Ep 14 - Culture Shock

12 snips

Nov 12, 2025

Jon Ewalt, founder of Roaster Tools and former coffee roaster, shares his transition from brewing beans to coding software. Now living in San Miguel de Allende, he discusses the challenges of building an ERP system for coffee roasters while prioritizing family time. Jon and Jordan explore the importance of a supportive founder community, lessons learned from nearly a decade of software development, and the significance of aligning business goals with personal values. They also reflect on mid-life entrepreneurial decisions and the balance between ambition and personal satisfaction.

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ANECDOTE

From Roastery To Struggling Software Founder

Jon sold his Portland roastery, hired developers, launched an award-winning product, and then realized he didn't know how to run a software company.
He says he's been "playing catch up" for nine years managing product, customers, and tech debt.

ANECDOTE

Family Move For Immersion Spanish

Jon moved his family to San Miguel de Allende to immerse their kids in Spanish and challenge the family culturally.
He recounts his kids' initial struggles, like not knowing how to ask for the bathroom, and eventual fluency.

INSIGHT

High-Difficulty Moves Build Resilience

Immersion forces character-building through uncomfortable experiences that pay off long-term.
Jordan and Jon both see language immersion as a high-difficulty, high-reward childhood challenge.

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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/