Servosity doesn't just store your data — they test, validate, and guarantee it’s recoverable every single day ►► https://bit.ly/43Gd3hI

What does it really take to grow an MSP to $30M+—without private equity, hype, or shortcuts? In this episode, I sit down with Mike Chaput, CEO of Endsight, who scaled his MSP to 150+ employees and over 20 locations across the U.S.

But his story didn’t start there. In fact, Mike’s first business ended in personal bankruptcy—and the lessons from that experience changed everything about how he built Endsight.

Today, Endsight is one of the most operationally mature, client-obsessed MSPs in the industry. And while there's many elements to their success, Mike puts an emphasis on one thing… a “secret” most MSPs ignore.

Here’s what you’ll learn in this episode:
✅ How hitting rock bottom reshaped Mike’s leadership philosophy
✅ Why most MSPs plateau (and how Mike broke through it)
✅ The hidden force that drives culture, clarity, and scale
✅ How Endsight scaled without taking a dime of private equity

Chapters:
0:00 - Intro
2:03 - Bankruptcy at his first business, then starting Endsight
10:49 - Where Endsight is now
14:50 - What he attributes to Endsight's success (it starts with vision)
39:55 - How do I create a BIG enough vision
46:44 - Growth through acquisition and how they did it
53:33 - How does he differentiate?
1:07:51 - Titan Questions

👉 CONNECT MORE WITH Damien and Mike:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/michaelchaput/

📺 Watch on YT: https://www.youtube.com/channel/UCbzzyR7yX9l9XQaZCBp0v0g

What happens if your backups aren't recoverable? With Servosity, we co-manage your data with you to ensure that never happens ►►https://bit.ly/43Gd3hI

👀 What if your biggest setbacks were actually your superpowers in disguise? That’s the story of Chris Friel, CEO of VoDaVi Technologies, who went from a blue-collar, hands-on upbringing and dropping out of high school… to building a respected, high-performance MSP known for elite customer service, deep trust, and fierce loyalty.

This episode isn’t just about business—it’s about resilience, owning your path, and building a company on your own terms.

Here are some powerful lessons I learned from Chris:

✅ You Don’t Need a Degree—You Need Drive
✅ You and Your Team Need Critical Thinking, not Just Technical Knowledge
✅ Success Comes From Owning Who You Are
✅ Efficiency Creates Capacity for Excellence

Chapters:
0:00 - Intro
2:05 - Starting his MSP
16:10 - Why is customer service to important to him?
40:32 - Overcoming being misunderstood
52:10 - MSP Titan Questions

👉 CONNECT MORE WITH Damien and Chris:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/frieltechnologies/

🎙 Listen on audio:
Apple Podcast: https://podcasts.apple.com/us/podcast/msp-mindset-with-damien-stevens/id1669572779
Spotify: https://open.spotify.com/show/5B1k3Z8qXBGBSCJeSScjBE?si=c5d185c306064520

#msp #managedservices #managedserviceprovider

Focus on your zone of genius and let us co-manage your backups with you ►►https://bit.ly/4lh8HUv

Most MSPs are still “watching” AI—Shane Naugher is already helping clients with it (and also buliding a second company around it!).

But, that's not where he started out. After nearly 25 years in business, Shane made a major pivot. He realized he wasn’t building a company—he was building a lifestyle business, something that wouldn't carry over to his family and loved ones. That realization kicked off a transformation: where he hunkered down and learned how to build his MSP into something that will last.

Also, Shane shares the many ways his MSP is embracing AI and helping clients take advantage of it. But we have to be careful that we're not learning it since it's the new flashy tool, but studying it to discover the business outcomes that your partners would benefit from.

Here are 5 powerful lessons I learned from Shane in this episode:
✅ Make your MSP into an Asset, Something that will last beyond you
✅ AI Is the Future—But Automation Is the Foundation
✅ Your clients want you to lead with AI
✅ You Don’t Need Developers to Build an AI-Enabled MSP
✅ Internal Automation Creates External Opportunity

Chapters:
0:00 - Intro
2:05 - Starting his MSP
10:02 - Switching from a lifestyle business to an asset
13:59 - Leaning into automation early
18:21 - How Shane is using AI now and what that looks like
49:39 - MSP Titan Questions

👉 Connect more with Damien and Shane:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/shanenaugher/

📺 Watch on YT: https://www.youtube.com/channel/UCbzzyR7yX9l9XQaZCBp0v0g

Lean more about how Servosity can secure your client’s data ►► https://bit.ly/3X1L8ED

👀 How do you go from $600K to $22 million in just 10 years—without private equity backing? That’s exactly what Aaron Underhill, CEO of Dedicated IT, pulled off. He’s adding over $100K in MRR every quarter and may be one of the fastest-growing MSPs in the country.

But Aaron’s growth isn’t about hype—it’s about strategy, sacrifice, and staying rooted in his why. From hyper-niching in healthcare to building pods for better client experience, his model is bold, refined, and deeply intentional.

Here are the five biggest lessons I learned from Aaron:
✅ Define the Destination First
✅ Vertical Specialization Drives Efficiency & Margin
✅ Scaling Requires Structure & Sacrifice
✅ Growth Without Cash Flow Strategy Will Break You
✅ You Must Grow First to Lead Others to Growth

Chapters:
0:00 - Intro
1:14 - From 600k to 20M in revenue
7:11 - Figuring out their niche
15:36 - What does he attribute to his growth (it involved his niche)?
21:11 - What does 100k MRR growth look like (per quarter)
25:30 - What he's learned from this growth (know your path and use your size)
32:05 - What challenges has he's faced?
40:00 - Leading yourself first
52:56 - MSP Titan Questions

👉 CONNECT MORE WITH Damien and Aaron:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/aaron-underhill-11b9b251/

📺 Watch on YT: https://www.youtube.com/channel/UCbzzyR7yX9l9XQaZCBp0v0g

Learn more about how Servosity co-manages your backups with you ►► https://bit.ly/43AIaeD

👀 What if you could build a fully remote MSP, dominate a niche, win dozens of culture awards, and have virtually zero turnover on your service desk? That’s exactly what Amber, CEO of Parasol Alliance, has done.

