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Episode Summary
In this episode of the Homegrown Hustle, host Matt Eickman sits down with Jim Keenan, CEO and Founder of POR, LLC (Emotional Wellness Services) and co-founder of Cannesota. We unpack Jim’s journey from clinician to entrepreneur—how he built a multi-service behavioral health company, leveraged those fundamentals into new ventures, and now navigates growth, regulation, and innovation in emerging markets. With PhD-level insight, Jim and Matt explore the intersection of mental-health services, business scalability, leadership mindset, and industry disruption. Expect deep dives into strategic timing, culture building, regulatory navigation, mission-driven entrepreneurship, and the hard lessons of launching complementary businesses across sectors.
Key Takeaways:
- Transitioning from practitioner to founder: stepping out of “doing the work” into leading the work.
- Building mission-driven culture in service-oriented businesses and sustaining it during scale-up.
- Choosing the right moment for diversification and how mental-health services principles apply to other industries.
- Navigating heavily regulated sectors: regulatory strategy, compliance, and growth channelling.
- Leveraging relationships, trust, and referral ecosystems as core growth engines in service enterprises.
- Dealing with failure, pivoting without losing integrity, and learning from operational mis-steps.
- Implementing systems and infrastructure early to support scale, without losing agility or mission focus.
- Practical tactics for founders: hiring for culture fit, investing in leadership development, building data systems, and balancing mission + margin.
Chapters:
0:00 – Introduction: Matt Eickman and guest Jim Keenan
3:15 – Jim’s early career: clinician roots, founding POR, LLC
11:40 – Defining mission and vision: how POR’s culture was built
19:55 – The shift: from service-provider to CEO-entrepreneur
27:30 – Launching Cannesota: timing, market conditions, regulatory context
35:10 – Regulatory dynamics: what to know in emerging industries
43:05 – Building a referral & relationship ecosystem – lessons from mental-health services
50:45 – Scaling challenges: infrastructure, leadership, systems
58:20 – Failure & pivot stories: what didn’t work and why
1:06:10 – Tactical advice for founders: culture, hiring, data, growth
1:14:30 – Future vision: where Jim is headed next, advice for listeners
1:18:50 – Close & key take-away recap
46:00 Defining Hustle
47:27 Balancing Family and Business
52:31 Finding a Business Mentor
Guest Resources:
Facebook:
http://facebook.com/jameswkeenan
https://www.facebook.com/POREmotionalWellness
Website:
https://poremotionalwellness.com/
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