The MSP Sales Podcast

By Brian GilletteTechnology

The MSP Sales Podcast episodes

July 27 Episode 52 - Money Treadmill: Why Working Harder Never Builds MSP Wealth (w/ Justin D Maxwell)
Revenue can climb for a decade.
Net worth can stay flat the whole time.
That gap is where most MSP owners get stuck.
Standard financial advice is built for salaried employees. Save a percentage, invest a percentage, wait for retirement. That breaks down when your income comes from a business and swings by six figures a year.
Justin D Maxwell has worked one-on-one with close to 1,000 seven-figure earners on this problem. He joins Brian to unpack the difference between money and wealth, and how a family office model turns profit into a system instead of a guess.
→ Why money and wealth are not the same thing
→ How a scarcity number mindset keeps high earners stuck
→ The shift from comfort driven thinking to impact driven wealth
→ Using the Ansoff Matrix to decide: push your current market, or expand
→ Why partnering before buying lowers the risk of a new market
→ Applying poker's estimated value thinking to marketing decisions
→ The two mistakes that keep profitable owners from building real wealth
This episode is for MSP owners making money that never turns into anything lasting. Justin lays out a deliberate way to turn profit into wealth.

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Learn more about Adam via his website.
Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
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#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen
54 min
July 20 Episode 51 - Foot in the Door, Not a Doormat: How to Win Mid-Market MSP Deals (w/ Adam Burke)
There is a quiet mistake sabotaging your biggest mid-market deals.
It is how you price the first project.
Most MSPs chase the big RFP.
Five hundred users, full boat, the whole suite.
It looks like the dream deal.
It is actually a bloody knife fight, and you only see three of the ten ways to lose it.
Adam Burke is VP of Sales and Partnerships at Quest, one of the largest MSPs in the country.
He skips the RFP fight.
He wins mid-market accounts by landing a small project first, then earning the bigger contract on trust.
→ Why full-boat RFPs are a losing bet for most MSPs
→ How one small entry project, like a single DBA fix, becomes the door to a bigger contract
→ Why foot-in-the-door pricing and a foot-in-the-door project are not the same thing
→ The four buckets every client rotates through, and how to sell into each one
→ Why you never price a contract on hope or on loyalty
→ Why flattery is more dangerous to a growing MSP than honest criticism
This one is for MSPs still trying to win by outbidding everyone on the big deal.
Land small, prove yourself, then get paid full price for the second job.

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Learn more about Adam via his LinkedIn.
Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
.
.
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen
58 min
July 13 Episode 50 - How Top MSPs Position vCISO Services (Guest: Erin McLean)
No mid-market CEO is waking up in a cold sweat hoping they can cut you a check for a list of cybersecurity frameworks and automated compliance reports.

Most clients aren't looking for a "vCISO." They're looking for someone who can reduce risk, guide better decisions, and help them navigate an increasingly complex cybersecurity landscape.
The problem? Many MSPs are still selling technical expertise instead of business outcomes.
In this episode, Brian Gillette sits down with Erin McLean to explore how top MSPs position and sell vCISO services in a way that clients actually understand and value. They discuss why language matters, how to shift from technical conversations to strategic ones, and what it takes to become a trusted security advisor.
We cover:
→ How to position vCISO services as strategic business guidance
→ Common mistakes MSPs make when selling cybersecurity
→ How to communicate value without overwhelming prospects
→ What separates trusted advisors from the
Whether you're launching a vCISO offering or refining an existing one, this episode will help you rethink how you position security, communicate value, and win more strategic client relationships.

