88: How 5x Founder David Cancel Builds & Sells Companies at Record Speeds - Founder of Drift

88: How 5x Founder David Cancel Builds & Sells Companies at Record Speeds - Founder of Drift

As the son of hardworking immigrants, David Cancel saw his parents working seven days a week to support their family. As an adult, he realized that not all people worked the way his parents did, which sparked in him a desire to make a living without getting a “job.” Cancel always knew that he wanted to be an entrepreneur, even if he wasn’t quite sure what that meant. As a kid, he found that flipping through the pages of Inc. Magazine and other early entrepreneurial publications didn’t offer much insight. He saw ads for get-rich-quick schemes and stories of businessmen who had reached amazing heights. Although he wasn’t quite sure what it meant to be an entrepreneur, he knew he wanted in. The term “serial entrepreneur” gets thrown around a lot, but few have lived a life that defines it as well as David Cancel. Building and selling companies has become a way of life; his obsessions around ideas or problems quickly snowball into companies. He has started and exited five companies in the past 16 years and is currently an advisor, investor, and/or consultant to several more, including BigCommerce, HelpScout, Rapportive, and Yieldbot. In this interview you will learn: What it takes to create a successful product How to listen to your customer and what you can learn from it What kind of feedback you should listen to and what you should ignore The secret to iterating effectively and how you can start improving your own products Where to find the right audience and what it means to serve them & much more!

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646: How Jesse Built A $450K/Year Brand Whilst Still Working in the Mines

646: How Jesse Built A $450K/Year Brand Whilst Still Working in the Mines

Most people with a full-time job, 14-hour shifts, and zero business experience don't start a brand — Jesse did, and he's closing in on half a million dollars a year to prove it. After 16 years work...

1 Apr 32min

645: (Solo) Why Your Email List Is Your Most Valuable Asset in 2026

645: (Solo) Why Your Email List Is Your Most Valuable Asset in 2026

Email marketing doesn't sound flashy. It's not the newest channel, not the trendiest platform, and it definitely doesn't get the same attention as TikTok, Instagram, or Meta ads. But that's exactly wh...

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644: This FBI Negotiation Trick Gets People to Say YES (By Saying NO) | Chris Voss

644: This FBI Negotiation Trick Gets People to Say YES (By Saying NO) | Chris Voss

Chris Voss spent decades as the FBI's lead international kidnapping negotiator, where a single wrong word could cost someone's life. After talking down armed bank robbers and negotiating with terror...

26 Mars 54min

643: (Solo) Why Profitable Businesses Still Fail (And How to Avoid It)

643: (Solo) Why Profitable Businesses Still Fail (And How to Avoid It)

Most founders think if their company is profitable on paper, they're safe. But here's the truth I learned the hard way: businesses don't fail because they're unprofitable. They fail because they run o...

23 Mars 12min

642: I Quit My 15 Year Career To Build a Jewelry Business — and Hit $400,000 in My First Year

642: I Quit My 15 Year Career To Build a Jewelry Business — and Hit $400,000 in My First Year

Rosie Collins had a Christmas epiphany about baby shower gifts—every present focused on the baby, never the mom. That single observation turned into Deja Marc, a multimillion-dollar personalized jewel...

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641: How Konnie Built A $60K/Month Swimwear Brand In 18 Months — Without Quitting Her Day Job

641: How Konnie Built A $60K/Month Swimwear Brand In 18 Months — Without Quitting Her Day Job

Most people spot a gap in the market and do nothing — Konnie Tsimiklis spotted one, had zero fashion experience, and built a brand around it anyway. A management consultant by trade, Konnie spent dec...

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640: (Solo) Why Community Beats Followers in 2026

640: (Solo) Why Community Beats Followers in 2026

Followers are easier to get than ever. But here's what most founders don't realize: genuine community and real relationships are becoming significantly more valuable. At Foundr, we've built an audi...

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639: From $60K in Debt to ICONIC $100M Fashion Label | Rebecca Minkoff

639: From $60K in Debt to ICONIC $100M Fashion Label | Rebecca Minkoff

Rebecca Minkoff arrived in New York City at 18 with no money, no degree, and a low-paid internship that paid $3 an hour. She lived in a relative's playroom just to make it work. Twenty-one years lat...

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