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 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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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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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.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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:

08:15 - Brian uncovers the unexpected culprit behind his health issues: Wheat

09:52 - From Chewy bars and Chipotle to pasta made of… beans?

18:49 - Banza gets a big break on national TV

23:16 - The 192-store order that Banza wasn’t ready for, and why retreating to a smaller manufacturer helped them meet it

30:52 - Banza’s first production run turns to mush when cooked. The solution? “Steep it like tea”

38:44 - The origin of the distinctive orange box

43:53 - Pizza anyone? Banza expands into thousands of stores and launches new products

47:10 - The food safety scare that Brian never saw coming

58:23 - 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.

Follow How I Built This:

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Website → guyraz.com

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today's callers: Carrie from Paris wants to turn interest into bookings for her boutique study-abroad programs for adults. Then, Grace from Nashville considers how to re-build relationships with interior designers she may have let down early on in her furniture upholstery business. And Angel from Indiana explores how to translate the emotional appeal of her self-care soap kits into stronger online sales.

Plus, Michelle explains why founders don't always need to raise outside capital, and why they shouldn’t go into business with an exit plan.

Thank you to the founders of Elective Study Abroad, Grace Ann Upholstery, and Sacred Pause Soap Company for being 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 Beyond Yoga’s founding story as told by Michelle in 2025.

This episode was produced by Carla Esteves 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.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today’s callers: Juliette in France wonders how to raise awareness of her “magical” cooling device—without a costly ad campaign. Then David in North Carolina looks to grow the wholesale channel of his engraved gifts business in light of thinning retail margins. And Kaitlin in California wants to leverage the virality of her supportive, bordered sheets and create an enduring sleep brand.

Plus, Kip reflects on The Container Store’s bankruptcy and acquisition, and plugs patience and persistence as the keys to sustainable growth.

Thank you to the folks at CoolaWand, Hazel Grove Customs, and Kaomi Sleep 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 The Container Store’s founding story as told by Kip and his wife Sharon in 2024.

This episode was produced by Alex Cheng 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 or on Substack.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.