Ep 14 - Culture Shock

Are you building a business that fits your personality or following someone else's playbook?

Jordan Gal hosts Jon Ewalt, founder of Roaster Tools, a comprehensive ERP system built specifically for specialty coffee roasters. After selling his Portland coffee roastery, Jon dove into software development nine years ago and has been "playing catch up" ever since. Now based in San Miguel de Allende, Mexico, Jon discusses the challenges of building desktop software with long development cycles while prioritizing personal time alongside business growth. How do you balance sustainable business practices with ambitious goals? Jordan and Jon explore the reality of mid-40s entrepreneurship, the value of a tight-knit founder community, and why Jon chose to move his family to Mexico for immersion Spanish education. Their decade-long friendship offers insights into building businesses aligned with your personality rather than chasing hockey stick growth.

In This Episode:
(00:00) From Coffee Roaster to Software Founder

(01:39) Why We Moved Our Families to Different Countries

(04:23) The Immigrant Experience and Core Memories

(09:30) Launching Too Early: Playing Catch Up for Nine Years

(18:45) Building Desktop Software vs Web Apps

(25:30) The Founder Mastermind That Predicted Our Paths

(33:56) Mid-40s and the Question of What's Next

(38:21) Moving Up the Abstraction Layer in Business

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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:

Jon Ewalt LinkedIn: https://www.linkedin.com/in/jonewalt/

Roaster Tools: https://www.roastertools.com/

Rosie AI: https://heyrosie.com/

Chapters

• (00:00:00) - Off-Site Podcast: The Place of Work
• (00:00:59) - Living as a Non-American in Mexico
• (00:06:19) - How To Raise An Immigrant Child
• (00:09:00) - How to Run a Coffee Company for 10 Years
• (00:13:03) - Tyler and Jordan on Their Differences
• (00:18:48) - Top Software Executives: How Do You Manage Your Team
• (00:25:19) - Roaster Company's Big Features
• (00:30:53) - Have You Had Any Negative Feedback From Your Partners?
• (00:33:09) - A Slack Group For Old People
• (00:38:52) - Have You Reached a Point Where You Can Exit Your Business?
• (00:39:59) - A Taste of Mexican food