ACES Conference 2026 Episodes

I sit down with Richard Wingfield, owner and head geek at Envision Design, to unpack how he turned a 30‑year Mac‑focused consultancy into a cross‑platform MSP with a clear path to retirement via a CTO buyout. We get into valuations, client transition, mastermind lessons, and why working yourself out of a job is the smartest thing you can do as an IT business owner.

I grab hallway conversations with Allen Edwards and Tim Fitzpatrick to unpack how MSP owners can get unstuck, build better relationships, and unlock hidden revenue in the business they already have. From learning how to be a normal human in a networking room to spotting fast track revenue opportunities, this one is all about getting back to fundamentals that still work.

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.