MSP To The Future

Hosted by Jeanne DeWitt

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Episodes

131

Latest episode

Aug 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

August 17, 202610 min

Why the Best MSP Salespeople Don't Feel Like Salespeople

The best MSP salespeople I've known all have something in common. Ironically...it isn't that they're great at sales. It's that they don't think like salespeople at all. That one realization changed the way I approached every sales conversation, and when I looked back at the clients we won over the years, it explained why they chose us. If sales has ever felt awkward or uncomfortable, I think this episode will change the way you think about it too. Hit play, and let's take your MSP to the future. When posting the podcasts, could you make sure to begin adding the following blurb after the description text? Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠The MSP To The Future Library | Cloud Services For MSPs⁠ ⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠ Click here to schedule a time.

August 10, 20268 min

The Questions I Wish I'd Asked Every Client Sooner

Have you ever found out a client was opening a new location... Hiring a bunch of employees... Buying another company... Or planning to retire......and your first thought was, "Why am I just hearing about this now?" After forty years in this industry, I've learned something that completely changed the way I meet with clients. It wasn't a new sales strategy. It wasn't a better QBR. It was one simple shift that uncovered opportunities I used to miss. If you've ever felt like you're the last one to know what's happening inside your clients' businesses, this episode is for you. Hit play...and let's take your MSP to the future. Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠⁠⁠The MSP To The Future Library | Cloud Services For MSPs⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠⁠⁠ Click here to schedule a time. ⁠⁠⁠⁠ ⁠⁠⁠⁠ Join our Cloud Academy ⁠⁠⁠⁠ , our completely free content suite designed to help you increase your MRR! Finally, subscribe to MSP To The Future so that you don't miss a single episode. While you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!

August 3, 202610 min

It's NOT Work, It's NETwork

What if the best networking advice you've ever heard... isn't really about networking at all? In this episode, I'll share one simple lesson that changed the way I think about relationships, referrals, and growing an MSP. Once you understand it, you'll never look at networking the same way again. Hit play... and let's take your MSP to the future. Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠The MSP To The Future Library | Cloud Services For MSPs⁠ ⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠ Click here to schedule a time. ⁠⁠ ⁠⁠ Join our Cloud Academy ⁠⁠ , our completely free content suite designed to help you increase your MRR! Finally, subscribe to MSP To The Future so that you don't miss a single episode. While you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!

July 27, 20269 min

Why Good MSP Clients Suddenly Leave

You know the call. The one that starts with... "We've decided to move in a different direction." And your first thought is always the same... "I never saw this coming." But what if you did? What if your clients were giving you clues long before they ever started looking for another MSP? In this episode, I'm sharing one of the biggest lessons I learned from building a seven-figure MSP—and one of the patterns I've seen over and over again while working with MSPs across the country. Because good clients rarely leave without a reason...and they almost never leave without warning. Hit play...and let's take your MSP to the future. Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠⁠⁠The MSP To The Future Library | Cloud Services For MSPs⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠⁠⁠ Click here to schedule a time. ⁠⁠⁠⁠ ⁠⁠⁠⁠ Join our Cloud Academy ⁠⁠⁠⁠ , our completely free content suite designed to help you increase your MRR! Finally, subscribe to MSP To The Future so that you don't miss a single episode. While you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!

July 20, 20269 min

The MSP Owner's Stuck Deal Rescue Plan

You know that proposal. The one sitting in your CRM that you were sure was going to become your next client. Great meeting. Great conversation. Proposal sent. Then... Nothing. So you follow up. And follow up again. Still nothing. But what if the deal didn't stall for the reason you think? After 40 years in this industry, I learned one question that completely changed the way I look at stalled opportunities and it's probably not the question you're asking. If you've ever looked at your pipeline and wondered, "What happened?" this episode is for you. Hit play...and let's take your MSP to the future. Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠⁠⁠The MSP To The Future Library | Cloud Services For MSPs⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠⁠⁠ Click here to schedule a time. ⁠⁠⁠⁠ ⁠⁠⁠⁠ Join our Cloud Academy ⁠⁠⁠⁠ , our completely free content suite designed to help you increase your MRR! Finally, subscribe to MSP To The Future so that you don't miss a single episode. While you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!

