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1.5K to 5K🎙 ~2x weekly·39 episodes·Last published 5d ago - Monthly Reach
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Recent episodes
Episode 47 - The Algorithmic Approach to Booking Meetings for MSPs (Guest: Nicole Bielanski)
Jun 22, 2026
52m 10s
Episode 46 - Why Most MSPs Don't Know If They're Profitable (Guest: John Risko)
Jun 15, 2026
58m 12s
Episode 45 - The MSP of the Future Will Be a vCISO (Guest: Jesse Miller)
Jun 8, 2026
46m 37s
Episode 44 - From Building to Closing: The Five Questions That Drive Revenue
Jun 1, 2026
18m 44s
Episode 43 - The Cyber Insurance Shield: De-risking Your MSP (w/Guest: Andy Runyan)
May 25, 2026
1h 01m 21s
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 6/22/26 | ![]() 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. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian'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 | 52m 10s | ||||||
| 6/15/26 | ![]() 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.comBrian'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 | 58m 12s | ||||||
| 6/8/26 | ![]() 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, 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.comBrian'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 | 46m 37s | ||||||
| 6/1/26 | ![]() 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. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian'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 | 18m 44s | ||||||
| 5/25/26 | ![]() 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.comLearn 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 | 1h 01m 21s | ||||||
| 5/18/26 | ![]() 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 more about Brian Kelly's services at Automated MSP - an MSP-native AI-powered outbound prospecting platform that helps managed service providers generate qualified leads, recruit talent, build strategic partnerships, and identify opportunities via cold email automation. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian'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 | 1h 02m 54s | ||||||
| 5/11/26 | ![]() 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 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.comBrian'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 | 25m 51s | ||||||
| 5/4/26 | ![]() 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 (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). _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian'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 | 57m 21s | ||||||
| 4/27/26 | ![]() Episode 39 - Is SaaS Replacing the Traditional MSP? (w/Guest: Omar Armenteros) | 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. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian'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 | 46m 43s | ||||||
| 4/13/26 | ![]() Episode 38 - Relax, Focus, Succeed: Karl Palachuk's Journey in Managed Services | 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. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian'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 | 47m 47s | ||||||
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| 3/30/26 | ![]() Episode 37 - Your MSP Will Only Grow as Fast as You Do, Here’s Why (w/Guest: Paul Vedder) | 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. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian'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 | 1h 09m 31s | ||||||
| 3/23/26 | ![]() BONUS Episode - A New Sales System for 6-Figure MSPs | 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 _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian'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 | 9m 14s | ||||||
| 3/16/26 | ![]() Episode 36 - The 3 Things Every MSP Needs to Grow (w/Guest: Tim Conkle) | Most MSPs don’t fail because of technology. They stall because the fundamentals of growth aren’t in place. In Episode 36 of The MSP Sales Podcast, Brian Gillette is joined by Tim Conkle to break down the three foundational elements every MSP needs if they want to scale beyond survival mode. This conversation dives into what separates MSPs that plateau from those that build real momentum - and why many owners focus on tactics before these core pieces are actually in place. In this episode, you’ll hear: → The 3 foundational ingredients every growing MSP needs → Why leadership maturity determines the ceiling of your business → Why sales and marketing discipline matters more than tools If your MSP feels stuck, overwhelmed, or inconsistent in growth, this episode explains what needs to change first. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian'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 | 1h 17m 37s | ||||||
