How I Built This with Guy Raz

Squarespace founder Anthony Casalena joins Guy on the Advice Line, where they answer questions from three early-stage entrepreneurs. Plus, Anthony shares how Squarespace is leveraging AI to help people bolster their sites and digital presence more effectively.

First we meet Bob in Connecticut, who’s wondering how to pump up awareness for his custom-made mattresses. Then Stacy in California asks how her new first aid products can stand out in a category dominated by legacy brands. And Mehek in New York strategizes about how to best launch a new digital companion she’s building: an app that supports people recovering from eating disorders.

Thank you to the founders of Custom Sleep Technology, All Better Co., and Kahani for being a part of our show.

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 Squarespace’s founding story as told by Anthony on the show in 2019.

This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was James Willetts.

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.

At 19, Ben Francis was lifting weights during the day and delivering pizza at night. He didn’t have money. He didn’t have fashion experience. He didn’t even know how to sew. What he did have was a front-row seat… to a new online trend. Before Instagram and influencers became a strategy, a handful of YouTubers were redefining gym culture — building identity and community online. 

With his gymwear brand Gymshark, Ben didn’t try to compete with Nike. He didn’t try to buy ads. He did something much more powerful: He built relationships. He sent free T-shirts to the Youtubers he admired. He learned what gym-goers actually wanted to wear: tapered tracksuits, and shirts that emphasized their muscles.

Today, Gymshark is valued at more than a billion dollars, and Ben is the youngest billionaire in the UK. But his story is not just about business. It’s about identity, discipline, humility—and learning to grow as fast as you can learn. 

What You’ll Learn: 

• How to build a brand by building community first 
• How to hire smart people without losing control of your company
• Avoiding imposter syndrome by creating your own apprenticeship program 
• How to get stronger by staying in your lane 

Timestamps: 

06:15 - The IT education that changed Ben’s life

17:48 - Gymshark’s first sale: a £2 profit that had him dancing in his bedroom

20:06 - Early apparel—Screen-printing T shirts, a single sewing machine 

23:50 - How YouTube bodybuilders became their best marketers 

40:48 - How Ben hired his own boss–and what he learned from him

47:44 - Expanding to the US: a bone-chilling trip to Ohio  

50:35 - The bodybuilder’s aesthetic: big shoulders, narrow waist

53:58 - The painful breakup between Ben and his co-founder 

1:04:49 - Why he earned the nickname “Hurricane Ben.” 

1:12:30 - A legacy company: Resisting the urge to grow beyond the gym 

1:19:19 - Small Business Spotlight 

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

Edited by Neva Grant, with research help from Alex Cheng.

Follow How I Built This:

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Chet Pipkin, former CEO and founder of the electronic goods company Belkin International, joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Chet and Guy drill into why solving problems for consumers is the key to success.

First, we hear from Daniel in Toronto, who’s wondering how to educate customers about his company’s plastic-free, dissolvable shampoo and conditioner tablets. Then Meredith in Long Island asks how to manage inventory for her booming backpack organizer business that keeps selling out to female athletes. And Ryan in San Diego asks for strategies to grow the B2B side of his therapeutic massage tool company.

Thank you to the founders of EarthSuds, Sideline Bags and Rolflex for being a part of our show.

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 Belkin International’s founding story as told by Chet on the show in 2019.

This episode was produced by Katherine Sypher with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was Cena Loffredo.

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

In his 20’s, working an office job he hated, Tom woke up in the middle of the night with a wild idea: why not take people on bike trips? No playbook. No investors. Just a sense that he could make a living doing what he loved. His first trip? Four guests riding through Death Valley, pitching their own tents. From there, Backroads scaled to hotels, while weathering a bike burglary, a van rollover in the desert, 9/11, the Great Recession, and a pandemic that brought tourism to a halt. 

Today, Backroads runs 5,000+ trips a year in 60+ countries.

This is a masterclass in savvy cash flow, scrupulous quality control, and dogged iteration. If you care about travel, brand, or building a services business at scale—listen to this.

