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If You're In a Creative Rut, Use This Founder's Surprisingly Simple Tip Harry's co-founder and co-CEO Jeff Raider derives inspiration from his team.

By Nina Zipkin

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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.

Jeff Raider knows a thing or two about ecommerce with a socially-conscious twist. As the co-founder and co-CEO of shaving company Harry's -- and the co-founder of eyewear brand Warby Parker -- Raider is on a mission to build beloved brands known for providing high quality, affordable products, while helping his customers give back.

Raider launched Harry's with Andy Katz-Mayfield in 2012, three years after Warby Parker got its start. The pair felt that they couldn't justify spending the kind of money on shaving products that didn't offer the durability and experience they wanted in something that was an integral part of their routine -- so they decided to make their own.

In four years, the company has gone from a fledgling 30-person startup operation in New York to an international business with a staff of more than 600. The leap was a big one, and happened barely a year into the company's tenure, when Raider and Katz-Mayfield decided to purchase a nearly century old factory in Germany to make their razors.

The company's shaving kits start retailing at $15 and one percent of every purchase goes towards non-profit organizations like City Year and Year Up. Since it's launch four years ago, the company has also expanded to include an online magazine and a brick-and-mortar barbershop in New York City.

We caught up with Raider to ask him 20 questions and figure out what makes him tick.

Related: This Introvert Founder Swears by This Management Tip

1. How do you start your day?
I roll out of bed and go to the gym. It helps get me focused and gives me energy for the day.

2. How do you end your day?
After my family goes to bed, I usually stay up for a couple of hours to work and think. I really like that quiet time at the end of the day.

3. What's a book that changed your mind and why?
Shoe Dog by Phil Knight. The book helped me appreciate how a small group of people can have such a big impact on the world by progressively dreaming bigger and bigger and taking risks to bring those dreams to life. It emboldens me to try to do more with Harry's -- to make bold decisions that could have more impact every day.

4. What's a book you always recommend and why?
The Hard Thing about Hard Things by Ben Horowitz. I think this book shared a particularly insightful view into what it takes to build a company and how hard it can be. I've given it to all of my direct reports to read.

5. What's a strategy to keep focused?
Every month I write down my priorities, and I send them to my co-founder Andy. He does the same to me. We discuss them together to ensure we're both focused on the most important things in the company.

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?
A professional basketball player. I had a good jump shot.

7. What did you learn from the worst boss you ever had?
I learned that inconsistency is really hard on teams. That saying one thing one day and another thing the next day without a clear explanation creates uncertainty and yield loss. I try to be consistent with our team at Harry's and when perspectives change -- and they inevitably do -- I make it as clear as possible about the new information that's driving the change.

8. Who has influenced you most when it comes to how you approach your work?
My Harry's co-founder Andy had a great piece advice for me on how to approach work: email is someone else's to do list for you. Focus on you and what you need to get done first. I've taken that heart.

9. What's a trip that changed you?
About 10 years ago I traveled all over China for a month. We were in cities I've never heard of that had a population with over 10 million people. It made me appreciate the scale and growth of another country and see first hand that we're living in an increasingly global world.

10. What inspires you?
Trying to have a positive impact on others -- on our team at Harry's, our customers and the community more broadly.

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 Warby Parker. We wanted to build an eyewear brand we'd sell directly to customers and that would try to be an agent for positive change in the world. We had the idea in business school, and we built the company in school. The experience changed my life.

12. What was an early job that taught you something important or useful?
I worked as a summer camp counselor at an overnight camp when I was 16 and 17. I was responsible for 15 other younger kids, and it taught me how to lead and motivate action. Getting a bunch of young kids to clean a bunk when all they wanted to do was sleep was one the hardest leadership challenges I've faced.

13. What's the best advice you ever took?
To buy our razor blade factory in Germany. We bought the factory to be able to expand supply of our razor blades and continue to drive innovation. We were less than a year old as a company and only about 30 people on our team in New York. All of a sudden we became a 450-person global company. It felt crazy then, it still feels crazy now, but I'm so glad that we did it.

14. What's the worst piece of advice you ever got?
A professor at business school told me and my Warby Parker co-founders that if we were going to build a global eyewear brand then we should build eyewear in the shapes of different continents of the world. We decided not to do that.

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

15. What's a productivity tip you swear by?
Carry a notebook with you and jot down any idea or question that comes to mind -- you never know when you'll have to go back to it.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I use Google Docs for all of my one-on-one meetings. We use it to set agendas and keep running notes of our conversations over months. It's really helpful and easy to refer back to.

17. What does work-life balance mean to you?
Having the flexibility to work when I want to and having that work not interfere with the most important things in my family life.

18. How do you prevent burnout?
Getting out of the city. Shutting down for a day or two and not engaging in work. It helps me continue to have a fresh perspective.

19. When you're faced with a creativity block, what's your strategy to get innovating?
Talk it out. I'm very verbal. I need new ideas coming from lots of places. I like to set time to talk with various people on our team, and try to get new ideas that might spark an insight that we can build on.

20. What are you learning now?
I'm constantly working to delegate more and more to our team to free me up to think more about the future. I used to be "doing" lots of things, then I was making lots of decisions, now I try to set a course for Harry's and trust our team to make lots of important decisions and drive the company forward. The nice thing is, our team inspires a lot of confidence.

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

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