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Welcome to the[STACK], the ultimate podcast for Managed Service Providers (MSPs) looking to elevate their game and stack up on success. Hosted by MSP veteran, Dan Tomaszewski, this podcast is your go-to resource for mastering the perfect blend of people, business, and technology in the MSP world.
Each episode, we delve into the intricacies of the MSP landscape, featuring interviews with top channel vendors, dissecting real-world MSP scenarios, and sharing actionable insights to help you build a thriving business.
Be sure to subscribe to keep up with the latest episodes!
Each episode, we delve into the intricacies of the MSP landscape, featuring interviews with top channel vendors, dissecting real-world MSP scenarios, and sharing actionable insights to help you build a thriving business.
Be sure to subscribe to keep up with the latest episodes!
94 Episodes
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The MSP industry isn't just evolving—we are rewriting the playbook. Greg Jones of Kaseya joins Dan to discuss the power of community and why collective collaboration is key to survival and success. Learn why a vendor relationship must be more than transactional, and how to challenge your partners to unlock underutilized resources like MDF funds and business support programs.
Before clients see your tech skills, they see your quote. Dan and Brian Laufer dive into how the quoting process shapes the way prospects perceive your MSP — and why it’s time to move beyond spreadsheets and static PDFs. Learn how to test quoting tools the right way, simplify your workflow, and deliver quotes that close deals faster.
Hope is not a strategy, and failure is your greatest teacher. Mary Hamilton offers a candid, granular look at where MSP processes often break down (even a year later) and the importance of inspecting what you expect. Discover why allowing customers to point out your vulnerabilities builds trust, and how a cultural shift towards accountability is the only way to genuinely deliver and execute.
If managing Microsoft 365 tenants feels like herding cats, this one’s for you.Derik Belair of Augmentt joins Dan to break down how to rein in policy chaos, improve security, and turn standardization into serious margin gains.
Smart MSPs don’t guess what clients want — they study the data.In this episode of the[STACK], Dan Tomaszewski talks with GTIA’s Carolyn April about the latest SMB Technology & Buying Trends Report. Discover what’s driving purchasing decisions, how tariffs and economic uncertainty are reshaping budgets, and why MSPs have a massive opportunity to lead clients through AI and cybersecurity adoption.Access the report here: https://go.everythingmsp.com/SMB-Tech-Trends
Migrations don't have to be a source of stress and sleepless nights for your team or your clients. Colin Hogg joins Dan Tomaszewski to explain how a defined process and the right tools turn complex moves into a profitable, confidence-building service. Discover why testing with pilot users and transparent, visible reporting are the keys to reducing surprises and building long-term client trust.
The process of moving a client is often messy, unsecure, and done in "dark rooms" through back channels. We discuss why MSPs should stop risking bad behavior and start treating client offloading as a strategic, secure business move. Matt introduces the MSPX marketplace, which provides structure, transparency, and escrow to ensure a smooth, monetized transition. Discover how this solution allows MSPs to better align their services, scale into new geographies, and reinvest client revenue.
Search is shifting from click-based SEO to AI-driven AEO and GEO, demanding authoritative, conversational answers. Join Dan Tomaszewski and Pete Busam to learn how to adapt your MSP's content to win the vital "zero-click moment" and be surfaced as the trusted source by AI engines like ChatGPT and Google. They break down the necessary pivot: from talking about solutions to focusing on persona-based outcomes and building a citable digital footprint.
Comfort was killing their momentum. Growth changed everything.Hear how Lisa and Brian Johnson of ABC Technologies shifted from “good enough” to intentional growth — and how that mindset helped them scale faster, hire smarter, and build a stronger MSP.
Adding another security tool won’t make your MSP safer — changing your process will. Dan Tomaszewski talks with Pax8’s Rich Richardson about what it means to “live security,” not just sell it. Hear how to get owner buy-in, build a culture of vigilance, and make security your daily habit.🚨 Special Offer for Listeners! Be among the first five respondents to win a 1-hour coaching session with Pax8 Security experts! This exclusive session will help you explore how to build and scale your security offerings.📧 To enter: Send an email to slsupport@pax8.com with "Pax8 Security Coaching interest" in the subject line.Don’t miss this chance to level up your MSP game with expert guidance!
Every MSP owner hits a ceiling — often because they’re stuck doing everything themselves. In this episode, Jason Thomas of Jatag Solutions shares how hiring an operations manager was the game-changing move that freed him from bottlenecks and unlocked real growth.
Cybersecurity isn’t 9–5, and neither are the threats targeting MSPs. In this episode of the[STACK], Dan Tomaszewski sits down with former MSPs Chris Wanamaker and Steve Weber of Sophos to talk MDR, real threat hunting, and how MSPs can deliver better security outcomes without burning out their teams.
Clients don’t care if the ISP failed — they call you when the internet goes down. In this episode, Dan talks with Steve Copeland of RYTHMz about the “business in a box” solution that delivers reliable connectivity in minutes. Learn how hive bonding, enterprise-grade hardware, and an effortless MSP model can transform connectivity from a liability into revenue.
Seventeen years, multiple acquisitions, and one simple philosophy: treat clients like friends. Justin Esgar of Virtua Consulting reveals how his Apple-focused MSP scaled by embracing creativity, hospitality, and a business-first mindset. Discover how trimming costs, deepening client relationships, and thinking differently led to exponential growth.
Slow proposals kill deals. If you're tired of spending hours logging into different distributors and manually building quotes, this episode is for you. Dan and Brian Laufer of QuoteWerks dive into how the right quoting tool can save you massive amounts of time and turn quoting from a bottleneck into a competitive advantage. Discover how QuoteWerks Web, with its new AI features and key integrations, can help you get accurate, margin-smart proposals out the door faster and win more business.
QBRs shouldn’t be glorified status updates—they should be strategy sessions that drive outcomes. In this episode of the[STACK], Dan Tomaszewski and Brian Doyle of vCIOToolbox dig into how MSPs can streamline QBRs, tie them to business goals, and add GRC into the mix. Learn how the right process and tools can transform your role from IT provider to trusted advisor.
Broadcom’s VMware acquisition has shaken the virtualization world, leaving MSPs scrambling for answers on costs, licensing, and long-term strategy. In this episode of the[STACK], Dan sits down with Mason Giles of Comet Backup to unpack what these changes mean for MSPs. From the rise of Proxmox to backup best practices that save time, storage, and sanity, this conversation is packed with insights you don’t want to miss.
It’s not the technology that makes MSPs sticky—it’s how deeply they understand their clients’ business. Tracy Pound of Maximity joins Dan to share how her company weathered a near-collapse during COVID and emerged with a more sustainable model. From embracing ERP solutions to embedding themselves into their clients’ operations, Tracy reveals the power of caring about outcomes, not just uptime.
What if the secret to operational efficiency and scalable security isn't just another tool—it's a fundamental change in how you operate? In this episode, Josh Hohbein of CentrexIT reveals his team's breakthrough moment of aligning to a cybersecurity framework. He explains why this strategic move is a game-changer and shares the one piece of advice every MSP needs to hear: "Don't let perfect be the enemy of good."
Not your average cybersecurity talk — this is the story of a hacker who flipped the script. Dan Tomaszewski talks with Jesse Tuttle, Chief Hacking Officer at AP2T Labs, about his past as a threat actor, his path to redemption, and the mission that drives his work today. From cyber wars to human trafficking takedowns, Jesse’s experiences offer MSPs a rare perspective on awareness training and protecting what matters most.
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