Bobyard founder Michael Ding joined Marty Grunder on The Grow Show to talk about landscapers deserving better tools, why the hard problems are the ones worth solving, and what AI actually changes for estimators.
Marty Grunder has built two of the most respected brands in the green industry: Grunder Landscaping and The Grow Group, and now has one of the most listened-to industry podcasts, The Grow Show. We were thrilled to have our founder, Michael Ding, on his latest episode.
They covered a lot of ground: the founding story behind Bobyard, why estimators are the most under-leveraged people in your business, what it takes to solve a problem no one else wanted to touch, and a hiring factor you might not have thought of.
Watch the full conversation on YouTube, or read our favorite moments below.
Marty kicked off the conversation with a conversation we get often: how does a CS major at Stanford end up founding an AI company for the construction trades?
“I was biking back and forth between my real estate class and a computer vision AI class, and I connected the dots between the two. Someone showed me a takeoff for the first time, and I was actually surprised that it was the standard way—the intended way—to do a takeoff. I thought, ‘there has to be a better way to do this.’ That real estate professor is now an investor and advisor for Bobyard.”
And why the name Bobyard? “I was one of those little kids that watched Bob the Builder,” Michael laughed.
Marty also asked why Bobyard started with the landscaping trade and what surprised Michael most about landscapers.
“Initially we had a bunch of different trades as partners across electrical, mechanical, and landscaping, but in defending everything, we defended nothing. Landscaping is one of the last trades to go in a big construction project, and by the time you start, the whole project might be off budget and timeline. On top of that, landscaping has such a fragile asset class—your plants die if you don't do logistics well enough. No other trade has that."
Michael was also blown away by the sophistication of operators. Running a landscape business is "stupidly hard,” something that resonated with Marty.
“I had a family member go to our office and say, ‘Oh my gosh, you have a real company,’” Marty explained. “I remember thinking, 'what exactly do you think I'm doing here!?' So I appreciate the respect you're paying our industry."
Beyond the estimating process bottleneck, there’s the estimator problem, too. Estimators are some of the most expensive and difficult people to hire in the business, and Michael saw the pain Marty has lived all too well: more than half their day is just spent clicking and counting.
"Estimators are some of the most sophisticated, savvy people in your company, and there's a huge labor war going on for them. We make sure estimators spend time doing things that only they can do. If your job is to bring in money but you're clicking and counting all day, that's not the highest-leverage activity for anyone." — Michael Ding
Marty connected this directly to Grunder Landscaping, where his son, Grant, uses Bobyard daily. The more bids he can get out the door, the more deals can close. Michael emphasized that Bobyard doesn’t replace an estimator, it helps them be a super estimator to drive sales, set better margins, and get more bids out, instead of counting plants.
When Marty asked whether Michael was surprised no one had built this before, Michael's answer was blunt: he was, which is why he rushed to found Bobyard. Reading landscape blueprints is a hard AI problem, full of ambiguity, and it's taken a team of PhDs from Stanford, Virginia Tech, and Princeton to solve breakthroughs that aren't even in the literature yet.
"At Bobyard, we try to pick problems where there are no shortcuts. If you're in a market with a shortcut, everyone will take it. But if you pick a problem that only has a hard solution, no one else can follow you except by doing the hard thing as well."
Marty has also lived this in landscaping. He told a story from a recent event in Boston where a contractor complained about a municipality that was impossible to work with because the permitting was so tough. Marty's take: “Grunder Landscaping has one of those in their own backyard, and once we figured out how to meet the standard, that same municipality actually started recommending us.”
"When you take the road less traveled, that's where a lot of reward is. People don't want headaches, but it sounds to me like Bobyard has embraced them." — Marty Grunder
Marty cautioned that the reason no one's doing it might be that it can't be done, and Michael agreed that you have to know when to stop, but pushing past the initial thought that something is too difficult might be where the opportunity lives.
When Marty asked Michael what he'd do if he were starting a landscaping company, Michael didn't talk systems or strategy, but people.
“Bobyard's hiring rule is simple: every new hire has to be better than the average of the company. That forces the current team to grow with every addition.” It's why Michael now spends most of his time on hiring and keeping people motivated.
In Bobyard’s earlier years, Michael said he'd find himself losing sleep over specific problems, so he sought to hire people who he could really trust to tackle it so he could sleep well.
"How easy does everybody else sleep knowing you're in charge of the things you're in charge of?"
Marty's admitted that at Michael's age, he was a dictator faking it till he made it, and that real growth came when he learned to listen.
It's the same standard Bobyard tries to bring to its product: when estimators can genuinely own and uplevel their work, it of course makes an impact on the business bottom line, but also in how they show up and do the work.
Marty and Michael covered so much ground in the full conversation (from the Wall Street Journal feature, private equity's impact on the green industry, and the "mom test" for product-market fit). Check out the full episode on YouTube, or wherever you get your podcasts.
Q: How much time can AI save on landscape takeoffs?
Customers like Grunder Landscape report saving 60–80% of the time previously spent on takeoffs. Commercial projects that took four to five hours can often be completed in 30 to 60 minutes.
Q: What is the biggest bottleneck in landscape estimating?
The manual takeoff process like counting plants, measuring areas, calculating material quantities can take half or more of an estimator’s time and workday. That leaves less time for the high-leverage work estimators are skilled at that drives the bottom line: pricing strategy, risk assessment, and closing deals.
Q: How hard is it to hire a good landscape estimator?
Skilled estimators are among the most difficult hires in the industry. They require significant training and experience, command high salaries, and are in short supply, making it critical to get maximum output from the estimators you already have.
Q: Do you need a technical background to use AI estimating software?
No. Bobyard is designed to be self-serve and intuitive for estimators without any data science or engineering background. The AI runs in the background while the estimator stays in control of the workflow and final numbers.
Q: What should landscape contractors look for when evaluating estimating software?
Look for AI-native software that handles the full manual takeoff workflow. Be cautious of tacked-on GPT or AI wrappers or outsourced manual work sold as “AI.” The best test is a direct comparison: run the same project through your current tool and Bobyard, and measure the difference in time and accuracy yourself. Bobyard’s demos are free and will run a takeoff on a real project you have.