Guy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. In each episode, founders reveal deep, intimate moments of doubt and failure, and share insights on their eventual success.&nbsp;How I Built This&nbsp;is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds.

How I Built This is part of the Vox Media Podcast Network.

How I Built This with Guy Raz

Today’s callers: Kohindo 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 Kohindo, 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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Advice Line with Seth Berkowitz of Insomnia Cookies

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. 

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Sweet Loren’s: Loren Castle. How A Recipe Makeover Built a National Cookie Brand

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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Advice Line with Tara Bosch of SmartSweets

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.

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Alamo Drafthouse Cinema: Tim and Karrie League (2023)

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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Advice Line with Nick Green of Thrive Market

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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10 Years of How I Built This:  A Decade of Innovation, Risk and Reinvention

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 hibt@id.wondery.com 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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Advice Line with Scott Tannen of Boll & Branch and Jamie Siminoff of Ring (2025)

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.

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Seventh Generation: Alan Newman and Jeffrey Hollender. A Partnership that Flourished—until it Failed. (2021) 

Today’s callers: Janell from Kentucky wonders how to build a sense of hospitality into her canned bourbon cocktail brand. Jade from South Carolina considers the upsides and risks of shipping her smoked salmon directly to customers. And Bar from Colorado considers strategies for bringing his protein-packed cous cous to quick service restaurants.

Plus Danny talks about the elements of a strong company culture as described in his new book, What Could Possibly Go Right?

Thank you to the founders of Ponyboy Slings, Angel Oak Smokehouse, and Boostcous for being a part of our show.

If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—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 hibt@id.wondery.com or call 1-800-433-1298. 

And be sure to listen to Shake Shack’s founding story as told by Danny on the show in 2020.

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

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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Advice Line with Danny Meyer of Shake Shack

Brian Rudolph started making chickpea pasta in his Detroit apartment because wheat made him feel sick. A decade later, Banza was in more than 25,000 stores, and today, it’s one of the most popular pasta brands in the country. Success was not automatic: The business barely got off the ground because the cooked pasta was turning to mush—and as Banza became known for its health benefits, a food-safety scare sent sales plunging by 30%.
In this episode, Brian explains why he was inspired to create a whole new category, how he turned chickpea skeptics into fans, and how the company rebuilt trust after a public relations disaster. 
What you’ll learn 

How Brian and his brother Scott launched Banza with only $100,000.

How they learned to stop chasing perfection and to ship something that was “good enough.” 

How crowdfunding and reality TV helped Banza land its first retail accounts. 

How packaging can become an important growth engine for a new brand. 

How transparency can rebuild trust after a PR debacle–but can’t restore it overnight. 


Timestamps:
05:50 - Brian uncovers the unexpected culprit behind his health issues: Wheat
07:27 - From Chewy bars and Chipotle to pasta made of… beans?
16:24 - Banza gets a big break on national TV
20:51 - The 192-store order that Banza wasn’t ready for, and why retreating to a smaller manufacturer helped them meet it  
26:12 - Banza’s first production run turns to mush when cooked. The solution? “Steep it like tea”
34:04 - The origin of the distinctive orange box
39:13 - Pizza anyone? Banza expands into thousands of stores and launches new products 
41:00 - The food safety scare that Brian never saw coming
52:13 - Even in the midst of a crisis, Brian says to “assume positive intent”

This episode was produced by Katherine Sypher, with music by Ramtin Arablouei.
Edited by Neva Grant, with research help from Kerry Thompson. Our audio engineer was Robert Rodriguez.


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