MSP To The Future

MSP To The Future

By Jeanne DeWitt

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!
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Currently playing episode

How Smart MSPs Get Past the Gatekeeper — and Get Invited In

MSP To The FutureNov 03, 2025
00:00
13:51
How We Used Education to Outsell Bigger MSPs
Aug 31, 202609:06
Want More MSP Clients? Stop Trying to Sell Them
Aug 24, 202606:38
 Why the Best MSP Salespeople Don't Feel Like Salespeople
Aug 17, 202610:23
The Questions I Wish I'd Asked Every Client Sooner
Aug 10, 202608:32
It's NOT Work, It's NETwork
Aug 03, 202610:04
Why Good MSP Clients Suddenly Leave
Jul 27, 202609:00
The MSP Owner's Stuck Deal Rescue Plan
Jul 20, 202609:06
Your Next Sale May Already Be Sitting in Your Help Desk
Jul 13, 202611:13
The 10-Minute MSP Audit That Finds Hidden Revenue
Jul 06, 202608:58
Decision Fatigue: The Silent MSP Killer
Jun 29, 202612:18
 The Top 10 Prospecting Mistakes MSPs Make

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!

Jun 22, 202611:60
How to Ask Better Questions Without Sounding Like You’re Selling

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!

Jun 15, 202615:26
Your MSP Marketing Isn’t Broken… It’s Not Boiling Yet
Jun 08, 202610:26
We Need to Talk About Frogs
Jun 01, 202609:10
Stop Skating on Thin Ice: The MSP Mistake That Looks Like Growth
May 25, 202612:10
The Growth Trap Most MSPs Don’t See Coming

The Growth Trap Most MSPs Don’t See Coming

May 18, 202610:04
The Purple Cow Problem: Why Your MSP Isn’t Standing Out
May 11, 202610:49
8 Prospecting Truths MSPs Ignore (What I Learned from the Queen of Cold Calling)

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.


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!

May 04, 202611:47
How Many Times You Should Follow Up (and Why Most MSPs Quit Too Soon)
Apr 27, 202610:06
When Hiring Isn’t an Option: How Smart MSPs Lighten the Load Without Adding Payroll

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

Apr 20, 202608:32
 The 8 Prospecting Rules MSPs Ignore (That Actually Work)

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.


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!

Apr 13, 202613:12
How to Exit a Bad Networking Conversation Without Feeling Awkward

How to Exit a Bad Networking Conversation Without Feeling Awkward

Apr 06, 202607:40
 4 Proposal Mistakes MSPs Make (And Why They Never Close)

4 Proposal Mistakes MSPs Make (And Why They Never Close)

Most MSPs think their proposals just need to be better.


-More detailed.
-More polished.
-More impressive.


So they spend hours putting them together…
Only to get ghosted.


Or hear, “We went with someone else.”


After building a seven-figure MSP, I can tell you — it’s not your proposal.


It’s what’s happening before you ever send it.


There are a few critical mistakes MSPs make in the sales process that quietly kill deals… and most don’t even realize they’re doing them.


In this episode of MSP To The Future, I’m breaking down the 4 mistakes that cause proposals to go nowhere — and how to fix them so more of your deals actually close.


If you’re tired of wasting time on proposals that never turn into clients…


You need to hear this.


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!

Mar 30, 202609:47
The Four Biggest Roadblocks to Selling More (And Why Most MSPs Stay Stuck)
Mar 23, 202609:46
Not Every Lead Deserves a Proposal: How Smart MSPs Qualify Without Chasing

Not Every Lead Deserves a Proposal: How Smart MSPs Qualify Without Chasing

How many proposals are sitting in your Sent folder right now that never turned into clients?


Be honest.


If you’re frustrated with prospects ghosting you…


If you’re tired of hearing, “We’re reviewing options”…


If you feel like you’re working harder than the buyer is…
This episode is going to hit home.


After building a seven-figure MSP, I can tell you this with confidence:


Most deals don’t fall apart at the proposal stage.
They were never qualified in the first place.
And the reason MSPs chase?


Because they mistake interest for commitment.


In this episode, I’m breaking down the shift that changes everything how to slow down your sales process, ask better questions, and stop giving proposals to people who haven’t earned them.


Because not every lead deserves your time.


And the smartest MSPs know exactly how to tell the difference.


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!

Mar 16, 202609:38
How to Respond When They Say “We Don’t Have The Budget”

How to Respond When They Say “We Don’t Have The Budget”

Every MSP has heard it.


You’ve had the meeting.


The conversation is going well.


They understand the risks.


They even agree with your recommendations.


And then it happens.


They lean back and say…
“We just don’t have budget for that right now.”


For most MSPs, that’s where the deal quietly dies.


But here’s the part almost nobody realizes — that moment isn’t the end of the conversation.


It’s the moment that reveals whether you’re leading the sale… or reacting to it.


In this episode, I’m going to challenge the way most MSPs think about the “no budget” objection — and why the response in that moment often determines whether the deal moves forward or disappears.


If you’ve ever walked away from a prospect wondering what just happened… this one 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!

Mar 09, 202609:13
Get on the Energy Bus: Why MSP Growth Starts with You

Get on the Energy Bus: Why MSP Growth Starts with You

Mar 02, 202610:39
Voicemails That Get Callbacks: The MSP Owner’s Playbook
Feb 23, 202610:31
The Kaizen Habit Behind Every Seven-Figure MSP

The Kaizen Habit Behind Every Seven-Figure MSP

This week on MSP To The Future, I’m sharing something I’ve noticed after 40 years of running, growing, and studying MSPs — something surprisingly consistent among the ones who break seven figures and stay there.