| 3/2/26 | ![]() Episode 35 - From MSP Operator to Visionary CEO (w/Guest: Shawn Freeman) | Most MSP owners don’t struggle because they lack technical skill. They struggle because they’re stuck operating instead of leading. In Episode 35 of The MSP Sales Podcast, Brian sits down with serial entrepreneur and MSP growth strategist Shawn Freeman to unpack what it really takes to transition from hands-on operator to visionary CEO. This isn’t theory. It’s about building scalable systems, integrating AI intentionally, and shifting your leadership identity so the business can grow beyond you. In this episode, you’ll hear: → Why MSP owners stall when they stay in operator mode → How AI and automation should actually be integrated into your firm → The leadership shift required to build something scalable → What resilient, future-ready MSPs are doing differently If you want to stop being the bottleneck and start building an MSP that scales with intention, this episode lays out the path. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comRecent News: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 | 52m 20s | ||||||
| 2/16/26 | ![]() Episode 34 - Not All Good Advice Is Good For You | In Episode 34 of The MSP Sales Podcast, Brian Gillette breaks down a hard truth. Most MSP owners learn the expensive way: not all “good advice” is good for you - at least not yet. Some advice is universal. Some is contextual. And some is only true in a specific sequence, after certain prerequisites have been put into place. In this episode, you’ll learn: → The 3 types of advice (and how to spot the difference) → Why “proven tactics” fail when your MSP is in the wrong stage → How MSPs waste money on PPC, lead gen, and automation too early→ Why hiring sales reps before your sales process is repeatable backfires If you’ve ever felt like you’re doing everything you’re told and still not seeing results, this episode will help you identify what’s missing: context, stage, and order. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comRecent News: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 | 32m 05s | ||||||
| 2/2/26 | ![]() Episode 33 - The Webinar Framework: Build a 24/7 Lead Gen Machine (w/ Guest: Scott Millar) | Word-of-mouth is the lifeblood of the MSP, but it is notoriously difficult to scale. In this episode, Brian Gillette sits down with Scott Millar (IT Rockstars), author of Virtually Irresistible, to discuss why webinars are the ultimate bridge between technical expertise and scalable relationship building. Many MSP owners avoid webinars due to "tech anxiety" or a fear of public speaking, but Scott reframes the process as a repeatable system rather than a performance. They dive deep into the tactical side of lead generation, explaining why Meta’s machine learning often outperforms LinkedIn for reaching decision-makers at a fraction of the cost. In this episode, you’ll learn: Why "dog whistle" copy is the key to attracting your ideal client profile How to overcome camera shyness by acting as a "guest expert" The technical "minimum viable process": Why audio quality matters most To upcycle one 40-minute webinar into two months of social media authority This episode provides the structural blueprint to move from accidental 'word-of-mouth' growth to an intentional, scalable inbound system. _____________________________________________________ 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/hJKoFxgLearn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen #Webinars | 1h 10m 20s | ||||||
| 1/19/26 | ![]() Episode 32 - From Survival to Scale: An MSP Growth Story (w/Guests: John Snyder & Neelesh Patel) | In Episode 32 of The MSP Sales Podcast, Brian Gillette is joined by John Snyder (CEO) and Neelesh Patel (President) of Net Friends for a candid, behind-the-scenes look at what it really takes to build a successful MSP - the wins, the mistakes, and the decisions that shaped where they are today. This isn’t a polished success story. It’s an honest conversation about growth through constraint, learning the hard way, and how a strong partnership became a competitive advantage instead of a liability. John and Neelesh share how they navigated leadership challenges, clarified roles, and built trust as the company scaled. Along the way, they dig into how Net Friends thinks about marketing, differentiation, and experimentation. This episode is packed with insights MSP owners can actually apply. In this episode, you’ll hear: ➡️ How a strong CEO–President partnership accelerates growth ➡️ The mistakes they made early - and what they’d do differently ➡️ Why clarity of roles matters more as MSPs scale ➡️ Creative marketing and AI ideas If you’re an MSP who wants to learn from people who’ve lived it - this episode offers a look at what sustainable success requires. _____________________________________________________ Have you heard the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"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/hJKoFxgLearn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining | 1h 06m 38s | ||||||
