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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!
116 Episodes
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"Shadow AI" is the new frontier of risk, and your clients are likely already using it without your guidance. Dan and Alex Farling discuss why MSPs must lead the AI charge by first mastering these tools internally to drive efficiency and security. Discover how to transition your technicians from simply closing tickets to spotting high-level business vulnerabilities before they become breaches.
MSPs who stop evolving risk getting left behind. In this episode of the[STACK], Dan Tomaszewski welcomes Miles Walker from Kaseya to discuss cybersecurity trends, the rise of phishing and downtime risks, and why security services continue to be one of the biggest growth opportunities for MSPs. They also explore new developments in the Kaseya ecosystem, including the addition of INKY and the launch of a new partner community. If you're thinking about how to future-proof your MSP, this conversation is packed with insights.
Most MSPs don’t have a technical problem. They have a positioning problem.This episode dives into speed-to-contact, data-driven prospecting, and why being first with meaningful insight dramatically increases your chances of winning. If growth has felt harder lately, this conversation will reframe how you approach sales in 2026.
CMMC is a marathon, not a sprint, and if you're waiting for your clients to bring it up first, you're already behind the curve. In this episode, Chris Henderson from Huntress joins Dan to debunk the "magic wand" compliance myths and explain why readiness is a 12–18 month journey of deliberate work. Learn how the final rules for Security Protection Assets (SPA) have changed the game, allowing smaller MSPs to support DoD clients without getting buried in FedRAMP costs. Stop reacting to deadlines and start leading the conversation with confidence.
You read the articles. You hear the interviews. Sometimes you think, “I could add more to this conversation.”This episode with CJ Arlotta dives into how MSPs can move from silent operators to recognized thought leaders by building real relationships with journalists, contributing expertise, and owning the AI and cybersecurity narrative.Stop hiding in plain sight.
Attackers know your backup is your escape hatch, which is why they’re targeting your storage keys before they ever hit the production data. Josh Flores breaks down the uncomfortable questions MSPs need to ask about their own internal hardening, MFA, and immutable storage. Learn how to practice what you preach so your own internal systems don't become the weakest link during a client crisis.
Migrating your clients from on-prem SharePoint doesn't have to be a fire drill; it’s an opportunity to modernize their business while driving revenue for yours. In this episode, Colin Hogg and Ramiro Millan from Movebot explain why the "junk drawer" approach to data migration is a mistake and how to use this transition to clean up permissions and legacy files. Discover a structured playbook that moves data at scale—up to 500GB per day—without the need for constant technician babysitting.
Why do most MSPs avoid Technology Business Reviews like the plague? In this episode of the[STACK], Brian Doyle from vCIOToolbox joins Dan Tomaszewski to break down the blockers that keep MSPs from staying consistent with their strategy. Learn how to ditch the "thud factor" of heavy technical reports and use intelligent automation to cut your TBR prep time from hours down to just minutes.
Most cyberattacks don’t start with malware — they start with reconnaissance. In this episode of the[STACK], Dan sits down with Joshua Mohr of ThreatLocker to break down how attackers map MSP environments long before a breach ever happens. Learn how network control and Zero Trust can stop threats at first contact — before they even connect.
Join Dan Tomaszewski and guest Mike DePalma of OpenText as they discuss the massive influx of enterprise vendors moving into the IT channel. Mike explains why global giants are finally prioritizing the SMB market and how MSPs can leverage this shift to gain more influence and better support. This session provides a tactical blueprint for taking control of your vendor relationships and using account managers as strategic assets to drive operational efficiency.
Email is still the #1 entry point for attackers—and misconfiguration is doing more damage than malware. Dan and special guest, Cody Ekle, break down why so many MSPs are scoring poorly on email health checks, even when they think everything is set up correctly. This episode shows how hidden email gaps can cost you security, trust, and even clients.
Dan Tomaszewski sits down with Pete Busam, Founder of Equilibrium Consulting, to explore the shifting landscape of MSP marketing and sales. Pete explains how to leverage AI as an enabler rather than a "lazy" replacement for your brand voice, while stressing the importance of getting back to human-to-human basics. Learn how the most successful MSPs are using data and discipline to align their brand message with the outcomes that drive long-term client loyalty.
The AI buzz is loud, but clarity is rare. In this episode, Dan is joined by Pax8's Dave Wiseman, and they unpack what AI actually means for MSP operations, service delivery, and client relationships. From simple automation to long-term strategy, they share practical ways MSPs can start small and scale smart. If you want actionable insight instead of hype, this episode delivers.
Passwords are still the #1 attack vector — and MSPs are paying the price. In this episode of The Stack, Dan Tomaszewski sits down with Danny Obaseki of KZero to break down why MFA isn’t enough anymore. We dig into passwordless authentication, how it reduces risk and tickets, and why identity is now the frontline of MSP security.
Are you losing money through missed billing? Andy Cormier joins Dan Tomaszewski to detail the shocking revenue leaks caused by manual add-on and license management, showcasing how "Universal Billing" eliminates this profit drain. Andy, an MSP veteran, also explores the need to integrate daily Microsoft tasks directly into your core RMM/PSA to streamline operations and deliver a consistently better client experience.
Your clients think they aren’t using AI—but they already are, and most of it is happening in the shadows. Dan and Joshua Liberman unpack how AI is slipping into everyday workflows, why that creates massive security and compliance risks, and how MSPs can turn this chaos into deeper client engagement. They explore the rise of weaponized AI, evolving business expectations, and what MSPs should be doing right now. This conversation will change how you approach AI with your clients.
What happens when an MSP stops chasing payments and starts automating them instead? Dan and Adam Crandall dive into the mindset and mechanics of fixing cash flow once and for all. They explore how early invoicing, automated reminders, and smarter payment options can reduce DSO dramatically. If predictable revenue and fewer Friday-night billing sessions sound good, tune in.
Are AI-driven compliance tools promising you the world? In this episode, we talk with the founders of Blacksmith InfoSec to cut through the baloney and find out what AI can really do for MSP compliance. Learn why automation can accelerate your journey, but why a human must always remain in the loop to prevent blind spots, non-deterministic risks, and costly hallucinations in security auditing.
AI adoption, SaaS overload, and surprise offboarding requests are creating new attack paths MSPs can’t see. Dan and Nathan Archie discuss why identity governance is now mission-critical and how providers can protect clients from massive liability. Plus, they reveal how MSPs can turn governance into a scalable, profitable new service.
AV and EDR are essential, but they’re no longer enough on their own. Dan sits down with ThreatLocker’s DeShawn Dortch to explain how application control strengthens your security posture without adding work or frustration for your team. From learning mode to end-user experience, they cover the practical realities MSPs face every day. It’s a clear, actionable breakdown you can apply immediately.
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