How I Built This with Guy Raz

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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Website → guyraz.com

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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 hibt@id.wondery.com 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:

Instagram → @howibuiltthis

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Facebook → How I Built This

Follow Guy Raz:

Instagram → @guy.raz

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Substack → guyraz.substack.com

Website → guyraz.com

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.

Randy Hetrick, former Navy SEAL and founder of the suspension training company TRX, joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Randy updates Guy on his latest venture, a mobile gym called Outfit that brings the workout to you.

First, we hear from Paige in Toronto, who’s wondering how to best capitalize on a major new retail account for her caffeine-conscious energy drink company. Then Kerri in British Columbia asks how to select the right strategic investor for her Australian-style meat pie bakery chain. And Katharine in Ontario wonders whether it's best to expand or narrow the focus of her adaptive clothing brand.

Thank you to the founders of Benny, Peaked Pies and Adaptt Apparel 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 TRX’s founding story as told by Randy on the show in 2017.

This episode was produced by Katherine Sypher with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineers were Robert Rodriguez and Kwesi Lee.

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

A decade ago, Allison Ellsworth was drinking apple cider vinegar for health reasons and doctoring it with fruit so she could stand the taste. Her husband Stephen helped her turn it into a business by adding carbonation on a hacked soda line in their Dallas townhouse. They called it “Mother Beverage,” and sold out every week at the farmers market…but then heard the words no founder forgets: “Your branding is…sh*t.” 

What happens next is one of the wildest CPG glow-ups of the 2010s: a Shark Tank deal with brand whisperer Rohan Oza, a full rebrand to Poppi, colored cans that jumped off the shelf, a launch derailed by Covid—and finally, an explosion fueled by Amazon, TikTok, and a Super Bowl moment that planted the flag: We’re soda–and we’ve left the farmers market for good.  

Five years after its rebrand,  Poppi was acquired by Pepsi for nearly $2B. This is the story of the messy bottling line, saying no to “dumb money,” baptism by Shark Tank, and building a generational brand while staying married.

In this episode, you’ll learn:

• How rebranding can rescue a beverage, and when to avoid early eye-rolls 
• The hit-and-miss of carbonating on a small scale (and why co-packers said no).
• How the risky decision to call Poppi “soda” unlocked a new retail set (functional soda).
• What a Shark Tank partner does during a rebrand window.
• How Allison seized on TikTok to spike sales during Covid 

Timestamps:

• 0:10:15 Meeting cute at a snowboard shop → engagement in 7 months 
• 0:14:00 How apple cider vinegar helped Allison’s health…but tasted terrible (early flavor hacks) 
• 0:22:36 DIY carbonation disasters: exploding bottles & the 40°F lesson 
• 0:37:48 Appearing on Shark Tank while nine months pregnant and the deal with Rohan: “your branding is sh*t.”
• 0:42:28 Selling out at the Dallas Farmers Market 
• 0:47:02 The nail-biting rebrand from “Mother” to Poppi: colored cans vs. white, and winning the shelf 
• 0:55:43 Expo West canceled by Covid → a massive turnaround fueled by Amazon, Shark Tank, and TikTok
• 1:07:51 Super Bowl ad– “We’re soda!”--and the road to a ~$2B Pepsi acquisition 
• 1:09:58 Growing a business while managing a marriage 

Follow How I Built This:

Instagram → @howibuiltthis

X → @HowIBuiltThis

Facebook → How I Built This

Follow Guy Raz:

Instagram → @guy.raz

X → @guyraz

Substack → guyraz.substack.com

Website → guyraz.com

This episode was produced by Rommel Wood with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Alex Cheng. Our engineers were Patrick Murray and Jimmy Keeley.

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.

Bobbi Brown, founder of Bobbi Brown Cosmetics and Jones Road Beauty, joins Guy on the Advice Line, where they answer questions from three early-stage entrepreneurs. Plus, Bobbi shares what drove her to found her new company — Jones Road — at the age of 62.

First we meet Mark in Chicago, an orthopedic surgeon who’s looking to promote his cabbage-based muscle and joint rub beyond the walls of his practice. Then Abby in Dallas, who’s wondering whether her popular social media livestreams are a sustainable way to market her trendy phone cases. And Henry in Charlotte, who wants to turn his mouth rinse for coffee drinkers into a mainstream oral care brand.

Thank you to the founders of Cabbage Labs, AbbyRose, and Tannin Oral Care 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 Bobbi Brown Cosmetics’ founding story as told by Bobbi on the show in 2018.

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

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.

Many of us don’t know our neighbors anymore — and Nirav Tolia wanted to change that. He walked away from millions in stock options at Yahoo and eventually co-founded Nextdoor, the hyperlocal social network where neighbors share local news and recommendations. Along the way, he learned that for a digital service, Nextdoor demanded a ton of manual work: drawing neighborhood boundaries with Sharpies, sending individual “invite” postcards by snail mail, talking to neighbors about the information they wanted. After 8 years of grind, Nirav stepped away as CEO, only to return 6 years later to spearhead an ambitious rebrand of Nextdoor, which now has 100 million users around the world.    

In this episode, you’ll learn:

• Why Nirav walked away from millions in stock options to launch his own business 
• How the failure of an early business helped fuel Nextdoor’s success 
• How not having an initial vision for your brand can be a superpower.  
• Why apps that focus on “local” are so hard to master 
• Why Nirav believes” local” is a massive untapped opportunity in tech.

This episode was produced by Casey Herman with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineers were Kwesi Lee and Jimmy Keeley.

Follow How I Built This:

Instagram

→ @howibuiltthis

X → @HowIBuiltThis

Facebook

→ How I Built This

Follow Guy Raz:

Instagram

→ @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.

Priority Bicycles founder and CEO Dave Weiner joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, Dave shares his strategy for keeping sales steady and positioning Priority Bicycles for continued growth in uncertain or declining markets. 

First, we meet Dave from Rhode Island who’s trying to figure out how to bring his oft-misunderstood coffee milk product to the national market. Then, Alex from Buffalo who is deliberating whether to scale her lavender farm and barn events venue or stay small, all while trying to reclaim more work-life balance. And finally, Sabrina from Boise who’s looking for creative ways to get her custom dog treats noticed by larger corporate brands and hospitality groups. 

Thank you to the founders of Dave’s Coffee, Kin Loch Farmstead, and Idaho Barkery 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 Priority Bicycle’s founding story as told by Dave on the show in 2023.  

This episode was produced by Carla Esteves with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineers were Maggie Luthar and James Willetts. 

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 summer of 2000, Razor scooters were everywhere—on sidewalks, in schools, even in Silicon Valley offices. At the center of it all was Carlton Calvin, an ex-lawyer turned toy mogul who had already ridden—and crashed—multiple crazes, from Pogs to yo-yos.

Carlton knew how to spot what kids wanted before the world caught on. But when Razor went from selling a million scooters a month to zero almost overnight, his business teetered on collapse.

This is a story about timing, obsession and instinct: knowing kids would snap up Slammers with scorpions inside, seeing the potential of a sleek new scooter from Taiwan, and learning how to turn a craze into a lasting global brand.

In this episode, you’ll learn:

• Why most “overnight successes” collapse as quickly as they rise
• The power of partnerships– and trust– in scaling quickly
• How to think like your customer (in Carlton’s case, a 10-year-old boy)

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 Maggie Luthar.

Follow How I Built This:

Instagram

→ @howibuiltthis

X → @HowIBuiltThis

Facebook

→ How I Built This

Follow Guy Raz:

Instagram

→ @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.