The Landscaper's Guide to Modern Sales & Marketing

You'll Learn:

• How Jays Landscape increased maintenance gross profit margins from 19% to approximately 40%.
• Why reviewing unprofitable contracts and crew labor hours can dramatically improve profitability.
• How setting clear company goals helps a family-owned landscape business grow.
• Why SEO, team videos, and transparent pricing help attract better-fit customers.
• How to build a repeatable sales and customer experience that doesn't depend entirely on the owner.

Connect With Today's Guest

Get Started With The Landscaper's Guide

Join us for the Landscape Leader of the Year Livestream - Thursday, 10/22/2026! https://landscapersguide.com/leader/

Is your landscape company losing high-value projects before you even get a chance to speak with the customer? You might have invested thousands of dollars in a professional website, beautiful project photos, and marketing that attracts affluent homeowners. But what happens when a potential customer calls your office or fills out your contact form? In this solo episode of The Landscaper's Guide, Jack Jostes, CEO of Ramblin Jackson, explains why your first impression could be costing you sales.

Jack introduces the Ramblin Jackson Secret Shopper Test, a personalized evaluation of how your company handles incoming leads, phone calls, follow-up, and the overall sales experience. He also shares a real example of how one landscape company's phone-answering experience may have been hurting its sales. Discover why small details matter when customers are considering projects worth tens or even hundreds of thousands of dollars.

You'll Learn:

• Why your office staff plays a critical role in converting high-end landscape leads.
• How your phone-answering experience can influence a customer's first impression.
• What the Ramblin Jackson Secret Shopper Test evaluates.
• Why response times and follow-up matter when converting marketing leads.
• How personalized feedback can help improve your sales process.

Connect With Jack Jostes

🌳 Ramblin Jackson: https://ramblinjackson.com/

👤 Jack Jostes on Instagram: https://www.instagram.com/jackjostes/ 

Jack Jostes on LinkedIn: https://www.linkedin.com/in/jackjostes/

🔎 Request Your Secret Shopper Test: https://ramblinjackson.com/secret

Get Started With The Landscaper's Guide

🎧 Watch the full episode + read the transcript: https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky: https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events: https://landscapersguide.com/events

What’s happening behind the scenes at Ramblin Jackson—and which AI tools are actually helping Jack Jostes run the business more efficiently? In this solo episode of The Landscaper’s Guide, Jack shares an inside look at his upcoming third book, The Landscaper’s Guide to Direct Response Sales and Marketing, a new implementation course, an updated marketing audit, and the systems Ramblin Jackson is building as the company enters its next stage of growth.

Jack also breaks down three AI tools he’s using in his day-to-day work: Superhuman for faster email management and AI-assisted replies, Claude for automating recurring internal workflows, and Gemini for research, travel planning, and organization. You’ll hear practical examples of how these tools save time, why strong systems still matter, and how improving your sales and marketing process can help you close more landscape jobs.

You’ll Learn:

• How Jack is turning his new book into a practical sales and marketing course
• Why Ramblin Jackson is updating its marketing audit and delivery systems
• How Superhuman helps Jack manage email and draft responses faster
• How Claude can automate recurring internal processes
• How Gemini helps with research, planning, and organization

Connect With Jack Jostes:

👤 Connect with Jack Jostes: https://www.linkedin.com/in/jackjostes/
📸Jack Jostes on Instagram: https://www.instagram.com/jackjostes/
🏢 Ramblin Jackson on Facebook: https://www.facebook.com/RamblinJackson/

🌳 Ramblin Jackson: https://www.ramblinjackson.com/ 

🌳 The Landscaper’s Guide: https://www.landscapersguide.com/

Get Started With The Landscaper’s Guide:

🎧 Watch the full episode + read the transcript: https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky: https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events:
https://landscapersguide.com/events

What does it take to build a landscape company that can eventually run without you?

In this episode of The Landscaper’s Guide, Jack Jostes sits down with Andy Sykes, owner of Garrett Churchill Inc., to talk about what he’s learned from more than 25 years in the landscape industry. Andy shares how his company has evolved from gardening and design-build into a growing operation with roughly 18–20 field employees during peak season—and why his next goal is building a company that doesn’t depend on him for sales, design, and day-to-day management.

Andy also reveals how Garrett Churchill is putting AI to work right now. In a single day, his team used AI to help create job descriptions, onboarding plans, and career paths—work Andy says could otherwise have taken him weeks. Jack and Andy also discuss video marketing, customer reviews, recruiting, employee development, and how landscape companies can use AI to give managers and field employees better access to the information they need.

