Free Live Virtual Event
Landscape Leader of the Year
Discover What’s Working Right Now In The Landscaping Industry, Vote For The Winner, And Win Over $1,000 In Live Prizes — Plus Unlock A Limited-Time Registration Bonus When You Sign Up Today.
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DATE
Thursday, October 22, 2026
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TIME
10:00–11:30 AM MT
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BROADCASTING FROM
Lyons, CO
MEET THE 2026 PRESENTERS & THEIR PRESENTATIONS
SCOTT BENSON — BENSON LANDSCAPE & DESIGN
Out of the Weeds: How Scott Benson Spent Thirty-Nine Years Building the Team That Will Take Benson Forward
Most owners step back because growth stalled — Scott Benson is doing it from a position of strength. He’s grown Benson Landscape & Design profitably for thirty-nine years with no outside investment, staying in the black even through the 2008–2010 housing collapse. His secret: fund roles, technology, and new service lines before the case is obvious. Learn how to invest ahead of your team’s belief, create room for others to lead without lowering your standards, and keep innovating for decades without ever putting your company at risk.
The $1 Million Habit: How Ruthless Punctuality Transformed Wickenburg Landscape Into THE Choice For High-End Residential Clientele
What if simply showing up on time could add $1 million to your bottom line? Aaron Wolfe transformed Wickenburg Landscape from a business plagued by missed appointments into the undisputed top choice for high-end residential clients by instilling relentless punctuality, unwavering follow-through, and core values of family, integrity, and Kaizen. Discover the exact, repeatable operational disciplines Aaron used to grow Wickenburg from $1M to $3.8M in under five years — and learn how to earn total client trust and scale your own business.
The Landscaper’s Guide to Direct Response Sales & Marketing
Jack Jostes, CEO of Ramblin Jackson and host of The Landscaper’s Guide to Modern Sales & Marketing, shares core strategies from his new book, The Landscaper’s Guide to Direct Response Sales and Marketing: how to shorten your sales process, attract “Hell Yes” customers without paying for online advertising, and step up your recruiting to win great employees. As host, Jack also moderates the day and keeps the conversation tactical and focused on what’s working now.
What is the Landscape Leader of the Year Livestream?
The Landscape Leader of the Year Livestream is a public speaking contest where two hand-picked finalists — both successful landscape company owners — share their most valuable, proven strategies for growing their businesses right now, followed by a special featured presentation from host Jack Jostes.
You’ll get:
- Real-world, current tactics you can take and apply to your own business immediately.
- The power to vote and crown the 2026 Landscape Leader of the Year.
A front-row seat to see who takes home the championship belt and a $500 donation to their nonprofit of choice.
Why You Need to Attend LIVE
Let’s be blunt—watching the replay might be nice, but attending LIVE is where the money is. Here’s why:
- YOU decide the winner of the Landscape Leader of the Year Award. Your vote counts.
- Over $1,000 in exclusive live audience giveaways you can’t get later. Miss the livestream, and you miss the prizes.
- Network in real time with other top landscape and snow company owners in our live chat.
- Satisfaction Guarantee: Walk away with at least one sales or marketing idea worth 10X the time you invest—or I’ll personally donate $100 to your favorite non-profit
The Winner’s Week Experience
These finalists aren’t just showing up on camera. They’re flying into Colorado for a Winner’s Week with Landscaper’s Guide podcast host and Ramblin Jackson CEO Jack Jostes.
Winner’s Week includes:
- A full-day business strategy session
- A group mastermind with the other finalists
- A professional video shoot in the Ramblin Jackson studio
- Time in the beautiful foothills of Lyons, Colorado—complete with hiking, BBQ, and creative inspiration
- Behind-the-scenes access to the Ramblin Jackson Video Studio where the livestream is broadcast
The result? Finalists walk away with valuable business assets, unforgettable memories, and nationwide recognition in the landscaping industry.
And you—watching live—get their best ideas for free.
You’ll see these leaders share their current winning strategies, live and unfiltered.
Previous Winners!
Ramblin Jackson has been hosting an annual Landscaper’s Summit since 2020 with a “What’s Working Now” contest. In 2024, we officially launched The Landscape Leader of the Year Contest, which includes bragging rights and a $500 donation to the non-profit of the winner’s choice. In 2024, Scott Lawn from Greenway Landscape Design & Build whose presentation of “How Reading and Leading Are the Keys To Landscape Success won him our championship belt.
2025 Landscape Leader of the Year Stuart Ward From Buckhead Landscape & Design
2024 Landscape Leader of the Year Scott Lawn from Greenway Landscape Design & Build
Previous What’s Working Now Winners include: