Most business owners spend years figuring out how to sell a trade business, and almost none of them plan for what happens the day after the money lands. Shanye Connolly did both, and he’s the first to admit the second part caught him off guard.
Shayne’s no stranger to The Site Shed. He was on the show once before, back when he was still running the business day to day. This time, Matt Jones catches up with him after the sale, to talk about the part most exit conversations skip entirely: what it actually feels like, and what you need to have sorted before you get there.
From Business Owner to Asset Owner
Shayne says the single biggest shift in his thinking happened two or three years before he sold. “I didn’t have a business, I had an asset,” he says. Once that clicked, everything changed, including how he ran the place day to day.
An asset isn’t just a bottom line. It’s something that can run without you, be handed to a manager, be folded into a bigger operation, or be sold outright. A business that depends entirely on the owner turning up every day isn’t really an asset yet, no matter what the P&L says. Shane points out the difference bluntly: selling a $100,000 mowing run isn’t selling a business, it’s selling a job to someone else.
That distinction is also why brokers struggled with his listing. When he first spoke to them, they didn’t understand what his business actually did or who’d want to buy it. It was an underwhelming conversation, and it’s a big part of why owners considering an exit need to build the “can run without me” case well before they start shopping the business around.
Knowing Your Exit Number
Before any of the mechanics, Shayne says the first real conversation needs to be with your accountant, not a broker. “You need to know how much of the money the government is going to want to take before you get to actually have it yourself,” he says. Get that number wrong and a headline sale price can shrink fast once tax is accounted for.
The second conversation is with yourself: what does the money actually need to fund? For Shayne, the exit number wasn’t a retirement figure, it was a bridge to the next thing. He knew building his dream house would use up most of what came from the sale, so by the end of that year he’d need another income-generating project running. Knowing that in advance shaped every decision that followed, including starting work on OwnerHQ before the ink on the sale was even fully dry.
“80% of businesses don’t sell,” Shane says, which is exactly why throwing around a fantasy number before you’ve done this work is a waste of everyone’s time. Have the honest conversation first.
The Part Nobody Talks About
The mechanics of selling a business are well covered ground. What isn’t, according to Shayne, is how it feels once it’s done. “I’ve never been personally so deflated in my life as the day that happened,” he says. “We thought that we’d be dancing around the room popping champagne corks, and it was like, oh, well, there it is. That’s it.”
Part of that was practical. The sale dragged on eight months longer than planned because of a slow bank, and by settlement Shayne and his wife had already mentally spent the money on their next chapter. There was no windfall moment, because the plan had already absorbed it.
But there’s a deeper reason too. Shayne compares selling a business to raising a child: you’re entwined in it, your identity gets wrapped up in it, whether you intend that or not. He’s spoken to several business owners who were genuinely devastated after selling, “even though they were sitting on a big pile of cash.” Without a plan for what replaces the business, purpose and identity, not just income, people can end up anxious, depressed, or full of regret. Working out what “useful” and “relevant” look like after the business is gone matters just as much as the sale price.
Why He Sold to Someone He Knew
Shayne didn’t end up going through a broker. The deal came together after he mentioned to a team member, Chris, that he was thinking about selling, and Chris said he might be interested. That one conversation, plus support from his lawyers at Legal Vision and his accountant, gave him the confidence to go down that path instead of paying someone else “50 grand” to sell his own business.
He also seriously considered not selling at all, putting a manager in and keeping the business as a cash-generating asset, or using it as a base to acquire complementary businesses and build toward a private equity exit worth $10 to 20 million-plus. He worked out that path was realistic. It just didn’t excite him. “I’m not a CEO,” he says. “I’m a bit of a junkie for the adrenaline of building something rather than watching it grow slowly.” Knowing which type of owner you are is as important as knowing your exit number.
Key Takeaways
- Start thinking of your business as an asset years before you plan to sell. It changes how you build it and what you can eventually do with it.
- Talk to your accountant before you talk to anyone else. Tax treatment can make or break what your exit number is really worth.
- Fix what’s broken before you list, not after you decide to sell. You need proof it’s fixed, not just a promise.
- Plan for what replaces your identity and purpose, not just your income. This is the part that catches most owners out.
- Know whether you’re a builder or a runner. It should shape whether you sell, hand over to a manager, or roll up into something bigger.
If exiting your trade business is on your radar, Shayne’s book, Exit Plan, digs into all of this in more depth, starting with the question he says most owners skip: do you really want to do this?
🫱🏻🫲🏼 Book a Free Strategy Call with Tradie Web Guys: https://tradie.wiki/tssyt