In this episode, she breaks down how her team of over 80 employees — spread across 9 states — landed on the MSP 501 list at #4, all by doing things differently than most MSPs.

Here are five major lessons I learned from Amber:

✅ Culture is EVERYTHING (Especially When You’re Fully Remote)
✅ Lead with Strategy, Not Just Support
✅ All-Inclusive Pricing Builds Trust
✅ Focus on One Niche to Scale Faster
✅ Don’t Wait to Fire Underperformers

🎧 Chapters:
0:00 - Intro
1:32 - How she started Parasol Alliance
9:09 - Having her team work fully remote
11:50 - How not knowing the industry helped her make a better MSP
13:20 - Why the senior living niche? + how they lead their clients with strategy
27:18 - Deep dive into their work culture
39:00 - Walls they've hit + how they handle standardization + diving deeper into their process
50:51 - How they're handling AI
55:53 - MSP Titan Questions

👉 CONNECT MORE WITH :
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/amberbardon/

📺 Watch on YT: https://www.youtube.com/channel/UCbzzyR7yX9l9XQaZCBp0v0g

Join my beta reader list for the upcoming book! ►► https://go.servosity.com/betareader

👀 What happens when an MSP is started by a finance and sales expert instead of an engineer? That’s exactly what Adam Barney and his business partner did with Framework IT, and the results speak for themselves.

Because they couldn’t do the tech work themselves, they were forced to scale/hire fast, build processes early, and master sales & marketing—leading to massive growth and a unique pricing model that rewards efficiency.

Here are five powerful lessons I learned from Adam about scaling an MSP strategically:

✅ Not Being a Tech Founder Can Be an Advantage
✅ The Wrong Clients Will Hold You Back
✅ A Unique Pricing Model Can Be a Game-Changer
✅ Fear Holds Back More MSPs Than Competition
✅ Peer Groups Can Accelerate Growth by Years

Chapters:
0:00 - Intro
2:07 - Starting an MSP with no IT background - had to hire fast
15:22 - Don't sale to just anyone + their unique pricing model
37:47 - How long it takes to get clients aligned on the pricing model
53:17 - Why peer groups are important
59:55 - MSP Titan Questions

👉 CONNECT MORE WITH:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/adam-barney-9810679/

📺 Watch on YT: https://www.youtube.com/channel/UCbzzyR7yX9l9XQaZCBp0v0g

Lean more about how my robust backup process and secure your client’s data ►► https://bit.ly/3X1L8ED

👀 What if your MSP could achieve world-class customer service, a rock-solid culture, and top-tier talent—all while scaling efficiently? That’s exactly what Bryon Beilman, CEO of IUVO, has done. With an NPS score of 80 (more than double the MSP industry average of 38!) and an average employee experience of 24 years, he's effectively built his MSP into the top 500.

Here are the five biggest lessons I learned from Bryon about scaling an MSP the right way:
✅ Leadership at the Edge Empowers Your Team
✅ Culture Isn’t a Buzzword—It’s a Strategy
✅ Customer Service is the Real Differentiator
✅ Think Long-Term: Invest in People & Process

Join my beta reader list for the upcoming book! ►► https://go.servosity.com/betareader

👉 CONNECT MORE WITH:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/bbeilman/

📖 Get Bryon's new book: https://a.co/d/4R7GIU6

Chapters:
0:00 - Intro
1:42 - Bryon's start
7:11 - Managing the process, not the employee
15:20 - How does his MSP differentiate?
25:42 - The importance of culture
31:05 - Leadership at the- edge
39:15 - MSP Titan Questions

📺 Watch on YT: https://www.youtube.com/channel/UCbzzyR7yX9l9XQaZCBp0v0g

►► Lean more about how my robust backup process and secure your client’s data ►► https://bit.ly/4ijcM8p

👀 How do you scale from an average MSP ($1.2M in revenue) to $18M all while slowly taking work off your plate? That’s exactly what Will Nobles, CEO of Vector Choice, did—and his secret wasn’t just hard work. It was a total mindset shift.

Will went from working non-stop to building a team and process that runs without him, unlocking the freedom to start multiple businesses, coach MSPs, and spend more time with his family.

Here are the five biggest lessons I learned from Will about breaking past growth plateaus and building a business that doesn’t own you:

✅ Get Out of Your Own Way
✅ Charge What You’re Worth—And Then Some
✅ Marketing Is a Process, Not a Gamble
✅ You Can’t Scale Without Letting Go
✅ Mindset Determines Everything

Chapters:
0:00 - Intro
1:36 - How Will got into IT
4:17 - Starting Vector Choice (his MSP) and growing to $18M
17:33 - His break throughs and overcoming himself
29:58 - Why your MSP needs an EA and why it's sooner than you think
34:00 - Why did he charge so little in the beginning?
39:20 - How Will manages to only spend 5-6 hours per week with Vector Choice
53:17 - Advice for those getting burnt out
59:37 - MSP Titan Questions

👉 CONNECT MORE WITH:
Damien: https://www.linkedin.com/in/dstevens
Will: https://www.linkedin.com/in/willnobles/

📺 Watch on YT: https://www.youtube.com/channel/UCbzzyR7yX9l9XQaZCBp0v0g

#msp #managedservices #managedserviceprovider