Episode 49 - Profiling and Tough Love: Rebuilding a Broken MSP Culture (Guest: Shawn Walsh)

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.   -------------------------------------------------------------------------------------------- Learn more about Shawn via his LinkedIn [https://www.linkedin.com/in/encorestrategic]. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com [https://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 [https://a.co/d/hJKoFxg] . . #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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.   -------------------------------------------------------------------------------------------- Learn more about Ashton via his LinkedIn [https://www.linkedin.com/in/ashton-fortuna-977b148b]. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com [https://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 [https://a.co/d/hJKoFxg] . . #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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.   -------------------------------------------------------------------------------------------- Learn more about Nicole via her LinkedIn [https://www.linkedin.com/in/nicolebielanski/]. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com [https://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 [https://a.co/d/hJKoFxg] . . #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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 [http://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 [https://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 [https://a.co/d/hJKoFxg] . . #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

Episode 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. -------------------------------------------------------------------------------------------- Learn more about Learn more about Jesse Miller [https://www.linkedin.com/in/secopswarrior/], the Founder of Powergryd [https://powerpsa.com/powergryd/]. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com [https://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 [https://a.co/d/hJKoFxg] . . #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen