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 [email protected] 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.

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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.

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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 [email protected] 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.

What happens when a charismatic home renovator marries a budding design whiz? You get the billion-dollar powerhouse that is Chip and Joanna Gaines.

The Gaines’ TV show Fixer Upper became a cultural obsession, turning shiplap and farmhouse sinks into a lifestyle movement that swept America.

When they walked away from that show at peak popularity, everyone thought they were crazy. Instead, they turned their business Magnolia into a thriving lifestyle brand, which includes a network, retail, restaurants, books, and a magazine. The Silos, their Waco headquarters, became an unlikely tourist destination, drawing millions.

Chip and Joanna proved that faith, small-town values and authentic storytelling could compete with coastal glitz. And they did it all while raising five kids.  

You’ll learn:

• What Chip and Joanna saw in each other—as business and life partners.
• How a miserable semester in New York sparked the idea for Joanna’s first store.
• How the Gaines’ almost went bankrupt after the 2008 housing crash—and refused to quit. 
• Why walking away from their TV show turned out to be a brilliant move.
• Why faith is as important as luck.
• Why betting on your hometown can be a superpower.

Time Stamps:

3:30 Chip’s failed dream of becoming a pro baseball player—and the unexpected path that followed.

8:20 How running a laundry in college taught Chip the economics of entrepreneurship.

14:35 Joanna’s Korean-American childhood, identity struggles, and how a toxic newsroom internship changed the course of her life.

24:10 The day Chip walked into her dad’s tire shop—and never left.

35:10 How Joanna’s first $25 “sale” encouraged her to open the first Magnolia store.

45:15 The housing crash that nearly ended their renovation business—and how they scraped their way back.

55:15 The moment HGTV called—and why Chip thought it was a scam.

1:09:10 How saying “no” to Fixer Upper opened the door to owning their own network—and their future.

1:13:09 The cultural backlash and the lessons that came with becoming America’s most famous fixer-uppers.

This episode was produced by Katherine Sypher with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Chris Maccini. Our engineers were Patrick Murray and Kwesi Lee.

Follow How I Built This:

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Stacy’s Pita Chips co-founder Stacy Madison joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Stacy talks about her hard-won experience of knowing when to stick with an idea… and when to walk away.

First up, Sam wants to figure out how to leverage his popular pizza instagram account into the go-to place for men to learn how to bake. Then, Alex wants to know how to make his Peruvian pisco brand stand out in a relatively unknown liquor category. And finally, Stephanie is eager to learn how she can rejuvenate what had been her family’s 88-year-old candy business. 

Thank you to the founders of Dough Guy, SUYO, and Stuckey’s 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 [email protected] or call 1-800-433-1298.

And be sure to go back and listen to Stacy’s episode from 2019 where she shares how a decision to make chips with the leftover pita from her sandwich cart led to a multi-million dollar snack category that didn’t exist before her. 

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

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. 

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

When identical twins Mike and Alex Faherty launched their clothing brand, they made a daring move– launching wholesale, retail, and online, pretty much at the same time.  Investors said it was outdated, maybe even doomed.

But that contrarian bet helped grow Faherty into a hugely popular brand, built on family, ingenuity, and obsession with detail.

The two brothers spent 12 years preparing for launch—Mike at Ralph Lauren learning the craft of fashion, Alex in finance learning the mechanics of business. In the early days they traveled the country in a beach house on wheels, pulling over on the PCH to sell bathing suits and board shorts. Mike’s designs—surf culture meets big-city chic—took hold online, in department stores, and even swanky boutiques in Japan, giving Faherty the momentum it needed to eventually grew to $250 million in sales. 

What You’ll Learn:

• Why the “all channels” strategy (wholesale + retail + online) can actually be a competitive advantage.
• The power of 12 years of preparation prior to launch.
• How to leverage factory relationships and suppliers as true partners.
• Why old-school, in-person sales can be a killer marketing tool 
• How family, trust, and resilience became a core advantage of the Faherty brand.

Timestamps:

(05:41) Mike discovers Bergdorf’s, cashmere, and fashion inspiration as a teenager in NYC

(08:19) Mike gets grief from his basketball teammates for studying fashion at Wash U

(13:38) Mike lands a job at Ralph Lauren to learn fashion from the inside

(21:28) The moment Alex’s mentor tells him that starting a clothing brand is “the dumbest idea I’ve ever heard”

(31:41) The brothers launch Faherty online from a borrowed apartment in Puerto Rico

(35:00) Roaming the country in a mobile beach house that doubles as their first store

(41:34) Early wins with specialty shops

(59:14) The brand nearly runs out of money and gets rescued by a man from Nantucket 

(1:07:14) A Covid-era gamble that pays off in massive growth 

(1:15:04) How the identical-twin bond became a superpower for the brand

Follow How I Built This:

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Dollar Shave Club founder Michael Dubin joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, Michael shares his latest career pivot into the screenwriting world.

First, Benita from New Jersey asks how to create a “guerilla-style” marketing campaign to introduce customers to her specialty Syrian Cheese. Then, Brandon from California wonders how he can encourage his mobile mini golf employees to become more emotionally invested in his business. And finally, Bria from Kansas wants to know the best way to scale her custom wildland firefighter uniforms. 

