The MSP Sales Podcast

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 the fake, take, escape pattern → Why fear, uncertainty, and doubt keep replacing trust in MSP sales → The one shift that breaks the adversarial cycle for good This one is for MSP owners and sales reps tired of feeling like the villain in their own pitch. Walk away with a name for the pattern working against you, and the first piece of what replaces it. -------------------------------------------------------------------------------------------- Interested in attending ScaleCon 2026? Register here with code FeelGood50 for a $50 discount: https://cvent.me/e9BBxL 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

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 three things: your objective, your motive, how they win This one is for any MSP owner who dreads walking into a room full of strangers. Walk out with the confidence to break the ice and build warm pipeline. -------------------------------------------------------------------------------------------- Interested in attending ScaleCon 2026? Register here with code FeelGood50 for a $50 discount: https://cvent.me/e9BBxL 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

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 judge the channel → Run several lead sources at once, never rely on one snare → Fire fast when someone cannot keep pace with the team's standards This one is for MSP owners waiting on one channel or one hire to fix their growth. You’ll walk away knowing exactly where your ceiling comes from. -------------------------------------------------------------------------------------------- Interested in attending ScaleCon 2026? Register here with code FeelGood50 for a $50 discount. Learn more about Taher Hamid via his LinkedIn. 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

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 bottleneck to business freedom. He rebuilt from absolute scratch by shifting his entire operational philosophy. Instead of micromanaging tasks, he started delegating by outcomes. Today, he runs two multi-million dollar MSPs and a global virtual staffing agency. He breaks down how he let go, why virtual talent is the cheat code for scaling, and how pairing AI with a VA multiplies your leverage. We cover: → Why most owners hand their team tasks instead of outcomes → Why you must treat offshore talent like full employees → How to do a proper "time study" to figure out what only you can do → Rejection proofing: How a stand-up comedy course can fix your sales Whether you are drowning in tickets or trying to make your first hire, Sergey's story shows what is waiting on the other side of letting go. -------------------------------------------------------------------------------------------- Learn more about Sergey Poltev via his LinkedIn. 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

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 process, and what to do instead. -------------------------------------------------------------------------------------------- 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

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 conference leaders because of one pattern they kept seeing: personal dysregulation is an epidemic in the channel, and it is costing operators more than they realize. In this episode, she reframes the work-life balance myth, explains why connection is the most underused performance tool in an MSP owner's toolkit, and walks through a practical transition protocol that anyone can start using today. We discuss how: → Overthinking is a coping mechanism for lack of trust → Work-life balance creates two competing forces. → When you come home dysregulated, you micromanage, disempower your team, and build dependency → Connection, not distance, is what actually regulates your stress → Tiny, intentional steps compound This episode is for the MSP owner who knows stress is affecting their performance but does not know where to start. You will walk away with a a reframe, and a reason to take the first step. -------------------------------------------------------------------------------------------- Learn more about Gabriela Embon via her website. 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

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 to look underneath the marketing, this episode is seven concrete, sub-$1,000 moves you can make this month. ** Access the link mentioned in this episode http://feelgoodmsp.com/apollo _____________________________________________________ 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 episode is seven concrete, sub-$1,000 moves you can make this month.

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 the same thing → How a scarcity number mindset keeps high earners stuck → The shift from comfort driven thinking to impact driven wealth → Using the Ansoff Matrix to decide: push your current market, or expand → Why partnering before buying lowers the risk of a new market → Applying poker's estimated value thinking to marketing decisions → The two mistakes that keep profitable owners from building real wealth This episode is for MSP owners making money that never turns into anything lasting. Justin lays out a deliberate way to turn profit into wealth. -------------------------------------------------------------------------------------------- Learn more about Adam via his website. 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

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 project, like a single DBA fix, becomes the door to a bigger contract → Why foot-in-the-door pricing and a foot-in-the-door project are not the same thing → The four buckets every client rotates through, and how to sell into each one → Why you never price a contract on hope or on loyalty → Why flattery is more dangerous to a growing MSP than honest criticism This one is for MSPs still trying to win by outbidding everyone on the big deal. Land small, prove yourself, then get paid full price for the second job. -------------------------------------------------------------------------------------------- Learn more about Adam via his LinkedIn. 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

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. They discuss why language matters, how to shift from technical conversations to strategic ones, and what it takes to become a trusted security advisor. We cover: → How to position vCISO services as strategic business guidance → Common mistakes MSPs make when selling cybersecurity → How to communicate value without overwhelming prospects → What separates trusted advisors from the Whether you're launching a vCISO offering or refining an existing one, this episode will help you rethink how you position security, communicate value, and win more strategic client relationships. -------------------------------------------------------------------------------------------- Learn more about Erin via his LinkedIn. 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

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. 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

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. 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

• Chapters

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.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

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.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

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.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

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.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

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 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

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.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

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.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

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.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