How I Built This with Guy Raz

Brian Chesky was 26 when he and his co-founders launched Airbnb, turning a few air mattresses in a San Francisco apartment into one of the most successful startups of all time.

But as Airbnb grew into a company worth more than $100 billion, Brian struggled to keep up. He hired experienced executives, trusted them to make decisions, and watched the company become increasingly chaotic. Looking back, he says Airbnb succeeded in spite of his leadership, not because of it.

Then COVID hit, and Airbnb lost 80% of its business in a matter of weeks. Facing the possibility of losing everything he'd built, Brian completely reinvented the way he ran the company—and soon after, much of his life outside work, too.

In this episode, Brian explains why some of the most common leadership advice can be disastrous for startups, what he learned from Steve Jobs and Barack Obama, and why the day after Airbnb’s IPO was one of the loneliest of his life. Plus, how Airbnb.org is providing free housing to people in crisis—and why Brian wants to expand that effort to one million nights a year.

What You'll Learn

• How an art school graduate with no business experience became the CEO of Airbnb
• Why Brian describes himself as “naturally a great founder but naturally a terrible CEO”
• How following conventional leadership advice created chaos inside Airbnb
• Why Brian believes "hire great people and get out of their way" can be a death sentence for startups
• How losing 80% of Airbnb's business during COVID forced Brian to reinvent his leadership style
• What studying Steve Jobs taught Brian about getting into the details
• How Barack Obama helped Brian understand and confront his loneliness
• Why reaching a $100 billion valuation left Brian feeling empty
• How Airbnb.org grew from helping people displaced by Hurricane Sandy into a global nonprofit—and an ambitious plan to provide one million nights of free housing annually
• How Brian thinks about Airbnb's future—and why he has no plans to stop building

Timestamps:

(00:03:23) - Airbnb goes public at a $100 billion valuation, but Brian wakes up feeling empty

(00:06:05) - From art school to Silicon Valley: How Brian became an unlikely tech founder

(00:10:37) - "I was a great founder and a terrible CEO": Brian's early leadership mistakes

(00:13:21) - Why hiring experienced executives and getting out of their way didn't work

(00:17:59) - The self-doubt and chaos of running a fast-growing company

(00:23:41) - How Barack Obama helped Brian confront his loneliness and reconnect with old friends

(00:33:55) - Why Airbnb's early success led to overconfidence and costly distractions

(00:38:10) - COVID wipes out 80% of Airbnb's business—and forces Brian to change

(00:40:05) - What Brian learned from Steve Jobs about hands-on leadership

(00:47:44) - Why Airbnb's leadership overhaul drove away much of its executive team

(00:50:54) - The 70 revisions of a single press release that helped Brian redefine excellence

(00:52:12) - How Brian gets honest feedback from employees who might be afraid to disagree

(00:57:38) - Why Airbnb is reconsidering some of its long-held beliefs about its business

(01:00:48) - Airbnb's plans to provide free housing for people in crisis

(01:05:09) - Why Brian hopes to keep building for the rest of his life

Production Credits

Our production is handled by Podcast Pointman.

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Today’s callers: Dominic in London faces challenges with profitability and scaling for his foldable bike helmet. Then, Ivana in Vancouver wonders how to maintain the momentum of her pet gear brand as she prepares for the arrival of her first child. Danny in South Carolina wants to expand her nail salon concept without making major trade-offs in her family life. And Justin in Boston grapples with prioritizing the many channels in which he sells his customized footwear.

Plus, Tope discusses Calendly’s new AI-powered scheduling assistant and how advances in technology are making it easier than ever to get new software applications off the ground.

Thank you to the founders of Newlane, Playfield, the Nail Room, and ISlide for being a part of our show.

Be sure to listen to Calendly's founding story as told by Tope on the show in 2020.

Some news: This is the final episode of the Advice Line. Thanks to all of the callers and returning guests who were a part of its run, and to all of you who tuned in — you make How I Built This great.

This episode was produced by Alex Cheng with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang.

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Heather Hasson and Trina Spear saw an opportunity nobody else seemed to notice: millions of healthcare workers were spending long days in uncomfortable, ill-fitting scrubs.

So they set out to reinvent them.

Heather was a designer with almost no money. To join her, Trina left a prestigious job at Blackstone and cashed out her retirement. They sold scrubs out of a car, got rejected by hundreds of investors, and eventually built FIGS into a multibillion-dollar public company.

Along the way, they paid $40 million to fight a lawsuit, navigated a pandemic, and watched their company’s valuation swing by billions.

This week, Heather and Trina share how they built the “Lululemon of Scrubs”—and why your net worth is not the same thing as self worth.

