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/ 

What does it really take to build a business that can thrive without depending on you every day?

In this special joint episode of The Landscaper's Guide Podcast, Jack Jostes sits down with his longtime business coach, Jason Swenk, founder of Smart Agency Masterclass and author of Operator to Owner. Together, they explore the five identity shifts every entrepreneur must make to grow from doing everything themselves into leading a company built on systems, leadership, and long-term value.

Whether you're running a landscape company, snow removal business, or any growing service business, you'll hear practical strategies for creating systems, hiring the right people, leading through outcomes instead of tasks, avoiding founder self-sabotage, and embracing AI without losing the human element that makes your business unique. Jason also shares why many owners accidentally become the biggest bottleneck in their companies—and what it takes to finally step into the CEO role with confidence.

You'll Learn

• The five identity shifts every business owner goes through while scaling.
• Why hiring alone won't fix your workload without documented systems.
• How to lead your team by focusing on outcomes instead of tasks.
• Practical ways AI can improve your business without replacing human expertise.
• How to stop being the bottleneck and build a company that can grow without you.

Connect With Today's Guest

🌳 Smart Agency Masterclass:
https://jasonswenk.com/index.html

👤 Connect with Jason Swenk:
https://www.linkedin.com/in/jasonswenk/

📸 Instagram:
https://www.instagram.com/jswenk/?hl=en

🏢 Check out the Operator to Owner Book:
https://operatortoownerevolution.com/

Connect With Jack Jostes

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

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

How do you prepare the next generation to lead a successful family business? In this episode of The Landscaper's Guide Podcast, Jack Jostes sits down with Sterling Lowe and his daughter, Madelyn Lowe, of IndusCo Facility Solutions to discuss leadership, succession planning, and growing a family-owned business across generations. They share how IndusCo expanded from commercial coatings into snow and facility services while creating opportunities for younger leaders to make a real impact.

You'll also hear Madelyn's perspective on entering the snow industry, building confidence through experience, encouraging more women to pursue careers in the trades, and how marketing, technology, and strong relationships continue to fuel IndusCo's growth. Whether you're preparing your children to join the business, developing future leaders on your team, or looking for ways to strengthen your company culture, this conversation is full of practical lessons you can apply today.

You'll Learn

• How to prepare the next generation to lead a family business.
• Why strong relationships continue to outperform traditional sales tactics.
• How marketing and a modern website strengthen commercial client relationships.
• Ways to create opportunities for women to succeed in the snow and landscape industries.
• Why confidence follows experience—and how great leaders help others take that first step.

Connect With Today's Guest

🌳 IndusCo Facility Solutions: https://induscofs.com/

👤 Connect with Sterling Lowe and Madelyn Lowe:
https://www.linkedin.com/in/sterling-lowe-a859475a/
https://www.linkedin.com/in/madelyn-lowe-871387254/

🏢 Company Facebook: https://www.facebook.com/IndusCoEnterprises/

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/ 

Winning commercial landscape and snow contracts isn't just about having the best equipment or submitting the lowest bid. It's about standing out, targeting the right customers, building trust, and creating a sales and marketing system that keeps you top of mind.

In this episode of The Landscaper's Guide Podcast, Jack Jostes shares five of the biggest lessons from a recent live virtual workshop with commercial snow and landscape contractors from across the country. You'll hear real stories from contractors who landed major accounts, learn why being specific about your ideal commercial client leads to better results, discover how "gold mining" your CRM can uncover your next customer, explore creative direct mail strategies that actually get noticed, and hear Jack's latest advice on preparing your company for AI-powered search. If you're ready to win more commercial maintenance and snow contracts, this episode is packed with practical ideas you can put to work immediately.

You'll Learn

• Why specializing in specific commercial property types helps you win more profitable contracts.
• How to identify your warmest prospects using your existing CRM and marketing data.
• Creative "lumpy mail" and offline marketing ideas that get commercial buyers' attention.
• Why sales and marketing should always work together—not separately.
• What landscape companies should be doing today to improve their visibility in AI search.

Connect With Jack Jostes

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

👤 Connect with Jack Jostes: https://www.linkedin.com/in/jackjostes/

📸 Instagram: https://www.instagram.com/jackjostes

🏢 Ramblin Jackson Instagram: https://www.instagram.com/ramblinjackson

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 would your health, family, and business look like if you started planning for the person you want to be at 80? In this episode of The Landscaper’s Guide Podcast, Jack Jostes hikes to the Royal Arch in Boulder, Colorado, with his business coach, Wayne Herring, owner of Business Builder Camp.

Wayne shares why his long-term goal is to complete a trail 10K when he is 80 and how ambitious fitness goals can help business owners make better decisions today. Jack and Wayne also discuss protein-focused nutrition, short-term fitness and business sprints, scheduling meaningful adventures, avoiding burnout, and using focused seasons to improve systems. You’ll hear how getting away from your computer can restore your energy, create urgency, and help you return to your team as a better leader.

You’ll Learn

• How long-term fitness goals can improve your decisions today
• Why protein is a practical priority for strength and nutrition
• How focused sprints can improve your health and business systems
• Why putting adventures and family experiences on the calendar matters
• How time away from work can increase energy, creativity, and productivity

Connect With Today’s Guest

🌳 Business Builder Camp: https://businessbuildercamp.com/
👤 Connect with Wayne Herring: https://www.linkedin.com/in/wayneherringjr/
📸 Wayne Herring Instagram: https://www.instagram.com/wayneherringcoach/

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