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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

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👀 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

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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