Landscaping CEO Who Grew From $1M To $35M: Finding Workers Is The Hardest Part Of This Business! | Bobby Jon Head
By Griffin Blackmon
May 4, 2026
Interview with Bobby Jon Head
Bobby Jon Head owns Rocky Mountain Custom Landscapes, a landscape design, commercial landscaping, and snow removal company in Eagle, Colorado. Born in Baxley, Georgia, he studied landscape architecture at the University of Georgia and learned the business side on the job. He prefers growth built on trust over anything that looks like a sales tactic.
Draft built from the interview notes. Answers are summarized and are not direct quotes.
Be cautious of labor-intensive service industries. The human resources headwinds are significant and the manual work ethic is declining.
Bobby Jon Head · Advice to his high school self
What was your biggest failure or mistake in your career, and what did you learn from it?
Learning Finance in the School of Hard Knocks
Head regrets skipping an MBA or business degree early on. He had to learn financial and corporate concepts, EBITDA among them, the expensive way, while running the company.
What non-academic skills mattered most?
Communicating from the top down and the bottom up, listening more than talking, and remembering personal details about the people he deals with, like their kids and hobbies.
How does he stay sharp and relevant?
Surrounding himself with people smarter than he is, joining industry peer groups of similar-sized companies as he scaled from $1M to $35M in revenue, taking constructive criticism well, and attending seminars and conferences.
What problem is he working on now?
Recruiting qualified project and account managers when housing in the Vail Valley costs more than most of them can afford.
What I Learned from Bobby Jon Head
Griffin writes this section in his own words after each interview.
The Head Framework
- 01
Grow Organically on Trust
He would rather earn the next contract than sell it.
- 02
Surround Yourself With Smarter People
Peer groups of similar-sized companies taught him how to scale.
- 03
Remove the Obstacles for Talent
Relocation help, subsidized housing, and onboarding support for families.
Playbook Success Interview Profile
- Interviewee
- Bobby Jon Head
- Date of Interview
- May 4, 2026
- Primary Industry
- Commercial Landscaping
- Based in
- Eagle, CO
- Born in
- Baxley, GA
- Education
- University of Georgia, landscape architecture
- Business
- Rocky Mountain Custom Landscapes
- Biggest Career Lesson
- Head regrets skipping an MBA or business degree early on. He had to learn financial and corporate concepts, EBITDA among them, the expensive way, while running the company.
- Advice for Young Entrepreneurs
- Be cautious of labor-intensive service industries. The human resources headwinds are significant and the manual work ethic is declining.
Griffin Blackmon
Hi, I’m Griffin. I’m a student entrepreneur and the host of Playbook Success. I interview successful entrepreneurs and millionaires, so you don’t have to. During the interviews, I distill their biggest wins and hardest lessons into the “entrepreneurial intel” we need to build our futures today. Join me as I decode what it actually takes to win in business before graduation. Check out the Playbook Success Blog for more interviews and entrepreneurial tips to help you turn your hobby into an empire. Thanks again for reading!