Could a single technical person who enjoys talking to customers really build a ten million dollar business alone?

Host Jordan Gal sits down with Jesse Hanley, founder of Bento, an email marketing platform, for an exploration of contrasting entrepreneurial approaches. Jesse operates solo from Fukuoka, Japan, building Bento into a single-digit-millions business through patience and deliberate choices. What drives a founder to stay lean while his company scales? The conversation traces back to 2012 when Jordan first met Jesse during his supplement store days, revealing how both founders evolved from those scrappy beginnings. They dissect everything from the arbitrage of living abroad to managing investor expectations versus staying bootstrap. Jesse's commitment to doing support on Twitter after years in business isn't masochism—it's strategy.

In This Episode:

(00:00) How Jordan and Jesse First Connected in 2012

(08:41) Why 2015 Was a Unique Era for Building Products

(10:18) Building Bento Through Grief and Finding Focus

(13:15) The Reality of Living and Working in Japan

(16:04) Customer Support as Long-Term Reputation Building

(24:07) Living Without Financial Goals or Ambition

(29:00) The Evolving Email Marketing Landscape

(42:29) Staying Solo While Scaling to Millions

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About the Show
Jordan Gal, founder and CEO of Rosie AI, hosts the Offsite Podcast where he teams up with rotating entrepreneur friends to explore what's happening in their work and beyond. After successfully building and selling CartHook, Jordan now leads a VC-backed company while sharing candid insights about the realities of startup life. The show combines real-time business updates with deeper conversations about founder psychology, growth strategies, and the personal side of entrepreneurship that rarely gets discussed publicly.

Resources:
Jesse Hanley: https://x.com/jessethanley
Jordan Gal: https://www.linkedin.com/in/jordangal/
Rosie AI: https://heyrosie.com/

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