How I Built This with Guy Raz

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

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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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: 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
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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.