Alexa von Tobel
Alexa von Tobel, founder of LearnVest, was inspired by her own struggle managing her personal finances. — Alexa von Tobel

Despite graduating from Harvard and working for Morgan Stanley, Alexa von Tobel didn't know what to do with her own personal finances.

"By all stretches of the imagination, [I] should have been good with finances," von Tobel said in a recent interview with CO—.

However, like many people, she wasn't sure what she should be doing with her money and how to balance her expenses.

Unable to find a suitable digital platform to help her put her finances in order, she decided to build her own. The idea behind her company, LearnVest, was to help people manage their money by educating and empowering them on their financial journey.

Delegating really is a critical skill.

Alexa von Tobel, entrepreneur and founder of LearnVest

Raising capital during the Great Recession

One of von Tobel's biggest struggles was getting the funding she needed to
launch her business. This common startup challenge was exacerbated by the timing: She was trying to raise money in late 2008, one of the lowest points of the Great Recession.

"Capital was tight," said von Tobel. "There wasn't a ton of venture money flowing around."

Despite the lack of available funding, von Tobel met with "anybody and everybody" who would talk with her about her business. After meeting with every potential investor, shel would ask if they knew anybody else who might be passionate or excited about LearnVest. This would often lead to one or two more intros, resulting in hundreds of meetings to secure seed capital.

Eventually, von Tobel was introduced to Ann Kaplan, the CEO and president of iFinance Canada Inc., who cared about financial literacy as much as she did.

"It really was like a blind date," von Tobel recalled.

After several meetings, Kaplan decided to give LearnVest some seed capital.

Learning to delegate

During the fundraising process, von Tobel quickly realized she couldn't do everything herself if she wanted to get LearnVest off the ground. She took all the help she could get, including part-time workers, volunteers and summer interns, so she could start delegating responsibilities to others.

"Delegating really is a critical skill," she said. "You have to be able to let things go, but you have to be really clear what you want people to accomplish. I would say, 'Here's what you're responsible for, here's what we need done by the end of the week. Go.'"

'There's no silver bullet'

Von Tobel's next priority was marketing LearnVest. To get her message out there, she used every marketing channel she could, including PR campaigns, press outreach, event attendance, campus recruitment and business partnerships.

"There's no silver bullet," von Tobel said, in regards to marketing. "You need a bunch of lead bullets."

Eventually, LearnVest began to gain a following, with more and more people signing up every single day.

"Fifty people would sign up a day, then 100 people, then 300 people," von Tobel said. "I would sit there and say, 'Wow I can't believe this is really working.'"

Achieving the dream of acquisition

After nearly five years of building the company from the ground up, LearnVest was acquired by Northwestern Mutual.

"It's every entrepreneur's dream," von Tobel said. "You build a company, it's working … [it has] great value and it gets acquired. It felt surreal."

Once the acquisition was finalized, von Tobel joined Northwestern Mutual's management team as the Chief Innovation Officer to support their vision of empowering Americans' wallets.

"[It's] very similar to what LearnVest was trying to do, but [Northwestern Mutual] has been doing it for 161 years," said von Tobel.

Today, von Tobel's responsibilities are to think through all the ways Northwestern Mutual can remain innovative.

"My job is to keep thinking through all the ways that we as a big company can be even more innovative for our clients and for the families that we care about around the country," she added.

Watch the full interview with Alexa von Tobel for more about her experiences and challenges starting LearnVest. This interview was conducted on behalf of CO— by C-Suite Network's Gregg Greenberg.

Alexa von Tobel interviewed for CO— by C-Suite Network's Gregg Greenberg. 

CO— aims to bring you inspiration from leading respected experts. However, before making any business decision, you should consult a professional who can advise you based on your individual situation.

Published February 27, 2019