You’ll Learn:

• How Andy is building Garrett Churchill to operate without depending on him
• How AI helped create job descriptions, onboarding plans, and career paths
• Why structured 30-, 60-, and 90-day onboarding matters for growing teams
• How reviews, photos, and video build trust before the sales appointment
• How AI can help landscape managers support more people without simply adding more management overhead

Connect With Today’s Guest

🌳 Garrett Churchill Inc.: https://garrettchurchill.com/

👤 Connect with Andy Sykes: https://www.linkedin.com/in/andysykes11/
📸Garrett Churchill Facebook: https://www.facebook.com/GarrettChurchillInc/
🏢 Garrett Churchill Instagram: https://www.instagram.com/garrettchurchill/

Get Started With The Landscaper’s Guide

🎧 Watch the full episode + read the transcript: https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky: https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events:
 https://landscapersguide.com/events

Schedule a 15-Minute Marketing Brainstorm with the Ramblin Jackson strategy team https://landscapersguide.com/brainstorm/

Andrew Lala started Yellow Wagon Landscaping when he was just 14 years old, pulling landscaping equipment around in a yellow garden wagon because he and his business partner weren’t old enough to drive. More than 20 years later, Yellow Wagon Landscaping has grown into an award-winning full-service landscape design, build, and maintenance company serving northern New Jersey.

In this episode of The Landscaper’s Guide, Jack Jostes talks with Andrew about the next stage of that growth: getting the owner out of the weeds. Andrew shares why spending nearly half his time on a division responsible for roughly 15% of company revenue was no longer sustainable, the challenge of hiring someone to take over responsibilities he has handled for years, and why documenting processes matters when scaling. They also discuss navigating a business partnership transition, investing in marketing, and using video to create consistent messaging as the company grows.

You’ll Learn:

• Why Andrew is working to replace himself in design, sales, and project management
• How documenting processes can make delegation and onboarding easier
• Why good business software is only valuable when someone owns the data
• How Andrew rebuilt his focus on growth and marketing after a major business transition
• Why video can help preserve your company’s message as your sales team grows

Connect With Today’s Guest

🌳 Yellow Wagon Landscaping: https://yellowwagonlandscaping.com/

👤 Connect with Andrew Lala: https://www.linkedin.com/in/andrew-lala-927a992a9/

📸 Yellow Wagon Landscaping Facebook: https://www.facebook.com/YellowWagonLandscaping 

🏢 Yellow Wagon Landscaping Instagram: https://www.instagram.com/yellowwagonlandscaping

Get Started With The Landscaper’s Guide

🎧 Watch the full episode + read the transcript: https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky: https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events:
https://landscapersguide.com/events

Schedule a 15-Minute Marketing Brainstorm with the Ramblin Jackson strategy team https://landscapersguide.com/brainstorm/

What happens when your customers research your company, study your pricing, and compare your proposal with competitors before you even get a chance to sell them? According to Chuck Harkins, Director of Sales at Miller Landscape & Outdoor Living, that’s already happening—and landscape companies need to adapt.

In this episode of The Landscaper’s Guide, Jack Jostes sits down with Chuck to talk about how Miller Landscape uses transparent pricing, video, marketing, sales metrics, and even AI to make the sales process easier. Chuck also shares how his role has evolved since joining Miller in 2009, why teamwork matters in sales leadership, and why today’s landscape companies can’t rely on old-school “belly-to-belly” selling alone.

You’ll Learn:

• Why publishing pricing can make landscape sales conversations easier
• How educated prospects can reach realistic budgets faster
• Why transparency builds trust with residential and commercial buyers
• How AI may change the way customers compare landscape proposals
• Why marketing, sales metrics, and teamwork must work together

Connect With Today’s Guest

🌳 Miller Landscape & Outdoor Living: https://millerlandscape.com/

👤 Connect with Chuck Harkins: https://www.linkedin.com/in/chuck-harkins-19835263/
🏢 Miller Landscape & Outdoor Living Facebook: https://www.facebook.com/MillerLandscapeInc/

Get Started With The Landscaper’s Guide

🎧 Watch the full episode + read the transcript: https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky: https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events:
https://landscapersguide.com/events

Schedule a 15-Minute Marketing Brainstorm with the Ramblin Jackson strategy team https://landscapersguide.com/brainstorm/

After more than 25 years in business, Frank Di Sandro, founder and owner of Di Sandro Landscape Group in Bucks County, Pennsylvania, has learned that growth isn't always about doing more. Sometimes, it's about becoming more selective about the work you take on.

In this episode of The Landscaper's Guide, Frank joins Jack Jostes to talk about evolving from mowing lawns and residential maintenance into higher-margin landscape construction, hardscaping, stormwater management, and new home construction. Frank shares how focusing on the right opportunities, applying the 80/20 rule, and making deliberate changes have helped his company evolve without sacrificing quality. They also discuss industry-specific marketing, the power of video, accountability, and why business owners need to make time to disconnect from work.

You’ll Learn:

• Why Frank transitioned away from lower-margin landscape work
• How the 80/20 rule helps Di Sandro Landscape Group choose better opportunities
• Why focusing on your ideal customer can improve margins and quality
• How accountability and deadlines make marketing partnerships more effective
• Why video can help landscape companies build trust and stand out online

Connect With Today’s Guest

🌳 Di Sandro Landscape Group: https://disandrogroup.com/

Facebook: https://www.facebook.com/DisandroLandscapeGroup

Get Started With The Landscaper’s Guide

🎧 Watch the full episode + read the transcript: https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky: https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events:
https://landscapersguide.com/events

Schedule a 15-Minute Marketing Brainstorm with the Ramblin Jackson strategy team https://landscapersguide.com/brainstorm/

What does it take to turn an exhausting 18–20-hour snow event into a 10-hour operation? For Logan Berns and Matt Cunningham of Berns Landscaping, the answer comes down to better planning, more manpower, reliable equipment, and smarter technology.

