MSP Acquisition Spotlight – Michael Wayland

1. What’s it like not being your own boss anymore? Did that take some getting used to?

It was certainly an adjustment at first. I joke that I traded my 80-hour-a-week job for a 50-hour-a-week one. I’m not sitting back and relaxing, but I do have a lot more time for hobbies I haven’t been able to enjoy for years. One big adjustment is that, when you’re used to making all the decisions, it’s different to step back and collaborate within a larger structure. But in a way, it’s also a relief—I can focus on my strengths and trust others to handle theirs. It’s all about finding that balance and embracing the change.

2. Selling your MSP is a big decision. Where did you go for guidance and advice?

First and foremost, it was a conversation with my wife about how the change would affect our family. Then I spoke with a mix of mentors, industry peers, my attorney, and my CPA. It was important to get advice from people who’d been through it, so I wasn’t flying blind. I also leaned on legal and financial experts to ensure every angle was covered.

3. How difficult was it to find the right buyer? What made you choose The 20 MSP in the end?

At the time, I was not in the market to sell my MSP. In fact, I had just experienced my own acquisition falling through at the closing table. It was challenging, no doubt. You want to ensure you’re leaving your company in good hands—not just financially, but for your team and clients as well. The 20 MSP felt like the right fit because of their reputation, the history my clients and I already had with them, and the culture they’ve built. It wasn’t just about the numbers; it was about where the business could grow from there.

4. How did you approach sharing your M&A plans with your team and clients? Were you surprised by any of their reactions?

For some clients, I made sure to communicate openly and early; for others, I informed them in person after we closed. I let my team know a little over a month before the scheduled closing date. Transparency was key—I wanted everyone to know they’d still be taken care of. Reactions varied: some were nervous, some excited, but overall, there was a lot of support. People appreciate honesty, and I believe that went a long way.

5.  What’s changed the most in your life since selling your MSP?

The biggest change for me has been the pace, variety, and type of work I do. It is nice to be able to focus and improve and get better at a smaller subset of tasks and skills.

6. Since selling your MSP, is there something – inside or outside of work – that you’ve been able to focus on more?

It has been nice to be able to pick up some of my hobbies again. I’ve managed to actually complete several games since Roll-Up. Also, knowing that when you do take a break on the weekend or on vacation I can actually shut my brain off and not worry about what is going on with the clients back at the office, that has been one of my favorite benefits so far.

7. What’s your best advice for someone thinking about selling their MSP?

Make sure you’re mentally ready for the change, not just financially. It’s a big shift, and you need to think about what’s next for you personally, not just for the business. And get good advisors—they’re worth their weight in gold.

8. Can you talk about your current role? How has your day-to-day changed since selling your company?

My current role is primarily as the Director of Managed Websites. I helped develop and build the new department and manage the day-to-day operations, including ongoing projects, maintenance, and ticket requests. In addition, I assist with some internal automations and tools.

9. In your opinion, what’s the most important quality for success?

Grit and perseverance with some humility and a desire to never stop learning.

10. What’s something most people don’t know about you?

I started college at the age of 15. Every year, I serve as a judge for the Mensa Mind Games Selection Committee, where I spend three days, 12–16 hours a day, playing new and pre-release tabletop board games to grade and select the three “best.”

11. Describe your dream vacation in 3 words…

Wood-Cabin, Coffee, Wife.