Thank you to the founders of Kasbo’s Middle Eastern Kitchen, Parrs Mobile Mini Golf, and Incidental Wildland 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 [email protected] or call 1-800-433-1298.

And be sure to listen to Dollar Shave Club’s founding story as told by Michael on the show in 2018. 

This episode was produced by Noor Gill 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.

What if the best startup isn’t sexy at all? In 2013, Vijen Patel left private equity to pursue “the least-worst idea”: dry cleaning. No patents. No app wizardry. Just laundry lockers in high-rises, ruthless unit economics, and a $1.99-a-shirt price that was seared into America’s brain.

From bootstrapping routes at 5 a.m. to breaking even in 6 weeks, Vijen and co-founder Drew McKenna scaled Pressbox to hundreds of locations, stared down well-funded competitors, and ultimately sold to Procter & Gamble, where Pressbox became Tide Cleaners (now ~1,200 locations). After the exit, Vijen launched The 81 Collection, a VC fund backing “boring” businesses that quietly power the economy.

This episode is a masterclass in building profit first, creating user behavior (not changing it), and protecting customer retention like your life depends on it.

What you’ll learn:

• How the “least-worst idea” found product-market fit
• How sidestepping rent + labor can flip margins from 15% to ~40%
• The efficiency insight that beat “Uber-for-X” rivals
• The new-residence edge: creating customer habits with a welcome-kit
• Why Pressbox had to set crazy-high retention goals (98%!)
• How to keep competitors close—and turn a Goliath into your buyer
• The post-exit premise: “boring” businesses are engines of the middle class

Timestamps:

• Choosing dry cleaning with a private equity lens: don’t do it for passion–focus on practicality — 00:09:30
• The SMS “app”: low tech, high convenience — 00:14:14
• Unit economics breakthrough: lockers (26 transactions per hr) versus scheduled pickup (4-6) — 00:18:55
• The $1.99 insight: a price everyone expected — 00:24:58
• How getting into Chicago’s top high-rise was a game-changer — 00:31:11
• Margins that work: if you’re a high-rise “amenity,” you don’t pay rent — 00:33:08
• Competing with Washio: convenience wins — 00:39:07
• Vertical integration: building the plant, staffing via Spanish newspapers — 00:41:48
• P&G looms: head-to-head, then the acquisition dance — 00:51:25
• Burnout, trade-offs, and life after exit: launching a VC fund that specializes in boring businesses — 01:03:28

This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Olivia Rockeman. Our engineers were Patrick Murray and Maggie Luthar.

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.

Tony Xu, founder of DoorDash, joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Tony updates Guy on his latest ventures: expanding into grocery and retail delivery - and taking on international markets.

First, we hear from Ron in Portland, who’s wondering about the right time to expand his product line - from kitchen knives to cutting boards.

Then Kathryn in Raleigh, North Carolina asks if it’s time to raise outside money to expand her line of date sweetened dark Chocolate bars. 

Finally, Yori in Stanford, Connecticut - wants to know the best way to educate customers about the benefits of buying grass raised beef. 

Thanks to the founders of Steelport Knife Company, Spring and Mulberry and Route 22 Meats 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 [email protected] or call 1-800-433-1298.

And be sure to listen to Doordash’s founding story, as told by Tony on the show in 2018.

This episode was produced by Kerry Thompson 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.

What if the founder of one of the internet’s most enduring brands… never wanted to run a company?

In 1995, Craig Newmark was a 42-year-old computer programmer in San Francisco who simply wanted to share local tech meetups with friends. He started an email list that became Craigslist—a website that reshaped how we find jobs, apartments, and community.

In this conversation, Craig opens up about how not having a grand vision (or a taste for power) led to one of the most popular platforms in the world. With fewer than 50 employees, Craigslist still generates hundreds of millions in revenue—while looking like a website frozen in 1996.

This is the story of an “accidental entrepreneur” who built a global brand by being in the right place at the right time—and why he now calls himself the Forrest Gump of the Internet.

In this episode, you’ll learn:

• Why keeping things simple is often the smartest design choice.
• How knowing your weaknesses can be the ultimate superpower.
• Why community beats marketing every time.
• How to monetize minimally—and still build a wildly profitable company.
• Why luck and timing matter more than you might think.

Timestamps:

• 07:10 Craig’s childhood struggles with social situations—and how local Holocaust survivors shaped his worldview
• 16:15 Discovering the early internet and becoming an “evangelist” at Charles Schwab
• 20:07 The simple email list that broke at 240 addresses—and became “Craig’s List”
• 29:16 Why Craig refused banner ads and said no to early monetization
• 35:00 Handing the CEO role to Jim Buckmaster—and how that decision led to Craigslist’s success
• 49:44 eBay buys a stake in Craigslist, then launches a competitor—sparking a messy legal battle
• 53:46 Was Craigslist really responsible for killing newspaper classifieds? Craig reveals his opinion
• 58:08 Why Craig gave hundreds of millions of dollars to support journalism, veterans, and… pigeons
• 1:03:10 Craig on money, meaning, and why billionaires are often miserable

Follow How I Built This:

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This episode was produced by Chris Maccini with music composed by Ramtin Arablouei.

It was edited by Kevin Leahy with research by Sam Paulson. 

Our engineers were Patrick Murray, Maggie Luthar and Robert Rodriguez.

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