6 Questions

6 Questions with Guy Raz

by Heather Freiser

Whether he’s taking his listeners on a narrative journey with some of the most inspiring TED speakers to ever hit the stage or talking to Mark Cuban about the impact of failure on success, NPR’s Guy Raz, host of the fastest-growing program in public radio history, is usually the one asking the questions. This time, we had some of our own.

07 Min Read Time


Uncertainty. It’s a word we hear often — uncertainty in the markets, in politics, in the current business climate. It’s a word entrepreneurs know well, and successful entrepreneurs know how to navigate better than anyone else.

Enter Guy Raz, host of NPR’s How I Built This and TED Radio Hour. He’s asked some of the world’s most well-known titans of industry about their triumphs and failures.

His goal? To offer his audience a sense of possibility in a time of uncertainty. Just call him the “optimist entrepreneur.” But as he tells us, being an optimist isn’t always easy.

Guy Raz

What are some of the lessons you learned from starting two of NPR’s most successful podcasts from the ground up?

I’ve learned that the way you think it is going to work out never matches the reality of how it works out. It’s always much much harder than you think it’s going to be.

I’ve also learned that even in a big organization that may have a certain way of doing things, you can push ideas through if you are committed to them, if you find a path. When I started I spent a lot of time reading about many different entrepreneurs, and I was so inspired by the people I was reading about. These weren’t people who got lucky. I was looking for stories of people who built it from the ground up and took big risks. It gave me the feeling that I shouldn’t give up on my ideas.

You’ve interviewed and profiled more than 6,000 people. Do you have any favorites?

The people who inspire me are often not the big names everyone has heard of. Cathy Hughes, founder of Radio One. She was a single mother at 19 and worked at [Howard University ] radio station. She was so determined that she rose to become station manager. Then she wanted to become the boss. And through total and sheer grit she raised the money to buy a radio station in Washington, D.C. She went to 32 banks to get a loan. They all rejected her. She never stopped. Bank number 33 approved her.

She bought the station, and it was soon losing money. She refused to give up. She slept on the couch of the station with her son. And they started to grow the company. They started to sell more ads, get higher ratings. Eventually her son went to Wharton [for his MBA]. He then helped her turn her company into a multimillion-dollar empire. It’s an amazing story. She’s an incredible philanthropist and businesswoman. And she started from the bottom. She had zero advantages. She built something because she was so determined.

What role does failure play in being a successful entrepreneur?

I don’t think you can fully realize your potential as an entrepreneur unless you have experienced failure. And not just experienced it, but really examined it. It’s not just failing, but failing and reflecting on it and coming to understand how it actually played a really important role in where you ended up.

One of the great examples of this was Instagram. You don’t typically think of it as a failure, but the beginnings of Instagram had nothing to do with photo sharing. It started as a check-in app like Foursquare called Burbn, and [founder] Kevin Systrom couldn’t get it to go anywhere. It was a failure. But that experience led him to think more deeply about how we share experiences. And that’s what steered him in the direction of developing a photo-sharing app at a time when people were not sharing photos as much on social media.

How important is “entrepreneurial spirit” in the workplace?

It’s super important. Being an entrepreneur doesn’t mean you have to only do it on your own or on the outside. An environment that encourages it is helpful. When a company is too rigid, it ultimately fails. When companies give people the space and room they need to grow, they are successful.

What are the common qualities of successful entrepreneurs?

It all comes down to hustle. Look at entrepreneurs like [Boston Beer founder] Jim Cook. He walked from bar to bar with a cooler telling bartenders to try his beer. If you believe in your idea, you will find a way.

Then an absolute, unshakable optimism. These entrepreneurs don’t have their heads in the clouds. They are realistic, too. There’s an ability they have cultivated to see beyond the immediate moment and know that it is going to be OK.

And finally, flexibility. Look at [toy company] Melissa & Doug. They started out making videotapes for children. They then morphed into making wooden puzzles and had enormous success with that. They’ve branched out so much since then.

You have familiarity with Melissa & Doug beyond just interviewing them. You’re also a father. How have your children changed how you look at the world and your purpose?

I am constantly trying to improve myself. We all have bad days and negative thoughts. Being happy is hard work. For some people it comes easily, but for most of us you have to put in the effort. You have to work at the way you think about the world. You have to commit time to the people you love. You have to exercise. You have to get your butt out of bed and go.

But the single most important thing I can do is to model a good partnership. My wife is the most important person in my life. If we can show our children that we have a mutually supportive partnership, when it comes time to find their own partners, they will find someone that helps them do that, as well.