It’s not a bigger team.
It’s not a better tech stack.
And it’s definitely not working more hours.


It’s something much smaller… and much easier to overlook.
In fact, most MSPs dismiss it entirely — and that’s exactly why they stay stuck.


If you’ve ever felt like you’re pushing hard but not moving fast enough…or you’re constantly trying to fix everything all at once…


this episode is going to shift how you think about growth.
Because real momentum doesn’t come from dramatic leaps.
It comes from a habit so simple, most MSPs never take it seriously — and yet it changes everything.


Curious?
You should be.


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!

Feb 16, 202611:36
Let Me Think About It Isn’t a No — It’s a Cry for Clarity
Feb 09, 202609:45
Stop Blending In: Branding Do’s and Don’ts with Steven Badorf
Feb 02, 202639:47
How to Get Over Call Reluctance (For MSPs Who Hate Calling)

How to Get Over Call Reluctance (For MSPs Who Hate Calling)

This week on MSP To The Future, we’re digging into one of the biggest hidden barriers to MSP growth — call reluctance.


Not the scripts.
Not the objections.
Not the tactics.


But the real reason so many MSP owners avoid the one activity that actually builds a pipeline.


After 40 years in this industry — and many years of successfully cold calling myself — I’ve learned that call reluctance has nothing to do with talent… and everything to do with momentum.


In this episode, I’m sharing the mindset shift that turns calling from dread to confidence, the warm-up routine that makes dialing ten times easier, and the one small action that breaks the fear cycle instantly.


If you’ve been putting off the uncomfortable work… if your pipeline feels lighter than it should… or if calling has always felt heavier than it needs to…


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!

Jan 26, 202612:36
The Hidden Skill That Builds a Seven-Figure MSP
Jan 19, 202608:04
The One Thing MSPs Can Never Own

The One Thing MSPs Can Never Own

Jan 12, 202619:25
The Gifts We Forget: A Christmas Message for MSPs

The Gifts We Forget: A Christmas Message for MSPs

This week on MSP To The Future, I’m stepping away from the tactics and the tech to share something we don’t talk about enough — especially in the middle of year-end chaos.


Because while you're juggling projects, shopping lists, and client emergencies… there’s something else happening all around you.
Something most MSPs miss entirely.


And no — it’s not a sales strategy, a marketing trick, or a cloud tip.
It’s a shift.
A perspective.


A gift that, once you notice it, changes how you lead, how you work, and how you show up every single day — not just during the holidays.


If you’re feeling stretched thin, rushing through December, or just trying to make it to the finish line…
this episode is the pause your brain didn’t know it needed.


Hit play, take a breath, and let’s take your MSP — and your life — 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!


Dec 22, 202505:38
The Secret to Easier MSP Sales

The Secret to Easier MSP Sales

Most MSPs think sales is hard because they need better scripts, better closers, or a better follow-up process.


But what if the real reason sales feels like a grind has nothing to do with your sales skills at all?


In today’s episode of MSP To The Future, I’m breaking down the single biggest factor that separates MSPs who struggle to close… from MSPs who walk into sales calls where the prospect is already halfway sold.


This is the same shift that completely transformed my own seven-figure MSP — the shift that took us from chasing clients to attracting the right ones, at the right price, without the endless back-and-forth.


And here’s the kicker: most MSPs are ignoring this part of their business entirely.


If you’ve been feeling stuck, stalled, or worn out trying to sell your services, this episode is going to flip the way you think about MSP sales on its head.


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!

Dec 15, 202511:16
Start Today, Sell Big Later: The MSP Playbook for a Profitable Exit
Dec 08, 202513:60
SNAP Selling — How Smart MSPs Sell to Busy, Distracted Decision Makers
Dec 01, 202516:18
The 10 Principles of Sustained Success — MSP Edition

The 10 Principles of Sustained Success — MSP Edition

Nov 24, 202511:02
The Only Sales Guide You’ll Ever Need — The Mindset of a 7-Figure MSP
Nov 10, 202513:31
How Smart MSPs Get Past the Gatekeeper — and Get Invited In
Nov 03, 202513:51
Stuck Selling and Still Starving: The MSP Owner’s Sales Trap
Oct 27, 202518:39
Think Horses, Not Zebras: Why MSPs Make Growth Too Complicated

Think Horses, Not Zebras: Why MSPs Make Growth Too Complicated

Ever notice how we MSPs love to overcomplicate things?


A ticket comes in, and suddenly we’re hunting for some rare, exotic issue when it usually ends up being a loose cable or a bad password.


In this week’s episode of MSP To The Future, we’re talking about why the simplest answer is almost always the right one and how you can use that same mindset to sell more, lead better, and stop drowning in busywork.


I’ll show you how to spot the “zebras” that are slowing down your business and how to focus on the horses that actually make you money.


Because success doesn’t come from adding more complexity it comes from simplifying what already works.


So tune in, think horses not zebras, and let’s take your MSP to the future!

Oct 20, 202513:27
MSP Marketing: It’s More Than You Think
Oct 13, 202513:59
Who Moved My Cheese? How Smart MSPs Turn Change into 7-Figure Growth
Oct 06, 202513:04
Networking for Introverts: How to Win Without Working the Whole Room
Sep 29, 202511:14
Insights from The Cloud Guy: Peer Groups That Grow Seven-Figure MSPs
Sep 22, 202519:26
SPIN Selling – Lessons Every MSP Should Steal
Sep 15, 202518:16
Speak Success Into Your Day: The 7 Lines That Built My MSP
Sep 08, 202514:06
 The Secret Weapon of Seven-Figure MSPs: Coaching
Sep 01, 202513:12