for your parents as you get older. We should all trust our parents earlier in our lives. It's a profound change, and your perspective changes so much, when you have a child. I can't even count the number of times I've been army crawling out of my daughter's room so I don't wake her up. And I'm lying in the dark, and I can't even be productive on a phone or tablet because my daughter will see the light from it. And I realize my mom did this for three kids and she worked full time. Definitely, I should have trusted her earlier. We should all trust our parents earlier.