What you’ll learn

•

How a trip to Kenya changed Heather’s view of uniforms–and led her to start her own scarf and tie business

•

How Heather spotted an opportunity in a stale category: healthcare workers want comfortable clothes, too

•

How free coffee became a tool for customer growth

•

How the founders endured hundreds of investor rejections and learned to pursue a quick no

•

How FIGS built a community that is “diehard obsessed” with their products

•

How it pays–and what it costs– to defend your company against competitor lawsuits

•

Why net worth shouldn’t determine self-worth

•

How Heather and Trina think about resilience, luck, and building a company that lasts

Timestamps:

07:05 - Heather’s dreams to become a surgeon and launch a handbag business fall through, so she takes a life-changing trip to Kenya

13:53 - Heather meets a healthcare friend for coffee: “What are you wearing?... This is garbage.”

20:46 - Trina beats Heather in a tennis match, and the two become business partners

29:38 - Trina walks away from Blackstone to join Heather, and everyone asks, “What are you doing?”

35:05 - FIGS launches: Healthcare workers get it, but investors don’t

47:56 - A big-time investor comes on board—from the movie business

52:17 - A competitor sues for $800 million, and Heather and Trina use anger to their advantage

59:46 - COVID hits… and a year later, FIGS goes public

1:08:22 - No major plans to diversify: FIGS is all-in on scrubs for now

This episode was researched and produced by Katherine Sypher with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineer was Robert Rodriguez.

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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.

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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 http://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 http://guyraz.com/ or on Substack.

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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.

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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.

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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
• Generation into a household name
• Why Jeffrey and Alan agree that having a co-founder isn’t for everyone

Timestamps:

7:55 - Jeffrey makes it big in Canada selling adult-learning courses…before he’s forced to leave the country

14:15 - Alan moves to Vermont on a whim, and winds up in a mail-order catalog business

26:56 - Alan and Jeffrey meet for the first time and find common ground: Alan needs capital and Jeffrey has it

32:38 - An atypical office for 1989: Ping pong table, nap room, and employees get prizes when they make mistakes

43:00 - Crisis hits … and tears Alan and Jeffrey’s friendship apart

48:06 - Jeffrey sends Alan a “Dear John” letter, and Alan leaves the company

54:40 - Seventh Generation grows to new heights… then Jeffrey is fired as CEO

1:29:06 - 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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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 http://guyraz.com/ and on Substack.

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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.

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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.

Karissa Bodnar had a dream job at L'Oréal when a close friend died from cancer at age 24. It shook her up and made her reassess what she really wanted to do with her life. The answer? Build her own beauty business with a mission of “giving back.”

The problem? Nobody seemed to want to carry her products. She pitched Sephora, Nordstrom, Ulta, and others—and kept hearing no.

She stuck it out, pouring tens of thousands of dollars of her own savings into it, and worked a full-time job to fund the formulation of new cosmetics.

Two years in, another life-changing event. Karissa posted a video of herself teaching make-up application to domestic violence survivors, and it went viral.

In this episode Karissa explains why mission alone will never save a bad product, how scarcity helped her build a better company, why she resisted raising too much money, and how she turned a deeply personal loss into one of the most distinctive brands in beauty.

What You’ll Learn:

• How Karissa's childhood experimenting with fruits and flowers led her to researching and formulating her own makeup
• How Karissa’s experiences at Nordstrom and Sephora set her up for a plum job in product development
• The importance of attracting an influential mentor or guide to career development, as Karissa did at L’Oreal
• How Karissa developed her unique line — like false eyelashes for people who had lost their natural lashes during cancer treatment
• Why the decision to keep sales DTC and ONLY online can be a great business move
• Why Karissa believes “scarcity drives focus”
• How to handle operations when sales explode
• Why mission helps customer loyalty — but performance drives the initial and repeat purchases

Timestamps:

05:30 – Making makeup in the kitchen at age 10 and Karissa’s first steps into research

08:55 – Learning the beauty business from the ground up

11:22 – How Karissa landed her dream job in product development at L'Oréal

14:48 – The career lessons that got Karissa noticed at L'Oréal

22:03 – How a tragedy made Karissa leave a dream job to start a company “with purpose”

31:36 – The one-person-at-a-time marketing strategy

33:01 – The viral moment that changed Thrive Causemetics

37:06 – Why failing to raise money became an advantage

42:33 – Mission versus product: which really matters?

44:34 – Why Thrive Causemetics stayed direct-to-consumer

This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by Andrea Bruce with research help from Chris Maccini. Our engineer was Jimmy Keeley.

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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 http://guyraz.com/ or on Substack.

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Kim’s inspiration to launch a business came from an unlikely source: Her son’s Crocs. She thought the durable, washable material would make a great beach bag. So she designed one. But after investing her savings—inlcuding some of her kids’ college fund—Kim was crushed when her first major shipment of Bogg bags was defective. It knocked her so off balance, that she put the entire business on hold.

