
I bought Geared for Growing about a year ago. It’s a full-service landscape company in Northern California. They had been building and maintaining properties since 1983. When I signed the papers, it was doing around $2.5 million a year. Six good crews, loyal clients, a name people around here trust.
I assumed I was buying a well-run business. What I was actually buying was a well-run business that lived almost entirely in a few people’s heads.
The estimating process took weeks and was backed up by a spreadsheet only the estimator understood. The schedule was a whiteboard with magnets in the shop and a running pile of text messages. If you wanted to know whether a job made money, you asked the foreman. He’d tilt his head and give you a number he felt pretty good about. He was close — sometimes. I found that out the hard way on a retaining wall job that ran 11 days when we’d bid six.
What I’ve learned is this is how most landscape companies our size actually run. It hit me hard early on in this transition: a business that lives in the owner’s head can’t grow past that person. Even if they’re a stellar employee, your operation is one bad back or one dead cellphone away from losing money.
I’ve spent the last year getting the company out of everyone’s heads and into something we could all see.
I’ve spent the last year getting the company out of everyone’s heads and into something we could all see. This wasn’t a giant software launch, or hiring a consultant, and certainly not a platform built for a company five times our size. I just tried to prioritize whatever was bleeding the most, one thing at a time.
Whether you’re a veteran owner who built a business from scratch or you just purchased one like I did, here are a few things I learned (the hard way) transitioning my business from the paper to the cloud.
You Can’t Fix What You Can’t Track
The mistake some owners make is deciding they need “a system,” forcing it on the crews, and two months later, everybody’s back at the whiteboard because the platform was too technical.
I did it backwards. I tried to really understand the three things holding me back from working “on” the business rather than “in” the business.
For me, it all started with time tracking. You can’t measure what you can’t track and if timecards are submitted at the end of the week, you can’t catch issues until it’s too late.
Then it was lead-flow. Leads dying after the estimate because they never received a followup phone call.
Finally, our crew schedules for construction, enhancements, and maintenance. By this time, I had grown the business from six crews to nine, and the white board didn’t scale.
That was my list. Everything else had to wait.
The Most Valuable Thing I did was Simplify
I got the customer list into one place. That’s it. That was the big move.
If your clients live in your phone, or your inbox, that’s priority number one. Pick one spot like a simple customer relationship management software (CRM), and put every lead, every proposal, every “call them back in Spring” note into it. Now when the phone rings, whoever picks up can see the whole story so a $40,000 install doesn’t evaporate because the one guy who knew about it lost his notebook.
The Whiteboard Had to Go
It had been on that wall for 20 years. My foremen loved it. But the whiteboard couldn’t tell me where the maintenance crews are right now. It couldn’t stop me from double-booking our one dump truck. It physically couldn’t fit an additional crew.
Get the schedule onto something everybody can pull up on their phone. Crews see their schedule and tasks the week before. The office sees every crew without having to call and leave a voicemail. When we flipped that switch, the constant “where are you, where’s the material, what’s the plan” calls stopped interrupting the work. It felt like somebody turned the volume down on the stress level across the company.
The Geared For Growing team. Since this photo was captured, about 5 to 7 more people have joined the company. Geared For Growing
If the Crew Hates it, It’s Already Dead
We were obsessing over estimating and invoicing, but the real leaks we found were in the boring daily stuff. Hours logged to the wrong client or sometimes not at all. A pallet of sod nobody wrote down. That retaining wall running five days over while everyone figures somebody else is tracking against the estimate.
The real leaks we found were in the boring daily stuff.
The goal seemed simple. With an operating system, we could capture the actual work: the hours, the materials, the daily profitability, the day it happens, by the people doing it using the phone they already have in their pocket. The idea was to see the real cost of a job while it’s still running, and while we could still do something about it.
From what I’ve learned, getting the crew on-board is where most of these efforts die. The owner gets fired up, rolls out five new apps at once, the crew mutinies and you’re back to printing more time cards. Our crews had been doing beautiful installs long before I came along, and the last thing I wanted was them feeling like I was giving them homework.
I introduced one concept at a time, and I made sure every single thing made somebody’s day easier, not just mine. The time tracking saves the crews time at the end of each day. The schedule gave them a clear view into the work they were responsible for that week. The CRM saved the office from digging through text messages. I saw first hand that when a tool actually helps the person using it, they use it.
You Don’t Need a Total Transformation
My advice: you don’t have to overhaul the whole company. Fix the three squeekiest wheels. Get that knowledge out of one person’s head. Prove to your crew the new way makes their day better. Then go do it again with the next problem.
We’re doing around $3.5 million now, up from the $2.5 million we were at when I bought the business a year ago. Software certainly didn’t do that on its own, but it has entirely changed the way our crews work. There is no way we’d have handled that growth on the old setup. A year in, the business runs on information anybody on the team can pull up. I can take a day off. My foreman can call in sick. And when I want to know if a job made money, I don’t ask anyone, I just look.
The landscape businesses we’re building are worth protecting. Getting a legacy business like mine off the whiteboard and out of our heads is how to protect it - and how you hand it to the next person in a better place than it is today.
What’s next? We’ve rolled out a client dashboard that empowers maintenance clients to submit their own work orders! Instead of navigating text threads and weekend voicemails, our clients are snapping a picture and clicking “submit” on new projects where they need help. It’s becoming a flywheel for new business.


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