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“Work Your Hardest When Times Are Toughest And The Good Times Will Come” With David Wolfe, CEO of Leesa Sleep

I had the pleasure to interview David Wolfe, the CEO of Leesa Sleep

What is your “backstory”?

“Simply by virtue of the fact that I am 55-year old CEO of a fast growing start-up, means I have a longer backstory than most. When I graduated from business school in 1987, it was unusual to want to start your own business. In those days nobody ever said, “I want to be an entrepreneur.” It was just in my blood. Interestingly, I don’t subscribe to the view that entrepreneurs are risk takers. The decisions we take look like risks to others but to us, the biggest risk is standing still. When you are almost tormented by constantly visualizing what success looks like and when failure is not an option in your mind, it is not difficult to take the plunge. At the age of 27, just nine weeks after becoming a partner at what is now BDO in London, I resigned to start my first fully independent business. I wanted and needed more of everything. I jumped into the unknown, but to me, not knowing what lies ahead has been the most exciting part of my life. I think my comfort with the unknown comes from the fact that I went to seven different schools before I went to University. I was always the new kid, so what we now call networking wasn’t something I wanted to do, it was a survival technique. My late father was a brilliant career executive who taught me to put people first and always lead with integrity. At almost 80, my mother is still an active lifelong community leader and volunteer. I often think that I am living their dream as well as my own by running a successful company that measures success as much by our impact on the world as by our financial performance.

Leesa is the 13th or 14th company I have started, where it began in London, England and now is based in Virginia Beach, Virginia. With the exception of one year, I have loved going to work every day of my life. I thrive on the belief that you have to work your hardest when times are toughest and the good times will come. I met my wife and best friend on my first day at college and we have been married for 33 years. We have two amazing and happy grown daughters. I work with an incredible group of young ambitious people and a business partner with whom I never argue. We sell a lot of mattresses, we are profitable and most importantly, we have donated over 20,000 mattresses to non-profits helping people seeking refuge from homelessness, domestic risk and human trafficking. I came to the US in search of the “American Dream” and found that I can achieve this by helping others sleep better and dream deeper. It’s been a humbling and wonderful journey so far and at 55, I feel like I’m just getting started.”

Can you share the funniest or most interesting story that happened to you since you began leading your company?

“I think the funniest thing is that building a mattress company is actually interesting. Who would have thought that?”

So, what exactly does your company do?

“On one level we design, make and and sell incredibly comfortable mattresses and sleep products online. On another, we donate mattresses to shelters, we plant trees and we constantly try to make the world a better and happier place. We like to say that we elevate life though better sleep.”

How have you used your success to bring goodness to the world?

“I honestly believe that anyone who sleeps on a Leesa mattress will sleep better and live better. But Leesa is also a B-Corp and our social impact program leads our industry. Our One-Ten program donates mattresses to those in need, our One-Earth program plants trees and our One-Community program supports our local communities with money and time.”

What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why.

“I have been incredibly lucky to have been guided by the best of the best in my life. At my age, I can tell you the 5 things that people did tell me that have guided me as the CEO of Leesa.”

1. Hire people much smarter than you, treat them well and set unrealistic expectations. They will surprise themselves but not you.

2. Work your hardest when times are toughest and the good times will come.

3. Every initiative needs to remain a strong green light until it is a red light otherwise you will be paralyzed by small setbacks which will slow you down.

4. Listening, not speaking, is the most important part of communication.

5. Contrary to popular belief, planning allows you to be fast, mobile and opportunistic which are key to entrepreneurial success.

The one thing I have discovered which is unexpected is how much fun this is and how much my life has been enriched by the people I work with and how much it has changed as a result of our social impact programs.

I have been blessed with the opportunity to interview and be in touch with some of the biggest names in Business, VC funding, Sports, and Entertainment. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this, or I might be able to introduce you.

“I’ve met some extraordinary people in my career many have sadly passed away but we are left with their extraordinary legacies. The highlight was probably meeting Estée Lauder.

Of the alive people I’ve met, it was always a dream of mine to meet Richard Branson, a dream that was realized in 2015 on a trip to Necker Island.

These days I dream different dreams. The most memorable people I met this last week were two homeless people, Larry and Richard who each had a story to tell. I also met an extraordinary woman who is one of the most impressive entrepreneurs I’ve ever met. I hope to partner with her on a business venture.

I think I would like to meet you for an off the record chat to ask you many of these questions. I think you must have some fascinating stories.

But my favorite breakfasts, lunches and dinners are with my family and friends and without technology. In this busy life we lead which has been cluttered rather than simplified by technology, you just can’t beat great times with family and good friends (without phones!)”