MSP Insider

 Running an MSP can feel like a never-ending sprint—until your mind and your motivation hit a wall. In this episode, I sat down with Scott Scrogin, Strategic Initiatives Director at ConnectWise, to talk about the thing no one builds a dashboard for: burnout. We covered the real stuff—what it looks like when you’re scaling fast and still feel stuck, what happens when your identity is wrapped up in the business, and how to build resilience that actually lasts.Scott’s been in the seat. From growing and exiting his MSP to now helping lead big-picture strategy at ConnectWise, he’s seen what burnout does to founders—and what it takes to get back in control.If your brain’s been running on fumes, this one’s for you. 🔍 What You’ll Learn • Why burnout hits harder than most MSPs admit • The mental weight of scaling fast • What no one tells you after you exit • Scott’s playbook for managing pressure and building clarity • How to reset your energy and lead with purpose • Turning mental wellness into business strategy ⏱️ Timestamps 0:00 – Why Mental Health Matters for MSPs 8:15 – Recognizing and Addressing MSP Burnout 16:40 – Post-Exit Identity Crisis: The Unseen Challenge 24:55 – Strategies for Mental Resilience During Growth 33:30 – Fostering a Culture of Empathy and Care 41:10 – Turning Mental Wellness into MSP Success This show is powered by Cyft.ai #MSPLeadership #MentalHealth #Burnout #ScalingMSPs

 You can’t outwork a broken model. That’s where this episode starts—and where a lot of MSP owners get stuck. I sat down with Arlin Sorensen (VP Ecosystem Evangelism of ConnectWise) to unpack the kind of growth that looks good on the surface… but still leaves you frustrated, burned out, or stuck at a ceiling you can’t break through. This one’s about the stuff we don’t talk about enough: → Plateaus that sneak up on you → Sales avoidance dressed up as delegation → Profitability that never shows up on paper → And what legacy actually means when the dust settles It’s part mindset, part strategy, and all experience. 🧠 What we cover: • Why delegation isn’t a shortcut to growth • The pressure of being the only one who knows the numbers • What happens when your hard work doesn’t equal real value • The 3-phase path to a healthy, intentional exit • Fulfillment, reflection, and planning for what’s next ⏱️ Timestamps: 0:00 – When growth looks good, but feels off 5:30 – The truth about owner-led sales 12:45 – The profit trap: working hard with nothing to show 18:20 – Breaking through plateaus 25:00 – Exit planning that doesn’t start too late 32:10 – Alignment between fulfillment and success 45:00 – Why reflection is a skill, not a luxury 

Is your MSP stuck in a pricing battle? Here’s the hard truth: if you’re still competing on price in 2025, you’re not scaling—you’re surviving. In this episode of MSP Insider, I sit down with Sagar Pandya to unpack the mindset shifts MSPs need to stay relevant and profitable. We go deep into how AI can give you an edge, why “consultative” isn’t just a buzzword, and what it takes to build client trust in a space moving faster than ever. If you’re tired of discounting your value—or trying to sell AI without really knowing how to use it—this one’s for you. 🎯 What You’ll Learn: • Why price-driven growth doesn’t scale • How to reposition yourself as a true advisor • Where AI fits (and doesn’t) in MSP operations • The real reason AI adoption is stalling • How to talk AI with clients—without overwhelming them • Practical strategies for sustainable MSP growth ⏱️ Timestamps: 0:00 – Intro 4:55 – Why competing on price is a trap 12:02 – Where AI actually helps MSPs grow 25:30 – Lessons from cloud → AI integration 37:14 – Real-world AI use cases for MSPs 49:38 – Building trust in a high-speed tech environment Powered by Cyft.ai – helping MSPs scale smarter

The MSP platform you’re using today? It might not get you where you want to go. In this episode of MSP Insider, I sat down with Chris Day to unpack what’s really broken in the MSP platform space—and where things are actually headed. We talk about: → Why “integration” is still mostly a buzzword → How AI is changing the way we manage data and deliver client value → What it really takes to create a platform that feels like it was built for you—not patched together for investors If you’ve ever felt like your tools don’t talk to each other—or that your stack is holding you back—this one’s worth your time. — Key Topics Covered: • Why traditional MSP platforms are falling behind • What true integration should look like • AI’s role in transforming client experience and operations • Building a scalable, context-aware customer journey • What to expect from MSP platforms by 2026 • What you can do today to close the gap ⏱️ Timestamps: 0:00 – Intro 1:20 – Chris Day on regrets and lessons learned 4:13 – Where MSP tools miss the mark 7:48 – Fixing broken integration 10:19 – Building a better client experience 14:03 – Behind the scenes at ScalePad 18:45 – AI, context, and the next big shift 26:37 – Why context wins 33:32 – Real steps to improve CX now

