Leslie Silverglide: “You Have to Embrace Ambiguity and Love Suspense”

Leslie Silverglide is a cofounder of Wello, a service that connects people with personal fitness trainers through online video chat. Silverglide and Ann Scott-Plante started Wello together in 2011 as MBA students at Stanford Graduate School of Business, and then ran the company for three years before selling to Weight Watchers in 2014 — the first non-franchise acquisition in the weight loss giant’s 50-year history. She is now a vice president there.

In 10 words or fewer, what is the big idea behind your business?

Leverage technology to help people live healthier, happier lives.

What is the best advice you’ve ever received?

Image

Leslie Silverglide | Courtesy

My mom told me you can do anything as long as you put your mind to it. A lot of parents say this, but she followed through by giving me the freedom to do so, as long as I could make a good argument for what I wanted to do and figure out how to get it done. When I was 14 I told her I wanted to spend two months in Africa doing community service. She told me to learn more about it and if I still wanted to go and could get in, she would let me go. The organization rejected me at first because I was too young but I kept applying. Eventually they said yes when I was 16. A month later I was on plane to Uganda. My mother was an entrepreneur, too, although that word didn’t exist in my vocabulary when I was a kid. I just knew if you wanted to do something and thought you could, you went and did it.

What was the most difficult lesson you have learned on the job?

Learning how to decide whether it is the right time to make a change. In 2005 I founded a company called Mixt Greens, a tossed-to-order organic salad restaurant chain. Nestle’s investment arm reached out and tried to acquire the company. We weren’t interested at first but eventually my partners — my brother and my husband — and I decided to do it in 2009. It was too early. We didn’t understand what we had: a bootstrapped, profitable business that fulfilled a need and delivered something that didn’t exist in the market. My brother and husband ended up buying it back two years later. Unfortunately, we lost two years of growth. As the founder of a young company, you can get so caught up in the day-to-day that you don’t pull your head out of the weeds. You need to carve out the time to step back, reflect, and take a larger view of where the company is going.

What advice would you give other entrepreneurs on how to build a great business?

Building a business is like diving into a pool blindfolded. You have to embrace ambiguity and love suspense.

If there was one thing that has enabled you to be successful as an entrepreneur, what would it be?

The support of my husband. He has been such an integral part of everything I’ve done.

How do you come up with your best ideas?

The biggest thing is questioning. I like to immerse myself in the world around me and think about what is missing. Why are things done this way? Is there a better way to do something? Can I do it? Do I want to do it?

What values are important to you in business?

There has to be fun. People get bored and move on. Incentives are important, and that includes treating your employees fairly. At Mixt Greens, of the first 12 employees we hired, 10 were still with us when we sold three years later. That is unheard of in the quick-service food industry. We always tried to make sure we were doing the best by our employees. Well before San Francisco mandated healthcare for workers, we offered all our employees healthcare. We also paid above-market wages and gave them good food they could take home to their families.

What impact would you like to have on the world?

To help people live healthier lives in a way they feel is positive, not negative. With Mixt Greens we gave people easy access to a healthy lunch: a kickass salad that is just as good as a cheeseburger. With Wello, we recognized that the majority of people abhor working out and they see it as a negative experience. We bring real people into your living room to bring accountability, motivation, and fun to your workout.

What was your first paying job?

Working at a nursing home as the assistant activities director when I was 14. Most people don’t really like the idea of nursing homes and find it sad and depressing. I loved going there because I loved the people. I knew I was making someone’s day better, even in a small way, and it felt good.

What is the best business book you have read?

I recently read Mindset by Carol Dweck. Some kids are told they are smart, so they don’t push themselves. Others are taught the growth approach, in which you learn and push yourself to be better. I’m always trying to create an environment where people are encouraged to grow and pushing them to do so.

What businessperson do you most admire?

Yvon Chouinard, the founder of Patagonia. I really respect that he started a business around his passion. Over the decades he was able to stand behind his principles and be a force for good.