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:

Instagram → @howibuiltthis

X → @HowIBuiltThis

Facebook → How I Built This

Follow Guy Raz:

Instagram → @guy.raz

Youtube → guy_raz

X → @guyraz

Substack → guyraz.substack.com

Website → guyraz.com

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:

Instagram → @howibuiltthis

X → @HowIBuiltThis

Facebook → How I Built This

Follow Guy Raz:

Instagram → @guy.raz

Youtube → guy_raz

X → @guyraz

Substack → guyraz.substack.com

Website → guyraz.com

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:

Instagram → @howibuiltthis

X → @HowIBuiltThis

Facebook → How I Built This

Follow Guy Raz:

Instagram → @guy.raz

Youtube → guy_raz

X → @guyraz

Substack → guyraz.substack.com

Website → guyraz.com