It’s not every day you get to interview one of the interviewing-greats about interviewing. Sitting down with Guy Raz, award-winning reporter and podcast host, was a bit surreal. Cue: some nerves, and a lot of excitement. Quickly, I realized that behind Raz’s approach to storytelling, there’s so much to learn about running a business.
And thankfully, Raz has a disarming way of making so many different types of people feel at ease. If you’re one of the 19 million listeners who tune into The Great Creators, Wisdom From the Top, Wow in the World or his other podcasts each month, you know what I’m talking about. On How I Built This, Raz goes deep with entrepreneurs — covering their early decisions and their most vulnerable and pivotal moments. Listening in, it’s like you’re right there with Raz and his guest, listening to an intimate conversation. And that’s intentional.
According to Raz, our brains process visualization lightning-fast. That means when you’re talking with someone face-to-face, it’s easy to focus on their expressions and lose the emotional resonance of their voice. “You don’t hear the cadence, the pauses and the variations in the voice that communicate things beyond just words,” Raz said. So he takes this into account when he holds an interview, even if it’s on video. “I’m constantly making sure that it doesn’t matter how you consume that conversation, it’s going to be powerful and rich,” he explained.
In the Square original series, “The Way Up,” Raz speaks with entrepreneurs from six of the fastest-growing local businesses in the country. Together, they talk through everything from opening a new location to winning a James Beard Award and reaching millions in sales. Watching Raz on set, I saw each guest relax in his presence, much like I did. After the conversation wrapped, several leaned in and thanked him in a whisper for making them feel so comfortable sharing their story.
Raz is an expert. He holds some of the most coveted awards in broadcasting, and Forbes describes him as “the greatest interviewer of his generation.” But having launched his own podcast, a book, and two media companies, he’s an entrepreneur in his own right. He shares a lot of the same experiences as the guests he interviews. So here’s our conversation about the business behind storytelling and, well, business.
Square: Thanks for sitting down with us today, Guy. We’re excited to learn about your background, and your career. Let’s take a page out of your book and start from the very beginning. You started out as a student reporter at your university. What inspired you to go into journalism?
Guy Raz: Yeah, I think all humans have a capacity to be curious. I wanted to make that my profession, and become a professional curiosity-seeker. What better way to make a living than to ask questions, and to learn about how people live, what they think about, what motivates them, how they improve their lives, how they endure, what their family stories are, than being a reporter and a journalist? What I do has changed in some ways, but the fundamentals of it are the same. I ask questions and I follow a thread, and then double click on certain answers and go down rabbit holes, which is just an incredibly interesting experience.
Square: That’s relatable. My curiosity has really guided my career path. But for you, going from war correspondent, to NPR reporter, to podcast host … It sounds like a lot has changed. Tell me a little bit more about your biggest trajectory-changing moments?
Guy Raz: I really wanted to be a print reporter early in my career, but I couldn’t get a job with any of the newspapers in the 1990s. It was very, very hard. I couldn’t get an internship or a foot in the door with the Washington Post or the Boston Globe or the LA Times or any of these places I dreamed of working for. But after multiple rejections, I did get my foot in the door with radio and ended up as a broadcaster, and then in television, and then over time in podcasting. All of those changes happened because of setbacks. I went into radio because I couldn’t get into print. I flourished in radio because I ended up loving it and then found that I had some challenges just trying to move beyond what I had been doing. And so I was recruited into television, and I did that for several years, and then I went back into radio, and then I had another setback, which was that I wasn’t selected to be the main anchor for the radio program.
So I went into podcasting, and that was like going into exile in 2011.
Square: That is a huge leap!
Guy Raz: Yeah, going into podcasting from being on national radio. It was like the end of your career. Who does that? But this thing that I got into just exploded in growth and popularity. During the course of doing this kind of work, I got out of the news and was really focused on ideas and began to get a lot of exposure to entrepreneurs 15 years ago. And that really started to change how I thought about what I wanted to do. It actually went right back to the fundamentals of what it was, which was to follow my curiosity and to find ways to use stories to inspire people. And that was really the transition to what I’ve now been doing for the past 10 years, which has been focusing almost entirely on entrepreneurs, on builders, on innovators, on people with big dreams who are changing the world, and I’m trying to use their stories to inspire people to hopefully do the same.
Square: Totally. I think in a lot of what you’re saying, there’s so much you couldn’t plan for but worked out in ways that even surprised you. There’s so much about this that feels like an entrepreneur’s story. Do you consider yourself an entrepreneur?
Guy Raz: Now when I reflect on my entire career, it’s clear to me that I was pursuing an entrepreneurial path. I mean, even when I was a reporter working for CNN, you drop into a country and you have to tell a story by a deadline, which might be four or 5:00 PM that night. And you have to use skills that entrepreneurs have to develop. You’ve got to be resourceful, you’ve got to figure out how to get information quickly. You have to find the right sources, you have to get the right shots, often you’re very constrained and you have to just figure it out.
Over time, those were the skills and tools that I developed just intuitively. And so when it came time for me to leave the world of mainstream media and start my own business and create programs, again, it wasn’t like I all of a sudden thought to myself, ‘I’m an entrepreneur, look what I’m doing.’ But it happened.
Square: I think that’s a very common experience for people. I hear that a lot when I talk with business owners. What they were doing wasn’t the original plan, but everything led up to that moment.