| 1/5/26 | ![]() Episode 31 - Reactive to Intentional: How MSP Leaders Actually Level Up (w/ Guest: Chris Day) | In Episode 31 of The MSP Sales Podcast, Brian Gillette is joined by Chris Day (CEO at ScalePad) for a no-nonsense conversation about the shift every MSP leader must make to move from reactive survival mode to intentional leadership. Too many MSPs remain dependent on the owner. Every decision, escalation, and bottleneck runs through one person. Chris breaks down why this happens, how it silently limits momentum, and what it actually takes to build an MSP that can operate and grow without constant founder involvement. Together, Brian and Chris explore: ➡️ Why reactivity keeps MSPs stuck (even when revenue is growing) ➡️ How intentional leadership creates leverage ➡️ How to build systems instead of dependencies ➡️ How to step out of the day-to-day without losing control of the business If you’re an MSP owner who feels indispensable to your business - or concerned that your growth still feels fragile - this episode will challenge how you think about what “leveling up” looks like. _____________________________________________________ Have you heard the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"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/hJKoFxgLearn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining | 47m 15s | ||||||
| 12/22/25 | ![]() Episode 30 - Building the Modern MSP: AI, Cloud & UX (w/ Guest: Jim Spignardo) | In Episode 30 of The MSP Sales Podcast, Brian Gillette sits down with Jim Spignardo, Director of Cloud Strategy & AI Enablement at ProArch, for a practical conversation about what it actually takes to build a modern MSP today. With over 25 years in IT across networking, cloud, cybersecurity, and consulting, Jim brings a grounded perspective on how MSPs must evolve beyond tools and tech stacks. Together, they explore how cloud maturity, AI enablement, and user experience now intersect - and how ignoring any of them creates friction for clients and internal teams. They discuss;➡️ Why “modern MSP” is more about experience than tech➡️ How AI is reshaping service delivery➡️ The role of cloud strategy in long-term MSP relevance➡️ Why UX matters just as much for internal teams as end users➡️ Common mistakes MSPs make when adopting AI If you’re an MSP owner, technical leader, or consultant trying to modernize your services, this conversation will help you think more clearly about where to focus. _____________________________________________________ Have you heard the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"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/hJKoFxgLearn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining | 59m 09s | ||||||
| 12/8/25 | ![]() Episode 29 - Selling Cybersecurity Without Fear In The AI Era (w/ Guest: Dor Eisner) | In Episode 29 of The MSP Sales Podcast, Brian Gillette sits down with Dor Eisner (CEO & Co-Founder of Guardz) for a grounded, myth-busting conversation about selling cybersecurity in an AI-shaped world. Too many MSPs feel pressured to become “cyber experts” overnight while many clients think cybersecurity is either too technical or too expensive to take seriously. Dor explains why both sides are looking at the problem the wrong way, and how MSPs can simplify, educate, and lead with confidence. Together, they explore: ➡️ Why MSPs overestimate how much clients want to know about cybersecurity➡️ How AI is already reshaping threat landscapes➡️ A practical path for MSPs who feel “outgunned” by the pace of innovation➡️ Why selling cybersecurity is really about risk reduction➡️ The common fears that stall customer decisions Whether you’re an MSP owner, vCISO, or someone trying to meaningfully add cybersecurity to your stack, this episode will help you communicate value more clearly, close deals more confidently, and protect clients more effectively. _____________________________________________________ Have you heard the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"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/hJKoFxgLearn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing | 32m 30s | ||||||
| 11/24/25 | ![]() Episode 28 - Profitable Packaging: Fueling Predictable Growth (w/ Guest: Brian Hoppe) | In Episode 28 of The MSP Sales Podcast, Brian Gillette sits down with Brian Hoppe (Strategic Advisor and Revenue Coach to MSPs) to unpack why pricing, packaging, and financial clarity shape the entire sales experience. Not through pressure, scripts, or gimmicks - but through alignment, transparency, and knowing your numbers. Together, they break down how the right packaging eliminates discounting, creates confidence in the sales process, and makes growth predictable instead of stressful. In this episode, you’ll learn: ➡️ How unclear packaging causes stalled deals and endless discounting ➡️ What finance numbers you must understand before you scale ➡️ The link between accountability, pricing, and recurring revenue ➡️ How your pricing model shapes your sales culture (for better or worse) ➡️ What good forecasting and predictable revenue look like inside an MSP This isn’t a conversation about “raising prices.” It’s a conversation about building a sales-ready business, one where your team can confidently sell, your clients know exactly what they’re paying for, and your growth becomes predictable instead of stressful. _____________________________________________________ Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"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/hJKoFxgLearn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing | 59m 35s | ||||||