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Learn more about Erin via his LinkedIn.
Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
.
.
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

59 min
July 06 Episode 49 - Profiling and Tough Love: Rebuilding a Broken MSP Culture (Guest: Shawn Walsh)
There is a common problem that sabotages your client relationships.
It is not your pricing.
It is not your tech stack.
It is you. Let me explain;
Most MSP owners blame turnover, blame difficult clients, blame the market.
Shawn Walsh did that too, until he lost three quarters of his tech staff in one week and watched them try to steal his customer list.
In this episode, Brian Gillette talks with Shawn Walsh, CEO of Encore Strategic and co-author of The Pumpkin Plan for MSPs.
Shawn built an MSP for 21 years, nearly destroyed it through his own leadership blind spots, then rebuilt it into a 400% growth story before exiting to private equity.
He breaks down the personality and EQ work that exposed why his team kept walking out, and how that same framework now helps other MSP owners spot the same patterns in themselves before it costs them their company. We cover;
→ Why undervaluing yourself shows up in pricing
→ Why raising your rates rarely costs you better clients
→ How personality and EQ profiling exposes leadership blind spots
→ How to tell if you are the common denominator in turnover
→ Why communicating your vision matters

This one is for MSP owners who suspect the problem might be closer to home than they want to admit.

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Learn more about Shawn via his LinkedIn.
Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
.
.
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen
46 min
June 29 Episode 48 - 8 Visits a Day: One MSP Prospecting System That Actually Works (w/Guest: Aston Fortuna)
This episode is for the MSP sales rep who's exhausted every digital channel and doesn't know what to try next.
And for the MSP owner who handed someone a blank slate and said, "Figure it out."
MSPs are sending emails nobody opens and making calls that go straight to voicemail. Every inbox is flooded with the same templates, sequences, and cadences.
But Ashton Fortuna found a different path.
After transitioning from cable puller to Sales & Marketing Lead at Valley Tech Logic, Ashton had no sales training, no playbook, and no coach. Through trial and error, he built a prospecting system that now generates 50% of the company's new MRR through in-person canvassing - helping grow from two new clients a year to eight.
In this episode, we cover:
→ How Ashton targets businesses by industry and geographic radius
→ Why the front desk is your greatest ally, not your biggest obstacle
→ How AI maps and verifies prospects before you ever knock on the door
→ How a part-time research VA can dramatically increase qualified visits
Brian also puts Ashton in the hot seat for a live pipeline coaching session, showing how a few small adjustments could double his results.
If you've been wondering what comes after cold email and cold calling, this episode gives you a practical prospecting system you can start adapting today.

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Learn more about Ashton via his LinkedIn.
Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
.
.
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

1 hr 7 min
June 22 Episode 47 - The Algorithmic Approach to Booking Meetings for MSPs (Guest: Nicole Bielanski)
If you look under the hood of a stagnant MSP pipeline you will usually find the same thing. They are focused entirely on the wrong metrics. Cold email is saturated. LinkedIn messaging stopped converting a long time ago. The volume of activity was never the point. The conversation was.
Nicole Bielanski is the Chief Revenue Officer at Frictionless IT. She started selling insurance at 19 and quickly topped a 400-person sales floor. She has spent nearly a decade building predictable go-to-market systems exclusively for MSPs. In this episode she reframes how we think about outbound and what pipeline actually means when the old channels no longer deliver.
We cover:
→ Why optimizing for conversations separates winners from losers
→ How smart list filtering eliminates wasted outreach
→ Why warm calling works when the prospect has a reason to take the call
→ How showing up in person is one of the highest-converting first touches
…and a lot more.
This episode is for the MSP owner grinding on outbound with nothing to show for it. You will walk away with a sharper picture of what a real go-to-market system looks like in 2026.

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Learn more about Nicole via her LinkedIn.
Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
.
.
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

