MSPs and accounting firms have a lot of shared DNA. My guest today thinks that accounting is paving the way for MSPs in AI adoption.  Peter McCarroll has spent over 30 years in public accounting, and he’s been helping other firm owners rethink how they price and deliver their work as AI takes over the…

Today we’re talking about something every MSP is running into right now: how do you let your team actually use AI without turning your ticket data into someone else’s training set. My guest today is Callen Sapien. Callen is currently building Synthreo, an AI infrastructure platform built specifically for MSPs and SMBs, and before that…

We’ve got a repeat guest on the show today. Alex Dow is back. Co-founder of Mirai Security, and currently an enterprise security architect for a large financial firm, and honestly one of my favorite people to talk security with. Alex has done federal security work, and securing the actual Olympics, now then a security consulting…

Josh Hobein, manager of cybersecurity and automation at Centrex IT, discusses how MSPs can be run like five-star restaurants by prioritizing service, empathy, and experience over mere SLA “checkbox” performance. Drawing on his background in restaurant management, he explains how hospitality skills translate to tier-one helpdesk and why culture is defined by what leaders tolerate,…

Evolve or Evaporate: Erik Bowles on MSP Branding, Anti‑Commoditization, and Human‑Led Marketing On the Evolved Radio podcast, Todd Kane interviews Erik Bowles about why many MSPs look identical online and how that commoditizes them into “line items.” Erik shares his background from early internet businesses to VAR/MSP-era engineering, MX Logic, and early Pax8, explaining that customers…

Automation as Core Strategy: Aarin Bailey on RPA, AI, and Scaling MSP Operations On the Evolved Radio podcast, Todd interviews Aarin Bailey, COO at Webit Services and former COO at MSP Bots, about treating automation as a core MSP operating strategy. Aarin describes how his automation focus accelerated around COVID by chaining PowerShell scripts, later…

Victor Lopez on Fixing Broken MSP Financial Plumbing with AI Todd interviews Victor Lopez, a former attorney and private credit professional at Blue Owl Capital who co-founded Flexpoint after seeing how clunky MSP financial tools were. Victor traces his “aha” back to Blue Owl financing Thoma Bravo’s 2018 acquisition of ConnectWise, which led him to…

Preparing to Sell Your MSP: Emotions, Valuation, Deal Structure, and Exit Planning with Amy Babinchak Today on the Evolved Radio podcast, I welcome Amy Babinchak, a 22-time Microsoft MVP and author of “20 Questions Every Owner Asks Before Selling Their MSP,” about planning an MSP sale years in advance. Babinchak describes the emotional impact of…

Ashley Cooper on Lovable, Local-First AI Apps, and Safe Agent Workflows for MSPs The host interviews Ashley Cooper (COO at Cyber Drain, VP of Community at Rewst) about her use of Lovable and other AI coding tools to build small, local-first, deterministic apps and learn through prompting. Ashley describes receiving a Lovable contributor gift after…

Ever wonder what really happens behind the scenes when a rocket-ship MSP vendor goes from scrappy startup to multi-billion dollar public company? Today, I’m talking with Michael Fass, former Datto general counsel and now CEO at Slide. Michael’s seen the vendor/MSP relationship from every angle—legal, operational, and now as a co-founder, building Slide for the…