IT Business Podcast Episodes

I sit down with Dan Spray from Precision IT to unpack how he took a small Nebraska computer shop and turned it into a nationwide MSP anchored by multiple business units and a new venture studio model. We talk about recurring revenue, no‑contract client relationships, and how he’s spun real‑world client problems into standalone companies under the Click Theory Capital umbrella.

Ray Cline from Tech Knowledge Worldwide joins me to unpack how an MSP-led community is transforming the original Ronald McDonald House in Philadelphia, and why technology is always the last thing funded—even for major nonprofits. We also dig into Ray’s consulting-first approach to MSP services and how he consistently saves clients more money than they spend with him.

NSITSP just hit its five-year mark, and I break down why this professional society still matters for MSPs, IT consultants, and service providers who want a real voice when security headlines, compliance rules, and industry standards start to shape how we work. The organization has grown from a grassroots response to unfair blame on “the IT people” into a formal professional society with elected leaders, active committees, and a clear mission to advocate for our profession, educate both members a...

I kick this one off with a real-world vendor story from my own MSP, talking through changes at Intermedia, CORE program fees, and what those decisions mean when you’re trying to protect margins while keeping clients fully supported. From there, I roll into a quick “know your network gear” segment that breaks down hubs, switches, modems, routers, firewalls, and Wi‑Fi access points in plain language you can use to train your team and design more secure, reliable networks. Then I bring on Paco Leb...

Ann Cloyd, CEO and co‑founder of Deep Tech Inc., joins me to share how she took a Mac‑focused niche supporting New York art galleries and turned it into a 30+ person, dual‑platform IT services company serving both Mac and Windows clients. She walks through why she positions Deep Tech as an outsourced IT department instead of “just an MSP,” how staying hands‑on with clients and committing to on‑site visits has built long‑term relationships and word‑of‑mouth growth, and why acquisitions became her...

Shadow IT and shadow AI are already inside our client environments, and in this conversation with Stanley Louissaint I dig into how MSPs can move from “roadblock” to trusted guide when users roll out tools without us. We also walk through real-world stories—from DIY law firm apps to interns shipping code with Claude—and wrap with practical OneDrive and sync configuration tips you can put into client environments today.

I open up about what’s been happening with my family, how it’s affected my focus, and why I’m choosing to put family first while still showing up for the MSP community. I also own up to some recent missteps around ThreatLocker, Microsoft updates, vendor calls, DNS changes, and even past data loss, using them to talk about accountability, respect, and culture in our industry.

I bring Mike Smith into the live studio to swap stories from the trenches about Adobe chaos, ISP contracts gone sideways, and a small office crippled by needless VLANs. Along the way, we share the tools, tactics, and talking points we use to keep clients secure without letting vendors quietly run the network for us.

Melanie Curtis and I dig into what it really takes to pivot from a “dream job” into coaching and speaking, without sacrificing family, fun, or your sanity as a business owner.

Melanie Curtis and I dig into how her world record skydiving career translates directly into how we handle risk, fear, and growth in our IT businesses. We talk about moving on from a “safe” job, planning big transitions, and why lasting MSP success comes from discipline, discomfort, and years of consistent work.

I sit down with ScalePad’s Ryan Sigouin to unpack how Lifecycle Manager’s new SaaS management gives MSPs real visibility into client cloud app usage, spend, and unused software—without adding another heavy agent to your stack. We also dig into ScalePad’s API-first, AI-enabled roadmap, including CSAT, NPS, and alignment tools designed to help MSPs build better QBRs and grow inside existing accounts.

I sit down with ScalePad’s Ryan Sigouin to unpack how Lifecycle Manager’s new SaaS management gives MSPs real visibility into client cloud app usage, spend, and unused software—without adding another heavy agent to your stack. We also dig into ScalePad’s API-first, AI-enabled roadmap, including CSAT, NPS, and alignment tools designed to help MSPs build better QBRs and grow inside existing accounts.

Victor Lopez from FlexPoint joins me in Salt Lake City to walk through how MSPs can streamline billing, collections, and payments without blowing up their QuickBooks workflows. We dig into same‑day ACH funding, flexible client financing, and new AI voice agents that take those awkward “you’re past due” calls off your plate.

I sit down with Gene Kim from Absolute Security to dig into how their firmware-embedded platform keeps MSP tools installed, self-healing, and recoverable—even when the OS is toast. We also talk about their Pax8 launch, why MSPs matter so much to their strategy, and how this changes the way we think about security, business continuity, and asset management.

I dig into real-world MSP stories, from fixing “just the Wi-Fi” for a court reporting client to wrestling with a digital logger at a small airport, and I share why I lean on Windows tools like netstat and NBTSTAT when you don’t have fancy test gear handy. I also draw a hard line on vendor etiquette, calling out aggressive outreach, hidden billing, broken partner portals, and the need for respectful, grown-up partner relationships.

Kim Simmonds from Cloud Contracts 365 and Law 365 joins me at Pax8 Beyond 2026 to break down how MSPs can use AI for contract review without trusting their entire MSA to uncounseled tools like Claude or Copilot. We dig into lawyer-verified templates, MSP-specific playbooks, and real-world examples where “AI contracts” quietly turned three‑year deals into 30‑day rolling time bombs that wreck valuation and revenue.

I sit down with Ramsey Sahyoun from Evergreen to unpack how his team acquires MSPs, keeps them independent, and still drives serious growth across more than 120 firms worldwide. We get into valuations, deal criteria, ERP expansion, and where AI and workflow automation are already moving the needle for MSPs.

I sit down with Ryan Walsh at PAX8 Beyond in Salt Lake City to break down the SMB Pulse Report, why so many small business AI projects stall out, and where MSPs can actually turn AI into real outcomes instead of hype. We get honest about partner feedback, trust, and what it really takes for MSPs and vendors to become customer zero and win that first secure, profitable AI agent with clients.

I’m joined by GTIA’s Dan Wensley and MJ Shoer live at Pax8 Beyond to break down why GTIA and ChannelCon 2026 in San Diego matter so much for MSPs right now. We get into industry self‑regulation, AI innovation awards, and the real ROI MSPs are seeing from GTIA membership, research, and cyber resources.

Sat down with Cynthia Schreiner at Pax8 Beyond to unpack her journey into channel engagement, how Pax8’s community and academy support MSP growth, and the very real ways AI is reshaping how she runs 90+ events a year.

I sit down with Gene Reich from Traceless to dig into how MSPs can lock down business communications, verify identity at the helpdesk, and stop high‑risk transactions from turning into wire fraud nightmares. We get real about voice AI phishing, data hygiene, and the practical ways Traceless plugs into your stack through Pax8 without blowing up your processes or your pricing.

David Schwartz, CEO of Pia, joins me at Pax8 Beyond in Salt Lake City to dig into how MSPs can use AI‑driven automation to scale service delivery without burning out their techs. We cover PiaChat for Teams, smart forms, automation hubs, and why “vibe‑coding” your own tools is usually a bad bet.

Regulations are shifting fast, and this NSITSP update walks through the new cyber laws, safe harbor protections, right to repair battles, and tax trends that are already reshaping how we run MSPs and IT service businesses. I break down what’s happening, why it matters, and where NSITSP is stepping in so you’re not blindsided by policy changes at the state level.

Brook Lee from Rev.io joins me at Pax8 Beyond to talk about what a PSA should really do for an MSP, and why leadership, vendor relationships, and community education matter way more than feature sheets.