Watch the Full Video
Episode Summary
In this episode of Homegrown Hustle, host Matt Eickman sits down with Wes Nichols, a bold operator who transformed his teenage side hustle into a thriving 30-person tree care enterprise. As the founder of Pro Tree Outdoor Services, Wes shares his raw and strategic journey from a high schooler tossing logs into pickup beds to a visionary building one of the most respected blue-collar brands in the Midwest.
This episode is a masterclass in entrepreneurial scale: from EOS implementation and financial systems to managing blue-collar talent and investing in fleet efficiency. Wes brings a practical, boots-on-the-ground perspective to business building—highlighting how true leadership is about evolving yourself so your team can rise.
Entrepreneurs will leave this conversation rethinking delegation, operational efficiency, and what it really takes to create a “destination workplace.”
Key Takeaways:
Start Where You Are: Wes turned a cash-under-the-table summer job into a legacy business by staying obsessed with the craft and constantly iterating.
Let Go to Scale: True leadership requires stepping back and trusting your team—even when their failure costs you money.
Culture Drives Performance: Pro Tree’s success hinges not just on equipment, but on culture, clarity, and accountability.
Data Beats Emotion: Profitability skyrocketed only after Wes implemented job costing and built systems around objective data.
EOS is a Game-Changer: Entrepreneurial Operating System gave structure, discipline, and ownership at every level of Pro Tree.
The Value of Mentorship: Relationships with more experienced operators became accelerants to Wes’s learning curve.
Efficiency is Strategic: Investing in infrastructure (like in-house mechanics and fuel systems) isn’t just ops—it’s margin.
Destination Workplace > Bigger Business: The long-term goal isn’t just scale—it’s to become the best place to work in the industry.
Chapters:
00:00 – 03:00 | Wes’s early days in tree care & how a summer job lit a lifelong spark
03:00 – 06:00 | The pizza hustle: how Wes’s sales mindset showed up early
06:00 – 09:00 | Landing government contracts (accidentally at first)—and how they transformed the business
09:00 – 12:00 | Navigating the mental shift from technician to CEO
12:00 – 16:00 | Implementing EOS (Entrepreneurial Operating System) and building a culture of accountability
16:00 – 19:00 | Letting go to let others lead—and learning through their failures
19:00 – 23:00 | Personal development as a CEO and why the inner work never stops
23:00 – 28:00 | Biggest bets: investing in cranes and managing a complex fleet
28:00 – 34:00 | The power of in-house mechanics and building resilience into operations
34:00 – 37:00 | Creating systems to control fuel costs, time theft, and field readiness
37:00 – 40:00 | Managing backlog and customer expectations in a seasonal service business
40:00 – 43:00 | Building Pro Tree into a destination workplace for arborists
43:00 – 47:00 | How Wes uses job costing and KPIs to drive margin and growth
47:00 – 51:00 | From intuition to data: the turning point in understanding profitability
51:00 – 54:00 | Lessons from seasoned mentors and the value of peer networks
54:00 – 59:00 | What’s next: scaling without compromising culture
Guest Resources:
Linkedin: https://www.linkedin.com/in/wes-nichols-1684ba71/
Instagram: https://www.instagram.com/wesnichols/?hl=en
Facebook: https://www.facebook.com/Protreeoutdoor
Website: https://pro-tree.com/
🎙️🎙️🎙️
