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Unlocking MSP Success: The Real Accountability Blueprint
14 Aug 2025
00:59:27
In this episode of MSP Insider, discover why most MSPs struggle with growth and learn the transformative power of accountability frameworks.
Summary: Join us as we dive deep into the realities of MSP leadership and accountability, with expert insights on how to navigate the challenges of scalability and team dynamics. Uncover why best practices often fall short and discover actionable strategies to revolutionize your MSP business.
🔍 Key Topics Covered: • The role of accountability in MSP growth and scalability • Breaking down the myths of MSP best practices • Transforming from a consultant mindset to a business leader • Developing a resilient MSP team through effective communication • Understanding the economy of scale and its impact on MSPs • Overcoming common MSP growth challenges with strategic insights • Building a profitable and sustainable MSP business
⏱️ Timestamps: 1. 00:00 - Introduction and Episode Overview 2. 05:55 - Understanding Accountability in MSPs 3. 11:20 - Breaking Down Best Practices Myths 4. 20:45 - Transitioning from Consultant to Leader 5. 31:10 - Building a Resilient MSP Team 6. 41:50 - The Power of Economy of Scale 7. 53:00 - Actionable Strategies for Profitable Growth
Why do so many MSPs struggle with growth despite possessing the technical prowess to succeed? The answer lies in financial awareness and sales strategies.
Summary: Dive into this eye-opening episode with MSP Insider's Jeffrey Newton as he sits down with strategic coach Brian Hoppe. Discover why most MSPs unknowingly sabotage their financial performance and avoid sales efforts, preventing them from achieving their full potential. Learn how to transition from a tech-focused mindset to becoming a sales-driven leader with insights that could reshape your business's future.
🔍 Key Topics Covered: • The hidden pitfalls of MSP financial blindness and how to overcome them • The critical difference between margin and markup: What you need to know • Why most MSPs avoid sales and how this prevents growth • Understanding client concentration and its impact on valuation • Building a successful sales-led MSP company • How to calculate gross margins for each line of business • Transitioning from a tech-first mentality to a sales-first strategy
⏱️ Timestamps: 1:12 – Brian Hoppe Introduction 5:15 – Why Coaching Unlocks MSP Potential 11:18 – The Reality of MSP Financial Awareness 17:31 – Avoiding Sales: The Hidden Obstacle 23:49 – From Technician to Sales Leader: Making the Shift 3 6:20 – How Client Selection Affects Your Business 41:50 – Preparing Your MSP for a Successful Exit
Escape the Grind: Building a Life-Friendly MSP Business
07 Aug 2025
01:03:50
Is the hustle and grind draining the life out of your MSP? Discover how to break free from the business prison and finally achieve the success you deserve!
Summary: Join Paul Green in this episode of MSP Insider as he unpacks the realities of MSP marketing, shares life-changing strategies to grow your business, and reveals the common traps that keep you stuck. Whether you’re struggling with sales or desperately trying to scale, this conversation is your roadmap to building a thriving, life-friendly MSP.
🔍 Key Topics Covered: • How to escape the "business prison" and create a life-friendly MSP • Debunking the biggest MSP marketing myths holding you back • Proven strategies for improving MSP sales with simple, actionable steps • The truth about how to effectively market in the MSP industry • How Reddit can offer an MSP reality check: are you on the right path? • Building sustainable growth through tried-and-tested marketing techniques • Avoiding common MSP marketing pitfalls and costly mistakes
⏱️ Timestamps: 1. (00:00) Introduction 2. (06:54) Meet Paul Green: Helping MSPs with Marketing 3. (10:00) The Business Prison: Why MSPs Feel Trapped 4. (20:03) Why Marketing is Key to MSP Success 5. (32:49) Overcoming Intimidation: The Reddit Reality Check 6. (43:23) MSP Marketing Lies and Finding Genuine Strategies 7. (54:55) Simplifying Your Marketing for Success 8. (1:03:08) Final Advice: Start Small, Build Big
Client Expectations vs. Reality: An MSP's Survival Guide
04 Aug 2025
00:52:49
Do you feel the tension between what your MSP promises and what it delivers? Discover how bridging this gap can set you apart from the competition.
