What happens when you achieve your goal but lose your purpose?

Jordan Gal sits down with his brother Assaf just two weeks after Assaf closed the sale of his six-location Crunch Fitness franchise empire. After 13 years building a 200-employee operation across Brooklyn, Bronx, and Queens, Assaf shares the emotional reality of transitioning from entrepreneurship to uncertainty. "Every day when you have a thing, you have a North Star, you have a purpose," Assaf reflects. "And now it feels like there's nothing." The conversation explores the ten-month deal process, the weight of managing 200 employees, and the challenge of finding what's next. What does freedom actually feel like when you've spent over a decade grinding? How do you process relief, guilt, and the search for new purpose?

In This Episode:

• (00:00) The Business Sale That Just Closed Two Weeks Ago
• (09:57) From Relief to Emotional Goodbye with 200 Employees
• (14:17) Why Some Exits Don't Feel Like Going to Disneyland
• (19:44) The Invisible Hand of Capital and Which Game You're Playing
• (26:41) Airplanes, Perspective, and Seeing the Bigger Picture
• (36:49) The Ocean of Capital That Needs to Find Returns
• (45:44) Why Everything Has Warts and Nothing Is Perfect
• (48:18) Italy, Tuscany, and Deciding Not to Be in the Race
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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:

LinkedIn: Assaf Gal https://www.linkedin.com/in/assafgal/

Jordan Gal: https://www.linkedin.com/in/jordangal/
Rosie AI: https://heyrosie.com/