MSP Success

Last month, I spoke at the Flow event in Nashville, an MSP conference hosted by Rewst focused entirely on AI and automation. Over several days I had the opportunity to talk with MSP leaders who are far ahead of the average MSP in adopting automation. I left with one overwhelming observation. AI technology isn’t our biggest challenge. Our business model is For more than a decade, the MSP industry has been built around support, security, and professional services.

Why EOL software and high-CVSS vulnerabilities are your biggest legal risks During a recent risk assessment for a regulated nonprofit healthcare organization, I asked its MSP whether the network contained any unsupported software. The answer was an emphatic “No.” I then reviewed the organization’s cyber insurance application and found that the MSP had instructed the CFO to answer “No” to the same question. Then we scanned the network and found the ugly truth.

There’s a version of your business that was built for a smaller scale. Fewer clients, a tighter team and a founder who could hold most of the critical knowledge in their head. That version worked until your business grew past it. We talked to MSP owners who’ve made this shift and asked what signaled that their previous approach was no longer effective. Here’s what they identified as the clearest warning signs and why recognizing them is the first step toward building something that compounds. 1.

Cyber insurance companies are quietly making their requirements more stringent. “We’ve seen [cyber insurance] become more complex,” says Mike Semel, compliance expert and President of Semel Consulting. “There was a time where if you could fog a mirror, you qualified for cyber insurance. We’re seeing more [requirements] included in the policies now.” The changes are driven, in part, by the fact that “insurance companies have figured out how much sprawl there is with technology,” Semel says.

The FAQ strategy that helps Google, ChatGPT and AI choose you over your competitors. If I could give you one thing to improve your chances of showing up in Google, AI search, and AI-generated answers, it wouldn’t be another SEO trick. It would be this: Keep the conversation going. Most MSP websites answer one question and then immediately ask for “the sale,” whether that’s a “Contact us” or “15-minute discovery call” or another call to action.

For years, the unofficial badge of honor in the MSP world has been availability; you are expected to answer every call, fix every problem, and sleep when you can. The idea of “hustle” was romanticized, and burnout was never an option. But a growing number of MSP leaders are now calling that model what it is: a liability.

After spending years building and leading an MSP, I’ve noticed something that separates the companies that scale from the ones that stay stuck. It isn’t having the best tool stack, the most certifications or even the best salespeople. It’s having a business plan that everyone understands—and a strategy your team believes in. Too many MSP owners keep the business plan locked away in their head or buried in a PowerPoint they created for a lender years ago.

Many MSPs start the same way: the owner handles most, if not all, of the technical work while getting the business up and running. That approach may get you off the ground, but it’s not how you scale. Long-term growth requires building a business that can succeed without relying on you for every decision or task. Here’s what three MSPs who have been in your shoes have to say about the importance of delegation, building a strong team  and stepping out of the daily grind.

Running an MSP means your name is on the line. Clients depend on you, so stepping away feels like a liability you can’t afford. But the leaders who’ve figured out how to genuinely disconnect share a consistent truth: the work they did to make unplugging possible, made their businesses stronger. We asked MSP owners to pull back the curtain on how they recharge and how they built the businesses that enabled them to do so.

Recently, I was reviewing some old Schnizzfest content. About ten years ago, we showed a Tony Robbins video called You Get What You Tolerate. In it, Tony talked about making a conscious decision about the standards we choose to live by. His point was simple: in both our personal and professional lives, we get what we tolerate. At first, that can sound harsh. After all, bad things happen. Sometimes extraordinarily bad things happen. Life isn’t always fair, and not every setback is our fault.