Guy Raz, called “one of the most popular podcasters in history” by The New York Times, introduced How I Built This in 2016 and quickly saw the show grow to be one of the most popular podcasts globally. The show focuses on entrepreneurship and each of the 100+ episodes features a notable founder, businessperson or innovator discussing their successes and failures in business. While there have been several interviews with iconic entrepreneurs like Mark Cuban and Howard Schultz, Raz isn’t afraid to also bring lesser-known names into the studio to share the stories behind a wide variety of companies. 

Raz has established himself as a great interviewer and storyteller through his other work on TED Radio Hour and All Things Considered and he’s able to draw big names into the studio to share never before heard stories about their companies. Entrepreneurs will love this show for the insight and advice, and those not in business will find it equally captivating because of the background it provides into some of the world’s greatest brands. 

1. Wikipedia: Jimmy Wales

Episode 70

This episode with Jimmy Wales is one of the exciting interviews from Guy Raz that features a founder that does not speak much publicly about the roots of their company. While we all use Wikipedia and surely are familiar with some aspects of how it runs, hearing Wales discuss the founding, politics and philosophy of the network he built is truly a great listen. Now the fifth most visited website in the world, Wales goes in depth into how the site grew since it was started in 2001 and shares why it has remained a non-profit with open source roots.

2. Bumble: Whitney Wolfe

Episode 116

Whitney Wolfe’s episode is full of drama, lively stories, and thought-provoking discussions. First, she begins by discussing the roots of her company, the Feminist angle it has taken, and how it grew from Tinder (where she was the former VP of Marketing). Although she is not able to discuss all of the details of her fallout with Tinder, she shares great stories about the guerilla style marketing that helped Bumble grow to be one of the top dating apps on the market.

She also spends a good portion of the interview discussing some of the politics of dating apps that we may not think about, including the decision to ban photos with guns from profiles and why the decision to only allow women to message first was made.

3. Ben & Jerry’s: Ben Cohen And Jerry Greenfield

Episode 60

If you are less interested in technology, marketing and finance and prefer feel good stories with a bit of humor mixed in, this episode is a great place to start. Of course, the lifelong friends share the history of the company and how they were able to grow it, but they also reflect on some of the quirkier aspects of the company like the unique flavor names and cult-following the ice cream has. Ben and Jerry also talk about the decision to stay political and to integrate humanitarianism into their brand when so many stay away from it. 

4. AirBNB: Joe Gebbia

Episode 6

Guy Raz has interviewed lots of tech founders, from founders of Instagram and LinkedIn to Reddit and Lyft, but Joe Gebbia’s discussion of starting AirBNB is one of the most engaging. Gebbia is a great story teller, and he spends much of the interview talking about the importance of community-building in his company and the growing role he sees it playing in the lives of travelers and hosts alike. 

5. Beyond Meat: Ethan Brown

Episode 24

When this episode was released in 2017, the Beyond Burger was hardly a well-known meat alternative and the plant-based meat market was not making news or gaining much traction. Now, thanks to Brown’s own company’s growth and numerous notable competitors, it is interesting to go back and hear the roots of Beyond Meat and his aspirations for the company before it blew up.

Another interesting aspect is the science that is shared, if you were ever curious how exactly a plant-based meat like Beyond offers is made and how it differs from your everyday veggie burger.

6. Southwest Airlines: Herb Kelleher 

Episode 11

87-year-old Herb Kelleher differs from some of the typical start-up founders and young entrepreneurs that How I Built This hosts, but his stories were just as engaging. As a veteran in the airline industry since the 1960s, Kelleher provided a great history of how Southwest has grown since he began the airline, but also how the world of aviation as a whole has transformed. 

Highlights of this episode are Kelleher’s reflection on the years of lawsuits Southwest initially faced, as well as the unique fact that the airline used to gift frequent flyers with a free bottle of whiskey whenever they flew Southwest.  

7. Buzzfeed: Jonah Peretti 

Episode 46

Few people understand the changing media landscape as well as Jonah Peretti. In addition to founding Buzzfeed in 2006, he was also a founder of the Huffington Post. In this interview from 2017, Peretti discusses his roots in media and “going viral,” which largely included pranks, trolling and ironic websites. However, he quickly took a more serious turn when he began studying and understanding how information spreads online. Peretti discusses the various ways Buzzfeed makes money, his goals for the future of the site and why he thinks his website and the polls, quizzes and other online content it creates is so popular. 

8. Spanx: Sarah Blakely

Episode 1

Sarah Blakely may not be as much of a household name as some other guests on How I Built This, but she became the youngest female billionaire in America by founding Spanx and certainly has a lot of great insight to share. Blakely largely built the company herself initially, developing her own prototypes and never taking investments, and it’s inspiring to hear how successful the company has been.  

9. TOMS: Blake Mycoskie

Episode 39

TOMS revolutionized the idea of a cause-driven business with the model of giving a pair of shoes for every pair of TOMS purchased. However, TOMS was hardly Mycoskie’s first business endeavor and while he does share a deep history of how a trip to Argentina inspired TOMS, he also talks about his personal life and what made him a serial entrepreneur. From laundry to reality TV, Mycoskie has certainly touched all sorts of businesses in his successful career and it’s fun to hear why he bounced around so much before settling on TOMS as his longest commitment to date. 

10. Burton Snowboards: Jake Carpenter

Episode 57

Truly a story of having a dream and following it, Jake Carpenter not only started Burton but is also considered to be one of the inventors of the modern snowboard. After his competitive skiing career ended in a car accident, Carpenter studied economics and went on to become one of the first manufacturers of snowboards. The boards he designed in the 1970s have changed slightly to become what we know today and the company has of course grown, but the culture of Burton remains committed to having a positive culture with plenty of ski breaks for employees.

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