July 13, 202611 min

Your Next Sale May Already Be Sitting in Your Help Desk

Most MSPs think their next sale is going to come from more prospecting. -More networking. -More appointments. -More follow-up. But what if some of your best opportunities are already sitting inside your MSP… and nobody’s noticing them? After 40 years in this industry, I’ve learned that clients often tell you exactly where they need help. The problem? Most MSPs are too busy solving tickets to hear what they’re actually saying. This week, I’m sharing one simple shift that changes the way you look at your help desk. Hit play…and let’s take your MSP to the future. Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠⁠⁠The MSP To The Future Library | Cloud Services For MSPs⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠⁠⁠ Click here to schedule a time. ⁠⁠⁠⁠ ⁠⁠⁠⁠ Join our Cloud Academy ⁠⁠⁠⁠ , our completely free content suite designed to help you increase your MRR! Finally, subscribe to MSP To The Future so that you don't miss a single episode. While you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!

July 6, 20268 min

The 10-Minute MSP Audit That Finds Hidden Revenue

Most MSPs think they have a lead problem. I’m not so sure. This week, I’m sharing a simple 10-minute exercise that helped us uncover opportunities hiding inside accounts we already had. No expensive campaigns. No complicated strategy. Just a smarter way to look at the clients already trusting you. You might be one conversation away from finding revenue you didn’t even know was there. Hit play… and let’s take your MSP to the future. Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠⁠⁠The MSP To The Future Library | Cloud Services For MSPs⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠⁠⁠ Click here to schedule a time. ⁠⁠⁠⁠ ⁠⁠⁠⁠ Join our Cloud Academy ⁠⁠⁠⁠ , our completely free content suite designed to help you increase your MRR! Finally, subscribe to MSP To The Future so that you don't miss a single episode. While you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!

June 29, 202612 min

Decision Fatigue: The Silent MSP Killer

Making decisions all day. Working hard all day. So why do some MSPs keep moving forward… while others stay busy but never seem to gain momentum? After 40 years in this industry, I’ve noticed a pattern and once you see it, you start recognizing it everywhere. This week, we’re digging into it. Hit play…and let’s take your MSP to the future. Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠⁠⁠The MSP To The Future Library | Cloud Services For MSPs⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠⁠⁠ Click here to schedule a time. ⁠⁠⁠⁠ ⁠⁠⁠⁠ Join our Cloud Academy ⁠⁠⁠⁠ , our completely free content suite designed to help you increase your MRR! Finally, subscribe to MSP To The Future so that you don't miss a single episode. While you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!

June 22, 202611 min

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. Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠⁠⁠The MSP To The Future Library | Cloud Services For MSPs⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠⁠⁠ Click here to schedule a time. ⁠⁠⁠⁠ ⁠⁠⁠⁠ Join our Cloud Academy ⁠⁠⁠⁠ , our completely free content suite designed to help you increase your MRR! Finally, subscribe to MSP To The Future so that you don't miss a single episode. While you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!

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. Thank you for being an engaged member of the MSP To The Future audience! Fill out a quick form on this page and download an E-Book of your choice from our Content Catalog: ⁠⁠⁠The MSP To The Future Library | Cloud Services For MSPs⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠ If you are an MSP or IT Service Provider and have a prospect or customer that needs cloud , let's talk. ⁠⁠⁠⁠ Click here to schedule a time. ⁠⁠⁠⁠ ⁠⁠⁠⁠ Join our Cloud Academy ⁠⁠⁠⁠ , our completely free content suite designed to help you increase your MRR! Finally, subscribe to MSP To The Future so that you don't miss a single episode. While you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!