In this episode of The Landscaper’s Guide Podcast, Jack Jostes sits down with Logan and Matt at the SIMA Symposium to talk about how their Michigan-based, family-owned landscape company has improved its snow operations while continuing to grow its commercial work. They share how pretreating properties, mobilizing larger crews, investing in newer equipment, and using Aspire have helped them work more efficiently. Plus, they discuss how they’re experimenting with AI, meeting-recording tools, and autonomous mowers—and why technology should make your job easier without replacing the personal touch.

You’ll Learn:

• How Berns Landscaping reduced long snow events to around 10 hours
• Why more manpower can actually reduce burnout and improve efficiency
• How newer, more reliable equipment impacts snow profitability and service
• How Aspire and AI are helping the team communicate and operate more efficiently
• Why Logan and Matt believe technology should support—not replace—the human side of the business

Berns Landscaping says bringing more people to large snow events means sites can be completed faster while reducing the grueling 18–20-hour shifts that can burn out employees.

Connect With Today’s Guests

🌳 Berns Landscaping: https://bernslandscape.com/

🏢 Berns Landscaping Instagram: https://www.instagram.com/bernslandscape/

🏢 Berns Landscaping Facebook: https://www.facebook.com/bernslandscaping/

Get Started With The Landscaper’s Guide

🎧 Watch the full episode + read the transcript: https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky: https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events:
https://landscapersguide.com/events

Schedule a 15-Minute Marketing Brainstorm with the Ramblin Jackson strategy team: https://landscapersguide.com/brainstorm/

What does it take to bet big on the right idea—and make AI actually useful inside your business? Jack Jostes sits down with Drew Dinkelacker, president of Marketing Accelerator, to talk about Drew’s 25-year journey from a video production background and growing up around his dad’s barbershop to becoming a fractional CMO. Drew shares how faith shaped his decision to start a business, why outside perspective can help owners overcome decision fatigue, and the simple lesson to “give people something they can say yes to.”

Then Jack and Drew unpack practical lessons from Cincy AI Week. They discuss why AI is more than another collection of tools—it can accelerate change management, expose broken processes, and create an advantage for teams that can clearly communicate how work gets done. For landscape and snow business owners, the takeaway is practical: get your processes right, use AI to improve the way your team works, and when you find an opportunity you truly believe in, be willing to bet big.

You’ll Learn:

• Why better decisions often start with giving someone something they can say yes to
• How AI can become a process and change-management tool
• Why AI can make broken workflows fail faster instead of fixing them
• Why clearly communicating your processes is becoming a competitive advantage
• When it’s time to stop taking incremental steps and bet big on an idea

Connect With Today’s Guest

🌳 Marketing Accelerator: https://marketingaccelerator.com/

👤 Connect with Drew Dinkelacker: https://www.linkedin.com/in/drewdinkelacker/

Get Started With The Landscaper’s Guide

🎧 Watch the full episode + read the transcript:
https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky:
https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events:
https://landscapersguide.com/events

Scott Benson started Benson Landscape & Design as a teenager in Rochester, New York, and has spent nearly 40 years building it into a 50-person residential landscape design, installation, maintenance, and snow company. In this episode, Scott joins Jack Jostes at the SIMA Symposium to share how the business grew from mowing neighborhood lawns and snowblowing driveways into a company with a leadership team, more than 40 service lines, and a strong reputation with residential clients.

Now Scott is taking on a new challenge: commercial snow removal. He explains why Benson is starting with carefully selected properties, repeated direct-mail touches, and a long-term approach instead of chasing every opportunity. Scott and Jack also dig into leadership, culture, team development, digital marketing, video, and why continued company growth creates more opportunities for employees.

You’ll Learn:

• How Benson built a profitable residential snow service and why they’re keeping it
• How Scott plans to enter commercial snow with targeted properties and repeated outreach
• Why growing from 35 to 50 employees made leadership, trust, and systems more important
• How Benson uses email, SEO, reviews, and video to educate clients about 40+ service lines
• Why continued company growth creates career opportunities for the team

Connect With Today’s Guest

🌳 Benson Landscape & Design: https://bensonenterprises.com/

👤 Connect with Scott Benson: https://www.linkedin.com/in/scott-benson-824738126/

🏢 Guest Company Facebook: https://www.facebook.com/BensonEnterprises

Get Started With The Landscaper’s Guide

🎧 Watch the full episode + read the transcript:
https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky:
https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events:
https://landscapersguide.com/events

Schedule a 15-Minute Marketing Brainstorm with the Ramblin Jackson strategy team https://landscapersguide.com/brainstorm/