Summary: In this episode of MSP Insider, we dive deep into the often-overlooked disconnect between MSP agreements and real-world client expectations. Mike Pedrick, an industry expert, reveals vital insights on how to navigate relationship dynamics, set crystal-clear expectations, and deliver truly remarkable service. This is an eye-opener for MSP owners looking to scale their operations smarter and retain their clients for the long haul.
🔍 Key Topics Covered: • The reality of aligning MSP agreements with client expectations • Strategies to prevent MSP-client relationship breakdowns • How to deliver consistent and reliable MSP services • The importance of clear communication in MSP-client dynamics • Understanding the role of people and process in MSP success • Techniques for reducing client attrition and boosting retention • Building a sustainable framework for MSP growth
⏱️ Timestamps: 1. 0:00 - Introduction 2. 5:03 - Bridging the Gap: MSP Agreements vs. Client Reality 3. 16:12 - Team Dynamics: People and Process in MSPs 4. 25:11 - The Heroic Fallacy: Consistency Over Heroics 5. 32:54 - Solving the Real Problem: Beyond Symptoms 6. 41:32 - Yes, If: The Art of Aligning Expectations 7. 51:08 - Wrap Up and Final Thoughts
The future of managed services is no longer a distant promise; it's an urgent call to action for MSP owners ready to transform and thrive. Learn why shifting your mindset is crucial to your MSP's growth.
Summary: In this episode of MSP Insider, industry veteran Tim Thomson joins us to discuss the transition to MSP 3.0, unlocking new growth opportunities through innovative mindsets and technologies. If you're ready to accelerate your MSP's success, it's time to tune in and learn actionable strategies that can be implemented today.
🔍 Key Topics Covered:
• MSP 3.0 Evolution: What it means for the industry and your organization • Strategic Mindset Shifts: Moving from reactive to proactive for true differentiation • Time Management: Breaking free from work traps to focus on business growth • Digital Work Analytics: Why it's the game changer MSPs can't ignore • AI and Productivity: Leveraging new tech for better client outcomes • Delegation and Outsourcing: Essential strategies to free your time and scale faster • Overcoming MSP Challenges: Common misconceptions that hinder growth
⏱️ Timestamps: • 00:00 Introduction • 02:00 Tim Thomson's Background • 08:00 Breaking Free from Time Traps • 18:00 The Rise of Digital Work Analytics • 25:00 MSP 3.0 Explained • 32:00 Key Strategies for 2025 and Beyond • 45:00 Closing Thoughts
Are you flying blind when it comes to your MSP's margins? Discover the hard truths that could transform the financial health of your MSP business.
Summary: In this episode of MSP Insider, Joe Burns, co-founder and CEO of Reformed IT, sits down to reveal the uncomfortable truths about MSP margins and why many MSPs are flying blind. We dive into understanding your numbers, making informed decisions, and reshaping your approach to pricing and client engagement. This episode is packed with essential insights designed to help MSPs scale smarter and increase profitability.
🔍 Key Topics Covered: • The critical importance of understanding your MSP margins • Common misconceptions about MSP pricing tiers • Why most MSPs are getting service margin calculations wrong • The impact of one-size-fits-all marketing in the MSP space • How to effectively transition clients to a more profitable pricing model • The underlying causes of MSP growth challenges you've overlooked
⏱️ Timestamps: 1. Intro – 00:00 2. Guest's Background – 01:01 3. Major Margin Misunderstandings – 06:21 4. Service Margin Deep Dive – 09:03 5. The Faulty Trio: Good, Better, Best – 25:15 6. Marketing Lies and Truths – 42:18 7. Final Takeaways – 52:00
Client Expectations vs. Reality: An MSP's Survival Guide
24 Jul 2025
00:52:09
Do you feel the tension between what your MSP promises and what it delivers? Discover how bridging this gap can set you apart from the competition.
Summary: In this episode of MSP Insider, we dive deep into the often-overlooked disconnect between MSP agreements and real-world client expectations. Mike Pedrick, an industry expert, reveals vital insights on how to navigate relationship dynamics, set crystal-clear expectations, and deliver truly remarkable service. This is an eye-opener for MSP owners looking to scale their operations smarter and retain their clients for the long haul.
