The MSP Sales Podcast

Oct 26, 2026

Episode 65 - Why Nobody Is Buying Your Managed Services

Why Nobody Is Buying Your Managed Services You know your tech is good. You know you can help the business. So why are prospects still comparing you on price, going quiet after discovery, or choosing the cheaper MSP? The problem might not be what you're selling. It might be how you're selling it. In this solo sales training episode, Brian Gillette breaks down where MSP sales conversations go wrong, and how to fix them. Here's what we get into: → Why selling your tech stack makes you sound like every other MSP → How to connect business problems to the outcomes you deliver → The "So What?" test f

Oct 19, 2026

Episode 64 - Money and Time: How to scale through the different phases of MSP Growth

If you look under the hood of an MSP that has been stuck for ten years, you usually find two things. No spare time and no spare money. Every growth move costs one or the other. So the owner spends the little they have on conferences, certifications, and half measures. Word of mouth becomes the plan. In this solo episode, Brian Gillette draws one chart with money on one axis and time on the other. He walks through the phases of MSP growth, from the first clients to the phase five chasm. Then he turns the chasm into arithmetic. Define the investments, price them, and work backward to the leads,

Oct 12, 2026

Episode 63 - How 750 Closed MSPs Taught Me to Stop Churn (w/ Nick Wolf)

Nick Wolf has heard that from hundreds of them. As employee #15 at Datto, Nick went on to close more than 750 MSP partners. At one point, he went 12 months without losing a single one of 160 active partners. What was behind that kind of performance? It wasn't some magic sales trick. It was how he built relationships, paid attention to details, and made sure people knew why he was calling. In Episode 63 of The MSP Sales Podcast, Nick and I get into: → Why your prospects probably don't see your MSP as different → How to make outbound calls that have an actual reason behind them → Why the handoff

Oct 5, 2026

Episode 62 - From Zero to $20 Million in Six Years (w/ Juan Fernandez)

Most MSPs say they don't want to compete on price. Then they spend the entire sales conversation talking about technology, comparing stacks, and trying to prove why they're worth more. Juan Fernandez took a very different approach. He built an MSP from zero to $20 million in six years by focusing less on what he was selling and more on whether he could actually solve the client's problem. In Episode 62 of The MSP Sales Podcast, Brian Gillette sits down with Juan, Chief Encouragement Officer at MSP As A Service, to break down how he thinks about discovery, pricing, positioning, and winning the

Sep 28, 2026

Episode 61 - Utility vs Asset: Selling Who They Become in MSP Sales

If you look under the hood of a stalled MSP sales call, you will often find a parts list. Backup cadence. Delta files. Portal logins. The client is nodding, but nothing is landing. That is the lowest level of connection. It leads straight to the price objection, and you have nothing left to say. In Episode 61, Brian Gillette closes out the Feel-Good Close Foundations series with pillar three: build connection. This solo lecture centers on the connection chart. The shift is simple. Stop explaining what the service does. Start speaking to who the client wants to become. → Buyers see MSPs at the

Sep 21, 2026

Episode 60 - Sausage Making: The MSP Sales Habit That Kills Trust

If you look under the hood of a stalled MSP sales call, you'll find the same habit every time. Too much talking. Not enough asking. Most discovery calls still run product-forward. XDR, RMM, endpoint detection. That's sausage making. Nobody wants to buy sausage by hearing how it's made. They care about what happens after they hire you. Brian Gillette continues the Feel-Good Close lecture series with pillars one and two. Focus on the solution. Fight for authenticity. He reframes discovery from product-forward to need-forward, and shows why curiosity, not charm, builds trust. He also unpacks the

Sep 14, 2026

Episode 59 - One of Three: Why Great MSP Closers Still Lose

There is a reason prospects lie to you before the pitch starts. It is not because they are bad people. It is because selling trained them to defend themselves. Most sales advice is tactics. Overcome objections. Handle pushback. Close harder. None of that explains why buyers show up guarded in the first place. This episode opens the Feel-Good Close Foundations series. Brian steps out of the interview chair to break down the adversarial sales complex, the pattern that turns sales conversations into a standoff. He names FUD as the fuel behind it, and empathy as the fix. → Why buyers default to th

