AI-First MSP Leadership: What I’m Seeing Across the Channel
AI-first MSP leadership is quickly becoming the difference between MSPs that scale and those that stall. From my conversations with founders, operators, and advisors, one thing is clear. This shift is not about adding AI tools. It is about changing how we think, lead, and build businesses. Let me break down what keeps coming up […]
AI-First MSP Leadership Lessons I Hear from the Field
AI-first MSP leadership is becoming the real differentiator in our channel. The best MSPs aren’t “adding AI.” They’re upgrading how they lead, decide, and scale, with AI accelerating everything. What follows is the most consistent set of lessons I keep hearing (and learning) from MSP operators, founders, and advisors. Why MSP Leadership Growth Starts with Perspective (Not Just Strategy) One of […]
Why MSP Leaders Can’t Wait to Feel Ready
In our industry, waiting feels responsible. Wait for the right hire. Wait for the market to stabilize. Wait until AI matures. Wait until the strategy is perfect. But here’s what I was reminded of in my recent conversation with Cara Moeller Poppitt: Waiting to feel ready is often the most expensive decision a leader can […]
What MSP Leaders Keep Telling Me About Building Trust, AI Adoption, and Real Growth
If you’re trying to grow an MSP business right now, the real differentiator isn’t your tool stack -it’s MSP relationships, trust, and how you show up as a trusted advisor in the AI era. That’s the biggest takeaway I’ve walked away with after having multiple conversations with MSP leaders across the channel. Different markets. Different […]
Why Connectivity Became the Conversation MSPs Can’t Ignore
Some conversations don’t start when the recording light turns on. This one started a few minutes earlier, when I wanted to make sure Rick and I were aligned on why we were having this discussion in the first place. This wasn’t about selling anything. It wasn’t about polished talking points. It was about continuous value […]
Sunny’s Silver Linings 2025: The Conversations MSPs Need to Have Heading Into 2026
Sunny’s Silver Linings wasn’t just an event. It was a moment of clarity. We came together to share ideas, challenge perspectives, and focus on what truly matters: people, purpose, and progress. And if there was one theme that kept surfacing across conversations, it was this: Even in change, there’s opportunity. Here’s a look back at […]
From Fixing Computers to Fueling Outcomes: A Conversation That Clarified the Future of the MSP Channel
I’ve had thousands of conversations with MSP leaders over the years, but every once in a while, a discussion cuts through the noise and brings clarity. Not hype. Not trends for the sake of trends. Just truth. That’s exactly what happened when I sat down with Paul Redding from NinjaOne. Before the microphones were even […]
From Chaos to Cash Confidence: Lessons from Benji Pays’ Adam Crandall
When I sat down with Adam Crandall for this episode of Sunny’s Silver Linings, I knew the conversation would be valuable, but I didn’t expect it to feel like looking into a mirror. Adam isn’t just a founder and CEO; he’s someone who has lived the accidental entrepreneur journey the way so many in our […]
Leadership, Security, Abundance & AI: My Deep Conversation with Tobias “Toby” Musser
When I welcomed Tobias “Toby” Musser to Sunny Silver Linings, I already knew this was going to be a special conversation. A couple of weeks prior, I had spoken with him privately, and immediately felt such a strong alignment: in mindset, values, leadership philosophy, and how we both view our responsibility as entrepreneurs. His lived […]
The AI Silver Lining From Managed Services to Managed Intelligence
When I sat down with my friend Terry Hedden, founder of Marketopia, for Sunny’s Silver Linings, I knew this wasn’t going to be just another business chat. Terry and I go way back in the MSP channel, and every time we talk, the conversation sparks new insight: that “aha” moment where experience meets vision. I’ve […]