How Many Times You Should Follow Up (and Why Most MSPs Quit Too Soon)

The Top 10 Prospecting Mistakes MSPs Make

Most MSPs think prospecting is the hard part. It’s not. The hard part is realizing that sometimes the reason prospecting isn’t working… has nothing to do with the market, the economy, or the people you’re calling. It has everything to do with small mistakes happening inside the conversation that most salespeople don’t even realize they’re making. And here’s the interesting part… These mistakes show up everywhere — in emails, in cold calls, in networking conversations, and even in follow-ups. They quietly shut down opportunities before the prospect ever has a chance to say yes. In this episode of MSP To The Future, I’m breaking down the 10 biggest prospecting mistakes, inspired by the work of Wendy Weiss — often called The Queen of Cold Calling. And I’ll show you how these mistakes show up specifically in the MSP world… and how fixing just one or two of them can completely change your sales conversations. Because prospecting isn’t about pressure. It’s about starting better conversations. Hit play… and let’s take your MSP to the future.

How to Ask Better Questions Without Sounding Like You’re Selling

Most MSPs don’t realize they’re doing it. A prospect asks a simple question…And within minutes, the conversation starts feeling salesy. The energy changes. The prospect pulls back. And suddenly the MSP is talking more… but connecting less. After 40 years of building a seven-figure MSP, I can tell you this: The best sales conversations rarely feel like selling. And the MSPs who close the easiest usually aren’t giving better presentations… They’re having completely different conversations. This week on MSP To The Future, I’m breaking down the subtle communication mistakes that make MSPs sound pushy without realizing it and how a few simple shifts can completely change the way prospects respond to you. If your sales conversations have ever felt harder than they should…You need to hear this one. Hit play. And let’s take your MSP to the future.

Your MSP Marketing Isn’t Broken… It’s Not Boiling Yet

You’re doing the work. You’ve tried the marketing. So why isn’t your MSP growing? Here’s the uncomfortable truth…It might not be your offer. And it might not be your market. In this episode, I’m sharing a pattern I’ve seen over years of building and working with MSPs—and why what looks like failure is often something else entirely. If your marketing feels like it’s going nowhere… don’t skip this one. Hit play…and let’s take your MSP to the future.

We Need to Talk About Frogs

There’s a reason I’m talking about frogs this week…And no—it’s not what you think. Years ago, I came across an idea that sounded ridiculous at first. But the more I paid attention…the more I started seeing it everywhere. Especially in MSPs. And it explains why some grow…while others spin their wheels. Don’t miss this one. Hit play…and let’s take your MSP to the future.

Stop Skating on Thin Ice: The MSP Mistake That Looks Like Growth

Most MSPs don’t realize they’re on thin ice…Because everything looks like growth. -More work coming in. -More opportunities. -More things you’re saying yes to. It feels like you’re building something. Until you look up one day…And realize you’re working harder than ever—and not making what you should. In this episode, I’m breaking down the mistake that quietly puts MSPs in this position…and why most don’t see it until it starts costing them. Hit play…and let’s take your MSP to the future.