Key Topics Covered: • The reality of aligning MSP agreements with client expectations • Strategies to prevent MSP-client relationship breakdowns • How to deliver consistent and reliable MSP services • The importance of clear communication in MSP-client dynamics • Understanding the role of people and process in MSP success • Techniques for reducing client attrition and boosting retention • Building a sustainable framework for MSP growth
⏱️ Timestamps: 1. 0:00 - Introduction 2. 5:03 - Bridging the Gap: MSP Agreements vs. Client Reality 3. 16:12 - Team Dynamics: People and Process in MSPs 4. 25:11 - The Heroic Fallacy: Consistency Over Heroics 5. 32:54 - Solving the Real Problem: Beyond Symptoms 6. 41:32 - Yes, If: The Art of Aligning Expectations 7. 51:08 - Wrap Up and Final Thoughts
Is your MSP ready for the AI revolution, or will you be left in the dust? Dive into the conversation that every managed service provider needs to hear.
Summary:
In this episode, we sit down with Mark, the manager of AI adoption at Hats.ai, to explore the untapped opportunities MSPs have in the rapidly evolving AI landscape. Discover how AI can transform your MSP business and why standing still might mean being left behind.
🔍 Key Topics Covered: • The equalizing force of AI for small and large businesses alike • Identifying MSPs' potential next big play with AI • Practical examples of AI use cases generating revenue for MSPs today • Understanding the risks of ignoring AI integration • The contrast between AI's bottom-up demand vs. cybersecurity’s top-down mandates • How to start transforming "butter-passing" jobs into strategic roles • MSP identity evolution in the wake of AI advancements
⏱️ Timestamps: • 00:00 Introduction and guest greeting • 02:20 The equalizing power of AI across industries • 06:15 Biggest opportunities for MSPs in AI • 12:30 Real-world AI use cases in MSP operations • 19:09 Addressing the AI apprehension in MSPs • 26:15 Future MSP framework: AI versus traditional approaches • 36:00 Transforming internal operations with AI
Curious why your MSP isn't growing as expected? You're not alone. Let's uncover the harsh truths holding many MSPs back from real success.
Summary:
In this episode of MSP Insider, Nick Wolf, a seasoned expert in the MSP sector, dives deep into the mindset, beliefs, and practices that can make or break your MSP growth journey. From flawed sales strategies to missteps in cyber insurance, discover actionable insights that will empower you to scale smarter. Explore how to transform your approach and avoid common pitfalls that stunt growth.
🔍 Key Topics Covered: • Critical MSP sales strategy mistakes and how to fix them • The importance of understanding your numbers for business success • Shocking truths about MSP and client cybersecurity practices • Why MSPs must embrace legal expertise for contracts • How outdated beliefs are costing MSPs money and clients • The role of cyber insurance in safeguarding your MSP • Strategies for managing and firing unprofitable clients
⏱️ Timestamps: (These are inferred and can be adjusted as needed) • 00:00 Introduction • 03:00 Dumbest Excuses MSPs Make • 08:30 Break-Fix vs. MSP: The Pricing Dilemma • 14:21 Cybersecurity: Misbeliefs That Hurt • 20:49 Delegating Right: How to Scale Successfully • 27:13 Legal Frameworks: Why They Matter
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Why Every MSP Needs a Disney Experience Approach
07 Jul 2025
01:42:12
Discover the hard truths about how MSPs sabotage their growth with common misconceptions in sales and operations. If you're tired of hitting growth plateaus, this episode is a wake-up call.
Summary: In this transformative episode, we dive deep into the operational challenges and cultural gaps that inhibit MSP growth. Our guest, Dean, reveals why the traditional hiring mindset fails and how a service-driven approach can turn the tide. Learn how to strike the perfect balance between sales and ops for a thriving MSP business.
🔍 Key Topics Covered: • The unspoken rift between MSP operations and sales teams • Why overdelivering may be silently killing your MSP's growth • Real-world examples of successful client experience transformation • The secret to sustainable scaling in the MSP world • Practical hiring strategies that attract the right talent • How MSPs can harness the competitive edge of a Disney-like client experience • Vendor event challenges and the untapped opportunities for learning
⏱️ Timestamps: 1. 0:00 - Introduction 2. 2:10 - The MSP Vendor-Event Paradox 3. 10:30 - Sustainable Scaling: Beyond Sales and Ops Conflict 4. 18:15 - Hiring Strategies for MSP Growth 5. 30:45 - The Real Cost of Overdelivering 6. 40:20 - Delivering a Disney-Level Client Experience 7. 50:10 - Wrapping Up: Key Takeaways
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Struggling to Scale? The MSP Owner’s Dilemma Explained
30 Jun 2025
00:33:33
Are you an MSP leader grappling with stagnation and scaling hurdles? Discover the hard truths and transformative insights that are holding you back in today’s cluttered market.