What you’ll learn:

• How a 5,000 mile solo bike trip laid the groundwork for Backroads 
• The first guided trip in Death Valley: four people, high winds, 50 miles/day 
• How to get your stolen bikes back: confront the thief yourself 
• The “collect early, pay late” flywheel that powered growth without investors
• How Backroads survived 9/11, 2008, and COVID—and what changed after each shock
• Avoiding the Instagram trap and delivering peak, uncrowded experiences

TImestamps:

• 7:24 – Tom’s epiphany and the eight pages of notes that started Backroads
• 10:15 – From cubicle to road bike: the solo trip that shaped the company’s DNA
• 12:46 – Trip #1: Making mistakes in Death Valley—and learning fast
• 24:47 – Tom’s DIY recovery operation after a warehouse burglary
• 29:21 – Cash without capital: spend your deposits, pay hotels later 
• 30:55 – The Nevada rollover: walking out of the ER…and running the next trips
• 40:06 – Recovering after 9/11 and the financial crisis—and rebuilding the company’s value prop
• 45:46 – Post-COVID surge, and avoiding the tyranny of the travel selfie 

This episode was produced by Casey Herman with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineers were Patrick Murray and 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.

Tariq Farid the founder of Edible Arrangements joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Tariq updates Guy on how he’s pivoting into a new industry while ushering in the next generation of leadership at the company. 

First, we hear from Jake in Virginia who’s wondering how he can make his Filipino-inspired banana ketchup mainstream in America. Then, Heather in Sweden wants to know if she should change the name of her luxury polar voyage company to distance themselves from cruises. And, Ryan in Texas wants to know how he can bump up his revenue without losing his company’s highly personalized customer service. 

Thank you to the founders of Fila Manila, Minimal Impact Cruises, and Kong Screen Printing for being a part of our show.

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 Edible Arrangement’s founding story as told by Tariq on the show in 2017.

This episode was produced by Rommel Wood with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was Robert Rodriguez. 

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

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

In 2010, software engineer Natalie Gordon was pregnant– and fed up with the overwhelming baby aisles in big box stores.  So she quit her computer job to code the registry she wished existed. No pink-and-blue giraffes. No allegiance to a single store. Just a universal list that let friends give the real help that new parents need—from strollers to diaper services to dog-walking.

Natalie coded the first lines of Babylist during her son’s nap time. She managed customer support, pitched bloggers from coffee shops, and learned growth the hard way—first through affiliates, then with a pivotal Pinterest bet, and finally by taking on her own inventory (and all the headaches that come with it). Along the way she wrestled with hiring, firing, fundraising, and the identity shift from founder to CEO. Today, Babylist is one of the most trusted parenting platforms in the U.S., with a retail arm, editorial content, and a program for providing breast pumps. 

This is a masterclass in living a problem–and building a solution. 

You’ll learn:

• How to spot a customer pain point and design an MVP around it
• The power of slow virality
• How to use a small seed round without losing control
• The painful path from affiliate revenue to first-party e-commerce
• Stumbles with hiring – and firing– as a first-time CEO
• How paid growth works on visual platforms like Pinterest
• How “controlling your destiny” justifies a hard shift in business model
• How coaching and feedback helps you evolve from founder to leader

Timestamps:

• 05:32 - Learning to solve hard problems at Amazon -
• 08:28 - Sabbatical in Latin America: Natalie’s first (failed) business and what it taught her
• 17:50 - A meltdown in a superstore → the Babylist “aha” moment
• 19:40 - Designing a universal registry, dog-walking included
• 24:42 - Blitzing the mommy blogs, a  “pregnant hacker” post on Hacker News
• 30:01 - Why $140/month revenue felt like a victory
• 39:18 - Going solo at an Accelerator, and the agony of early hiring and firing
• 49:29 - From “slowly viral” to real scale, and how Pinterest helped
• 58:09 - Affiliate links to in-house inventory → piles of bassinets in the office 
• 1:01:57 - COVID’s unexpected windfall,  the health wedge (breast pumps & beyond)

This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineers were Patrick Murray and 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.

