How I Built This with Guy Raz

Today’s callers: Dominic in London faces challenges with profitability and scaling for his foldable bike helmet. Then, Ivana in Vancouver wonders how to maintain the momentum of her pet gear brand as she prepares for the arrival of her first child. Danny in South Carolina wants to expand her nail salon concept without making major trade-offs in her family life. And Justin in Boston grapples with prioritizing the many channels in which he sells his customized footwear. 

Plus, Tope discusses Calendly’s new AI-powered scheduling assistant and how advances in technology are making it easier than ever to get new software applications off the ground. 

Thank you to the founders of Newlane, Playfield, the Nail Room, and ISlide for being a part of our show.

Be sure to listen to Calendly's founding story as told by Tope on the show in 2020.

Some news: This is the final episode of the Advice Line. Thanks to all of the callers and returning guests who were a part of its run, and to all of you who tuned in — you make How I Built This great.

This episode was produced by Alex Cheng with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack.

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Heather Hasson and Trina Spear saw an opportunity nobody else seemed to notice: millions of healthcare workers were spending long days in uncomfortable, ill-fitting scrubs.

So they set out to reinvent them.

Heather was a designer with almost no money. To join her, Trina left a prestigious job at Blackstone and cashed out her retirement. They sold scrubs out of a car, got rejected by hundreds of investors, and eventually built FIGS into a multibillion-dollar public company.

Along the way, they paid $40 million to fight a lawsuit, navigated a pandemic, and watched their company’s valuation swing by billions.

This week, Heather and Trina share how they built the “Lululemon of Scrubs”—and why your net worth is not the same thing as self worth. 

What you’ll learn 

Timestamps:

07:05 - Heather’s dreams to become a surgeon and launch a handbag business fall through, so she takes a life-changing trip to Kenya

13:53 - Heather meets a healthcare friend for coffee: “What are you wearing?... This is garbage.”  

20:46 - Trina beats Heather in a tennis match, and the two become business partners

29:38 - Trina walks away from Blackstone to join Heather, and everyone asks, “What are you doing?” 

35:05 - FIGS launches: Healthcare workers get it, but investors don’t

47:56 - A big-time investor comes on board—from the movie business 

52:17 - A competitor sues for $800 million, and Heather and Trina use anger to their advantage

59:46 - COVID hits… and a year later, FIGS goes public

1:08:22 - No major plans to diversify: FIGS is all-in on scrubs for now 

This episode was researched and produced by Katherine Sypher with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineer was Robert Rodriguez.

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Today’s callers: Kahindo from New York is looking to reboot her African-rooted fashion brand after losing a few key retailers. Then Tara from San Diego considers avenues to educate consumers about the benefits of her wool sauna hats. And Carol from Houston wonders whether to market her collegiate purses and accessories l to students or their gift-giving family members. 

Plus, Seth lays out his ambitions to quadruple Insomnia’s locations and become a global chain — without turning to franchising.

Thank you to the founders of Kahindo, Sauna Societé, and Desden for being a part of our show.

Be sure to listen to Insomnia Cookies’ founding story as told by Seth on the show in 2024.

This episode was produced by Casey Herman with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack.

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Loren Castle started baking cookies after surviving cancer in her early twenties. Five years later, Sweet Loren’s refrigerated cookie dough was generating just $350,000 a year. But instead of giving up, she listened to customers, and reinvented the dough without gluten, dairy, eggs or nuts.  That transformation turned a small regional business into a national brand sold in more than 30,000 stores.

WHAT YOU'LL LEARN

• How surviving cancer at 22 inspired Loren to rethink her career and develop a passion for healthier food.
• What working at New York’s Levain Bakery taught her about the enormous appeal—and profitability—of cookies.
• Why Loren decided to sell ready-made cookie dough instead of cookies 
• Why she was totally unprepared for her first Whole Foods meeting—but went anyway 
• Why raising her first $1 million from friends and family was much harder than she expected.
• Why hundreds of customer requests revealed an unmet need for allergen-free cookie dough.
• Why growing slowly may have saved the company.
• Why Loren isn't rushing to sell Sweet Loren’s

TIMESTAMPS: 

8:40 – After her mother's leukemia diagnosis, Loren is diagnosed with Hodgkin's Lymphoma at 22. 

