IT Business Podcast Episodes

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.

Synology made some big moves that hit MSPs right in the wallet, so I break down what changed, why trust is taking a hit, and what I’m doing about it in my own stack. I also walk through managed switch best practices and share my real‑world take on the Fluke LinkIQ Duo versus the NetAlly tools I actually carry in my bag.

I’m live at Pax8 Beyond 2026 in Salt Lake City with Acronis Channel Chief Officer Alex Ruslyakov, breaking down how Acronis is protecting GenAI, simplifying MSP operations, and helping partners scale smarter. We talk AI security, automation, CyberFrame, and a new partner program that bakes business growth tools right into the Acronis platform. From there, we zoom out to the bigger Acronis platform strategy: automation, agentic AI, third‑party integrations, and a unified console designed to cu...

Shadow AI and Copilot can leak your clients’ salaries and sensitive data long before an attacker hits the network, and in this conversation I dig in with Check Point’s David Meister on how MSPs can actually secure AI agents, browsers, and end users without swapping out their whole stack.

I sat down with ConnectWise Chief Product and Technology Officer David Raissipour at Pax8 Beyond to talk about the new ConnectWise platform, agentic AI, and how they’re backing it all with a 15‑minute SOC SLA for MSPs and MSSPs. We get into culture change, product execution, and what it really takes to deliver security outcomes without over‑promising to partners.

I sit down with consultant and “kick-ass marketer” Megan Killion to unpack why so many MSPs chase leads, revenue, and endpoints while staying miserable and barely profitable. We dig into building a business you’d actually buy, diagnosing where growth is really stuck, and using real client conversations and AI to drive intentional, sustainable marketing.

I sit down with Nick Ross from Cloud Capsule to talk about how he’s helping MSPs automate Microsoft 365 security, compliance, and remediation at scale. We dig into his journey from Pax8 and the T-Minus 365 YouTube channel to building a platform that turns painful tenant assessments into fast, repeatable, evidence-driven security workflows.

AI is no longer something MSPs should be planning for someday. It's happening right now. Rob Rae joined me at Pax8 Beyond 2026 to discuss how partners are turning AI from a talking point into a business opportunity and what comes next for the channel. From MCP servers and AI agents to partner growth and industry transformation, this conversation offers a practical look at where MSPs can find value in a rapidly changing market.

Pax8 Beyond delivered a clear message that MSPs need to move from managing endpoints to managing intelligence, and I break down what that actually looks like in the real world. I also share my favorite (and not-so-favorite) swag from the show and walk through practical network performance testing strategies you can use without buying expensive gear.

I’m joined by longtime friend of the show Tim Golden as we unpack how he built Golden Iris, a platform that captures your ideas, organizes them, and turns them into on-brand content without adding another dozen tools to your stack. We talk about AI, workflows, approvals, and what it really takes for MSPs and agencies to get their marketing out of their heads and into the world.

I sit down with Robin Robins to tear apart the myths MSPs believe about marketing, pricing, and growth, and dig into what actually moves you from referral-dependent to building a profitable, sellable business. We get real about self-doubt, bad packaging, weak follow-up, and why you must own your strategy instead of bouncing from one “easy button” vendor to the next.

Andrew Hartman, founder of Time Boss, shares how he built a framework to help MSP leaders escape burnout and regain five hours per week while reducing stress by treating time like cash instead of credit. His system delivers a 40% productivity jump by creating peace instead of chaos, even for solo techs drowning in client fires.

Most MSPs roll out new services by buying a shiny tool, slapping on a price, and then wondering why nobody buys. I brought back industry legend Rayanne Buchianico from ABC Solutions to walk through a better playbook, using her Goldman Sachs 10,000 Small Businesses lessons to help you assess risk, define customer pain, and know if a service will actually make you money before you launch it.

I bring Chris Skipworth from Passpack on to talk candidly about the invoice you never want to receive, the true downstream cost of a breach when your MSP is at the center of your clients’ credential universe. Chris walks through how Passpack evolved from a consumer tool into a B2B zero knowledge password and credential manager that simplifies policies, improves accountability, and actually gets adopted by normal business users.

I sit down with Tim Fitzpatrick from Rialto Marketing to talk about why most MSPs don’t really have a lead problem, they have a broken marketing engine problem. We get into strategy vs tactics, niching, referrals, and how to stop leaving money sitting in your existing client base.

I’m recapping my Money, Marketing, and Growth series with five core pillars every MSP needs to shore up before chasing leads, from fixing your foundation to protecting margin and using AI the right way. Along the way I share real client wins, an FBI flash alert, shout outs to ThreatLocker, TruGrid, OneStream, Domotz, and some fun behind‑the‑scenes plans for conferences, reviews, and an all‑MSP August.

I sit down with Justin Maxwell from Big Life Financial to dig into the money side of running an MSP, from proactive tax planning to getting your accountant, advisor, and legal team actually rowing in the same direction. We talk about picking a real wealth target, escaping scarcity mode, and turning your business into an asset that outlasts your ticket count.