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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621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

Nala was built by two founders with no fashion background who invested $200,000 before making a single sale and went on to sell over 400,000 pieces in just two years. In this interview, Chloe and ...

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620: (Solo) The Secret to Making Bold Business Moves With Confidence

620: (Solo) The Secret to Making Bold Business Moves With Confidence

One of the biggest challenges founders face — especially at the end of the year — is knowing what to do next and feeling confident that the move you're about to make is the right one. Certainty feels ...

6 Tammi 11min

619: Airline Charged Me $65 - So I built a $250M Competitor | Adam Ewart

619: Airline Charged Me $65 - So I built a $250M Competitor | Adam Ewart

Adam Ewart turned a £50 excess baggage fee into a global bootstrapped logistics company operating in 145 countries and staying profitable for 15 straight years. In this interview, Adam breaks down ...

1 Tammi 48min

618: (Solo) What 5 World-Class Founders Taught Me This Year

618: (Solo) What 5 World-Class Founders Taught Me This Year

Every year I sit down with some of the world’s most fascinating founders — but this year’s interviews hit me harder than most. Reinvention, resilience, copycats, failure, loneliness after exits, scrap...

30 Joulu 202511min

617: How A Failing Skincare Brand Became An 8-Figure Makeup Empire | Aliett Buttelman

617: How A Failing Skincare Brand Became An 8-Figure Makeup Empire | Aliett Buttelman

Aliett Buttelman spent eight years grinding in the dark before a single viral moment with Taylor Swift turned Fazit into an overnight seven-figure brand. In this interview, Aliett breaks down the ...

25 Joulu 202554min

616: (Solo) 5 Honest Business Lessons I’m Taking Into 2026

616: (Solo) 5 Honest Business Lessons I’m Taking Into 2026

2025 has been one of the most eye-opening years of my founder journey — personally, professionally, and strategically. Instead of sharing a highlight reel, I want to share the real lessons that moved ...

23 Joulu 20258min

615: Stop Chasing Sexy Businesses - This Boring One Made Me $500M+ | David Royce

615: Stop Chasing Sexy Businesses - This Boring One Made Me $500M+ | David Royce

David Royce went from a broke college kid in a door-to-door pest control job to building and selling four service businesses for nine-figure exits by applying Silicon Valley systems to an unsexy blu...

18 Joulu 20251h

614: (Solo) Running on Fumes? Reset Your Mindset Before The Year Ends

614: (Solo) Running on Fumes? Reset Your Mindset Before The Year Ends

If you’re dragging yourself toward the end of the year feeling exhausted, overwhelmed, and mentally drained, you’re not alone. This is one of the toughest stretches for founders — you’re still runni...

16 Joulu 20259min

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