Weston Zimmerman
The Cost of Doing Business
The Cost of Doing Business Podcast is here to help business owners find the path to profitability. We look beyond the glamour and glitz of the Instagram highlight reel by digging into the behind-the-scenes work necessary to achieve our goals. Your host, Weston Zimmerman, is the co-founder of SynkedUP. This award-winning landscape business management software is making a real difference for owners looking for a budgeting and overhead recovery tool and helps with estimating and job costing.
Author
Weston Zimmerman
Category
Podcast website
Latest episode
Jul 6, 2026
Where to listen?
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Episodes
Ep 104. Don't Rush Your Next Hire | Dan & Emily Gagnon 06.07.2026 59:01
The wrong hire can set your business back fast. In this episode of The Cost of Doing Business, Dan and Emily Gagnon talk about the burnout that comes from trying to do everything yourself and how that pressure can lead to hiring too fast. They also share why knowing your numbers can change the way you grow your business and help you avoid desperate decisions. Check out their instagram: https://www...
Ep 103. Why That $10K Job Should've Been $19K | Kabe Hockema 22.06.2026 35:33
In this episode, Weston Zimmerman sits down with Kabe Hockema of Hockema Landscape Design & Build to talk about the costly mistake of underpricing jobs and why so many contractors leave money on the table. It's a great reminder that working hard isn't enough if you don't know your numbers. Give Kabe a follow on Instagram: https://www.instagram.com/hockemalandscape Check out his website: https://...
Ep 102. We Asked Contractors: What's The Hardest Challenge You've Overcome? 08.06.2026 10:18
What's the most difficult challenge you've overcome? We asked that question to contractors and business owners from across the industry, and the answers weren't what you'd expect. Some talked about losing money. Some talked about learning to say no. Some talked about letting go, finding balance, and getting out of their own way. The common theme? Growth usually comes from the challenges you'd neve...
Ep 101. Hiring Great Employees With The Right Attitude 25.05.2026 36:20
Most landscaping companies have a hard time finding and keeping good workers. In this episode, Sean and Kerry Sweeney from Blue Ribbon Companies talk about why skilled workers actually WANT to work for their company. Their team members show up with good attitudes, useful skills, and a willingness to learn. As a family-run business, the Sweeneys explain how treating employees well and investing in...
Ep 100. The Cost of Starting My Business Too Early | Kory Jones 11.05.2026 46:50
Most people romanticize starting a business early. Nobody talks about the stress it puts on your family when you're not prepared. In this episode, Kory Jones talks about what he wishes he knew before starting his landscaping business… from cash flow struggles to hiring challenges to learning that passion alone isn't enough. One of the best lines from the episode: "You can do the right thing at the...
Ep 99. 30 Years in Business and Thinking About the End Game | Mark Arsenault 27.04.2026 36:41
Most guys don't think about the end when they start a business. In this episode, Weston sits down with Mark Arsenault from Green Monster Landscapes to talk about what changes when you've been doing this for a long time… and start thinking about what comes next. Mark shares his path through nearly three decades. Building crews, going through a full reset, and rebuilding the business in a way that a...
Ep 98. I Almost Quit Landscaping After Years of Losing Money | Jason Nolt 13.04.2026 37:42
Running a landscaping business isn't always what it looks like from the outside. In this episode, Weston sits down with Jason Nolt of Authentic Homescapes to talk about the early years of his business… and how close he came to quitting altogether. Jason shares what it actually looked like behind the scenes. Losing money, wearing every hat, growing too fast, and hitting a point where it just wasn't...
Ep 97. When Is Enough Enough in Business? | James Doyle 30.03.2026 37:56
In this episode, Weston sits down with James Doyle of Innovative Lawn & Landscape to talk about what happens when growth comes fast and the pressure to keep pushing never really goes away. James shares what it's been like building his company over the last 9 years, the struggle of never feeling satisfied, and the question a lot of owners don't talk about… when is enough actually enough? We also ge...
Ep 96. Pressure Is the Price of Running a Business | Wes Roberts 16.03.2026 25:16
Running a business comes with pressure. That's part of the deal. In this episode, Weston sits down with Wes Roberts of Wes Roberts Landscaping to talk about the mindset it takes to keep going after nearly three decades in the industry. Wes shares how the biggest obstacle in business is often yourself, why challenges never really go away as you grow, and how pressure can actually give purpose to th...
Ep 95. The Hard Part of Scaling Nobody Warns You About | Jordan Daneker 02.03.2026 58:42
Scaling a business sounds great on paper. In reality, it can get harder before it gets better. In this episode, Weston sits down with Jordan Daneker, co-owner of Evolve Design + Build, to talk about the side of growth most contractors don't expect. Jordan shares what it's really like scaling fast, why more revenue doesn't always mean more money, and how cash flow, confidence, and systems become cr...
Ep 94. I Was Winning Jobs and Still Losing Money (Here's Why) | Cody Adkins 16.02.2026 20:58
Most contractors don't lose money because they're bad at the work. They lose money because they don't actually know where it's going. In this episode, I sit down with Cody Adkins of Tri-State Outdoor Living to talk about what it looks like when you're winning jobs, staying busy, and still coming up short, especially when winter hits. Cody shares how square foot pricing left him negative on jobs, t...
Ep 93. Why Charging More Didn't Hurt My Business | Thomas Vanamerongen 02.02.2026 27:47
Most contractors don't undercharge on purpose. They just don't see everything that's actually coming out of their business. In this episode, I sit down with Thomas Vanamerongen of Niagara Waterscapes to talk about the wake-up call that came when he realized his pricing didn't reflect reality. Thomas shares how starting out at $65 an hour quickly turned into $90, then $110, once all the hidden cost...
