Built a 7-Figure Handyman Company in 12mo, Scaling in public to a $100M exit

Joined February 2025
Replying to @TimFlynnLeary
Can confirm this works. Have done it twice successfully
2
1
3
481
Hey you should read this if you’re at a $250k a year corporate job thinking your road to unlimited PTO via business acquisition will be as easy as securing a loan and signing up for Servicetitan + Claude Cowork
Today is my 3 yr anniversary of purchasing a construction company as sole owner. The past 3 yrs have been the hardest of my professional life. I'm both proud to have survived so far and embarrassed that I got myself into this situation in the first place. I purchased in 2023 via SBA 7a, underwritten as a $3M rev business. QofE and my own diligence missed two main things: the seller's second business was floating most cashflow issues and their local reputation was unusable. I rebranded to "Cooper" within 95 days on Jan 1, 2024. This industry runs on relationships and reputation. I instantly became an unknown entity and revenue dropped 95% overnight compared to what was underwritten. There are a lot of stories to tell about 2024, but tl;dr I scratched and clawed back to only $1.7M rev by the end of the year. I emptied my savings and depended on hard money to survive. Throughout that year, I made fundamental changes to our sales and operations. We focused on municipal work because I could personally handle the administrative burden and the playing field felt more fair. But our bid -> sale -> collection timeline ballooned to around 9-12 months. Changes wouldn't bear fruit for a long time. In Q2 2025, our 2024 efforts started to take effect. By EOY, we had grown to $3.65M in rev while improving gross margins. However, we were completely cash poor due to growth capital needs and crazy interest payments. We leaned on MCAs to get through because we couldn't compromise all our new client relationships. This year, we professionalized further, increasing both sales and GM. Our annualized revenue is ~$6m and this will be the first year with substantial EBITDA ($1.2M). We took some less horrible debt and I'm working on a larger refi to stabilize a bit. I am still just trying to maintain overall debt coverage. All this time, I haven't paid myself a cent. My team has remained underpaid. Everything has depended on selling the vision to both employees and clients. Selling the future to fund the present. As I reflect on the last 3 years, I feel optimistic about the future. I am a MUCH better operator than in 2023. My team is lean and loyal. And any further growth should be upside I can capture. But if you asked if it was all worth it, I'm not sure how I'd respond. For the past 3 yrs, I've chronically felt nauseous about paying bills, payroll, potential liability/conflict in our work. I've been less present at home. I've been very boring with friends. My health has taken a backseat to the needs of the business. Not to mention my net worth has tanked compared to pre-purchase levels. Our conservative plan is to hit $8M in '27, $12M in '28, then $19M in '29. I know it will continue to be hard, but I'm excited to outgrow the first phase of ownership and work on a fresh set of challenges. Here's to the next three years.
11
22
593
144,343
this is a hard road. Stay in the game, avoid the catastrophic events if you can, and keep chopping wood. rooting for you all
20
2
118
6,040
Tim Leary retweeted
Most trade businesses stay stuck under $5M because the owner refuses to make the hard personnel cuts. They let a lazy manager slide because he was an early hire. They let an uncoachable tech run over dispatch because he turns wrenches fast. When you protect low performers or excuse bad attitudes, your best people notice. They get tired of carrying dead weight and walk out the door. The crew that got you off the ground is rarely the crew that takes you to scale. Set the standard, hold everyone to it, and stop letting loyalty bankrupt your culture.
10
4
1
60
3,809
If you currently work for a meta ad agency on ad buying/creative side: I want to hire you. 6 figure OTE. I need an absolute weapon to help me build out HSA V2. Seriously, if you’re at an agency and feel like your talents are being wasted (they probably are) DM me.
6
3
1
38
7,738
Tim Leary retweeted
If you supported my business in the early stages, I haven’t forgotten. I’d take a bullet for the people who stepped up in the early days. You know who you are!
18
7
1
163
8,848
My work clothes stack: - Carhartt for shirts. - Ariat for pants. - Brunt for steel toe boots. - Sunglasses: Shady rays with the big wrap around lenses to protect the eyes. - Hats: I change these out, but today it’s a Seager hat. (I will wear your company hat if you send me one.) I don’t stray from these.
16
2
6
89
15,845
Everyone’s adding. Few are refining. Do one thing exceptionally. That’s the real growth play.
1
1
1
329
The people who win aren't the ones with all the answers. They’re the ones who keep asking better questions. Curiosity scales.
1
1
1
70
Most businesses lose jobs because they’re too slow. @TimFlynnLeary breaks down how speed, curiosity, and focus win. Most businesses lose jobs by being slow. Same-day service isn’t just a perk. It’s a conversion weapon. Fast beats fancy — every time.
1
2
10
1,111