MSP Mindset with Damien Stevens

In this episode of MSP Mindset, Damien Stevens sits down with Chance Weaver, former MSP owner turned VP of AI Adoption at Pax8, to uncover the true revenue opportunity behind AI. This isn't about flipping on Copilot—it’s about becoming a trusted business consultant, building real automation, and generating measurable outcomes for clients.

Connect with Damien and Chance:
Damien:
Chance: https://www.linkedin.com/in/chanceweaver/
https://www.linkedin.com/in/dstevens

📺 Watch on YT: https://www.youtube.com/@mspmindset

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Mike Jackson bought an MSP (one man shop) with zero tech background and scaled it into a Top 500 provider in less than 10 years. In this episode, Mike opens up about the bold choices that shaped his growth, including why he deleted all his spreadsheets, fired half his clients, and rebuilt culture from the ground up.

Chapters
0:00 Intro
1:01 - Starting his MSP
13:07 - Year one as an MSP
18:40 - Hitting the top 500 in 7 years
26:14 - Resetting Core Values
29:03 - Issues from their fast growth
34:10 - Culture wins and losses
47:03 - Engaging with the team during rapid growth
49:35 - MSP Titan Questions

Connect more with Damien and Mike:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/mike-jackson-1871711/

📺 Watch on YT: https://www.youtube.com/@mspmindset

What does it really take to go from zero to $2M in revenue in less than two years?

In this episode of MSP Mindset, Damien interviews Julian Gelfand, co-founder of Always Beyond, a Calgary-based MSP that’s scaling fast—without following the usual rules. Julian shares how he skipped the "build-as-you-go" method and launched with full infrastructure, strategic leadership, and a culture-first mindset that’s helping him smash growth ceilings most MSPs never break through.

Connect with Damien and Julian:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/julian-gelfand-13117a21/

📺 Watch on YT: https://www.youtube.com/@mspmindset

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What happens when a visionary tech founder has to throw out his own business model to grow? This episode with Matthew Held, CEO of Manawa Networks, is a brutally honest roadmap through business reinvention, founder separation, and the uphill battle to learn real sales.

Matthew shares the journey from a failed Uber-style IT model to building a proactive MSP that thrives on process and people. He opens up about the hard lessons, including parting ways with a longtime business partner, facing a sales function that wasn't producing, and how building structure was the only path to growth.

Chapters:
0:00 - Intro
1:23 - Starting Manawa
13:49 - Biggest challenge in the beginning
24:55 - What's working now + letting go of a partner
41:23 - What's next after losing your partner?
1:01:55 - MSP Titan Questions

Connect with Damien and Matthew:
https://www.linkedin.com/in/dstevens
https://www.linkedin.com/in/matthewheld/

📺 Watch on YT: https://www.youtube.com/@mspmindset

In this episode, John Snyder—CEO of a Top 500 MSP—explains why routine conversations with customers remain essential, and why if you're not doing this simple tasks, you'll lose. He also shares discovering that his sales team was pitching the wrong service, how he's learning to clarify his vision to curb “drift,” and what it's currently taking to implement EOS smoothly across the organization.

Time stamps:
0:00 - Intro
1:51 - How compliance unintentionally prepared them for Covid
14:33 - Staying focused on customers
27:26 - How do we drive value
41:41 - MSP Titan Questions

👉 CONNECT MORE WITH:
Damien: https://www.linkedin.com/in/dstevens
John: https://www.linkedin.com/in/johnsnyder-netfriends/

🎙 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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Feeling stalled while competitors surge ahead? Discover how Michael Goldstein, CEO of LAN Infotech, flipped the switch with his MSP—tripling marketing spend, doubling community reach, and future-proofing with AI.

Chapters:
0:00 - Intro
1:23 Burnout as a VAR & Pivot to MSP
6:18 Service Over Shiny Tech
10:26 Pricing Transparency & Relationships
24:32 Pandemic Pivot: Remote & Virtual Events
33:49 Marketing, Marketing, Marketing
44:54 AI & Copilot: First-Inning Opportunities
54:24 MSP Titan Questions

Connect with Damien and Michael:
Damien: https://www.linkedin.com/in/dstevens
Michael: https://www.linkedin.com/in/michaelagoldstein/

📺 Watch on YT: https://www.youtube.com/@mspmindset

What does it take to grow an MSP to $96M in under six years?

Maryann and Jason share the raw, real, and sometimes chaotic journey from launching their business with two people and two cell phones to becoming one of the fastest-growing MSPs in the country. Their story is packed with hard lessons, bold risks, and relentless focus on values, trust, and service. If you're an MSP owner or tech leader looking to scale, this episode is your blueprint.

Connect with Damien, Maryann, and Jason:
Damien: https://www.linkedin.com/in/dstevens
Maryann: https://www.linkedin.com/in/maryann-pagano-62293657/
Jason: https://www.linkedin.com/in/jason-caparoso-b8036114/

📺 Watch on YT: https://www.youtube.com/@mspmindset

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In this week's episode, Damien digs into how Ben Debow, CEO of Fortified Data, scaled a niche, database-focused MSP to 50+ staff with near-zero turnover (accomplished this after one crucial hire), mid-market ($1 B+) clients and a culture that prizes unique abilities—all while having the time to start up a new SaaS business.

Chapters:
0:00 - Intro
1:23 - How he started Fortified Data
9:51 - Who's his ideal client?
13:02 - Embracing remote culture
14:41 - Culture - solving the turnover problem
26:44 - Culture - neurodivergent hires
44:40 - Freeing up his time by hiring a President
53:23 - Having an abundance mindset
1:02:04 - His SaaS company
1:10:41- MSP Titan Questions

Connect with Damien and Ben:
Damien: https://www.linkedin.com/in/dstevens
Ben: https://www.linkedin.com/in/bendebow/

📺 Watch on YT: https://www.youtube.com/@mspmindset

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Is your MSP stuck circling the same revenue ceiling? Greg Zimmerle smashed his by doubling sales in four years—all from a mindset shift. Live from Pax8 Beyond, Damien unpacks Greg’s step-by-step shift from “chaos operator” to high-growth CEO. If you’re an MSP owner hungry to scale past your current ceiling, this conversation is for you.

Connect with Damien: https://www.linkedin.com/in/dstevens
Connect with Greg: https://www.linkedin.com/in/greg-zimmerle/

📺 Watch on YT: https://www.youtube.com/@mspmindset

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In this episode, Anderson Technologies’ Managing Partner Farica Chang reveals how she rocketed from $12-an-hour proofreader to co-owner, doubled headcount to 30, then weathered a brutal revenue cliff when two PE-backed clients pulled back. Hear the tactics, mistakes, and mindset shifts that kept her team—and culture—alive.

Chapters:
0:00 - Intro
1:14 - Getting into Anderson Technologies
8:00 - Her journey to becoming partner
22:30 - From 15 to 30 team members under her leadership
30:50 - Losing 50% of revenue from two clients
36:45 - Learning to let go and trust the team
55:03 - MSP Titan Questions

Connect with Damien and Farica:
Damien: https://www.linkedin.com/in/dstevens
Farica: https://www.linkedin.com/in/farica/

📺 Watch on YT: https://www.youtube.com/@mspmindset