Ep 92. Growing Too Fast Almost Broke My Landscaping Business | Dan Wanders 19.01.2026 22:38
Growing a business fast sounds great until the bills start stacking up. What matters is what you do once you realize something's off. In this episode, I sit down with Dan Wanders from Raymar Landscapes to talk about what happens when growth gets ahead of cash, systems, and planning. Dan shares how pushing too fast led to some tough seasons, and how slowing things down, tightening up his process, a...
Ep 91. Working Hard Only Works for So Long | More 2025 Highlights 05.01.2026 33:53
This episode brings together more honest moments from The Cost of Doing Business podcast, featuring contractors talking openly about pricing, job costing, and the limits of working harder to make a business work. These aren't theories or shortcuts. They're conversations about guessing at pricing, learning the difference between gross profit and real profit, and realizing how small mistakes compoun...
Ep 90. I Thought I Was Profitable Until I Looked at the Numbers | 2025 Highlights Part 1. 22.12.2025 30:44
This episode brings together some of the most honest moments from The Cost of Doing Business podcast in 2025. Real contractors sharing real experiences about pricing, profit, and the lessons they learned once they finally looked at their numbers. These aren't theories or quick tips. They're conversations about underbidding, burnout, growth, and the realization many contractors have after years of...
Ep 89. How Tussey Landscaping Built a Crew That Stays for 10–20 Years | With Matt Martin 08.12.2025 56:20
Building a crew that sticks around is not luck. It comes from leadership, culture, and doing the small things right year after year. In this episode, Weston sits down with someone who played a huge role in his own start in the industry: Matt Martin from Tussey Landscaping. Weston spent 15 years working under Matt and the Tussey team, and a lot of who he is as a leader today came from those early s...
Ep 88. How to Stand Out in a Landscaping Company | Ben Zimmerman 24.11.2025 1:08:38
When you work in the trades, it's easy to just show up, do the work, and call it a day. But sometimes the way you carry yourself and the pride you put into your craft quietly set you apart. That has been the case for Ben Zimmerman of Tussey Landscaping. In this episode, Weston and Ben talk about what it really looks like to grow inside a landscape company. They get into developing skill through re...
Ep 87. Letting Go to Grow: How Trust Built NVS Landscapes | Sean Hotaling & Wes Trumpler 10.11.2025 33:06
When you've built your business from the ground up, letting go isn't easy. But for Sean Hotaling, it was the only way to grow. In this episode, Weston sits down with Sean and Wes from NVS Landscapes to talk about what it really takes to go from a one-man show to a thriving team. They talk about learning to trust others, giving your crew the freedom to figure things out, and trusting your gut when...
Ep 86. Choose Your Hard: Building a Thriving Business Without Burning Out | Nate Butler 27.10.2025 37:25
"Choose your hard." That's the phrase Nate Butler lives by. After decades in landscaping and even a stint in the North Dakota oil fields, Nate started Summit Ridge Landscape with one goal: to build something lasting without burning out. He shares how focusing on systems, communication, and hard-earned lessons helped him grow from a one-man show to a thriving design-build company. It's about more t...
Ep 85. Time Kills Deals: How to Actually Close More Jobs w/ Kalei Duke 13.10.2025 57:43
Kalei used to send a bid and wait, hoping the client would call back. Now he gives every quote a short deadline and it completely changed how many jobs he closes. It's not about pressuring people. It's about keeping the conversation moving while the excitement is still there. Time kills deals. The longer they think about it, the colder it gets. Give Kalei a follow on Instagram: https://www.instagr...
Ep 84. Building Resilience: Lessons from the Journey of Conklin Landscape Solutions 29.09.2025 43:41
In this episode I sit down with Logan Conklin, co-founder of Conklin Landscape Solutions , to dive deep into the real-life challenges and triumphs of growing a small business. Logan shares candid stories about starting his landscape company, weathering financial setbacks, learning the importance of contracts, and finding success through strategic improvements and faith. Discover how a near busines...
Ep 83. Building Success from the Ground Up: Chris Huser's Lessons in Landscaping and Leadership 15.09.2025 37:49
I sit down with Chris Huser, founder of Huser's Outdoor Design + Build, for an honest conversation about the realities of running a landscaping business. Chris shares his three-decade journey from mowing lawns to mastering hardscapes, revealing the challenges, pivotal moments, and mindset shifts that fueled his company's growth. Discover how Chris navigated industry changes, embraced new technolog...
Ep 82. Investing in Success: Elliot's Journey from Playing It Safe to Scaling Up 01.09.2025 37:11
Elliot shares how embracing risk and investing in his business; from marketing and coaching to the right tools, transformed his journey from cautious growth to real success. Hear candid stories about overcoming self-doubt, learning the value of spending money to make money, and the mindset shifts that helped him scale his landscaping company. This episode is packed with practical advice and inspir...
Ep 81. Scaling a Profitable Landscaping Business: Marketing, Niching Down, and Project Management with Jesse Weidner 18.08.2025 42:13
I sit down with Jesse Weidner in this episode, owner of Weidner Landscape Solutions , to uncover the real journey behind building a successful landscaping business. In this episode, Jesse shares actionable insights on scaling from a solopreneur to a thriving team, the power of niching down, and how to create a steady flow of qualified leads through intentional marketing strategies. Discover how le...
Ep 80. From the Ground Up: Building a Thriving Landscaping Business with Clayton Canby 04.08.2025 1:06:16
In this episode of The Cost of Doing Business Podcast, I sit down with Clayton Canby, owner of Mountain Lake Landscaping LLC, to dig into the real-life challenges and rewards of growing a successful landscaping company. Broadcasting from a historic West Virginia dairy farm, Clayton shares his journey from humble beginnings and long days in the field to leading a dedicated team and building a busin...
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