The Adventures of Lee The SME Owner

Lee sat at his desk, a cup of coffee growing cold beside him as he stared out at the busy yard below. The question of his exit had been looming larger every day, and now that he’d worked through the basics with John, the real decisions were coming into focus.

But the more he thought about it, the harder the choices became.

On one hand, he had a young, competent management team. Troy, in particular, had shown real leadership potential, and the rest of the crew had stepped up when it counted. With the right development and guidance over the next few years, they could be an excellent option to buy him out. They knew the business inside and out, had earned his trust, and had a vested interest in seeing the company thrive.

But there was a catch, Lee thought as he rubbed his temples. If he went that route, he wouldn’t be able to walk away clean. He’d likely have to leave a significant amount of money in the business to make the buyout possible, which meant his payout would be delayed or staggered. That wasn’t ideal—he’d been working hard for decades, and the idea of waiting even longer to fully cash out didn’t sit well. Plus, it carried risk. If the business hit a rough patch or if the team couldn’t manage without him, he could be left holding the bag, financially speaking.

And then there was Glenn.

The thought of his son taking over the business stirred something in Lee that was deeper than money. It wasn’t just about the business staying in the family—though that had always been something he’d envisioned when he first took it over from his own father. It was about seeing Glenn finally pull himself together, finding a direction in life, and rising to the challenge. It would be satisfying beyond words to see Glenn become the man Lee knew he could be, to watch his son succeed where he had once struggled.

But that was the problem, Lee reminded himself, tapping his fingers on the desk. Glenn hadn’t shown any signs of being ready for that kind of responsibility. He was still drifting, his personal life in chaos, and their relationship was strained at best. Sure, there was potential, but there was also a mountain of risk—probably even more risk than with the management team.

Glenn wasn’t prepared, and Lee wasn’t sure he ever would be. The idea of handing over the business to Glenn in its current state felt like setting both his son and the company up for failure. Lee had built the business with blood, sweat, and tears. Could he really risk watching it all fall apart just for the sake of keeping it in the family?

And then there was the cleanest option of all: putting the business on the market.

Selling outright would mean less emotional baggage, fewer complicated dynamics, and potentially the highest payout in the shortest amount of time. He could set a fair price, find the right buyer, and walk away with his head held high, knowing he’d built something valuable. It would give him and Julie the freedom they hadn’t had in years—time to travel, relax, and spend with the grandkids. The idea of a clean break was appealing.

But it also felt... final. Like closing a door that could never be reopened. Would selling to a stranger mean losing control over what happened next? Would the new owners care as much as he did about the team, the clients, the reputation he’d worked so hard to build? He’d heard horror stories about businesses being sold, only for the new owners to strip them down for parts, laying off staff and ruining the culture.

He sighed and leaned back in his chair. Every option had its risks, its rewards. But the truth was, none of them felt perfect. And maybe that was the problem—there was no perfect solution.

If he sold to the management team, he’d have to trust that they could handle the weight of running the company and accept a delayed payout. If Glenn somehow got his life together, it would be the most emotionally satisfying choice, but the chances of that happening seemed slim. And if he sold outright, it would be the simplest path, but it came with the risk of losing control over what happened next.

Lee sat in silence for a long time, staring at the yard and watching his team go about their work. Troy was out there, directing one of the younger guys, and Lee could see the confidence in his movements. Maybe the team could handle it. Maybe this was their time to step up.

And then, as if on cue, his phone buzzed with a message from Glenn—something vague about coming by for a chat. Lee felt a familiar knot form in his stomach. What now?

The dilemma wasn’t going away. But one thing was becoming clearer: whatever decision he made, it would shape the future—not just of the business, but of his family, his legacy, and his life.

Lee knew he couldn’t put this off forever. The clock was ticking, and while he had time to figure things out, the weight of the decision was settling heavily on his shoulders.

It was time to have some hard conversations—with his team, with Glenn, and most importantly, with himself.

If you or anyone you know is considering exiting their business and would like a confidential, free of charge conversation about readiness, just sing out. [email protected] www.regeneratiohq.co.nz