MSP To The Future

Hosted by Jeanne DeWitt

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Episodes

121

Latest episode

Jun 2026

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About the show

Great Scott! Another MSP Podcast? Welcome to MSP To The Future, hosted by 38-year tech experts Jeanne DeWitt and David Hood! Join us each week as we share insights and guidance from building a successful 7 figure MSP to help your MSP grow and thrive. We'll have insights into recommended marketing strategies, service offerings and more; plus, learn from the Cloud Guy himself, David Hood, where he shares his technology expertise in our segment Cloud Conversations. Where we're going, we don't need servers... subscribe and blast off to a successful future for your MSP!

Listen to episodes

60 recent

June 15, 202615 min

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.

June 8, 20269 min

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.

June 1, 20269 min

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.

May 25, 202612 min

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.

May 18, 202610 min

The Growth Trap Most MSPs Don’t See Coming

Most MSPs don’t have a growth problem.They have a trap they don’t even realize they’re stuck in.It looks like progress.It feels productive.But behind the scenes… it’s quietly holding them back.In this episode of MSP To The Future, I’m breaking down a pattern I’ve seen over and over again one that keeps MSPs busy, frustrated, and wondering why things aren’t clicking.This is something I had to learn the hard way building my own seven-figure MSP… and once you recognize it, it changes how you operate completely.If you’ve ever felt like you’re doing all the right things… but not seeing the growth to match…This episode is for you.Hit play…and let’s take your MSP to the future.

May 11, 202610 min

The Purple Cow Problem: Why Your MSP Isn’t Standing Out

If your MSP disappeared tomorrow…Would anyone notice?That might sound harsh—but after 40 years in this industry, I can tell you… most MSPs are invisible and don’t even realize it.They’re doing the work.They’ve got the tools.They’ve got the experience.But to the buyer?They all look the same.In this episode, I’m breaking down a powerful idea that completely changed how I think about marketing—and why it explains the biggest growth problem MSPs face today.Once you see it… you won’t be able to unsee it.Hit play… and let’s take your MSP to the future.

May 4, 202611 min

8 Prospecting Truths MSPs Ignore (What I Learned from the Queen of Cold Calling)

Most MSPs don’t have a prospecting problem…They’re just ignoring the truths that actually make it work.They’ve convinced themselves:“No one answers.”“Decision-makers are too busy.”“Cold calling doesn’t work.”And those beliefs are exactly why their pipeline is inconsistent… and their growth feels stuck.After building a seven-figure MSP—and learning directly from my mentor, Wendy Weiss—I came face-to-face with 8 simple truths about prospecting…Truths most MSPs ignore.And once you understand them, getting conversations, appointments, and new clients becomes a whole lot easier.If you’re tired of waiting on referrals and want a more predictable way to grow your MSP…this episode will change how you think about prospecting.Hit play…and let’s take your MSP to the future.

April 27, 202610 min

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

How many times should an MSP actually follow up?Once?Twice?Five times?Most MSPs guess and then quit way too soon.In this episode, I’m breaking down the real follow-up numbers, why MSP sales take longer than you expect, and exactly where most MSPs give up even though they’re closer than they realize.If you’ve ever thought, “I don’t want to bug them,” or “If they were interested, they’d call me back,” this episode will change how you think about follow-up and your pipeline.Hit play, and let’s take your MSP to the future.

April 20, 20268 min

When Hiring Isn’t an Option: How Smart MSPs Lighten the Load Without Adding Payroll

You’re working harder than ever…Long days. Late nights. Constant tickets.So why does it still feel like your MSP isn’t moving forward?Most owners think the answer is hiring.Another tech. More help. Bigger payroll.But what if that’s not the solution at all?What if the real problem is hiding in how you’re spending your time every single day?In this episode of MSP To The Future, I’m breaking down the shift that separates overwhelmed MSP owners from those who actually scale—without burning out or overhiring.If you’ve ever felt stuck between doing everything yourself and not being able to afford to grow…This is the episode you need to hear.Hit play…and let’s take your MSP to the future.

April 13, 202613 min

The 8 Prospecting Rules MSPs Ignore (That Actually Work)

Most MSPs think their growth problem is marketing.They think they need more leads… better campaigns… a stronger message.They don’t.After building a seven-figure MSP, I can tell you—most growth problems don’t come from a lack of marketing.They come from avoiding one activity that actually creates clients.And here’s the part most people don’t want to admit…It’s not complicated.It’s not new.And it still works.But most MSPs won’t do it.Because it’s uncomfortable.In this episode, I’m breaking down a set of prospecting principles that have been around for years—but almost no MSPs are actually using them today.And once you see what’s missing…you’ll understand exactly why your pipeline feels inconsistent.Hit play…and let’s take your MSP to the future.