Wayfair co-founder Niraj Shah joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs about how to bet on themselves – and define themselves to consumers. Plus, Niraj explains why Wayfair is expanding into large-format brick-and-mortar stores.

First up, Valerie in Washington, D.C., is looking for a better way to educate consumers about her dehydrated chicken stock. Then, Bree in Utah wants to know when to seek investment in her improved mineral sunscreen brand. And finally, Tess in San Antonio is wondering if she should quit her day job and go all-in on her networking and accommodation app for solo women travelers.

Thank you to the founders of Cookstix, Daily Shade, and HerHouse for being a part of our show.

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 go back and listen to Niraj’s original episode from 2018, where he shares how he and his college roommate Steve Conine turned 250 single-product websites into one giant billion-dollar brand.

This episode was produced by Alex Cheng with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was Cena Loffredo.

You can follow HIBT on Twitter & 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.

A century ago, Jeff Braverman’s grandfather opened a peanut shop in Newark, New Jersey. By the early 2000s, the family business was doing $1M in sales and struggling to stay afloat. Jeff had a high-paying job in finance, but walked away from it to reinvent the business. His strategy? The internet. Something his dad and uncle knew nothing about.

What happened next is wild: an AdWords experiment that blew the doors off the budding online business; a slip on national TV where Rachael Ray accidentally renamed the company; 40,000 pounds of protest peanuts that crashed servers and landed them in the New York Times; a hilariously polarizing rap jingle; and a COVID surge that tested leadership—and humanity—every single day.

This is the blueprint for transforming a dusty, low-margin business into a profitable, $100M+ direct-to-consumer brand—while keeping it family-owned. It’s also a masterclass in earning trust, making risky bets, and scaling without losing your soul.

You’ll learn:

• The mechanics of a paid-search playbook that 10x’d orders overnight
• How to win over skeptical family members (and when to demand the keys to the store)
• The exploding-deal etiquette of buying a premium domain
• How an improvised rap-jingle can be stickier than a professional ad  
• How Nuts.com built a robust B2B business alongside DTC
• Crisis leadership lessons from the COVID floor 
• When and how a leader should hire their replacement

Timestamps:

• 00:07:08 — Cash registers, code words, and a Newark childhood inside the peanut shop
• 00:13:42 — The “build a website” pitch at a Jersey diner 
• 00:29:40 — December 4, 2003: from 3 orders/day to 30 
• 00:31:19 — Dad panics –”shut it off!”– Jeff doubles down on demand and ops
• 00:35:26 — Losing the storefront to a hockey arena—and going all-in online
• 00:42:29 — Jericho fans send 40,000 lbs of peanuts to CBS: press, links, and leverage
• 00:48:38 — Rachael Ray calls them “Nuts.com” by accident… and the $700k domain deal that followed
• 01:00:51 — The notorious Nuts.com rap jingle: how an earworm took hold
• 01:03:11 — Offices, microbreweries, and building a sticky B2B engine
• 01:05:08 — COVID hits: 70% call-outs, factory safety, and leading from the floor
• 01:10:18 — Handing the reins to a new CEO: leaning into strengths, not ego

This episode was produced by Sam Paulson with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Olivia Rockman. Our engineers were Patrick Murray and 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.

Lyft co-founder John Zimmer joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, John talks about his recent decision to step away from the company he founded in 2012.

First, Alan from England asks about the best strategy for expanding his patented shower innovation to the U.S. Then, Teri from California looks for advice on raising money because her weighted “rucking” vest for women keeps selling out. And finally, Kobi from New York wants to know how to prioritize work-life balance while growing his craft chocolate company. 

Thank you to the founders of ShowerSpaah, RUKSTR, and slowcocoa for being a part of our show.

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 Lyft’s founding story as told by John on the show in 2017. 

This episode was produced by Chris Maccini with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was James Willetts.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com.

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