Sep 7, 2026

Episode 58 - How to Break the Ice at Your Next Networking Event

You walk into a networking event and start selling. That is the fastest way to leave with nothing. MSPs treat these rooms like a numbers game, pitching everyone and hoping something sticks. People feel the agenda and shut down before you finish your sentence. In this solo episode, Brian breaks down how he actually breaks the ice, at events and on cold calls. The reframe: you are not there to close. You are there to earn a second conversation. → Invite yourself into a conversation circle instead of hovering → Ask two or three follow up questions before you pitch anything → Run cold calls on thr

Aug 31, 2026

Episode 57 - Fire Fast, Grow Faster: Taher Hamid's Team-Building Playbook (w/ Taher Hamid)

If you look under the hood of a stalled MSP, you rarely find a bad market. You find one lead source, one excuse, and zero accountability. Most owners want one channel to save them. When SEO does not hit in three months, they blame the tactic. When leads come in and they cannot close, they blame the agency. Taher Hamid is back on the podcast - our first repeat guest! He runs MSP Camp, the Apex agency, and the ScaleCon conference. He and Brian break down why growth ceilings are almost always self-imposed. Not the market. Not the vendor. The owner. → Give SEO and AEO twelve months before you judg

Aug 24, 2026

Episode 56 - What One Man Can Do: Rebuilding an MSP After Losing It All (w/ Sergey Poltev)

If you look under the hood of an MSP that never grows, you will usually find one owner trying to do it all. That was Sergey Poltev, and it almost cost him everything. He was overworked, stuck in the tickets, and running his life on empty. The burnout cost him his marriage and his house. Then, a bad partnership deal collapsed and cost him half of his clients, leaving him with barely enough to survive. If you are an MSP owner, there is guaranteed to be something you can relate to in Sergey's story. He is a computer science grad who had to learn the hard way that a technical ego is the ultimate b

Aug 17, 2026

Episode 55 - These Six Sales Myths are Killing Your Results

If you look under the hood of a stalled MSP sales process, you'll usually find the same six pieces of advice. Advice that sounds right. Advice that's been recycled from forum posts and LinkedIn threads until nobody remembers where it came from. Most MSPs never test it. They just repeat it, and it slowly caps their growth. In this solo episode, Brian pulls apart six sales myths making the rounds in the MSP space right now. This one's for any MSP owner who's been quietly following advice they never actually stress-tested. Walk away knowing which of these six myths have been sitting in your sales

Aug 10, 2026

Episode 54 - Overthinking to Clarity: Life Engineering for MSP Owners (w/ Gabriela Embon)

If you look under the hood of a stagnant MSP, you will find a dysregulated owner. Not a broken sales process. Not a bad tech stack. MSP owners carry a level of pressure that shows up on their faces, in their bodies, and inside their teams. When stress goes unmanaged, it does not stay at the office. It drives micromanagement, fractures relationships at home, and builds a team that depends on you instead of functioning without you. Treating work and life as two competing forces makes it worse. Gabriela Embon is a certified professional coach and chemical engineer who was sought out by MSP confer

Aug 3, 2026

Episode 53 - 7 MSP Investments to Make Before Marketing

If you look under the hood of a stalled MSP pipeline, the wiring problem usually isn't marketing. It's everything sitting underneath it. Ads and outbound only work as well as the foundation holding them up. Bad lighting on a sales call, no real CRM, no owned data list. These quietly cap what any campaign can do. In this solo episode, Brian Gillette walks through seven investments, each under $1,000, that build trust and confidence before a single pitch happens. None of it is more marketing spend. It's what marketing can't fix on its own. For MSP owners frustrated with their numbers and ready t

Jul 27, 2026

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 th

Jul 20, 2026

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 pro

Jul 13, 2026

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.

Jul 6, 2026

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%

Jun 29, 2026

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

Jun 22, 2026

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 pipelin

Jun 15, 2026

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 pro