 Is your MSP actually ready for the AI revolution? We unpack why ignoring AI could be the biggest risk to your business as we dive into the hard truths and strategies for leveraging AI and compliance in the MSP industry. Summary: In this episode, we dive deep into how MSPs can navigate the challenges of compliance and the transformative potential of AI. Learn how to transition your business strategy to stay competitive, overcome common misconceptions about AI, and simplify compliance by strategically implementing AI solutions. 🔍 Key Topics Covered: - Transformative AI strategies that increase MSP efficiency - The pressing role of compliance in MSP growth - Proven methods for integrating AI into MSP operations - Overcoming AI skepticism in the MSP community - Streamlining MSP processes with AI technologies - Preparing your MSP for 2025 and beyond - Utilizing AI to tackle cybersecurity challenges ⏱️ Timestamps: [00:00] Introduction to AI and Compliance in MSPs [07:30] The Compliance-Driven MSP Strategy [14:45] AI Misconceptions and How to Overcome Them [23:10] Practical AI Applications for MSP Efficiency [32:00] Planning for a Hybrid Workforce: AI and Humans [45:14] Future Trends and Recommendations for MSPs - This show is powered by Cyft.ai#MSPInsider #JeffreyNewton #Randy Blasik #VCISO #MSPGrowth

Think compliance automation has you covered? You might be walking into a false sense of security. In this episode, I sat down with Tim Golden, founder of Compliance Scorecard, to unpack the real risks of relying too heavily on automation—and what it actually takes to build a scalable, secure compliance program as an MSP. This one’s for MSP leaders who want to grow and protect what they’ve built. What we cover: • Why automation alone isn’t enough to keep you (or your clients) safe • What a real compliance foundation looks like • Turning compliance into momentum—not just maintenance • What the FTC safeguards really mean for your MSP • How to create a compliance-first culture that scales • Real examples of what’s working in the field Timestamps: 00:00 – Intro 05:00 – The compliance myths holding MSPs back 12:00 – What strong compliance actually looks like 22:00 – FTC safeguards: what you need to know 30:00 – From “check the box” to continuous monitoring 40:00 – Building a culture that gets it 55:00 – Final takeaways Powered by Cyft.ai  #MSPInsider #JeffreyNewton #TimGolden #VCISO #MSPGrowth 

 In episode 15 of MSP Insider, host Jeffrey Newton sits down with Jesse Miller, founder of Power PSA Consulting, for a no-BS conversation about why most MSPs fail at cybersecurity sales. Through candid discussion, Jesse reveals why obsessing over security tech stacks instead of business risk is killing your margins, how his own first security program "bled cash" until he changed his approach, and why "comfort zone thinking" is the true barrier to MSP growth. Key Topics Covered: • Why technical cybersecurity stacks alone are impossible to sell profitably • How to transition from technical expert to strategic risk advisor • The critical difference between vCIO and vCISO conversations with clients • Why "professional perfection" mentality kills MSP cybersecurity programs • How to structure security offerings that clients actually understand and buy Timestamps: 0:00 - Introduction to cybersecurity challenges for MSPs 4:03 - Jesse's journey from technical expert to strategic advisor 10:17 - Why most MSPs get stuck in their comfort zones 16:35 - The critical difference between vCIO and vCISO services 22:06 - Why "professional perfection" kills cybersecurity programs 31:22 - Building flexible frameworks vs. rigid security packages Whether you're struggling to make cybersecurity profitable or looking to expand your existing security practice, this episode delivers practical advice about what it really takes to sell and deliver security services that clients actually value and pay for. This show is powered by cyft.ai #MSPInsider #JeffreyNewton #JesseMiller #VCISO #CybersecurityServices #MSPGrowth #RiskManagement

 In episode 14 of MSP Insider, host Jeffrey Newton sits down with Damian Stevens, host of MSP Mindset and founder of Scarcity, for a raw conversation about why most MSPs are getting hiring completely wrong. Through brutally honest discussion, Damian reveals why four-year degree requirements are killing your talent pipeline, how to spot "high trajectory" candidates that conventional hiring processes miss, and why obsessing over technical skill sets often leads to culture disasters that cost you far more in the long run. Key Topics Covered: • Why conventional hiring processes filter out the most innovative potential employees • How to identify "unconventional hires" with higher growth trajectories than traditional candidates • The critical shift from "time-to-hire" thinking to "time-to-performance" measurement • Why culture problems are usually the real constraint in MSP growth (not tech or leads) • How to build a hiring process that reflects your actual culture, not generic corporate templates Timestamps: 0:00 - Introduction to MSP hiring challenges 4:12 - Why conventional job descriptions are killing your talent pipeline 8:35 - Identifying "high trajectory" unconventional hires 14:27 - The shift from "time-to-hire" to "time-to-performance" thinking 22:06 - Culture as the hidden constraint in MSP growth 28:43 - Building a hiring process that shows your true culture Whether you're struggling with finding good technical talent or constantly dealing with culture mismatches after hiring, this episode delivers uncomfortable truths about what it really takes to build an MSP team that drives sustainable growth in 2025 and beyond. This show is powered by cyft.ai #MSPInsider #JeffreyNewton #DamianStevens #MSPHiring #TalentAcquisition #MSPCulture #UnconventionalHiring

 In episode 13 of MSP Insider, host Jeffrey Newton sits down with Jonathan Schofield, a no-nonsense sales pro in the IT services space, who tells it like it is about those painful moments when your prospect's eyes glaze over. Jonathan cuts through the BS about why your monologuing is killing deals, how to spot the exact moment you've lost someone, and his battle-tested techniques to snap prospects back to attention. Key Topics Covered: • The telltale signs your prospect has mentally left the building mid-pitch • Jonathan's "pattern interrupt" technique that forces re-engagement (even if they don't want to) • The mutual expectations framework that prevents tune-out in the first place • Why most MSPs waste thousands on marketing "silver bullets" that never hit the target • How to get brutally honest about who your ideal customer actually is (hint: it's not "SMEs with 20+ employees") Timestamps: 0:00 - Introduction to sales engagement disasters we've all experienced 3:57 - The exact moment you realize you've lost your prospect's attention 8:18 - The pattern interrupt technique that works every time 14:53 - Why "accidental entrepreneurs" struggle with sales ownership 22:31 - Getting real about your ideal customer profile 31:05 - "Where thy prospect is, there thou shalt also be" If you're tired of watching opportunities slip away as prospects check email during your pitch, this episode delivers the uncomfortable truths about what it really takes to keep decision-makers locked in during sales conversations in 2025 and beyond. This show is powered by cyft.ai #MSPInsider #JeffreyNewton #JonathanSchofield #SalesEngagement #MSPGrowth #SalesStrategy #ITServices

 In this episode of MSP Insider, host Jeffrey Newton sits down with Robert Gillette, founder of MSP Dojo, for a candid conversation about why most MSP sales programs fail and what actually drives results. Through honest discussion, Robert reveals why making hundreds of cold calls isn't enough, how lack of confidence impacts sales meetings "like body odor," and the psychological barriers preventing MSP owners from achieving sales success. Key Topics Covered: • The three critical levers of MSP sales success beyond activity volume • Why most MSP owners sabotage their sales hires from day one • How compensation plans can either motivate or destroy sales momentum • The psychological "pucker effect" that kills rainmaker relationships • Why sales is a journey of self-development, not just tactics Timestamps: 0:00 - Introduction to MSP sales challenges 7:22 - The three critical levers of sales success 12:05 - Why hiring a sales rep usually backfires 18:33 - The psychology of successful sales 22:19 - Building effective compensation plans 27:46 - Protecting your rainmakers Whether you're struggling with making your first sales hire or looking to improve your existing sales process, this episode delivers uncomfortable truths about what it really takes to grow an MSP through effective sales in 2025 and beyond. This show is powered by cyft.ai #MSPsales #JeffreyNewton #RobertGillette #salestraining #ITchannel #MSPgrowth #salesstrategy #managedservices