Guy Raz, host of NPR’s “How I built this,” on what it takes to be an entrepreneur

Original photo by Kara Frame/NPR

Guy Raz, host of NPR’s “How I built this,” on what it takes to be an entrepreneur

Guy Raz is the host of the NPR podcast “How I built this,” where he interviews entrepreneurs, innovators, and executives from all over the world about the companies they’ve built and the stories behind their success.

We were lucky enough to talk with Raz about his own career, his experience hosting the show, and what he has learned from talking to so many innovators and business leaders. The conversation is below. It has been lightly edited for clarity.

Do you have to be optimistic to be an entrepreneur?

I think the short answer is yes. But, it’s also cultivated. I think optimism comes easy for some people, there’s no question. I mean, if you are somebody like Marc Cuban, he is just optimistic. He thought from the beginning that he was going to make it. He never had a doubt. He had a book on his shelf called “how to retire as a millionaire at age 35” that he bought when he was 17, so it was always his intention and expectation that he would be wealthy and successful. But I think for the most part most entrepreneurs have to work at it. They have to remind themselves that things will work out and that they will somehow figure it out. But there is no doubt that for many of the entrepreneurs that I’ve talked to there are crisis periods, there are trough, and times when they really aren’t sure whether it is going to work.

Are there themes that you can pick out, that you think run through successful entrepreneurs lives? Are there traits that you can pick out, that unite entrepreneurs?

I think if there is one meta-characteristic, one overarching characteristic that unites all of them it is optimism and the unshakeable belief in the thing that they are working on or the thing that they’re doing. And it may not ultimately be the thing that they succeed in, but there is an unshakeable belief in it.

The other thing is, whether its’ Vice Magazine, or Spanx, or Sam Adams beer, or Southwest airlines or Patagonia, every person who is involved in creating those things loved the actual thing. I mean, any other person other than Herb Kelleher would have given up on Southwest airlines. It took them 4 years since the time the company was founded to launch the first airline because they were challenged every step of the way by the major air carriers. Herb Kelleher fought a lonely battle. He was a lawyer and he basically fought and fought for four years. They ran out of money, he was doing it for free for a while, but he really believed that people should have this option of flying for much cheaper than was available, that the monopoly should be broken. He wanted to create this airline. He had this unshakable confidence and optimism in it. It doesn’t mean that there aren’t moments where some of these people have doubts. I mean with Vice Mag they basically had their peaks and troughs as well. They were a clothing company, and they went bankrupt right after 9/11. In many other cases, whoever was behind a company like that would have just walked away. They would have said this is done, that was fun. They sort of swept up the ashes and rebuilt it, I mean Suroosh Alvi and Shane Smith, and turned it into what it is today.

A common thread among the people you interview is that they all have hustle. Do you think that hustle is a necessary component of starting a business?

I think it is the most important part of starting a business. I think it is a really hard part, because the hustle component tends to favor extroverts over introverts, but many of the people who are have been featured on the show are introverts. I mean, Angie Hicks is a great example of that, you know, she co-founded Angie’s list. You know, Neil Blumenthal of Warby-Parker isn’t super extroverted. Melissa Bernstein from Melissa and Doug, she’s super introverted. But what they’re able to do is focus on product development and on other kinds of innovations and partner with a cofounder who has the skills to make the deals and make the sales but ultimately everyone is hustling, everyone is trying to prove that what they have to offer is worth considering, is worth looking at.

Whether it’s hustling for investment funds or hustling to convince people that this idea will work, I mean, to me a classic example of that is Jim Cook. He was working for Boston consulting company and he quit, he just left, and he started to brew beer based on a great-great grandfather’s recipe. And he literally walked around the south end of Boston with a small cooler. And he would walk into bars at 4:00 in the afternoon, before the dinner rush after the lunch-time crowd left, and he would chat up bar backs and bartenders and say, “hey, will you try this beer.” And they would often say, well, just leave me a couple of bottles and I’ll try it later. But he would have a cooler, so the beer was cold and he would have chilled glasses in the cooler, and he would say “no, you have to try it with me, come on, one drink.” He knew that when you offer a bartender a drink, it’s rude to decline. So that’s how he got them to try Sam Adams. So he would just walk from bar to bar. He would literally bang on doors, and you know some of them would say “no, not interested,” they’d say “thanks but no thanks,” but over time he convinced enough people that this was worth trying. And that to me is sort of the classic kind of hustle.

Or Melissa and Doug Bernstein who started this incredibly successful toy company driving from toy store to toy store throughout New England to pitch their products. They had to do that, they had to make their case and prove that it was worth carrying their wooden puzzles at a time when parents were focused on battery powered toys.
Read the entire interview.