The MSP Sales Podcast

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. _____________________________________________________ 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/] Learn more about Andy Runyan [https://www.linkedin.com/in/andy-runyan-ccis/] 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 [https://a.co/d/hJKoFxg] . . #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

Episode 42 - Stop Acting Like Spam: An MSP Guide to Cold Email (w/Guest: Brian Kelly)

Most MSPs think cold email stopped working. The reality? Most outbound campaigns fail before anyone even reads the message. In this episode, Brian Kelly breaks down why deliverability has become the real bottleneck in MSP marketing, and why most providers are still approaching outbound the wrong way. Brian shares how he applied a technical, engineering mindset to sales and built systems focused on one core principle: “The best way to avoid being treated like spam is to stop acting like spam.” We cover: → Why most MSP emails never reach the inbox → The real impact of AI on outbound marketing → The role of context, timing, and relevance in outbound → How MSPs are doing the right things in the wrong order If your outbound strategy feels inconsistent, overcomplicated, or ineffective, this episode will challenge a lot of assumptions.     _____________________________________________________ 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/] Learn more about Brian Kelly's services at https://www.automatedmsp.com/ [https://www.automatedmsp.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 41 - How I'd start an MSP in 2026

How would you start an MSP in 2026? Most would copy what’s already been done. Same services. Same pricing. Same positioning. That’s the problem. In this solo episode, Brian Gillette [https://www.linkedin.com/in/brian-gillette/] breaks down exactly how he’d go from $0 to $1M ARR today - without reinventing the tech, but completely rethinking how it’s packaged and sold. → The 3 core offers I’d build: MSP, AI as a Service, and vCSO → How to sell outcomes (time, growth, productivity) instead of tools → How to reframe managed services as “insurance” (but why you shouldn’t lead with it) → Why most MSP marketing fails - and how to fix it without changing your stack This isn’t about doing more. It’s about saying the right thing, to the right audience, in the right order. If I were starting over today - this would be the playbook. _____________________________________________________ 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 40 - Why Most MSPs Get Compliance Completely Wrong (w/Guest: Tim Golden)

Most MSPs get compliance completely wrong. They treat it like a product. They overcomplicate it. Or they try to charge a premium for something they can’t clearly define. In this episode, Tim Golden [https://www.linkedin.com/in/timothygolden/] (Founder and CEO of Compliance Scorecard) breaks down what compliance actually is - and how MSPs should be using it. → Why compliance is a process, not a tool → How to position yourself as a facilitator, not just a fixer → The simple framework for delivering compliance without complexity → How compliance uncovers gaps that turn into real revenue This isn’t about adding another service. It’s about changing how you think about value, risk, and your role in the client relationship. If you’re trying to move upstream, get a seat at the table, and stop being seen as “just IT” - this is the shift. Looking for Tim's FTC Safeguards CaaS Facilitation Workflow Document (mentioned in the episode) ? Get it here [https://content.app-us1.com/aQYOv/2026/05/03/8bb653ee-933b-44ca-bf7f-3c1b407f4a23.pdf]. It's a practical playbook to help Managed Service Providers (MSPs) guide small and midsize businesses through the legal requirements of the FTC Safeguards Rule (16 CFR 314.4). _____________________________________________________ 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 39 - Is SaaS Replacing the Traditional MSP? (w/Guest: Omar Armenteros)

In this episode, Brian Gillette [https://www.linkedin.com/in/brian-gillette/] talks with Omar Armenteros [https://www.linkedin.com/in/omararmenteros/], CEO and founder of Virtuworks, about the future of managed services and how SaaS is changing the game. With over 30 years in the industry, Omar shares how his company shifted from traditional break-fix models to software-driven solutions that scale and automate to meet today’s demands. They discuss how this change is reshaping the way MSPs operate, why automation is essential for growth, and how customer expectations are evolving. Omar also explains why the traditional MSP model is fading, making way for a new, software-centric approach to IT services. In this episode, you’ll learn: * How Virtuworks adopted SaaS to improve operations * The importance of meeting changing customer expectations in 2026 * Why automation is crucial for growing an MSP business * How to adapt to the shift from service to software Listen in to hear how the managed services landscape is evolving, and why embracing software might be the key to staying ahead. _____________________________________________________ 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