Then something unexpected happened.The few thousand customers who already had a bag….clamored for more. So Kim decided to start over. She borrowed $120,000, found another factory, shared trade show booths with four other founders, and slowly built Bogg Bag into a $100 million phenomenon.

What you'll learn:

• How getting nowhere with Crocs gave Kim the motivation to make Bogg Bag herself.
• Why her first $30,000 production run nearly killed the company.
• Why a founder isn’t always the best judge of her product
• How Superstorm Sandy gave new life to Bogg Bag
• How Kim built Bogg Bag for years while keeping her full-time job and raising two kids.
• How COVID turned Bogg Bag from a beach product into a “beach and beyond” product.
• How Kim got a massive acquisition offer–and why she turned it down.
• Why Kim thinks Bogg Bag can eventually become a billion-dollar brand.

Chapters:

06:36 - Growing up without financial security

08:17 - From high-school dropout to a six-figure career

17:19 - Reading “Mommy Millionaire” and dreaming of inventing something

19:41 - The Crocs-on-the-beach moment

24:56 - Kim hits a wall with Crocs, so she decides to make Bogg Bag herself

33:33 - The early prototypes and a nervous visit to a boutique: “I don’t know what this is, but I think I need it.”

41:16 - The first big shipment, a $30,000 defect, and a decision to pull the plug

47:13 - A massive natural disaster presents an opportunity

52:15 - “Now I gotta make this damn bag”

54:45 - A factory showdown in China

59:52 - Starting over with $120,000

01:01:51 - The trade-show “timeshare” in a tiny booth

01:07:12 - Finally quitting her day job

01:10:42 - COVID boosts the business

01:13:28 - The acquisition offer that could have changed everything

01:23:40 - Learning to lead a much bigger company

01:26:13 - The dream of a family legacy

This episode was produced by J.C. Howard, with music by Ramtin Arablouei.

Edited by Neva Grant, with research help from Sam Paulson.

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Today’s callers: Darin from North Carolina seeks guidance on consumer education as his ghee-based snack brand grows into major retailers. Then Sarah from Massachusetts explores scaling pathways for her ‘never-frozen’ gluten-free baked goods. And John from Ohio considers whether online sales can turn around his local food co-op.

Plus, Ben comments on the drivers of Olipop’s nearly $2 billion valuation, and critiques a common piece of business advice that often holds founders back.

Thank you to the founders of Gheelish, Sarah’s Gluten Free Goods, and Bexley’s Natural Foods 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 Olipop’s founding story as told by Ben in 2024.

This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineers were Cena Loffredo and Robert Rodriguez.

You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at http://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.

Nicole Bernard Dawes spent much of her childhood hanging out in her dad’s potato chip factory on Cape Cod.

She liked his kettle-cooked chips a lot more than the flavorless snacks in her mom’s health food store. But when she started her own business, she wanted the best of both worlds: a snack made with natural, organic ingredients…that still tasted good.

Nicole launched Late July Snacks in 2003, when most consumers barely knew what “organic” meant. For years, sales limped along. Then, in a moment of crisis, she made a company-saving pivot by launching a brand new product – organic tortilla chips. Within just a few years, Late July grew to over $100M in sales, and Nicole decided to launch a new brand in an even more challenging category: soda.

You Will Learn:

• How growing up in a family business can help–and hurt–when you launch your own
• The pros and cons of financial vs. strategic investors
• When to cut a product that isn’t working
• Why the fine print in a contract is so important
• How the hardest decision might be the best one for your family and the business

Timestamps:

07:22 - The car crash that launched a potato chip company

21:00 - Pregnant and craving crackers: The birth of Late July Snacks

36:54 - The organic cookies that tasted great but nearly sunk the business

40:49 - Tragedy and crisis: a father’s death and a $3 million loan in default

50:31 - A tortilla chip Hail Mary

57:29 - Nicole’s first big sales call… and her last chance to save the company

1:08:49 - “The big fish eats the small fish.” A food giant acquisition

1:13:36 - Nicole launches a new brand, moving from a hard category–to an even harder one

This episode was researched and produced by Chris Maccini with music composed by Ramtin Arablouei. It was edited by Neva Grant. Our engineer was Robert Rodriguez.

Follow How I Built This:

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Today’s callers: Cristopher from Chicago wants to expand his family’s salsa brand from farmers markets into retail. Next, Darcy in Australia considers adapting his protein bar brand’s messaging to reach beyond his core enthusiasts. Finally, Seema in Canada seeks strategies to increase B2B sales for her ethical kitchen linen company.

Plus, Daymond and Guy talk about what makes a great Shark Tank pitch, and why Guy decided to start How I Built This 10 years ago.

Thank you to the founders of Sabor a Mexico, Raised Nutrition and Cooks Who Feed for joining us on the 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 FUBU’s founding story as told by Daymond on the show in 2018.

This episode was produced by Katherine Sypher with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Kwesi Lee.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at http://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.