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

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.

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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 Brian Kelly's services at 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 .

. #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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 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.

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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

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 (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. 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).

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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

In this episode, Brian Gillette talks with Omar Armenteros, 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.

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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

In this episode, Brian Gillette speaks with Karl Palachuk, a prolific author and two-time MSP business owner, about his journey in the managed services industry. With over 25 books under his belt, Karl delves into his philosophy on success, focusing on relaxation, focus, and sustainable growth.

Karl also reflects on his battle with health challenges and how they influenced his approach to business and life. He shares how he transformed from focusing solely on hard work to understanding the importance of balance and focus. The discussion moves into the evolving managed services landscape and why MSPs must adapt to stay relevant.

In this episode, you’ll learn:

• How relaxation and focus lead to success
• Why work-life balance isn’t a myth, but a necessary pursuit for MSP owners
• The shift in managed services towards solving bigger business problems
• Insights from Karl's success in building and selling MSPs

Tune in to gain valuable advice on balancing business growth, personal health, and staying ahead in the fast-paced MSP world.

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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

What does personal growth have to do with business success? A lot! Join Brian Gillette and Paul Vedder, CEO of VXIT, as they dive into how overcoming personal challenges fueled his professional achievements. In this raw, honest conversation, Paul shares the pivotal moments when shifting his mindset and committing to physical fitness reshaped not only his life but his MSP business.

Paul opens up about his journey - from battling addiction to becoming a marathon runner - and how these personal victories directly translated into business triumphs at VXIT. Learn how small daily habits and a commitment to self-improvement are the key to sustainable business growth.

In this episode, you’ll learn:

• The personal habits that lead to professional success
• How your health can supercharge your business
• Why overcoming personal limitations is essential
• How to build a thriving business with the right mindset

Don’t miss this inspiring conversation about the power of personal growth in business success.

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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

This is a bonus episode - and a different one.

If you’re here for a standard interview or tactical breakdown, feel free to skip this one. We’ll be back with a regular episode next week.

But if you’re an MSP owner who’s been following the podcast and thinking, “This makes sense, but I’m not ready for a full coaching program yet” - this is for you.

In this episode, Brian introduces MSP Sales Foundations - a new, self-serve membership designed specifically for six-figure MSPs who want to build a real sales engine without the time or financial commitment of 1:1 coaching.

This is built for MSPs who need to fit sales into a busy schedule - and want a clear, practical system to generate consistent growth. Get notified when it's available and an invite to our online launch party: https://go.feelgoodmsp.com/msp-sales-foundations

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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)", has just been released in 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