Robert Clinkenbeard of Wilson360 shares how he grew his landscaping business to $20M by fixing three things: people, financial blind spots, and sales execution. He breaks down exactly how to spot what’s holding you back—and what to do about it.
“The landscape industry is such a great industry—people are more than happy to share their knowledge if you ask.” — Robert Clinkenbeard
Wilson360 – Robert’s coaching and consulting firm focused on scaling green industry businesses.
Commercial Landscaper Podcast – Robert’s show featuring industry leaders and insights: search on your favourite platform.
The Ultimate Sales Machine by Chet Holmes – Book that transformed ILM’s sales strategy.
Simple Numbers by Greg Crabtree – Financial strategies and insights for growing companies.
Who Not How by Dan Sullivan – Book about unlocking growth through the right people.
Entrepreneurs’ Organization (EO) – Global peer group network for business owners.
Inner Metrics / Advanced Insights – Personality assessment tools Robert uses to match people to the right roles.
Scaling Up Talent Assessment Tool – A quadrant chart for evaluating team fit and performance (ask Robert for access).
[00:00] Meet Robert Clinkenbeard
From Scotland to Arizona, Robert’s 40-year green industry journey spans ValleyCrest, ILM, and now Wilson360.
[01:47] What Wilson360 Does
Peer groups, coaching, and consulting for landscape businesses ready to scale.
[03:12] The #1 Growth Constraint: People
Growth problems always come back to team issues—especially at the leadership level.
[06:00] Common Blind Spots in Landscape Businesses
Misplaced loyalty, no financial visibility, and zero sales strategy top the list.
[09:45] Fixing Loyalty Problems with Org Charts + Assessments
Don’t assign names—assign roles first. Then match team members to the right seats.
[14:14] Your Financials Might Be Lying to You
If your profit is under 8%, you're bleeding—and your team probably thinks you're rich.
[19:59] Where to Find $150K in Waste
Robert breaks down a case study in savings from optimizing truck routes and idle time.
[22:27] Sales Execution Wins
Fact sheets, fast proposals, and budget spreadsheets skyrocketed close rates from 30% to 70%.
[28:38] No Ads, Just Relationships
Robert used events, partnerships, and a Top 50 target list to grow ILM’s client base.
[32:57] Right People, Right Seats: Talent Assessment Tool
The simple quadrant Robert uses to separate A-players from costly C-players.
[36:44] The Power of EO + EMP
Why joining EO and attending the Entrepreneurial Master's Program was a game-changer for Robert.