Is the era of grinding and hustling finally over for smart founders?Jordan Gal hosts fellow entrepreneur Christian Genco in this candid conversation about the "two wolves" battling inside every founder. Genco, creator of File Inbox and seasoned bootstrapper, brings 12+ years of SaaS experience to discuss the eternal tension between "enough" wealth versus relentless growth. Both founders dig into their personal motivations, from Gal's immigrant drive to "slay the dragon" to Genco's struggle between minimalist philosophy and capitalist ambition. What drives someone to want "millions of dollars post-tax in a personal bank account"? How do you balance family life with business obsession? The conversation reveals the raw psychology behind entrepreneurial success and the frameworks top founders use to navigate major decisions.
In This Episode: 

(00:00) The Two Wolves Inside Every Entrepreneur
(13:00) Shoveling Coal vs Strategic Thinking
(23:00) How Fatherhood Changes Business Ambition
(31:00) File Inbox: The 12-Year Dragon Hunt
(44:00) AI Revolution in Marketing and Automation
(52:00) The Era of the Idea Guy
(59:00) Zuckerberg's Hundred Million Dollar Chess Game
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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:
Christian Genco: https://x.com/cgenco
File Inbox: fileinbox.com
Jordan Gal: https://www.linkedin.com/in/jordangal/Rosie AI: https://heyrosie.com/
Chapters
(00:00:00) - Off-Site Podcast: The American Wolf(00:00:41) - Christian Genko on The First Time He Met Jordan(00:01:26) - In the Elevator With Carthook(00:04:39) - Why Do I Need a Million-Dollar Budget?(00:10:21) - The Workaholic's Challenge(00:14:12) - Pushing a Direction Change(00:18:49) - Have You Learned to Find Time for Yourself?(00:22:59) - How to Limit Yourself to Limited Focus(00:27:43) - Having a Team at Work(00:31:06) - Slack's Ad Spending Slow Down(00:35:50) - How Much Advertising Should We Spend?(00:40:12) - Should You Diversify Into Other Channels?(00:41:23) - The Bullseye Method for Going To Market(00:44:30) - Go to Market: The Claude Model(00:50:27) - The Future of SaaS Is in the Ideas(00:52:52) - Zuckerberg's OpenAI Battle(00:59:20) - Facebook's Next Evolving Paradigm(01:02:07) - Drop In: File Inbox(01:02:44) - Offsite: Where Everything Clicks

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