MSP Mindset with Damien Stevens

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➡️ Can improv comedy and boxing make you a better MSP CEO? For Jason Vanzin, the answer was a life-changing yes.

In this episode, Jason Vanzin—founder of Right Hand Technology Group and builder of a Top 500 MSP—gets radically honest about overcoming fear, learning sales as an introvert, and scaling his cybersecurity-first business through process, partnerships, and learning to overcome his fears. From dragging his wife to networking events to crafting a vCISO coaching model, Jason drops real strategies for MSP growth.

👉 Connect with Damien and Jason:
Damien: https://www.linkedin.com/in/dstevens
Jason: https://www.linkedin.com/in/jasonvanzin/
Website: https://www.righthandtechnologygroup.com/

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

#msp #managedservices #managedserviceprovider

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👀 Could you grow faster by hiring people with zero tech experience?

I sat down with Danny Perry, CEO of IT Cubed, to learn how he and his co-founder built a Top 500 MSP—by recruiting from the service industry, not résumés. In just three years, they scaled from a startup to a nationally ranked MSP. Danny breaks down the real playbook behind operational maturity, culture-first leadership, and why you may be overlooking your best hires.

If you want a behind-the-scenes look at MSP growth, this one’s a must-watch.

✅ How hiring from hospitality unlocked growth
✅ Why documentation—not certifications—drives team performance
✅ The COO role most MSPs overlook (until it’s too late)

Chapters:
0:00 - Intro
1:20 - From history major to IT business owner
21:39 - His role in their success and how unique hiring helped
35:36 - How they got to the top 500 in 3 years
41:20 - Being intentional about diversity
45:55 - Investing in unconventional hires
1:07:35 - MSP Titan Questions

Connect with Damien and Danny:
Damien: https://www.linkedin.com/in/dstevens/
Danny: https://www.linkedin.com/in/dannyaperry/

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

What if the biggest bottleneck in your MSP isn’t a tech stack, a sales strategy, or a new hire... but you?

In this week's episode of MSP Mindset, we sit down with Kayvan Yazd, founder of TruAdvantage, the top-ranked MSP in the San Francisco Bay Area. Kayvan shares how a single mindset shift—starting with a 5AM wake-up and a commitment to internal growth—transformed not only his personal life but also his MSP’s trajectory.

Chapters:
0:00 - Intro
2:04 - His internal change and health journey
17:00 - Internal change before external
29:00 - Daily habit tracker
34:35 - Kayvan's hiring process
40:53 - Why he changed from health care to non-profit
48:46 - Helping his clients with AI
53:06 - His role currently with AI
1:00:21 - MSP Titan Questions

👉 CONNECT MORE WITH Damien and Kayvan:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/kayvanyazdi/

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

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In this week's episode, Alex Markov (CEO, Red Key Solutions) shares how losing his right-hand executive pushed him to rethink how he invests in his team, both professionally and personally. But Alex shares so much more:

🟢 The real reason he walked away from 280 break-fix clients
📈 The power of standardization for MSPs
🧠 Why you should teach “life operational maturity" to your team
🛠️ The 11 Pillars of MSP Success

Chapters:
0:00 - Intro
1:25 - Why he let go of 280 break fix clients
7:42 - Focusing in on one business model
11:30 - Why he prefers staying lean
15:34 - The loss of a team member & taking care of your team
29:50 - The importance of learning from others
39:12 - The importance of process and standardization
48:10 - The 11 Pillars of MSP Success
1:00:07 - MSP Titan Questions

👉 CONNECT MORE WITH Damien and Alex:
Damien: https://www.linkedin.com/in/dstevens
Alex: https://www.linkedin.com/in/alex-markov/
Red Key Solutions: https://www.redkeysolutions.com/
Strategy Overview: https://www.strategyoverview.com/

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

Don't let your backups ruin your reputation, let Servosity co-manage them with you ►► https://bit.ly/43Gd3hI

In this episode, Wade shares how he and his team used a simple red-yellow-green system to objectively rate every client. What it revealed... 75% of their client base weren't good fits.

But instead of clinging to bad-fit business, Wade built a plan to off board those clients over a year—while simultaneously tightening their sales process and only bringing on new clients who matched their green profile. The result? They didn’t just survive the transition—they grew.

Wade breaks down exactly how they executed this shift without sacrificing revenue, and why their service, employee morale, and long-term growth all improved because of it.

Chapters:
0:00 - Intro
0:59 - Why he started his MSP
13:18 - Why he let go of 75% of his clients
31:36 - How he's able to standardize and scale
37:29 - How does he manage transitions and staying fluid as a business?
50:14 - MSP Titan Questions

👉 CONNECT MORE WITH Damien and Wade:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/wadeyeaman/

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

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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

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👀 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