How I Built This with Guy Raz

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.

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

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:
7:38 A lightbulb switches on at an NYC bodega: “Oh my God, look at all those cherries!”
11:52 The moment Stitch Fix founder Katrina Lake realized she should start her own business.
13:50 The difference between scary and dangerous, and why it matters for founders
21:17 Eileen Fisher’s first, terrifying trade show: “I couldn’t speak. I just stood there.”
26:56 “Everything was on one computer?” The chaotic launch of Instagram
31:15 How Sara Blakely sold her first Spanx
35:45 The marketing genius behind Liquid Death
42:22 Why 2008 was the worst year of Joe Gebbia’s life
50:01 How the co-founder of Banana Republic fell asleep at the wheel—literally
58:39 Makeup mogul Bobbi Brown on selling to Estee Lauder: “I am not a follow-the- leader-kind of person.”
1:06:59 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
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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