The Weekly Grind: Issue 01

👋 Welcome to the grind

Hey, John here. If you’re in the MSP community, this is your new Friday ritual. Every week, I’ll be sharing what I’m seeing in the industry: from LinkedIn takes to event recaps to the tips that are actually helping MSPs win.

My goal? Help you think bigger, move faster, and avoid the noise. Let’s get into it.

🎤 MSP Geek Con 2025: My Recap

MSPGeekCon was an absolute hit, and hands down one of the best events out there for technicians looking to find a real sense of community. If you’re in the trenches of MSP work and want to surround yourself with people who truly get it, this is the event to be at.

The conference grew out of the MSPGeek community, which originally started as a gathering place for MSP technicians (back when many of us were still proudly calling ourselves “break-fix”). I wasn’t part of that original crowd, but I found my way in when I launched Saaslio to serve the MSP space. That was five years ago, and from day one, this community welcomed me like I’d always been part of it.

What’s incredible about MSPGeek is that it’s not just a loose group of people chatting about tech. It’s a robust, thriving community held together by a team that truly cares. The event had its behind-the-scenes hiccups like any live show, but you’d never know it as an attendee. That’s thanks to the powerhouse admin team: Mendy Green, Kyle Spooner, Ashley Cooper, Kevin Dutkiewicz, Martyn Keigher, Darren White, Michael Priest, Kelvin Tegelaar, and Amanda Lachapelle. These folks are the glue that keep both MSPGeek and MSPGeekCon running like clockwork.

The tracks this year were top-notch and built specifically for the technician audience. This isn’t your typical conference geared toward execs and sales pitches. It’s for the people actually doing the work, solving problems, rolling up their sleeves, and living in the weeds. The vendor presence was more grounded too, with real product people ready to dive into the details. The result was a collection of unique talks, practical insights, and real conversations you won’t find anywhere else.

Eddie Chow nailed it during the Monday morning keynote. He summed up what MSPGeekCon is all about in one word: love. Love for our customers. Love for solving problems. Love for helping others without expecting anything in return. That’s what ties this community together.

That’s why I’ll be back in 2026—because of the love that flows through this community and the people who make it what it is. If you’re a tech looking for your people, this is where you’ll find them.

✈️ Did you go to MSPGeekCon too? Hit reply and tell me your biggest takeaway.

☕️ Coffee Chats Recap: Community, Connection & the MSP Flywheel (Live from MSPGeekCon with Ashley Cooper)

Live from Orlando at MSPGeekCon, Ashley Cooper shared a powerful perspective on what real community means for MSPs—and why it's more than a strategy. Don’t miss the insights 👇

𝗪𝗵𝗮𝘁 𝗪𝗲 𝗟𝗲𝗮𝗿𝗻𝗲𝗱:
Community isn’t a marketing tactic—it’s human nature. Ashley Cooper illuminated how true communities grow from authentic needs, not business plans, and how MSPs can nurture this grassroots power through intention, consistency, and belonging. From IRC forums to MSPGeekCon, the evolution is clear: people show up for each other because it matters.

𝗕𝗶𝗴𝗴𝗲𝘀𝘁 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀:

• Community ≠ Strategy: Real community isn’t manufactured; it emerges when people find shared struggles and rally to solve them together.

• Measure What You Can, Feel What You Can’t: While ROI is tough to track, the ripple effect of helping “just one person” can be transformational.

• Small Groups = Big Impact: Micro-communities and “in-jokes” (like the now-famous MSPGeek boots) help scale authenticity while preserving intimacy.

• Lurkers Are Listening: Don’t mistake silence for absence—many find deep value in observing quietly until the moment’s right.

𝗥𝗲𝗰𝗼𝗺𝗺𝗲𝗻𝗱𝗮𝘁𝗶𝗼𝗻𝘀:

• Stay engaged between events through micro-interactions like follow-up posts, DMs, or casual digital meetups (yes, even a remote D&D session counts).

• Prioritize authentic follow-ups—ditch the generic emails and lead scans. Build real, human continuity.

• Give space for “quiet” community members. Assume impact even when it’s invisible.

Huge thanks to Ashley for showing us how to build communities that feel like home. Let’s carry that energy forward until the next GeekCon! 🧠💬

🎯 🎯Why I’m All In on GTIA (And Why You Might Want to Be Too)

Why? Because GTIA reminds me of the kind of community that helped me get my start in tech. It’s built on a mission that resonates deeply with me. GTIA empowers technologists from every walk of life, especially those with limited access, to break into the industry and thrive. In my own words, GTIA is about opening doors and lifting people up.

Now that the certification programs have spun off, GTIA stands at a crossroads. There’s a new identity to shape, and honestly, that’s exciting. The next chapter kicked off with a major announcement this week: Dan Wensley is stepping in to lead the charge.

If you’ve been around the industry for a while, you’ve probably heard the buzz and speculation about what GTIA might become after the split from CompTIA. I’ve had my own questions too. But never doubt. I know the team that’s still in place. They’re talented, mission-driven, and ready. With Dan stepping in as the new leader, I truly believe this is the moment GTIA steps into its next evolution.

I haven’t had the chance to meet Dan personally yet, so I won’t try to speak for him. But I can share the vibe I picked up this week at MSPGeekCon and from the conversations happening online. People are excited. Really excited. Dan has a strong track record, he’s accomplished a lot, and most importantly, he is one of us. He comes from the community and is here to serve the community. That matters.

With ChannelCon just around the corner, the timing could not be better. I can’t wait to see how this momentum plays out on that stage.

Looking ahead, it’s hard not to feel optimistic about where GTIA is heading. The recent appointment of Scott Barlow to the Board of Directors is a smart move. Internally, leaders like MJ Shoer and Tracy Pound continue to steer GTIA forward with clarity and openness. Sure, every transition comes with a few bumps and differing opinions. That’s normal. But I trust this team and I’m proud to support them as they move ahead.

If you’re heading to ChannelCon this year, let’s connect. The theme is Connect with Your People and Evolve with Technology. Let’s make that happen together.

Let’s keep building.

🎙️ I’m Live This Week

I’m going live May 15 with Jimmy Hatzell, CEO of Hatz.AI, to talk about how MSPs can monetize AI without losing focus on client value

Why this chat matters:
MSPs are under pressure to “do AI” — but how do you balance that with solving real problems for real people? Jimmy’s been deep in both sides: building AI products and running an MSP.

What you’ll hear:
• Where AI fits (and doesn’t) in a services business
• How to differentiate when everyone’s shouting “AI!”
• Avoiding tech-first traps and focusing on outcomes

🎧 Register here

🔗 Stuff Worth Clicking

• ConnectWise CEO: MSP Market To See ‘Double-Digit’ Growth Over Next Five Years

• Here Are The Emerging Technologies That MSP 500 Execs See Offering The Biggest Opportunities In 2025

• The IT trends 2025 industry report: why IT is long on challenges but short on time

📬 Hit Me Back

Were you at Geek Con? Have thoughts on AI, pricing, or tools I should check out? Reply and let me know—or tell me what you want to see in next week’s grind.