Summary: Join us in this episode of MSP Insider as we dive into the core challenges MSP owners face in scaling their business. Ron Losavsky shares his extensive coaching experience, revealing key barriers to growth and providing a roadmap for meaningful transformations in your MSP operations. If you’re ready to surpass mere survival and build a thriving MSP asset, this episode is your blueprint.
🔍 Key Topics Covered: • The psychology of MSP owners: How personal traits impact business growth. • Services Gross Margin: An overlooked metric crucial for MSP success. • Execution vs. Strategy: Why focusing on action leads to better results. • Building an MSP Asset: Transitioning from managing a job to running a business. • Execution strategies for teams: The importance of clarity and focus. • Toxic Leadership Patterns: Identifying and overcoming growth obstacles. • Transforming MSP Dynamics: How Ron's coaching leads to positive change.
⏱️ Timestamps: • [00:00] Introduction and Jeff's journey with Ron's mentorship. • [04:45] Diving into execution, accountability, and the MSP owner’s challenge. • [09:00] The true metric MSPs are lying to themselves about: Services Gross Margin. • [15:30] Breaking through the 15-employee wall: The leadership growth spurt. • [22:00] Managing stubbornness: Leadership patterns that block MSP growth. • [28:00] Facilitating meaningful, positive transformation in MSP teams.
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Dive deep into the changing tides of the MSP industry, where private equity's influence and the evolving nature of industry events are reshaping how MSPs scale and succeed.
Summary: In this episode of MSP Insider, Jeff and Gene explore the strategic shifts that are redefining the MSP landscape. From the impact of private equity and the importance of refining sales strategies, to adapting to evolving trade shows and embracing true service hospitality, discover the key insights that could transform your MSP's growth trajectory.
🔍 Key Topics Covered: • The transformative impact of private equity on MSPs • How MSPs can refine sales strategies for maximum growth • Navigating the evolving landscape of MSP trade shows • Distinguishing between service and hospitality in MSP settings • Leveraging industry consolidation for MSP success • Challenges and opportunities in the current MSP market • Innovative strategies for MSP scalability
⏱️ Timestamps: 1. Introduction and Guest Overview 2. Private Equity's Role in MSP Growth 3. Revamping MSP Sales Tactics 4. The Shift in Trade Show Dynamics 5. Service vs. Hospitality in MSPs 6. Consolidation: A Blessing or Curse? 7. Final Thoughts and Future Trends
CTA Section: 📩 We go even deeper on email every week: https://mspinsider.beehiiv.com/insider-access
MSP Automation: Unlocking Efficiency with AI With Ashley Cooper
16 Jun 2025
00:55:11
In this episode of MSP Insider, we're diving deep into the often overlooked but massively impactful world of open source and how it's revolutionizing the MSP industry.
Summary: Learn how community-driven resources and open source tools can transform your MSP, streamline operations, and enhance service delivery. Plus, discover why AI isn't just a buzzword but a powerful ally for scaling your business smarter.
🔍 Key Topics Covered: • The hidden benefits of open source for MSPs • How community engagement boosts MSP growth • AI tools that are redefining MSP operations • The pitfalls of ignoring open source solutions • Real-world examples of successful MSP automation • Steps to integrate open source in your MSP strategy • Why 2025 will be a turning point for small MSPs
⏱️ Timestamps: 1. [0:00] - Introduction to the power of open source 2. [5:12] - Community as a strategic asset for MSPs 3. [12:34] - AI tools that transform MSP operations 4. [21:44] - Overcoming common MSP challenges with open source 5. [34:19] - Building a future-proof MSP strategy
CTA Section: 📩 We go even deeper on email every week: https://mspinsider.beehiiv.com/insider-access
This show is powered by Cyft.ai
From Invisible to Irresistible: Transforming Your MSP Brand With Crystal Conkle
09 Jun 2025
00:58:11
Most MSPs don’t have a marketing problem.