13:12 – Watching people line up for cookies at Levain Bakery: “I think this is America’s favorite food.” 

14:54 – Selling baked goods at Smorgasburg: customers ask if they can just buy the dough 

26:52 – Just as Whole Foods agrees to carry her cookie dough, Loren loses her mom  

37:41 – What happens after Sweet Loren’s gets on The Today Show:  “The whole country is excited by this.” 

50:19 – Loren reconsiders her recipes after customers ask for dough without gluten, dairy, eggs. 

56:24 – Loren takes the leap: discontinuing her original product line and going allergen-free for all. 

1:05:41 – From one Whole Foods to 30,000 stores–the company expands nationally. 

1:07:46 – After years of struggle, Loren explains why she wants to keep building the company instead of pursuing an exit.

This episode was produced by Carla Esteves, with music composed by Ramtin Arablouei.  It was edited by Neva Grant. Our audio engineer was Jimmy Keeley. 

Follow How I Built This:

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Today’s callers: Lindzi from Chicago wants to expand her gourmet marshmallow brand into retail without cannibalizing her high-margin DTC sales. Then, Vivi from Hawaii considers how to best tell her sustainable swimwear brand’s story to a digital audience. And Aly from Los Angeles wonders whether a subscription model is best for her whimsical curated experiences. 

Plus, Tara talks about her latest entrepreneurial venture, Snackish, and how starting a new company feels different the second time around... 

Thank you to the founders of XO Marshmallows, Vivi’s Vacation, and Romanticize Collective for being a part of our show.

Be sure to listen to SmartSweets’ founding story as told by Tara on the show in 2024.

This episode was produced by Chris Maccini with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack.

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In the early 1990’s, Tim League spent $50,000 in savings to lease an abandoned movie theater on the wrong side of the tracks—a shaky experiment that eventually grew into a thriving national chain. As Tim and his wife Karrie built theaters in Austin and beyond, they made a name for themselves by offering dinner with the movie, creative pairings (like sake with Godzilla), and roadshows where movie-goers could watch Deliverance in canoes, or Rocky on the famous steps in Philly. Alamo Drafthouse Cinema now has dozens of locations across the country, but there have been plenty of bruises along the way: a failed first theater, a fractious lawsuit with business partners, and a swan dive into the red during the pandemic.

This episode was produced by Carla Esteves, with music by Ramtin Arablouei.

Edited by Neva Grant, with research help from Carla Esteves.

Follow How I Built This:

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Today’s callers: Mercedes in Utah tries to find harmony between quality and speed as she scales her concert attire brand for musicians. Then Danny in Colorado grapples with the tradeoffs of growing his sustainable and functional coffee brand. And Riya in Illinois wonders how to build awareness for her app that aids people affected by speech loss.

Plus, Nick’s insights on how AI is changing the way we fill our grocery carts — and how grocers respond to food and nutrition trends.

Thank you to the founders of Blackstrad Concert Attire, Peak State Coffee, and Voice Back for being a part of our show.

And be sure to listen to Thrive Market’s founding story as told by Nick in 2024.

This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang.

You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack.

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Stories about starting a business are almost always full of drama. They’re about ambition, loss, triumph, catastrophe, resilience. And they’re also full of life lessons – which is why Guy Raz launched How I Built This 10 years ago: He wanted to host a free master class in entrepreneurship, one conversation at a time. Ten years on, he’s conducted over 600 interviews with some of the world’s most successful founders, and on today’s show, he replays some of the most memorable moments and lessons. Joining him is Jamie Siminoff, the founder of RING and a former guest on the show. Why Jamie? He’s a friend, a fan, and – as you may remember from his first interview - he doesn’t hide his emotions.

