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Behind a $100 Million Mattress Startup, Casper Co-Founder Shares Advice on Finding Success as an Entrepreneur For our series '20 Questions' Jeff Chapin of mattress startup Casper dishes on the strange book that changed his outlook on life, his simple trick to staying on task and what his worst boss taught him about life.

By Lindsay Friedman

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.


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

For Jeff Chapin, bringing ideas to life is what makes him tick and excites him. "I get pride in seeing people creating great stuff whatever their area is," he says.

As the former designer at famed innovation firm IDEO, Chapin definitely got to see his fair share of dreams turn into reality. Yet, after having worked on big projects, Chapin was ready to tackle his own passion project: turning the mattress industry on its head.

"There's a big issue in society that people only get a few hours of sleep a night, which can have huge life and productivity impact," he says. "It's a huge potential business opportunity to create a market in that realm."

Chapin did just that. He, along with four others, saw an opportunity to disrupt the mattress industry after witnessing customers continually overwhelmed by the multiple mattress options, lack of customer service and complicated return policies.

So, in 2014 the small team launched New York City-based Casper, an ecommerce mattress startup focused on creating a streamlined and simplified experience through an "all size fits all" mattress and a seamless return policy. In doing so, the Casper team seized the chance to disrupt the $14 billion mattress industry.

"The opportunity we saw was just to try to help people sleep better and change how they balance sleep with the rest of the decisions in their life," Chapin says. "Being underslept in New York City, seeing focused companies tackle industries and the success they were having, combined with our past experience got us excited to give it a shot."

Now, after recently surpassing $100 million in business, the company has gone from a staff of five to 150 employees in less than three years. It has expanded to include sheets and pillows, while also currently experimenting with more products focusing on the practice of sleeping overall.

Now looking at the long-term game, idea-man Chapin is excited by the myriad of possibilities Casper aims to explore as it works to go international.

To understand what made this entrepreneur tick and his keys to success and growth, we caught up with Chapin and asked him 20 questions:

1. How do you start your day?

I have a dog named Alta, so I start by running with my dog around 6:30 or 7 in the morning. I try best not to check my phone or email until I at least do that and have breakfast.

The reason being is my default is to do many things at once, or rush to the next thing. Real life rarely allows us to get a full eight hours of sleep or an entire hour to run with the dog in the morning, but that doesn't mean we can't use those six hours of sleep or 30 minutes to run and clear the head, right?

2. How do you end your day?

Some nights I watch Game of Thrones, but when I'm better behaved, I read. I read a lot of nonfiction, so I can keep learning. Mostly I read about science, technology, design and sometimes history. Anything that tells me how the world works.

3. What's a book that changed your mind?

Tower and the Bridge, a professor of mine in college wrote it.

When I started college, I was headed down the path of becoming a chemist. I'd always wanted to wear a lab coat and work in a lab. But when I read this book in my first year of college for a class about structural art -- essentially, the beauty found in architecture and engineering -- it was so captivating I switched majors and pursued a civil engineering degree focused on structures. To this day, it's still a reference for me in my work, even though I've switched from structures to products and work on a much smaller physical scale.

4. What's a book you always recommend?

Making of the Atomic Bomb, a story of the U.S. effort to build the atomic bomb. It's a beautifully written book about the science and technology behind it. I don't think many people think of a non-fiction book as page turner, but it sucked me in.

There's incredible science (described in a very understandable way), tension around the morality of building an atomic bomb, egos and personality conflicts, along with the fact that many of the scientists were Jews expunged from Nazi Europe creating the ultimate weapon to destroy Nazism. It's a good read. A lot of people haven't had great experiences with non-fiction, so I think it surprises them.

5. What's a strategy to keep focused?

I have to remove distractions. It's pretty simple. Headphones and music with no words and an office where there's no people.

6. When you were a kid what did you want to be when you grew up?

I thought I was going to be a scientist. I wanted to wear a lab coat and be in a science lab, all clean and pure. I started in college as a chemical engineer and then I took this guy's class who created this notion that form follows art, the idea engineers and scientists can create beautiful things.