They have a clarity problem
Crystal Conkle (CMO at The 20 MSP) breaks down what that really means—and how to fix it.
If your growth feels stuck, or your marketing still sounds like everyone else… this is your episode.
We cover: → Why invisibility is the real cost of copy-paste marketing → The shift from “engineering-first” identity to market relevance → How to build an organic engine that compounds over time → And what it really takes to create a message people remember
Timestamps: 00:00 – Introduction to Crystal Conkle and key challenges in MSP marketing 08:19 – Realizing the MSP industry's marketing misunderstanding 15:50 – Breaking free from the engineering-first identity 24:05 – Core systems for scalable MSP marketing 36:10 – The future of MSP growth and marketing strategies 45:35 – Addressing MSP owners' fear of standing out 52:40 – Building your MSP's organic growth engine
How Soft Leadership is Hurting Your MSP Success With Dale Walls
02 Jun 2025
00:56:18
Hard truth: It’s not your tech that’s holding you back. It’s your leadership.
In this episode, I sat down with Dale Walls (founder of Corsica Technologies) to break down the real reason MSPs hit a wall.
It’s not lack of effort. It’s not lack of ideas. It’s lack of clarity, courage, and consistency at the top.
This one covers: → The quiet cost of soft leadership → Building trust as your core currency → Retention strategies that actually work → The 10-year vision most MSPs avoid defining → How to lead without needing to have it all figured out
Timestamps:
00:01 – Intro 04:00 – Dale on Leading with Clarity 10:35 – Where MSP Leadership Breaks 18:24 – Trust, Vision, and Retention 25:00 – Mapping the Next 10 Years 38:15 – The Anti-Playbook Approach 52:00 – Closing Takeaways
Ending MSP Burnout: A Mental Health Roadmap to Breakthrough
26 May 2025
00:55:28
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
The Hard Truth About MSP Profitability and Exit Strategy with Arlin Sorenson
19 May 2025
01:08:08
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
Unlocking Profit: How AI Transforms MSP Revenue in 2025
12 May 2025
01:12:22
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 Future of MSP Platforms: AI, Integration & Growth | Chris Day
05 May 2025
00:53:11
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
AI Compliance for MSPs: The Untapped Potentia
28 Apr 2025
01:06:57
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
Why Most MSPs Fail at Compliance and How to Break the Cycle
21 Apr 2025
01:05:29
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
The VCISO Approach That Transforms MSP Profitability with Jesse Miller
14 Apr 2025
00:59:20
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.
Stop Chasing 'Silver Bullet' Tech and Fix Your People Problem” with Damien Stevens
07 Apr 2025
00:53:39
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.
Stop Losing Prospects Mid-Pitch: Sales Recovery Tactics with Jonathan Schofield
31 Mar 2025
00:53:55
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.
Why Your MSP Sales Training Is Garbage (And What Really Works) - Robert Gillette
24 Mar 2025
00:52:29
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.
Fix Your Service Leaks Before Turning On The Sales Faucet - Keith Marchiano
17 Mar 2025
00:45:18
In this episode of MSP Insider, host Jeffrey Newton sits down with Keith Marciano, Senior Executive Coach at Pax8 Academy, for a practical conversation about the operational foundations MSPs need before focusing on sales growth. Through candid discussion, Keith reveals why generating more leads without fixing service delivery creates bigger problems, how to approach modern buyers who've already done their research, and the specific metrics that indicate MSP health.
Key Topics Covered: • Why your service foundations must be solid before ramping up marketing • The "Results Selling Framework" that focuses on client business outcomes • How to identify if unprofitable clients are "your problem" or "their problem" • The benchmark metrics every MSP should be tracking (50-60% margins, 6.5 billable hours) • Why specializing in 1-3 industries creates more value than being a generalist
Timestamps: 0:00 - Introduction to MSP operational challenges 4:09 - Understanding the modern buyer journey 10:22 - Strategic ways to engage decision-makers 16:30 - The Results Selling Framework 27:03 - Critical operational metrics to track 33:21 - Addressing unprofitable legacy clients
Whether you're struggling with service delivery efficiency or trying to increase your managed services margins, this episode delivers practical advice about what it really takes to build a profitable MSP in 2025 and beyond.
