IT Business Podcast Episodes

I sit down with world record skydiver and keynote speaker Melanie Curtis to unpack what jumping out of planes at scale can teach us about fear, growth, and leading a business when the stakes feel sky-high. We connect her decades of skydiving and coaching with the everyday reality of MSPs and IT business owners navigating tough clients, burnout, and high‑pressure decisions.

Live from the ACES Conference in Minneapolis, I sit down with longtime friend and Apple MSP veteran Brian Best to dig into what makes this business‑focused Apple event so different from the typical tech show. We talk real‑world lessons from twelve years of ACES, scaling a Mac‑centric MSP, and how Windows and Apple shops can actually win together instead of avoiding each other’s worlds.

Clients are not firing MSPs because of bad tools; they are walking away because they feel ignored, unseen, and “not important.” Lisa Shorr joins me to show how better soft skills, branding, and intentional AI use can turn your team into high‑trust, client‑facing pros who keep MRR growing instead of leaking out the back door

I sit down with my friend Colin Knox from Gradient to talk about where MSPs are leaking revenue, how Managed Billing Reconciliation actually protects your margins, and why so many of us still struggle to show up consistently in our marketing. We also get real about AI-driven content, social media “autopilot,” and the lies we tell ourselves about growth as MSP owners.

In this episode, I kick off our Money, Marketing & Growth Month with a candid conversation with Laura Johns, founder of The Business Growers and host of the “Get More MSP Leads” podcast. We get real about why so many MSPs keep throwing money at random tactics—Google Ads, canned social, cold-calling vendors—without ever building a true growth engine underneath.

I walk through a real client project that pushed me into the cloud with VULTR instead of AWS or Azure, and then pull back the curtain on what’s really happening with vendors, margins, commissions, and partner programs in our world. Along the way, I talk about SLIDE vs Datto, AppRiver’s partner changes, solo tech “trunk slammer” stigma, Money Marketing and Growth Month, and how I’m keeping MB Systems steady while the industry keeps shifting.

I sit down with Brian Higgins from Aditum Connect to break down how MSPs can turn multi-tenant buildings into high-margin, white-labeled ISP revenue without becoming full-blown telcos. We walk through the business model, contracts, tech stack, and real-world numbers so you can see exactly how this becomes a long-term, low-touch recurring revenue stream.

Hitting 1,000 episodes gave me the perfect excuse to bring back some of the original Podnutz Pro crew, look at how far the MSP and IT world has come, and share some real talk about burnout, work–life “balance,” and sticking with this crazy business. We get honest about the basics too—why DHCP, DNS, and real troubleshooting still matter, even in a cloud‑first, AI‑obsessed world.

I’m joined by Brian Weiss from iTech to dig into the real reason Copilot is “failing” for so many MSPs and clients: adoption, not technology. We walk through AI readiness, data governance, Purview, and how MSPs can turn Copilot into a strategic business tool instead of another line item.

A candid conversation with Larry Cobrin from MSPCFO on what your PSA is really telling you about client profitability, contribution per hour, and which customers you should probably fix or fire. We also dig into AI, private equity expectations, and why bad data can still wreck your decisions even with the best tools.

Most MSP owners wait too long to get serious about an exit, then wonder why their “baby” doesn’t get the valuation they expected. In this conversation with Amy Babinchak, we dig into her book “20 Questions Every Owner Asked Before Selling Their MSP” and break down what really drives value, what kills deals, and how to treat your MSP like the nest egg it actually is.

Vendors love to pitch “better, cheaper” tools, but Tom Wyant and I break down the real, often hidden cost of changing your MSP stack, from migration and data ownership to client disruption and staff confusion. We talk honestly about when it actually makes sense to switch, why I’ve stuck with my N-Able‑centered stack plus ThreatLocker and Liongard, and how to evaluate tools without blowing up what already works.