7. What did you learn from the worst boss you ever had?

I had a boss who was both sexist and racist. I observed him treating women and African Americans terribly and making bad candid comments to me. It was extreme.

Everyone deserves a fair shot regardless of their background. You just can't judge anyone from their background. It was shocking to work with someone like that, because I had not been exposed to that before. I didn't keep the job long.

8. Who has influenced you most when it comes to how you approach your work?

My parents. They were builders. It was their passion and hobby to always be making things and fixing the house. It was this notion to not overthink something and just take an initial idea, build it and improve it over time. Nothing is permanent; you can make it better later.

9. What's a trip that changed you?

In 2009, I moved to Cambodia for six months and worked with a nonprofit to do a rural sanitation project.

I had always been a part of an institution. I learned you can do something on your own, even though you've always been a part of these institutions. You don't need them; you can go on your own to learn, grow and continue to succeed.

10. What inspires you?

I'm inspired by good citizens -- people who contribute to their communities. So much of society relies on good citizens to function, but it's not talked about all that much.

They're everywhere in the country, filling holes that our government can't fill. I am blown away by dedicated people helping hold society together.

11. What was your first business idea and what did you do with it?

In grad school, we were all surfers in New England. We made a dry glove for surfing and called it Furance Surf. It still exists.

Eventually I peeled out. We were all very much the same people, and you really should start a business with people different from yourself. There are a lot of reasons for that, but I'll boil it down to two. One, since there are so many different things that need to get done, it's incredibly helpful to be able to divide and conquer, Second, I believe you don't need more than one expert on any one topic. We all have opinions on everything, and we all share them and listen to them, but we each get a final say on our own area of the business. It helps us make decisions quickly and move faster.

12. What was an early job that taught you something important or useful?

My most influential job was working at IDEO for such a long time. I started there when I was 25 or 26 and worked there for 10 years.

One useful thing I learned was how to present. You're always standing up telling your story, presenting your ideas and showing clients your work. That repetition took something that, for me, used to be very nerve-wracking, and now I enjoy it. It was a massive change.

13. What's the best advice you ever took?

In undergrad we went to do a tour of an architecture office. Someone there advised us not to get married too early. It's weird advice, but if you want to build a career it's hard to do if you have family pressures and kids early on. I'm 39 and still not married, so maybe I took it too much to heart. But I am engaged now.

14. What's the worst piece of advice you ever got?

When I was thinking about leaving IDEO there was a senior person who told me I was making a big mistake leaving, and I'd never find another place like it. I think it's healthy for people to move on and find something new. If I waited even just a month or two, I wouldn't have been here.

15. What's a productivity tip you swear by?

I ignore a lot of emails. For better or worse, it helps with my productivity, so I can focus on the task at hand.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?

I still use sticky notes to make daily to-do lists. I make a list of what I need to do and check it off. Pencil and paper works for me better than anything I've seen.

17. What does work-life balance mean to you?

I have a good signal for whether or not I'm doing good at this or not. If I go to bed and I'm not thinking about work, then I'm doing OK in the work-life balance. It's about being able to shut off work at certain times.

18. How do you prevent burnout?

I like working, so I'm not that at risk at burnout. I'm focused in the specific job I have and the field I've chosen. We always take on new projects and for every new project there's things to learn about materials or functionality. As long as you're doing that, it's hard to burn out, because the next thing is exciting.

19. When you're faced with a creativity block, what's your strategy?

You're not going to be that creative sitting at your desk. Whatever it takes to do something with your body and hands and experience it is the solution. You have to create the right environment to do that and it's on us to create that environment now.

I leave the office and go to stores, talk to people in their homes, go to tradeshows.We also have a workshop, and you can go play around in the workshop and play with materials.

20. What are you learning now? Why is that important?

Most of my learning and thinking right now is about how to build and design the right office. I have to learn how to build a design culture, how to inspire people, how to enable them to come up with new ideas. It's becoming larger and past the point where I actually know what everyone's working on. For long-term sustainability, we have to get that infrastructure and attitude correct.

This interview was edited for clarity and brevity.

Lindsay Friedman

Staff writer. Frequently covers franchise news and food trends.

Lindsay Friedman is a staff writer at

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