A few hundred shirts came off the press in the wrong colours.
Michael Hobart’s print shop was running a New England Patriots logo. Everyone in that building was from New England. Everyone knew exactly what that logo looked like. Two colours in the spec were inverted, the flesh tone and the brown, and the job went straight through production without anyone catching it.
Michael threw a screen across the shop and frustrated with himself and his staff, most of them his friends. Then he walked up to his office, pulled up the artwork, and saw the mistake was his.
“I learned to be a manager by being really bad at it,” he told me, and dug deep to become a great manager, I know this because I had a brief time working with him at his last startup.
Today Michael is an engineering manager at Toast with seven engineers and an eighth on the way. No CS degree, no bootcamp. His way in was being the customer first. He ran a small business for almost ten years and built the tools it needed because nobody sold them. By the time he walked into tech, he already knew the problems engineers are paid to solve.
If you’re trying to break into tech right now, that’s the path I’d study.
How I know Michael
We met at Trust & Will, where Michael was an engineering manager and helped onboard me. Our first conversation was supposed to be twenty minutes on the lay of the land. It ran another forty-five, mostly about being a parent. We’ve still never met in person.
The print shop
Michael didn’t love school. He loved making show flyers and shooting photos in the punk, BMX and skate scenes. That became a graphic design degree, then a job at a tiny apparel printer serving the underground music scene.
About a year in, one owner walked away. The silent partner asked Michael if he wanted to run it. Michael didn’t want to write a CV or sit through interviews, so he started his own shop with the equipment stuffed in his basement. His landlord kicked him out. He moved into a corner of a warehouse and found a business partner who floated him cash. He ran the business for about nine and a half years. At its peak it had two to four employees, a 4,000 sq ft warehouse and automated presses, and it printed merch for convention clients like PAX and Rooster Teeth.
The tools came before the title
About four years in, the shop was too big for mom-and-pop tools and too small for enterprise software. So Michael built his own.
Excel and Google Sheets first. Then an order form on Airtable with a screen showing every order on the production floor. Then an inventory tracker and web sales tracking. Then a demand projection that took a client’s past sales, the headcount of their next event and a market tier (Boston versus rural Kansas), and used them to flatten the spikes of convention season.
He learned from YouTube and Stack Overflow, and by trying and failing. The tools were internal, so rough edges were fine as long as the business problem got solved and this is something I love seeing in self taught folks, is this focus on solving problems more than the tech.
That’s where he found what he calls his career tagline: he loves “solving business problems with tech.” Running the business was the part he didn’t love. People in tech told him to learn the business and translate its problems into technology. He’d been doing both for years.
Hundreds of applications, one reply
He sold the equipment and inventory, took website work at a private school, then a second school role. He applied to hundreds of tech jobs and heard crickets.
The reply that changed things landed while he stood at the base of a crag on a climbing trip. Catalyst, a small restaurant point-of-sale company, said his history was interesting. He answered on the spot. They needed someone who understood the tech and the business - first full time technical role.
Next came Trust & Will. A friend’s wife worked there and told him about a manager-player role on a new team, at a time when engineering was about fifteen people, and well before AI blew up. He knew nothing about estate planning. He reasoned that every business needs revenue, users and customers, and started there.
He reckons about half his roles came from people he knew and half from cold applications. Getting the interview is the hardest part these days so standing out is even more important.
At Toast he works in Embedded Finance, building financial tools that help restaurant owners with cash flow. His current product is bookkeeping, still pre-alpha. As a shop owner, Michael had a bookkeeper who’d call asking what a receipt from sixty days ago was for. Now he builds for both of them.
Four things I’m taking from this conversation
1. Be the customer before you’re the engineer.
Michael’s advantage at Toast is that he has been the small-business owner staring at a receipt he can’t place. AI is making prototypes faster and cheaper. He thinks that pushes the value towards understanding the problem and explaining it to sales, product and execs in their language. You may not need to know Docker inside out to ship an MVP. “People want to understand how you’re gonna solve their problems,” he said.
The obvious pushback: that’s fine for a manager, but a junior still needs hard skills to get hired. Michael agrees skills matter. He puts them third.
2. Leadership starts the day you own the mistake.
No book taught Michael more than the Patriots shirts did. His early advice came from his dad, a long-time business owner, and from an old-school former boss. Some of it belonged in the bin, but it pointed him somewhere. Asking for help didn’t come naturally, so he treats it as a skill he practises.
3. Decide honestly whether you want the top seat.
Michael’s friends in the trades talk about going solo, and he asks them to run the numbers:
- Can you cover insurance for your family and anyone you hire?
- Can you go six months without pay?
He once ate $15,000 from a client because his attorney’s fees to chase it would have cost more than he’d recover. And when the job finishes at 2:30, running the business is a second job that pays nothing.
I know this one. When I freelanced full-time, I priced a family holiday by the billable hours it cost me, and my wife told me I needed a full-time job so I could just relax. Some people love owning a business. Knowing which kind of person you are is the skill.