20 Questions

This Entrepreneur Shares Her Surprising Secret to Fighting Decision Fatigue

LearnVest founder Alexa von Tobel explains how she conserves her energy for the things that require the most brainpower and creativity.
This Entrepreneur Shares Her Surprising Secret to Fighting Decision Fatigue
Image credit: Courtesy of Alexa von Tobel
Entrepreneur Staff
Staff Writer. Covers leadership, media, technology and culture.
11 min read

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

For so many of us, there are few things more daunting than getting a handle on money matters. Not for Alexa von Tobel.

In 2009, at the height of the recession, von Tobel launched LearnVest to create a hub of information and resources to help customers relieve some of their financial stress.

During that time, Von Tobel dropped out of Harvard Business School to start the company, with just her conviction, a year of research and a 75-page business plan in hand.

She raised $75 million in funding for the company, and in 2015, the business was acquired by Northwestern Mutual for $250 million. Today, in addition to leading LearnVest in the role of CEO, von Tobel recently was named Northwestern Mutual’s first ever chief digital officer.

We caught up with von Tobel to ask her 20 Questions and find out what makes her tick.

Related: This Introvert Founder Swears by This Management Tip

1. How do you start your day?
I have my little mantra for my day, which is, "get up, dress up, show up." Get up early, dress the part -- it'll help you feel better if if you're put together -- and show up with a good attitude. It just really makes a difference.

2. How do you end your day?
Now that I have a toddler my evening involves cooking dinner at my house and then it's book time with my daughter. Parents always tell you that the end of the day is when kids tend to confess things; I think that is the most precious time of my day. After she goes to bed, my husband and I spend one-on-one time together, and we either take a walk, go for a glass of wine or eat dinner together. Then I love to watch a 30-minute show to clear my head.

3. What’s a book that changed your mind and why?
The Inevitable by Kevin Kelly. I put it in all my family members stockings. It simply is an exploration of the 12 technology trends that are changing the world. I genuinely geek out over where the world is going to be in 10 years, and I love that exercise of thinking about how are we going to live? What's going to be different?

4. What’s a book you always recommend and why?
The Purple Cow by Seth Godin. It's about phenomenal product development. The idea is if you're going to create something, create something truly exceptional that doesn't exist. It's called the Purple Cow, because if you saw purple cow, you would never forget it and you would tell everybody. It's a great example of like what Amazon is -- you get your stuff faster, cheaper and you love it and then tell everybody.

5. What’s a strategy to keep focused?
First is when I'm at home, I'm at home, and when I'm at the office, I'm at the office.

The other simple thing is to work smart. I spend a lot of time thinking about about how to optimize my days and all my meetings. I don't have any one-hour meetings; I schedule them for 45 minutes. I schedule many 15-minute meetings, because they don't need to be 30. By doing so, you get a lot more done.

The other work smart thing is I don't take a break to go get lunch, because I'd rather have a nice meal with my husband at a reasonable hour.

Related: Use This Founder's Top Tip To Make Your Meetings Work For You

6. When you were a kid what did you want to be when you grew up?
I used to think the coolest people ever were CEOs of companies. I used to think they were all rock stars, and people who invented and created and ran corporations. I was always fascinated by that as I got older.

7. What did you learn from the worst boss you ever had?
I'm fortunate that I've never had a terrible boss. What I will say I've learned is I try to be as sensitive as I can when I'm working with people and proactively say work-life balance matters. When you're here, do your best work. But I believe everybody needs a day to fully recharge, where you're not focused on work, where you're reading, sleeping, exercising, relaxing. I think we're more creative when we're happy, engaged and inspired as opposed to worried and fearful.

8. Who has influenced you most when it comes to how you approach your work?
My mom has worked close to every day of my life. She is 69 years old and works as a pediatric nurse practitioner. She has somehow also raised three kids without any help, while working full time. She made breakfast, packed our lunches, made a home-cooked dinner and ironed everything including boxers and jeans.

She did it all with a smile and grace. I think the kind of the core takeaway is just an extreme work ethic and always making time for your family. You don't make excuses and you find the time to make things work.

9. What’s a trip that changed you?
I dropped out of Harvard Business School in the heart of the recession with no income. I read Richard Branson's book Losing My Virginity, which is all about him starting Virgin.

What was really powerful for me is one of my investors took me down to Necker Island, Richard's island, where I got to spend five days with Richard and a group of amazing people doing everything from beach Olympics to late night dancing and having the most fun ever.