Timestamps:

5:10 A lightbulb switches on at an NYC bodega: “Oh my God, look at all those cherries!” 

9:33 The moment Stitch Fix founder Katrina Lake realized she should start her own business.

12:04 The difference between scary and dangerous, and why it matters for founders

19:35 Eileen Fisher’s first, terrifying trade show: “I couldn’t speak. I just stood there.”

22:59 “Everything was on one computer?” The chaotic launch of Instagram

27:32 How Sara Blakely sold her first Spanx

31:16 The marketing genius behind Liquid Death

39:40 Why 2008 was the worst year of Joe Gebbia’s life

44:51 How the co-founder of Banana Republic fell asleep at the wheel—literally

53:40 Makeup mogul Bobbi Brown on selling to Estee Lauder: “I am not a follow-the- leader-kind of person.”

1:01:59 Luck, skill, and staying on the surfboard

This episode was produced by Casey Herman, with music by Ramtin Arablouei.

Edited by Neva Grant. Our audio engineer was Robert Rodriguez.

Follow How I Built This:

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CEO and co-founder of Boll & Branch, Scott Tannen joins Ring founder Jamie Siminoff and Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Jamie and Guy talk about how creating repeat customers often comes from creating social good.  

First, we hear from Melita in Toronto who's wondering whether to continue bootstrapping her organic clothing business. Then Eric in the Sunshine State asks which direction to take to grow his sunscreen apparel lines. And Chris in Alpine Meadows, California, is trying to figure out how to get his sleek binoculars into the hands of more people.

Thank you to the founders of Q for Quinn, L Cubed Lifestyle, and Nocs Provisions. 

If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [email protected] or call 1-800-433-1298.

And be sure to listen to the story of how Jamie founded Ring from our episode back in 2020, as well as his appearance on the Advice Line in 2024.. And how Scott and his wife Missy started Boll & Branch, a story they told on the show in 2024.

This episode was produced by J.C. Howard with music by Ramtin Arablouei.

It was edited by Andrea Bruce. Our audio engineer was Jimmy Keeley.

Follow How I Built This:

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Facebook → How I Built This

Follow Guy Raz:

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Youtube → guy_raz

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With its eco-friendly paper towels, diapers, and cleansers, Seventh Generation was one of the first—and most successful—green household brands to hit the market. But in the early 1990s, its two founders had a bitter falling out.

Alan Newman and Jeffrey Hollender have barely spoken since that time, but they both agreed to come on the show to talk about the business they were both passionate about, and the delicate nature of partnership.

What you'll learn: 

• Why Alan says his great strength—and his greatness weakness—is his tendency to say “yes.”
• How Jeffrey and Alan lost their friendship and business partnership after only three years.
• How Jeffrey grew Seventh Generation into a household name—and then got fired.
• How two formerly estranged partners feel about partnership now.

Timestamps:

5:30 - Jeffrey makes it big in Canada selling adult-learning courses… before he’s forced to leave the country

11:50 - Alan moves to Vermont on a whim, and winds up in a mail-order catalog business

24:31 - Alan and Jeffrey meet for the first time and find common ground: Alan needs capital and Jeffrey has it 

30:13 - An atypical office for 1989: Ping pong table, nap room, and employees get prizes when they make mistakes 

40:35 - Crisis hits… and tears Alan and Jeffrey’s friendship apart

45:41 - Jeffrey sends Alan a “Dear John” letter, and Alan leaves the company

50:00 - Seventh Generation grows to new heights… then Jeffrey is fired as CEO

82:56 - Jeffrey and Alan reflect on why their partnership failed, and what it takes to have a good one  

This episode was produced by Casey Herman with music by Ramtin Arablouei. 

It was edited by Neva Grant.

Follow How I Built This:

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Facebook → How I Built This

Follow Guy Raz:

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Website → guyraz.com

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