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.

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
• 0:42:28 Selling out at the Dallas Farmers Market
• 0:37:48 Appearing on Shark Tank while nine months pregnant and the deal with Rohan: “your branding is sh*t.”
• 0:47:02 The nail-biting rebrand from “Mother” to Poppi: colored cans vs. white, and winning the shelf
• 0:53:44 Expo West canceled by Covid → a massive turnaround fueled by Amazon, Shark Tank, and TikTok
• 1:05:51 Super Bowl ad– “We’re soda!”--and the road to a ~$2B Pepsi acquisition
• 1:07:58 Growing a business while managing a marriage

Follow How I Built This:

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X → @HowIBuiltThis

Facebook → How I Built This

Follow Guy Raz:

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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.