The Cost of Doing Business

Hosted by Weston Zimmerman

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Episodes

107

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Aug 2026

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About the show

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.

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60 recent

August 31, 202644 min

Ep 108. Why the Best Leaders Start in the Field | Bryce McCloskey

Bryce started at Affinity Outdoors sharpening mower blades. Fourteen years later, he's helping run the entire operation. In this episode of The Cost of Doing Business, Bryce shares how growing through the ranks of the business made him a better leader and prepared him for more responsibility. Sometimes the best leaders are the ones who've done the work themselves. If you enjoyed this episode, join us at the SynkedUP Contractor Summit in Pittsburgh on September 10–11. Bryce and the Affinity team will take us inside their operation through a virtual tour. Visit synkedup.com/contractor-summit for the details. Check out Affinity Outdoors on IG: https://www.instagram.com/affinitylawnandlandscape/ Learn more about SynkedUP: https://www.synkedup.com #contractor #leadership #landscaping #employeegrowth #synkedup

August 17, 202632 min

Ep 107. He Went From $630K to $2M in 3 Seasons | David Esh

Tripling your business in three seasons doesn't happen by accident. In this episode of The Cost of Doing Business, David Esh talks tracking his numbers from day one and staying focused on executing the changes that build a successful business. Knowing your numbers could be the difference between just doing the work and growing your business. Give David a follow on Instagram: https://www.instagram.com/david208.lux/ Learn more about SynkedUP: https://www.synkedup.com #businessgrowth #contractor #landscapingbusiness #knowyournumbers #synkedup

August 3, 202645 min

Ep 106. His Side Hustle Is Now A $1M Business | With Dylan Stephenson

Every contractor reaches a point where they have to bet on themselves. In this episode of The Cost of Doing Business, Dylan Stephenson shares the mindset shifts that helped him grow Brilliant Gardens from a side hustle into a million-dollar business. Your next opportunity could be one decision away. Learn more about the 2026 SynkedUP Contractor Summit: https://www.synkedup.com/contractor-summit Give Dylan a follow on Instagram: https://www.instagram.com/brilliant_gardens/ If you're interested in learning more about SynkedUP, check us out: SynkedUP - Landscape Business Management Software https://synkedup.com/ Follow us on Instagram: @SynkedUP #synkedup #contractor #businessgrowth #mindset #landscapeconstruction

July 20, 202635 min

Ep 105. Why I Stopped Paying My Crew Hourly | Alex Bulow

Most contractors pay by the hour. Alex Bulow doesn't. In this episode of The Cost of Doing Business, Alex shares why he switched most of his crew to salary, how it changes the way they work, and why it's helped build a stronger business. Build a crew that wants to win, and the business will follow. 💡 Check out Alex on Instagram: https://www.instagram.com/inca_stone/ If you're interested in learning more about SynkedUP, check us out: SynkedUP - Landscape Business Management Software https://synkedup.com/ Follow us on Instagram: @SynkedUP #synkedup #contractor #businessgrowth #knowyournumbers #landscapingbusiness

July 6, 202659 min

Ep 104. Don't Rush Your Next Hire | Dan & Emily Gagnon

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.instagram.com/gagnonlandscapeco/ If you're interested in learning more about SynkedUP, check us out: SynkedUP - Landscape Business Management Software https://synkedup.com/ Follow us on Instagram: @SynkedUP #contractors #businessgrowth #hiring #leadership #synkedup

June 22, 202635 min

Ep 103. Why That $10K Job Should've Been $19K | Kabe Hockema

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://hockemalandscape.com/ If you're interested in learning more about SynkedUP, check us out: SynkedUP - Landscape Business Management Software https://synkedup.com/ Follow us on Instagram: @SynkedUP #contractor #pricing #knowyournumbers #estimating #jobcosting

June 8, 202610 min

Ep 102. We Asked Contractors: What's The Hardest Challenge You've Overcome?

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 never choose for yourself. Watch the full compilation and let us know. What's been the toughest challenge you've overcome in your business? Featuring: https://www.instagram.com/suttonoutdoorllc/ https://www.instagram.com/nunezoutdoorliving/ https://www.instagram.com/rcoutdoor/ https://www.instagram.com/pandolfilandscapeconstruction/ https://www.instagram.com/anthonygrouphardscapes/ https://www.instagram.com/derbycitypools/ https://www.instagram.com/wesrobertslandscaping/ https://www.instagram.com/stone_craftdesigns/ https://www.instagram.com/innovativelawnandlandscapellc/ https://www.instagram.com/gregwittstockthepondguy/ If you're interested in learning more about SynkedUP, check us out: SynkedUP - Landscape Business Management Software https://synkedup.com/ Follow us on Instagram: @SynkedUP #contractor #businessowner #businessgrowth #synkedup #knowyournumbers

May 25, 202636 min

Ep 101. Hiring Great Employees With The Right Attitude

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 their team has helped them grow their landscaping business to $3 million without losing their company culture. Give Blue Ribbon a follow: https://www.blueribbonnh.com https://www.facebook.com/blueribboncompany/ https://www.instagram.com/blueribboncompanies?igsh=MWNidTltb2ExZG15MQ== If you're interested in learning more about SynkedUP, check us out: SynkedUP - Landscape Business Management Software https://synkedup.com/ Follow us on Instagram: @SynkedUP #contractor #hiring #businessowner #synkedup #knowyournumbers

May 11, 202646 min

Ep 100. The Cost of Starting My Business Too Early | Kory Jones

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 wrong time." Give Kory a follow: https://www.instagram.com/jonesoutdoors.ut/ If you're interested in learning more about SynkedUP, check us out: SynkedUP - Landscape Business Management Software https://synkedup.com/ Follow us on Instagram: @SynkedUP #contractor #landscapingbusiness #businessowner #synkedup #knowyournumbers

April 27, 202636 min

Ep 99. 30 Years in Business and Thinking About the End Game | Mark Arsenault

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 actually fits how he wants to work. They get into something that hits for a lot of contractors. A lot of owner operators aren't building something they can step away from… they're building a job. When you start thinking about retirement, that reality hits a little different. Give Mark a follow: https://www.instagram.com/greenmonsterlandscapes/ If you're interested in learning more about SynkedUP, check us out: SynkedUP - Landscape Business Management Software https://synkedup.com/ Follow us on Instagram: @SynkedUP #contractor #landscapingbusiness #businessowner #synkedup #knowyournumbers