The Power of Peer 

Early in my career, I was the IT Manager for a nonprofit. Like many IT professionals at the time, I was responsible for everything technology-related and whatever else I had an aptitude for. I wanted to become better at my craft, but my resources were limited. Until I found a book by Harry Brelsford, founder of SMB Nation.

I reached out and Harry responded, introducing me to Roger Otterson, a former Microsoft Small Business Server MVP. Roger had experience building technical communities and offered one simple piece of advice: find a Microsoft event, ask for a few minutes on stage, and invite people to a meeting. So that’s exactly what I did.

I still remember taking the train into Manhattan, scribbling talking points on a piece of paper, hoping someone would show up. I gave my speech. A few weeks later, in a small conference room, a handful of people came for our first meeting.

What started with a few IT professionals grew into a community of nearly 300 members, with more than 50 of them regularly attending our monthly meetings. Several of those early attendees eventually became leaders within the group. Looking back, I thought I was building a technical user group. What I was really discovering was the power of peer.

Over the years, that lesson has only become more meaningful.

Today, MSP owners have access to more information than ever before. You can watch webinars, listen to podcasts, attend conferences, join online communities and ask AI almost any question imaginable. Information is everywhere, but perspective is not. That’s why peer matters.

Every MSP owner eventually reaches a point where technical expertise alone isn’t enough. The questions become less about configuring a firewall or troubleshooting a server and more about building a leadership team, pricing services, retaining talent, navigating acquisitions, developing managers, preparing for an exit or deciding how AI fits into the future of the business. Those aren’t questions with one right answer they’re leadership questions—and we all know leadership can be lonely.

Your employees look to you for direction. Your clients expect confidence. Your vendors want your business. But who challenges your thinking? Who can tell you they’ve made the same mistake you’re about to make? Who can celebrate your successes while also asking the difficult questions that help you continue growing?

After years of facilitating peer communities for MSP owners, I’ve noticed something interesting: the members who get the most value are the most curious people in the room. They’re willing to admit they don’t have all the answers. They ask thoughtful questions. They openly share what’s working—and what’s not. They come ready to learn just as much as they come ready to contribute.

I’ve also learned that the most valuable conversations rarely happen at the front of the room. They happen when one owner says, “Here’s what happened to us.” They happen in the hallway. In a matter of minutes, someone can save another business owner months of frustration or help them avoid an expensive mistake altogether. You can’t Google that kind of wisdom. It comes from experience, trust and a willingness to help someone else succeed.

I’ve watched members solve operational challenges, rethink pricing strategies, improve leadership and gain the confidence to make decisions they had been putting off for months. But the greatest transformations weren’t in their businesses, but in the leaders themselves. Confident leaders build stronger teams. Stronger teams create better client experiences. Better client experiences build better businesses.

This reminds me of a great peer member, DenaliTek’s founder Todd Clark, who participated in both TruPeer and Producers Club. He built an exceptional MSP, no longer needs a peer group and successfully exited the business. Yet he chose to stay.

He’s now serving as an elder and coach, helping the next generation of MSP owners navigate the same challenges he once faced. To me, that’s the greatest measure of success. Peer isn’t just about what you receive. It’s about who you become and, eventually, it’s about what you give back.

When I think back to that train ride into Manhattan, I smile. Not because I started a successful community. But because someone I had never met took the time to answer an email, offer encouragement and point me toward others who were willing to help. That single act of generosity shaped my career.

Today, I see that same generosity every time an experienced MSP owner shares a hard-earned lesson, encourages a fellow member through a difficult season or chooses to mentor the next generation. Technology will continue to evolve and the challenges facing MSPs will continue to change. One thing never will: the strongest leaders don’t grow alone, they grow together.

That’s the power of peer.

Learn more about what is going on with your MSP peers in the Kaseya Community. Check out What’s new in the Kaseya Community: May 2026 roundup.