Landscape Leader of the Year 2025
Discover What’s Working Right Now in the Landscaping Industry, Vote for the Winner, Win Over $1,000 in Live Prizes—Plus Unlock a Limited-Time Bonus at Our Famous Pizza Lunch.
LIVE Online – Thursday, October 9 | 9:00 AM MT
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
What is the Landscape Leader of the Year Livestream?
Imagine sitting in on a high-stakes, what’s-working-now mastermind—where the best ideas are revealed, the audience decides the winner, and the stakes are real
The Landscape Leader of the Year Livestream is a public speaking contest where three hand-picked finalists—all successful landscape company owners—share their most valuable, proven strategies for growing their businesses right now.
You’ll get:
- Real-world, current tactics you can take and apply to your own business immediately.
- The power to vote and crown the 2025 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.
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.
This is the only time this year you’ll see these three leaders share their current winning strategies, live and unfiltered.
Registration Bonus – Immediate ROI
When you register today, you’ll get instant access to Ramblin Jackson’s Instant Marketing Diagnostic. This quick, powerful tool gives you immediate feedback on your sales and marketing so you can identify exactly where to focus to get better leads, close more sales, and stop wasting money.
You could improve your business before the event even starts.
Meet the 2025 Finalists & Their Presentations
Michael Fisher – Dutchies Stoneworks & Outdoor Living
From Price-Shoppers to Premium Clients: How a High-Converting Website Transformed Our Sales
Discover how Michael’s team filters out tire-kickers, attracts high-end outdoor living clients, and frees up valuable sales time to focus on building dream projects instead of chasing quotes.
Building a Culture That Fuels Growth
Dominick will share how cultivating a family-oriented, positive work culture has powered Tri Valley’s growth, improved retention, and created a team that loves coming to work.
Defining and Developing an Effective Sales Process
Stuart reveals his proven process for guiding high-value leads from first contact to project kickoff, how it’s helped fill every key position in his company, and how it’s supported steady growth and more complex projects.
Host & Moderator
Jack is the CEO of Ramblin Jackson, a green industry branding and marketing agency that helps landscaping companies attract more qualified leads. He’s the host of The Landscaper’s Guide to Modern Sales & Marketing and the author of The Tree of Good Fortune. As moderator, Jack will guide the conversation to keep the discussion tactical and focused on what’s working now.
Ramblinjackson.com
Event Agenda – Thursday, October 9
Times in Mountain Time (MT)
9:00 AM MT – Welcome to the Landscape Leader of the Year Livestream
with Jack Jostes, CEO of Ramblin Jackson
9:05 AM MT – From Price-Shoppers to Premium Clients – Michael Fisher
9:20 AM MT – Building a Culture That Fuels Growth – Dominick DePadre
9:35 AM MT – Defining and Developing an Effective Sales Process – Stuart Ward
9:50 AM MT – Live Audience Prizes + Vote for the Landscape Leader of the Year Award
10:00 AM MT – Optional Ramblin Jackson Pizza Lunch with Jack Jostes
Want to shortcut your results to having your sales and marketing dialed in and generating more Hell Yes Customers? Join this 30-minute virtual lunch with Jack Jostes to learn how Ramblin Jackson’s proven, done-for-you marketing agency services can help you grow. Jack will share quick case studies of clients who’ve achieved measurable results working with Ramblin Jackson, along with a limited-time bonus offer for attendees.
Stay until the end, and we’ll send you two gourmet Lou Malnati’s pizzas ($72.99 value) to enjoy on us.
Who Should Attend
- Landscape business owners serious about growth
- Sales managers and marketing leaders ready for proven strategies
- Anyone who wants to see exactly what’s working now in sales, marketing, and leadership
- Ramblin Jackson clients AND staff
Your Next Step
Don’t wait—these giveaways, networking opportunities, and the power to decide the winner disappear the second the livestream ends.
Secure your spot, claim your Instant Marketing Diagnostic, and mark your calendar for Thursday, October 9.
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.