The Painful Truth About Why Most MSPs Can't Sell - Brian Gillette
10 Mar 2025
00:58:34
In Episode 10 of MSP Insider, host Jeffrey Newton sits down with Brian Gillette, founder of Feel Good MSP and host of the MSP Sales Podcast, for a raw conversation about why most MSPs struggle with sales and the uncomfortable truths about what it takes to grow. Through candid discussion, Brian reveals why technology often creates distance between MSPs and their clients, and how to rebuild the human connection that drives real growth.
Key Topics Covered: • Why most technical founders struggle with sales psychology • How to overcome the "victim mindset" in MSP sales • Why adding more technology often hurts client relationships • The critical importance of human connection in managed services • Practical steps for facing sales fears and taking action
Timestamps: 0:00 - Introduction 7:46 - The Victim Mindset in MSPs 15:29 - Overcoming Sales Fear 32:11 - The Human Side of Service 42:07 - Technology vs Connection 54:26 - Key Takeaways
Whether you're struggling with sales or looking to rebuild genuine client relationships, this episode delivers uncomfortable truths about what it really takes to grow an MSP in 2025 and beyond.
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Stop Running Your MSP Like Everyone Else: A Marketing Expert's Warning - Kevin Clune
03 Mar 2025
00:53:38
In Episode 9 of MSP Insider, host Jeffrey Newton sits down with Kevin Clune, founder of MSP Growth Hacks, for an eye-opening discussion about why traditional MSP models are failing to meet modern business needs. Drawing from his experience building and selling his own MSP, Kevin reveals why stepping outside the industry echo chamber might be the key to your success.
Key Topics Covered: • Why traditional MSP models don't work for many clients • How to identify what customers really need (not what you want to sell) • Creating buyer personas that actually drive results • The evolution of managed services and what's next • Practical steps for differentiating your MSP
Timestamps: 0:00 - Introduction 3:13 - Breaking Free from MSP Echo Chamber 16:39 - Rethinking Service Models 22:56 - Building Effective Buyer Personas 35:08 - The Future of Managed Services 47:53 - Key Takeaways
Whether you're struggling to differentiate your MSP or looking to break free from traditional service models, this episode delivers fresh insights about meeting customers where they are - not where the industry says they should be.
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The Brutal Truth About MSP Marketing (And How to Fix It) - Katie Vreeland
24 Feb 2025
00:48:11
In Episode 8 of MSP Insider, host Jeffrey Newton sits down with Katie Vreeland, founder of Luminary Creative, for a candid conversation about why most MSPs struggle with marketing and how to actually get started. Drawing from her experience on both sides of the industry, Katie breaks down the common pitfalls and provides actionable steps for MSPs ready to invest in growth.
Key Topics Covered: • The real reason most MSPs fail at marketing • How to start marketing without getting overwhelmed • Why focusing on problems beats talking about solutions • Practical steps for identifying your ideal client profile • The truth about marketing accountability in MSPs
Timestamps: 0:00 - Introduction 3:44 - The Brutal Truth About MSP Marketing 6:36 - Getting Started with Marketing 15:51 - Problems vs Solutions in Marketing 27:07 - Identifying Your Ideal Client 40:02 - Marketing Accountability 46:31 - Key Takeaways
Whether you're just starting to think about marketing or looking to improve your current efforts, this episode delivers practical insights without the typical marketing fluff.
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The Most Expensive Thing Killing Your MSP's Growth - Tim Conkle
17 Feb 2025
00:53:20
In Episode 7 of MSP Insider, host Jeffrey Newton sits down with Tim Conkle, CEO of The 20, for a raw conversation about ego, accountability, and why most MSPs are their own worst enemy. With decades of experience scaling MSPs and building one of the industry's largest peer groups, Tim delivers unfiltered insights about what really holds companies back from growth. Through candid discussion, Tim challenges common industry excuses and explains why "ego is the most expensive thing in business." From the myth of the lifestyle MSP to the real reason companies stay small, this episode cuts through the noise to deliver uncomfortable truths about what it takes to build a successful managed services business.
