Could sharing your most shameful moment actually accelerate your career?  Jordan Gal teams up with fellow entrepreneurs to discuss work and life beyond business. In this episode, Jordan sits down with returning guest Christian Genco,a software engineer and entrepreneur navigating the challenges of scaling products while maintaining focus. Christian recently welcomed his second child and shares insights on balancing creative work with reactive demands. What's the real cost of constant interruptions on engineering productivity? The conversation explores vulnerability as a business asset, the concept of "Sanskara" (emotional wounds from Sanskrit that block growth), and practical strategies from 37signals' Shape Up methodology. Christian opens up about getting fired from a startup and how sharing that vulnerability created unexpected opportunities. Can founders really separate engineering focus from customer chaos?  
In This Episode:   

(00:00) How Sharing Shame Creates Unexpected Business Opportunities 


(05:48) Christian Announces His Second Child 


(13:52) The Creative Satisfaction Problem in Business 


(24:52) Managing Reactive Engineering vs Deep Creative Work 


(42:19) Founder Intentions and Life Philosophy Beyond Money 


(56:22) The Engineering Productivity Challenge Every Startup Faces 


(59:37) 37signals' Approach to Protecting Engineering Focus 


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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 X: https://x.com/cgenco   37signals (company) - basecamp.comRosie AI: https://heyrosie.com/ 
Chapters
(00:00:00) - Off-Site Podcast(00:01:52) - Why I Talk About My Mistakes on My Podcast(00:05:48) - Baby Luca's First Birthday(00:08:39) - What Do You Need To Know For A 3-Year-Old(00:10:54) - Has Having a Baby Impact Your Worklife?(00:14:40) - Sponsoring an AI startup(00:15:05) - How to Focus On Work and Family(00:16:50) - "You Ruined My Wedding!"(00:18:46) - How to Stop Reacting to Customer Support Emails(00:23:51) - Patrick Collison on His Personal(00:28:28) - The Secret to A Nice House(00:31:10) - How to Let Go Of Envy(00:34:47) - "I Can't Control My Own Life"(00:38:12) - The Lean Startup on Postmortem(00:42:42) - A Boss Had a Fight With His Employee Over Communication(00:47:32) - How To Deal With Conflict In Your Relationship(00:51:03) - How to Manage Expectations in the Software Development Process(00:56:30) - How to Manage a Non-Technical Team(00:59:37) - Software Development: The Hill Chart

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