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The Landscaper’s Guide to Modern Sales and Marketing Newsletter
OCTOBER 2025
WHY I SKIPPED THE BIGGEST INDUSTRY EVENT TO HUNT ELK AND SLEEP IN The Secret to Outlasting Everyone in Business
I didn’t go to the Equip Expo this year. Yeah, the landscape industry’s biggest trade show, formerly known as GIE Expo, where thousands of outdoor professionals gather. For five years, I went religiously. Made deals, gained clients, shook a lot of hands. It helped build my business exponentially each time. But for the last five years? I’ve skipped it. Instead, I’ve been in the high country of Colorado, sleeping in, hunting elk, and waking up to mountain silence instead of hotel alarms. That’s my time, and my decision to “miss out” has made me a better business owner, a better leader, and a happier human. I call it the Last Man Standing mindset. In business and life, it’s not about who sprints the hardest. It’s about who still has the strength, clarity, and desire to keep going 10, 20, 30 years in. It’s not about the biggest grind, it’s about longevity. So, while the hunt is great, it’s not really about the elk at all. What I’ve learned over time is that the real value isn’t the meat in the freezer; it’s the mental clarity, the deep sleep, and the reset button that I so desperately need as a CEO. Because here’s the truth we don’t talk about enough: Business ownership can be crushing. I’ve known business owners who didn’t make it. Not metaphorically: They’re gone. Two men I knew personally, successful in their fields, couldn’t carry the weight anymore. One left behind a wife and kids. Another died on the job. You can’t tell me burnout isn’t fatal. You can’t tell me rest isn’t survival. My elk hunt? It’s locked in every year because the season dates are fixed, and you have to win a lottery to get a spot. It takes effort and planning, which is exactly why it works. Planning time away gives me something to look forward to. It breaks the cycle of “just one more week” and forces me to prepare my team, delegate, and step back.
My hunting partner is my client-turned-friend Rich Leeman, owner of Landscape Technology Group. Funny enough, even when we sleep in and start our hunts late, we always seem to hit our target. We’ve gotten a deer or elk every year together. He reminds me that you don’t always have to be up at 4 a.m. to win; you just have to be consistent, intentional, and present. That’s a lesson I’ve brought back to business. So, yeah, I missed Equip. I slept in. I hunted. I laughed with a friend who shares my love for the mountains. And guess what? We still land clients. We still grow. Why? Because we’ve built systems, processes, and a brand that frees me from being the only one driving the bus. That’s our mission at Ramblin Jackson: to brand your sales process so you can step out and live your damn life. If you’re doing all the selling, you’ll never take time off, and eventually, that’ll catch up with you. You’ll see your competitors at every show, on every social feed. You’ll wonder if you're falling behind. But here’s the truth: You’re not falling behind when you’re catching your breath. You’re not failing when you say no to a “great opportunity” so you can say yes to your health, your family, your hobbies, or hell, even a hideous Hulk Hogan-style mustache contest with your buddies (which I am in fact doing …). This job will eat you alive if you let it. So, don’t. Schedule the trip. Build the systems. Say no more often. And be proud of it. That’s how you stay the last man standing.
JACK JOSTES, CEO RAMBLIN JACKSON
RamblinJackson.com • 1
Read It in Your Truck on a Rainy Day
RING THE BELL SPOTLIGHT High Prairie Outdoors and Pools Claimed Their True Identity, and the Leads Followed
We knew High Prairie Outdoors and Pools wasn’t your average landscaping company from the jump. This was a team building luxury outdoor spaces from the ground up, including certified pools, intricate masonry, and architectural-grade carpentry. But you wouldn’t have known that by their name or website. That had to change. And change it did. We looked hard at how the market saw them and where opportunities were being lost. The solution? A strategic name shift and branding transformation that said what they actually do, loud and clear. And because we walk the talk, we brought CEO and Owner Robyn Schmitz to our Colorado office so she can work directly with Jack for the brand transformation and to film a custom video series. While Robyn may have had her doubts before, it was this in-person collaboration that changed everything. We built trust, confidence, and most importantly, a client bond that allows us to be of service for years to come.
Here’s what Robyn had to say about our rebrand:
“We’re absolutely thrilled with our new homepage design and the collaboration it took to get here. Since the name change, we’ve even noticed an increase in pool leads. While we can’t attribute all of that solely to the name, it’s clear this shift is fueling momentum. We’re incredibly grateful to the Ramblin Jackson team for their insight, guidance, and partnership in helping us better tell our story.” That’s what we’re here for: helping you tell the full story of what you do, and who you are. Whether it’s revisualising your brand to reflect your authority or building a site that leads in looks and rankings, we bring clarity, precision, and bold moves. Because in business, perception is everything. And when your brand finally aligns with your craftsmanship? That’s when the leads roll in. Want to see what your business could become? Visit RamblinJackson.com/services to learn how we can help you build a brand that reflects the quality of your work.
“When Ramblin Jackson first suggested adding ‘and Pools’ to our name, I was hesitant. We’ve always valued simplicity, and making our name longer seemed counterintuitive. But they helped us see that this change wasn’t about adding words — it was about adding clarity. Too often, people assumed we were just another landscape company, unaware of our extensive expertise in certified pool building, complex construction, carpentry, masonry, and stonework. “In a highly competitive, legacy-driven market, positioning matters. The new name helps homeowners immediately recognize the craftsmanship, customization, and quality we provide — work that meets standards far above base code regulations. This change represents transparency, opportunity, and the future for Kansas City homeowners who value enduring design and construction excellence.