Guy Raz: Yes, It sort of evolved very organically over time. I started a production company. I started a second one where we make children’s programs. I started one where we make business programs and shows about inspiring people, whether it’s the Great Creators or Wisdom From the Top or How I Built This.
So much of it is about serendipity and it’s about looking around at opportunities, and it’s about surrounding yourself with people who are smarter than you and who you can build things with and create things with. And that’s what I’ve been very lucky to have in my life. I now see myself as an entrepreneur. But it took me a while before I was comfortable calling myself that, because I thought an entrepreneur was somebody who starts something from the beginning in a store at a brand or a business, and it’s not always so clear cut.
Square: I’m curious, are you surprised that the skills you’ve developed in one world have actually helped you in the other? What are the skills that you find are analogous between the two, between being both a successful interviewer and podcaster and being a successful entrepreneur?
Guy Raz: I’m not a better interviewer, I’m not smarter, I’m not more knowledgeable than lots of other people and I don’t ask better questions than anyone else. The reason why I have developed an ability to tease out deeper ideas and stories from people is because I’m a very good listener. And that actually is a superpower that the interviewer needs to develop. It’s actually not what you say, but it’s how you listen to what somebody else is saying when you get an incredible interview. It’s the same in business. It’s not what you say, it’s how you listen to people and how you follow their thread.
So I don’t go into an interview with prepared questions. I go into an interview very prepared, knowing about that person’s life. For the most part, any questions that I have written down are sort of out the window because I am following a thread. I’ll ask a question, and the person will answer. I will hear something in that question that is worth exploring more. And oftentimes people want to explore more. They want to go deeper, but they’re not sure if you do.
When you kind of double click on that answer and you go down certain rabbit holes, you’re signaling to that person, I respect you, I respect your ideas. I want to learn from you. And you are not saying that. You’re just signaling that and that person’s responses to you are not just powerful and meaningful, but you are also deepening over the course of that conversation, your connection with that person. It’s critical in business too.
Business is all about relationship building and listening to the signals all around you, whether it’s a customer or a partner or even a piece of data. When you can develop a bond with somebody quickly, it can and often will be transformational for your business.
Square: I like to tell my friends really great journalists would make really excellent entrepreneurs, in part because of this ability to listen. It’s about building the relationships around you, and also a relationship with the customer that you’re looking for, and really listening to that customer about what they need. At Square, we think about business owners’ stories, where they are in their lives so we can develop a point of view of how to help them. When you think about the six business owners that you spoke with on this series, is there anything that stood out to you about their journeys?
Guy Raz: Serendipity plays a role in every single one of these stories. And I think sometimes people confuse the word serendipity and an effortlessness, and they’re not the same things. Serendipity still requires a lot of effort, and it still requires a lot of backstory and struggle. We can’t plan for exactly what’s going to happen in our lives. We can dream, and hope, and think about maybe one day doing so. But if you look at all of these stories, none of them were planned.
Charles didn’t say when he was 17, leaving Charlotte, the outskirts of Charlotte, ‘I’m going to have a restaurant called Charles Pan-Fried Chicken one day, and it’s going to be legendary.’ Pete didn’t say, ‘I’m going to own one of the most important bookstores in San Francisco.’ Jenny Nguyen didn’t even see herself as an entrepreneur until recently. She was in kitchens. I mean, even Alex at Rustler Hat Co., she was working in real estate. So none of these businesses were planned. They all happened because out of circumstance or frustration or some kind of change in life or an opportunity that presented itself. But that opportunity presented itself because all of the people, all these stories were waiting for them. I mean, they were eyes-wide-open. They were perceptive to the possibility of those opportunities coming to them.
Square: I love that, each story kind of requires a big key moment. I’d love to dig a little bit deeper into the qualities that you find in yourself as an interviewer and the folks that you mentioned. What personal traits do you see in these folks that you possess as well as an entrepreneur, and an interviewer?
Guy Raz: What virtually every entrepreneur I’ve interviewed shares is an absence of ego. Shamelessness is another good word for it. It’s like if somebody says ‘no’ or ‘I’m not interested in your product,’ or ‘please leave, stop trying to sell me.’ They’ll move on.
No one likes to be rejected, including the entrepreneurs I’ve interviewed, including all of these entrepreneurs. But they have figured out that it is part of the process. And when your ego is wounded and it prevents you from moving forward, that can be an obstacle. But when you’re not too worried about your ego or feeling like everybody always has to treat you a certain way and respect you in a certain way, but you’re really focused on a mission on something that is bigger than you, it could be your business, it could be your employees, it could be building something to create an awesome community for people, like The Sports Bra.
Square: You’re absolutely right. They’re all so incredibly driven, and resilient. It’s really inspiring.
Guy Raz: I think that’s what enables successful entrepreneurs to become successful. Not that they’re born with this trait, but that they have developed this skill. It’s taken me a long time to develop myself. They can do things like brush it off. If somebody is sort of skeptical or even mocks their idea, they can move on and go to the next person or try again, or maybe even come back to that person in the future.
I have told so many stories in the show where a founder will go seek out investments and will be laughed out of the room in many cases. And then two, three years later when they’ve shown that there’s traction and there’s potential in their business, have gone back to those same investors who have said, ‘Wow, you really proved me wrong. I want to be part of this now.’ And that’s remarkable. I mean, that’s the sign of a really great entrepreneur who can go back and say, ‘Okay, let’s try again.’
Square: Amen.