I sit down with N-Able Head Nerds Ben Lee and Marc‑Andre to talk about how MSPs can move beyond “another AI chatbot” and start building real services, automation, and governance around AI. From internal efficiencies to client-facing AI packages, we dig into what mature MSPs are actually asking about, and how Enable is trying to meet them there.

Michael DePalma, OpenText's VP of Business Development, dives into their massive channel revamp after a full year, covering Secure Cloud upgrades and killer MSP partnerships like Hats AI. He breaks down real MSP pain points from 2025 and how OpenText listens to deliver value without the salesy BS.

I sit down with Robert Johnston from N-able (formerly Adlumin) to talk about how MSPs can realistically deliver SIEM, MDR, and true business resilience without trying to build their own 24×7 SOC. We get into the talent gap, compliance-driven security, and why pre-breach hardening and post-breach recovery need to be just as baked into your stack as endpoint tools.

Lewis Pope and Stephanie Hammond from the N‑able Head Nerds team join me live at Empower in Fort Lauderdale to talk about shifting from selling tools to leading with business resilience, governance, and real executive conversations your clients actually care about. We dig into CMMC, compliance, EBRs, and why MSPs need to stop hiding behind tech jargon and start stepping up as advisors.

Frank Colletti from N‑Able joins me live at Empower 2026 in Fort Lauderdale to talk about AI, UEM, security, and how MSPs can turn all of this innovation into real, profitable services. We dig into N‑Able’s partner-first strategy, global Empower roadshow plans, and how peers and head nerds are shaping the next wave of MSP growth.

I sat down with Mike Wise from Clockwork Networks and we got into what it really looks like to run a lean, highly efficient MSP without chasing headcount. We covered niching, compliance, and how smart standardization can outperform traditional growth models.

In this episode, I sit down with Dawn and Dave Sizer to walk through the messy, honest reality of running and rebuilding a growing MSP. We talk about what happens when you think you’re mature and buttoned up… until one key person leaves and exposes every crack in your processes, documentation, and service delivery. If you’re an MSP owner, IT leader, or service manager trying to scale without losing your mind, this conversation is going to hit close to home.

In this episode, I sit down in-studio with my good friend Tim Coach from Cynomi to talk about how MSPs can finally get cybersecurity, vCISO services, and compliance under control without drowning in frameworks and spreadsheets. We dig into what Cynomi actually does for partners, how it turns risk assessments into clear action plans, and why it helps MSPs package and price security in a way clients actually understand. If you’ve ever struggled to move beyond “tools and alerts” into real security outcomes, this one’s for you.

If you’re still turning off noisy alerts and hoping your basic patching policies are “good enough,” this episode is your wake‑up call. Frank and I talk tough love for MSPs: knowing every IP, understanding real exploitability, documenting what you do and don’t cover, and having the guts to walk away from clients who refuse to secure their environment.

Rick Harber joins me to break down how his MSP uses automation, AI, and solid process to triage tickets in seconds, report real value to clients, and grow without constantly hiring more techs. We also swap real‑world stories about Liongard, DNS disasters, billing for Active Directory accounts, and how to turn tools into true IT solutions instead of just more noise in your stack.

I caught up with Jared Casner of Blacksmith InfoSec after MSP IT Expo to unpack what’s really working for MSPs around security, compliance, and client education. We talk about starting small with CIS IG1, mapping your existing stack to NIST CSF, and using QBRs to show progress instead of just ticket counts. If you’re wrestling with pricing, packaging, and monetizing cybersecurity and compliance services, this conversation gives you concrete strategies you can put to work fast.

I sit down with Jerem Morris from Datatek to unpack how he built a seven‑figure, security‑first MSP in one of the most competitive markets in the country. We dig into people‑first service, all‑in pricing, cybersecurity stacks, 3‑2‑1‑plus backup, and why almost all his managed services business comes from referrals, not flashy marketing. Jerem also shares how QBRs, AI guardrails, and real‑world training keep his clients protected, compliant, and calling him before they make big technology decisions.