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

CTA Section:

• 📩 Download your free MSP Insider workbook: https://mspinsider.beehiiv.com/insider-access

This show is powered by Cyft.ai

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.

CTA Section:

• 📩 Download your free MSP Insider workbook: https://mspinsider.beehiiv.com/insider-access

This show is powered by Cyft.ai

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

This show is powered by Cyft.ai

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

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

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

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