53 min
June 15 Episode 46 - Why Most MSPs Don't Know If They're Profitable (Guest: John Risko)
Most MSP owners think they know their numbers.
The problem is... most don't.
If you look under the hood of a stagnant MSP, the problem usually isn't sales.
It's visibility. You can't improve profitability if you don't know where it's actually coming from.
Many MSPs chase growth without understanding which customers, agreements, or services are making money. The result is more complexity, more work, and often very little improvement to the bottom line.
In this episode, Brian Gillette sits down with John Risko of MSP CFO & Accounting to unpack the connection between strategy, operations, and profitability. They discuss why specialization creates leverage, why many MSPs don't actually know their numbers, and how better visibility leads to better business decisions.
We cover:
→ Why strategic focus matters more than adding revenue
→ How saying "no" improves profitability
→ The hidden cost of custom solutions
→ Why many MSPs struggle to measure profit
→ Ways to identify unprofitable customers
…and more.
If you're trying to build a more profitable MSP, this conversation will challenge how you think about growth, metrics, and what it actually takes to scale.
Get in touch with today's guest, John Risko, at www.MSPCFOandAccounting.com
Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
.
.
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen
59 min
June 08Episode 45 - The MSP of the Future Will Be a vCISO (Guest: Jesse Miller)
This was probably one of our most impactful and actionable interviews to date. Jesse Miller is, for my money, the absolute voice on vCISO. If you are trying to figure out where this industry is heading next, Jesse lays out the exact roadmap to stop playing the commodity "tech guy" game and start acting like a true strategic advisor.
The Big Takeaways?
“The Death of the "Tech Guy" Value Proposition: Why the MSP of the future will either be a vCISO or won't exist at all, and how to stop selling tool stacks so you can start translating technology into business risk.
The "Monkey Paw" Entry Offer: How to use universal baseline needs—like incident response planning and tabletop games—as the ultimate foot-in-the-door strategy to land larger accounts and displace incumbent competitors.
SaaSifying Your Strategy and Pricing: Why pricing security on a per-user basis means you are going to lose your shirt, and how to structure modular flat-rate monthly retainers from $3,500 to $15,000.
Climbing the 5-Layer AI Risk Pyramid: How to cut through the chaotic market FOMO and leverage AI governance to create a three-to-five-year runway of high-margin, enterprise-level advisory work.
If you're trying to figure out where MSPs are headed next, this episode provides a roadmap.
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Learn more about Learn more about Jesse Miller, the Founder of Powergryd.
Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
.
.
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen
47 min
June 01 Episode 44 - From Building to Closing: The Five Questions That Drive Revenue
Are you building a sales process or just avoiding doing the hard work?
A lot of MSP owners are stuck trying to build the perfect AI-powered Rube Goldberg machine. They want a system that sells for them. They obsess over tools, CRMs, and complex automations.
In this solo episode of The MSP Sales Podcast Brian Gillette breaks down why the exact skills that make you a great engineer are actively killing your sales numbers. He strips away the noise and brings it back to the five foundational questions you must answer before any marketing can work.
If nobody is buying your product it is time to sell a different product.
We cover:
→ The 5 fundamental questions every MSP must answer
→ How to repackage managed services as the foundation for AI adoption
→ Why you must clarify your positioning before you spend a dime on lead gen

If you are tired of overcomplicating your growth and want a straightforward path to closing deals this episode is for you.
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Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
.
.
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

19 min
May 25 Episode 43 - The Cyber Insurance Shield: De-risking Your MSP (w/Guest: Andy Runyan)
If you are like me you hate talking about insurance.
You do not like the checkboxes. You do not like the technicalities. You certainly do not like the liability.
For a long time it felt like cyber insurance providers were just looking to make the MSP the scapegoat.
But the market has matured.
In Episode 43 of The MSP Sales Podcast Brian sits down with Andy Runyan from UKON Insurance to break down the real relationship between MSPs, cyber liability, and security sales.
Andy explains why hiding from the insurance conversation is actually increasing your E&O risk. He also explains why playing the "cowboy consultant" and giving unlicensed advice is even worse.
Instead of avoiding the topic smart MSPs are using insurance requirements to force the hand on security controls and they are turning local agents into massive referral engines.
We cover:
→ Why you should never ignore cyber insurance
(and why you can't fill out the application for them)
→ The real reason claims got denied during the ransomware explosion
→ Why "sub-limits" are leaving your clients massively underinsured
→ The critical difference between cyber warranties and cyber insurance
→ How to use tabletop exercises to sell Incident Response (IR) planning
→ Why local insurance agents are the ultimate untapped referral source
If you want to stop getting stuck in the crossfire of liability and actually use compliance to drive revenue this episode is for you.
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Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com
Learn more about Andy Runyan on LinkedIn

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!
It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now at Amazon.com https://a.co/d/hJKoFxg
.
.
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

1 hr 2 min

About The MSP Sales Podcast

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The MSP Sales Podcast digs into the philosophy, strategy, sales training, and techniques that allow a managed service provider to meet their maximum sales potential. For managed service providers who…