Delegate, Automate, and Reclaim Your Freedom YOUR SALES SYSTEM SHOULD WORK SO YOU CAN LIVE
At Ramblin Jackson, one of our core values is Craftsmanship in Life & Work, Especially on Fridays , and we mean every word. This isn’t about the polish on a logo or the precision of a marketing funnel. It’s about building your business with such intention and efficiency that you can actually live your life, too. That’s the real edge.
On the front page this month, Jack talked about skipping out on industry events to go elk hunting, on purpose. Why? Because chasing joy outside of work isn’t a luxury. It’s essential to stay strong, sane, and sharp as a business owner. Whether you’re rucking in the mountains or hunting elk in the wilderness like Jack or playing with your kids in your backyard, it’s vital you craft the life you want. This is why we obsess over sales systems. When you can delegate follow-ups, automate bookings, and trust your marketing to do its job, you’re free to step away. Confidently. Guilt-free.
Craftsmanship isn’t just about your landscaping projects. It’s how you schedule your time. How you eat. How you rest. And yes, how you close sales on a Friday afternoon while your competitors are already checked out.
Want to Ring The Bell in business and life? Book a Marketing Brainstorm with Alyssa, our Landscape Marketing Guide, at LandscapersGuide.com/ brainstorm .
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LandscapersGuide.com/events Nov. 13, 10–11 a.m. MT • Virtual Workshop In partnership with the Texas Nursery & Landscape Association Fireside Chat: Ask Jack Anything About Sales & Marketing Dec. 11, 10–11 a.m. MT • Free Virtual Q&A ChatGPT for Landscape Sales Pros and Owners: A Hands-On Intro to Close More Sales Nov. 5, 9:00–9:45 a.m. MT West Building, 100 Level, Room 105 See Jack speak at NALP ELEVATE NALP ELEVATE Conference Nov. 2–5 • Phoenix, AZ Visit us at Booth #1531! Oct. 9, 9-10 a.m. MT • Virtual Event Livestream via Zoom from Lyons, CO The Landscaper’s Guide to Selling to the Affluent With Direct Response Marketing Landscape Leader of the Year Livestream UPCOMING EVENTS
Schedule a 15-minute Marketing Brainstorm with one of our Landscape Marketing Assistants. In just 15 minutes, they will: • Offer game-changing feedback on your marketing ideas. • Find gaps in your existing campaigns. • Discuss your best marketing strategy. • Share next steps for success! This is a quick, easy, no-pressure call — and we’ll even send you beef jerky or candied almonds for your time. Visit LandscapersGuide.com/brainstorm to schedule your Marketing Brainstorm today. Ready to Level Up Your Marketing and Get More Hell Yes Customers?
TAKE A BREAK
RamblinJackson.com • 3
uck on a Rainy Day
PRST STD US POSTAGE PAID BOISE, ID PERMIT 411
1 Last Man Standing: The CEO’s Guide to Saying No and Surviving Business 2 High Prairie Outdoors and Pools Didn’t Tweak Their Brand, They Transformed 2 Craftsmanship Isn’t Just for the Jobsite, It’s for Your Life Too 3 Upcoming Events 4 The Follow-Up Move That Closes More Landscaping Deals, Fast INSIDE PO Box 1429 • Lyons, CO 80540 (303) 544-2125 • RamblinJackson.com
USE CHATGPT TO FOLLOW UP FASTER AND CLOSE MORE PROJECTS This 60-Second Sales Hack Will Set You Apart If you walk out of sales appointments and wait until the end of the day (or worse, the end of the week) to follow up, you’re leaving money on the table. Period. Too many landscapers are losing deals because they’re not following up fast enough. And in a competitive industry, speed and clarity are the name of the game. Here’s one simple tip that’s helped me and the landscapers we work with close sales faster and stand out in the best way possible: use the ChatGPT mobile app to voice-dictate your follow-up emails . Not next week, not when you’re back in the office, but right after your sales call, while it’s still fresh. The Fastest Way to Stand Out Using ChatGPT on your phone allows you to voice dictate a detailed follow-up email immediately after a sales appointment, no typing, no delay, no excuse. Here’s exactly how top landscape businesses are doing it.
Open the ChatGPT app. Tap the mic and speak freely about what was discussed, such as scope, timing, budget, and pain points. Then use this exact prompt: “Help me write a professional follow-up email outlining what the client wants and what date I will be sending them a detailed proposal. Include a call to action to read our reviews on our website.” Within 60 seconds, you have a polished, client-facing email ready to send. And guess what? It works. Ramblin Jackson clients are using this strategy to gain trust, demonstrate professionalism, and close sales faster than their competition. This little move alone will set you apart. Just ask our podcast guest and owner of Greener Concepts, Jacob Peffer; he won over a client just because he followed up. That’s it. A simple, thoughtful, fast email that most of his competitors never send. Want more tips that close deals? Come see me speak live at NALP Elevate in Phoenix. I’m giving a workshop loaded with practical, no-fluff strategies that’ll help you and your sales team close faster and communicate better immediately. Workshop Title: ChatGPT for Landscape Sales Pros and Owners: A Hands-On Intro to Close More Sales When: Wednesday, Nov. 5, 2025, 9:00–9:45 a.m. MST Where: West Building, 100 Level, Room 105
See you there. Let’s Ring The Bell.
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