Key Topics Covered: • The truth about "lifestyle businesses" and other excuses • How ego prevents collaboration and growth • The critical importance of accountability • Why communication is the root of all business failures
Timestamps: 0:00 - Opening Thoughts on Ego 4:15 - Why Ego is Your Most Expensive Asset 14:45 - The Power of Better Together 21:39 - Communication as the Root of All Failure 31:11 - The Problem with Tool Obsession 42:27 - The Truth About Lifestyle MSPs 48:39 - Why Most Peer Groups Fail 50:24 - The Importance of True Accountability
Whether you're struggling to scale your MSP or looking to break through to the next level, this episode delivers straight talk about what's really holding you back - and it might not be what you think. Connect with Tim: the20.com
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From Ransomware Victim to Industry Leader: An MSP's Journey Through Hell - Robert Cioffi
10 Feb 2025
01:11:17
In Episode 6 of MSP Insider, host Jeffrey Newton sits down with Robert Cioffi, CTO and Co-founder of Progressive Computing Inc, for a raw conversation about surviving a devastating ransomware attack and its aftermath. As a 32-year industry veteran, Robert shares the brutal reality of what happens when cybersecurity theory meets real-world crisis.
Through candid discussion, Robert reveals how a catastrophic security incident transformed not only his business but his entire approach to MSP leadership. From stepping back from leadership to rebuild account management from the ground up, to becoming a vocal advocate for industry-wide security education, Robert shares hard-earned wisdom about what really matters in building a resilient MSP.
Key Topics Covered: • The harsh reality of recovering from a major ransomware attack • Why traditional VCIO services may be doing more harm than good • How to build and scale genuine account management excellence • The danger of title inflation in MSPs • Practical steps for creating consistent service delivery Don't miss this compelling conversation about vulnerability, humility, and what it really takes to protect both your MSP and your clients in today's threat landscape. Robert's journey from crisis to becoming a leading voice in cybersecurity education offers essential lessons for every MSP leader.
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Measuring Metrics That Actually Matter In Your MSP
03 Feb 2025
00:27:53
In Episode 5 of MSP Insider, host Jeffrey Newton draws from his extensive experience with TruMethods, Service Leadership Index (SLI), SLIQ, and Sea-Level Operations to challenge conventional wisdom about MSP metrics and performance tracking.
With 18 years of hands-on experience implementing various methodologies - from TruMethods' Operational Maturity Level (OML) to Service Leadership's industry benchmarks - Jeffrey breaks down which frameworks actually deliver results and which ones can lead your MSP astray. Through candid analysis of his time working at five different MSPs across seven roles, he reveals why blindly following industry "best practices" can make you hate the company you built.
Key Topics Covered:
A detailed comparison of TruMethods, SLI, SLIQ, and Sea-Level Operations approaches
Why 90% of MSPs track metrics but only 35% feel confident they're tracking the right ones
The truth about NPS scores, utilization rates, and other overrated metrics
How competing KPIs between teams destroy profitability
Practical ways to measure what actually matters for MSP growth
Whether you're currently using TruMethods, Service Leadership Index, or another framework - or just starting to track metrics - this episode cuts through the noise to help you focus on numbers that actually drive business success.
Watch now to learn why choosing the right framework and metrics - not just following industry standards - is critical for building a sustainable MSP.
The Last Mile - Human-AI Integration In MSP Delivery
03 Feb 2025
00:14:35
In this MSP Insider Whiteboard Series, host Jeffrey Newton breaks down a powerful concept from his conversation with David Powell (VP of Sales Strategy at Pax8) about AI integration in MSPs.
Learn how to think about "the last mile" - where human expertise meets artificial intelligence in modern service delivery.
Key Concepts Covered: • The three-layer framework for AI integration in MSPs • Understanding "butter passing jobs" and how to identify them • Why human discernment remains irreplaceable in service delivery • Practical steps to start implementing AI in your MSP
This whiteboard session transforms high-level concepts into actionable insights, showing MSPs how to balance automation with human expertise. Perfect for MSP owners who know they need to adopt AI but aren't sure where to start.
Whether you're just beginning your AI journey or looking to optimize your current approach, this breakdown provides a clear roadmap for integrating AI while enhancing, not replacing, your team's capabilities.