| 11/10/25 | ![]() Episode 27 - Lead Generation for MSPs: What Actually Works | In Episode 27 of The MSP Sales Podcast, Brian Gillette kicks off the new Lead Generation Series- a focused, no-nonsense deep dive into what actually works for MSPs looking to build a reliable pipeline. Don’t waste time on the gimmicks, shortcuts, and “one weird trick” advice floating around out there. This episode breaks down the fundamentals of consistent outbound lead generation - how to use calls, emails, and events in a repeatable, measurable way to drive sales conversations. Want to know what separates MSPs who get consistent leads from those who stay stuck in “feast or famine” mode? Learn; ➡️ The truth about why most outbound fails ➡️ How to balance short-term outreach with long-term brand building ➡️ What to measure (and what not to obsess over) If you’ve ever wondered why your lead gen feels unpredictable, this episode lays the foundation for this series. Because real growth doesn’t come from hacks. It comes from doing the right work, consistently. _____________________________________________________ "How To Sell a Sh*tload of Managed Services (without selling your soul)" <--- A new book now available at Amazon.Written by Brian Gillette, Founder of Feel-Good MSP and host of the MSP Sales Podcast - it’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.Get it now https://a.co/d/hJKoFxgLearn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #MSPLeadGen #LeadGeneratio #LeadGen | 25m 27s | ||||||
| 10/27/25 | ![]() Episode 26 - Lessons from Building, Selling, and Starting Over (w/ Guest: Colin Knox) | What do you do after you’ve reached the top?You’ve achieved the dream - built the business, and made the exit.The pressure’s gone, and the question becomes - what now?In Episode 26 of The MSP Sales Podcast, Brian Gillette sits down with Colin Knox (Founder of Gradient MSP, Passportal, & MSPCentric) for a conversation that gets down to the realities of entrepreneurship — what drives us, what drains us, and what’s waiting on the other side of “making it.”Colin opens up about his own journey and shares hard-earned lessons from building, selling, and starting over — including: ➡️ Why chasing money rarely leads to fulfillment ➡️ How to define success beyond the spreadsheet ➡️ Why impact and purpose are stronger motivators than profit If you’ve ever wondered what separates “busy” from “fulfilled,” or what happens after the big win, this episode is the one.Because sometimes, the real work begins after you’ve already “made it.” _____________________________________________________ Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"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/hJKoFxgLearn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com You can reach our guest Colin Knox on LinkedIn.#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing | 59m 47s | ||||||
| 10/13/25 | ![]() Episode 25 - Marketing Works. Yours Doesn’t. Here’s Why. (w/ Guest: Johnathan Schofield) | Too many MSPs are still waiting for someone else to grow their business for them. In Episode 25 of The MSP Sales Podcast, Brian Gillette sits down with Johnathan “Skofi” Schofield, founder of FindMyITPartner.com, to unpack why so many MSPs feel stuck when it comes to growth. They break down why 77% of MSPs still rely on referrals, and what MPSs can do to start building trust on purpose instead of waiting for it to happen.They dig into the truth behind MSP marketing: ➡️ Why “marketing doesn’t work for MSPs” is a myth ➡️ How consistency beats complexity every time ➡️ Why referrals aren’t a growth strategy (and what to do instead) ➡️ How to manufacture trust before a prospect even talks to you This one’s a practical look at what it really takes to turn activity into traction.Because marketing works. Sales works.The only question is: are you working it? _____________________________________________________ Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"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/hJKoFxgLearn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing | 55m 49s | ||||||
| 9/29/25 | ![]() Episode 24 - Standing Out in a Sea of MSP Sameness (w/ Guest: Paul Green) | In Episode 24 of The MSP Sales Podcast, Brian Gillette sits down with Paul Green — one of the most respected voices in the MSP community — to unpack why so much MSP marketing looks the same and how to finally break free. When every website, offer, and stock photo blends together, it’s harder than ever for prospects to tell you apart. Paul shares practical, battle-tested ways to brand yourself more authentically and make your marketing unmistakably yours: ➡️ Put your name and face front and center to build real trust➡️ Create authentic content (even on a small budget)➡️ Avoid “AI slop” - human stories always beat generic copy➡️ Build charisma and confidence, even if you’re introverted If your campaigns feel invisible or prospects ghost you after the first touch, this episode will show you how to stand out, connect more deeply and become the MSP people actually remember. _____________________________________________________ Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"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/hJKoFxgwww.FeelGoodMSP.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing | 52m 06s | ||||||
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