As an entrepreneur, I think mentors matter. And for me, Richard Branson was someone that was a mentor who lived up to what I thought he would be. He has a zest for life, zest for family. He has comfort with big risks and boldness and deep belief and conviction. And at a time that was everything I wanted for LearnVest: to empower Americans to have a financial plan and make everyone's life better. Being able to meet an idol of mine was pinch-me cool.

10. What inspires you?
I believe that we were put on this earth to make the world a better place, and I believe that if we are capable of making the world around us better, we should. So, I think what inspires me is this deep belief that every day the world can be better -- and to raise the bar of the standard of living for people.

The second thing that really inspires me is other people who have given me that spark of their greatness. When I hear a story or listen to a challenge they've prevailed through, or what what they created or overcome, I just get inspired.

Related: The Founder of Bumble Reveals How the 'Question of Nine' Can Help You Stay Focused

11. What was your first business idea and what did you do with it?
My first business idea was instead of having a lemonade stand, I sold everything I could find on the golf course, including things that I was not supposed to sell like inexpensive art from my house.

My first true business idea that I took to full time was  LearnVest. I wrote a 75-page business plan before starting LearnVest. It resulted in a multi-hundred million dollar business that got acquired. I am very proud of that work.

12. What was an early job that taught you something important or useful?
My dad was a specialized behavioral pediatrician for kids with autism and Down Syndrome. My parents took me to work in my dad's office where I filed charts, cleaned up the playroom and interacted with the kids.

From that job, my dad taught me, that as a doctor, your job is to observe people.

It also taught me this interesting listening skill, which was observing people for their full selves, not just for what they present. My dad also taught me that every human you interact with has something to teach you, and it was my job to learn what they could teach me.

13. What’s the best advice you ever took?
The best piece of advice I've ever taken is a quote attributed to Winston Churchill. It says that "courage is what it takes to stand up and speak; courage is also what it means to sit down and listen.” Learning to really listen to people is actually more courageous than speaking.

14. What's the worst piece of advice you ever got?
I've had plenty people tell me that pursuing my dreams and starting a company was too risky or dangerous. I had plenty of people say that it was going to fail, or it wasn't a good idea. You're too young. You don't have enough experience. I just had to trust my gut, and go with my own instincts.

15. What’s a productivity tip you swear by?
I automate everything from my Amazon Prime subscription to my food subscriptions to even what I wear.

The more tasks that are low excitement, like ordering paper towels, that can be taken off my plate and fully automated, the better. I then have the energy and the brain power for things that are real decisions I need to make.

Related: This Beauty Founder Shares the Secret Leadership Skill to Making a Company Thrive

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I'm obviously super biased, but I use my LearnVest financial app every morning to stay focused. But also those apps that just remind me of the things that I need to do every day. I have Fitbit [for my step count] and my Jawbone tells me how much I've slept -- those types of things.

17. What does work-life balance mean to you?
There is no such thing as work-life balance, but it particularly feels acutely bad when you don't love your job. And I love my job. As a result, when I'm working, I'm not feeling like I'm not home and sad. Feeling like you're really loving what you do is what creates that balance, because it gives you that vigor and energy to combat every day.

18. How do you prevent burnout?
I think you need vacations; you just come back a different human. You have energy, you're revived. You've gotten sleep. I really believe in getting out of the office and shutting your phone off, your email off or not checking it.

The other thing is exercise; I am very committed to that. Even 20 minutes on an elliptical can just totally change your attitude, so that you you can come back feeling refreshed.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
My biggest creativity comes when I'm doing things that have nothing to do with my job, like visiting a company that's innovating on a totally different topic. Or going on long drives when there is nothing going on. Or learning about a fundamentally different industry or going to an interesting conference. My creativity comes from not being in front of a computer or at a desk, but being out there in the world doing and talking about things that are fundamentally different than my own industry.

20. What are you learning now?
I believe that leadership is never done. I think it is something you revisit often. And I feel like the older you get, the more humility you feel. I am constantly asking myself, “what are the things I could do better?”

This interview was edited for brevity and clarity. 

Related video: How to Impact Your Industry, According to a Multimillionaire

My Queue

There are no Videos in your queue.

Click on the Add to next to any video to save to your queue.

There are no Articles in your queue.

Click on the Add to next to any article to save to your queue.

There are no Podcasts in your queue.

Click on the Add to next to any podcast episode to save to your queue.

You're not following any authors.

Click the Follow button on any author page to keep up with the latest content from your favorite authors.

Jimmy Choo's Co-Founder Explains Why There Are No Small Jobs