Timestamps: 0:00 - Introduction 1:04 - The Last Mile Concept 3:52 - Three-Layer Framework 8:47 - Human Excellence Layer 10:35 - Finding Butter Passing Jobs 12:38 - Key Takeaways
Death of the Small MSP: Why 2025 Will Change Everything - Matt Lee
27 Jan 2025
00:46:38
In Episode 4 of MSP Insider, host Jeffrey Newton sits down with Matt Lee for an unflinching look at the future of managed services and why many MSPs won't survive the coming changes. As an industry veteran and cybersecurity expert, Matt delivers a powerful wake-up call about the critical challenges facing MSPs in 2025 and beyond.
This episode tackles tough questions about why MSPs must move beyond selling tools to delivering provable outcomes, the dangers of ignoring foundational security practices, and how private equity's growing influence will reshape the industry landscape. Matt delivers practical insights about starting where you are, being honest about organizational weaknesses, and the importance of continuous improvement in surviving the industry's inevitable consolidation.
Key Topics Covered:
Why most MSPs aren't ready for coming compliance and regulatory changes
The critical importance of proving historical security controls
How private equity will drive industry consolidation
Practical steps for surviving the "year of the haves and have-nots"
Don't miss this compelling conversation about why "ignorant people die ignorantly" and what MSPs must do now to avoid being part of the coming industry shakeout.
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The VCIO Lie: What MSPs Get Wrong About Strategic Services - Alex Farling
19 Jan 2025
00:47:51
In Episode 3 of MSP Insider, host Jeffrey Newton sits down with Alex Farling, co-founder of Empath, for an unfiltered conversation about the state of managed services and why most MSPs are getting it wrong.
With over 20 years in the industry, including founding and selling both an MSP and Lifecycle Insights to ScalePad, Alex brings a unique perspective as a non-technical owner who's been in the trenches. His journey from sales professional to MSP owner to industry innovator provides a fresh lens on common industry challenges.
This episode dives deep into controversial topics like why the VCIO model is fundamentally broken, the real reasons client relationships fail, and how misaligned incentives are holding MSPs back from growth. Alex shares practical insights on building sustainable client relationships, proper role definition, and why continuous improvement matters more than industry "best practices."
Key Topics Covered:
Why most MSPs are approaching VCIO roles completely wrong
The critical importance of relationship building in client retention
How to stop treating sales as "black magic" and start driving results
Practical steps for scaling your MSP without losing quality
If you're tired of the typical industry echo chamber and ready for honest conversation about what really drives MSP success, this episode delivers actionable insights you can implement today. Don't miss this candid discussion with one of the industry's most thoughtful voices.
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Stop Fighting AI: How MSPs Should Actually Use Automation - David Powell
10 Jan 2025
00:57:47
In Episode 2 of MSP Insider, host Jeffrey Newton sits down with David Powell, VP of Sales Strategy at PAX8, to dive deep into the transformative role of AI in managed services. With years of experience leading growth in the MSP space, David shares his perspective on how AI is creating new opportunities for efficiency, scalability, and client satisfaction.
This episode unpacks the real challenges MSPs face when it comes to adopting AI, including resource constraints, fear of failure, and navigating data-driven decisions. Learn how to bridge the gap between innovation and execution, and discover how AI can empower your team to focus on high-value work.
Key Topics Covered:
•Why MSPs can’t afford to ignore AI
•How AI is driving efficiency and automation in managed services
•Real-world applications of AI to enhance MSP operations
•The importance of data governance and actionable ideas for implementation
If you’re ready to move beyond the buzzwords and learn how AI can help you stay competitive, this episode is packed with actionable insights to get you started. Don’t miss this must-watch conversation with one of the industry’s leading voices.
AI & The Future Of MSPs: Adapting To Stay Ahead
05 Jan 2025
00:15:52
Discover how AI is transforming the MSP industry and what it means for the future of managed services. In this video, we explore the game-changing potential of artificial intelligence in streamlining workflows, improving ticket management, and boosting overall efficiency for MSPs.
Whether you’re an MSP owner, manager, or technician, staying ahead of the curve is critical. Learn how AI-powered tools can help you adapt to industry challenges, enhance client satisfaction, and reclaim valuable time for strategic growth.
Key Topics Covered: • How AI is reshaping the MSP landscape • Practical ways MSPs can leverage AI for efficiency • The future of IT workflows powered by AI • Real-world examples of AI improving MSP operations
If you’re ready to embrace the next evolution of managed services, this video is for you. Don’t fall behind—discover how AI can revolutionize your MSP today.