Evolved Radio

Oct 5, 2026

AI, Accounting, and MSPs - ERP143

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 routine stuff. His view is that accounting is the canary in the coal mine for professional services, with MSPs next in line. Today we're looking at what's already happening in his industry and what MSP owners can learn from it before it reaches them. This episode is brought to you by Opsleader Pro

Sep 14, 2026

Using AI Safely At Your MSP - ERP142

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 he was Chief Strategy Officer over at MSPbots. Here's how I've been framing this one. We spent a decade dragging our clients to the cloud. Then we spent a decade dragging them to security. And now our clients are dragging us into AI, whether we're ready or not. S

Aug 31, 2026

Security in the age of AI - ERP141

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 firm. If you've been listening a while, you might remember Alex from way back in episode 11 and then again in episode 96. Today's round three, and we're going fully nerd-out mode on the OpenAI/Hugging Face hack. Walking through the signals and understanding how this ty

Aug 3, 2026

From the Kitchen Rush to Cyber Risk: Lessons in Leadership and Service - ERP140

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, requiring top-down standards, accountability, recognition, and sometimes letting misaligned people go; Centrex’s ESOP model also supports ownership and buy-in. On security, he describes a simplified five-stage maturit

Jun 29, 2026

Building Personal Brand To Win at Marketing - ERP139

Evolve or Evaporate: Erik Boles on MSP Branding, Anti‑Commoditization, and Human‑Led Marketing On the Evolved Radio podcast, Todd Kane interviews Erik Boles 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 care about outcomes and experience more than products or stacks. He argues brand is a result created by people, presence, and “lore,” and that templated marketing gets ignored due to pattern recognition and how th

Jun 15, 2026

AI, RPA, and MSP Automation - ERP138

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 expanding into Python, GUIs, and modular systems connected via RESTful APIs, with much of the computation running outside the RMM on servers (including SQL and Python) while the RMM remains mainly a monitoring and job-push layer. They discuss wh

Jun 8, 2026

Beyond Service: AI's Role in Business Efficiency - ERP137

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 question why PSAs mix ticketing/project work with invoicing while still requiring separate accounting software. They discuss how most AI talk in the MSP industry centers on service delivery, but Victor argues owners should also apply AI to operation

May 25, 2026

Selling your MSP - ERP136

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 selling—often resembling grief—and stresses having a purpose and plan for life after the exit. They discuss avoiding pressure to "time the market," noting there is always demand for a well-run profitable business, and the need to prepare both operation

May 11, 2026

ERP135 - AI Assisted Coding

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 ranking in the top 0.01% of users, her early failed attempt to rebuild community software, and her shift to rapid, browser-based prototypes like JSON-to-CSV converters, receipt/expense and food trackers, and a webhook-driven PSA time-entry timer. She

Apr 27, 2026

ERP134 - Navigating Rapid Change in the MSP Channel

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 MSP channel. If you want a brutally honest look at what hypergrowth actually looks like from the inside, why most MSPs never get past "just technical," and how to avoid being the cobbler with ragged shoes, this episode is for you. You'll

Apr 6, 2026

ERP133 - AI-Driven MSPs: Integrating Technology for Better Service

Today, we have a unique perspective on AI, courtesy of our guest, Jeff Gaines with Treeline.ai. In this episode, we're exploring what it truly means to be "AI-first" in the MSP space—not just adding AI as a feature, but building it into every layer of the operation for a fundamentally different approach to service delivery. If you've been following the rapid changes in software, automation, and managed services, you won't want to miss this episode. We're getting into operational strategy, technology adoption, and the future of MSPs in the age of AI. This episode is brought to you by Opsleader

Mar 23, 2026

ERP132 - VibeOps

In today's episode, I'm joined by John Capobianco to talk about what John calls "VibeOps." If you've ever wondered where network automation and AI intersect—or how the next evolution of IT operations could look almost like managing a team of digital coworkers, you're going to love this one. Hear how John went from working in an aluminum factory to managing the network for the Canadian House of Parliament. John explains VibeOps and J shares practical advice for MSPs, how to get started with agentic tools safely, and where he thinks the whole industry is headed. If you're curious about building

Mar 2, 2026

ERP131 - Health and Wellness in IT

Today's topic is close to my heart and, honestly, one that doesn't get enough airtime in the IT industry: health and wellness. Joining me for this conversation is my Paul Vedder, CEO of VXIT, a return guest you might remember from a Episode 77. We're talking about what it takes to prioritize our physical and mental health—while juggling the endless demands of business ownership, parenthood, and life in the tech world. Paul unpacks his personal journey: from the challenges of work-life balance and struggles with unhealthy habits, to discovering the power of change through things like the 75 Har

Feb 2, 2026

ERP130 - Project Delays and Failures, Breaking the Cycle

Today I'm speaking to Mike Psenka, CEO of Moovila, once again. If you missed our previous episode together, Advanced Project Management—episode 104—I highly recommend checking it out for some great insights. Today, we're diving into a topic that's been top of mind for me and, honestly, I believe not enough people in the MSP industry are paying close attention to it: project management and profitability. We'll break down some eye-opening stats about how 25% of the MSP channel is either breaking even or losing money—and how poor project management is often the hidden culprit, even when service d

Jan 14, 2026

ERP129 - Less Admin, More Impact: AI for MSPs

Today I'm joined by Matt Tougas, CEO of Mizo. We'll explore how Matt's background as a software engineer and MSP operator led him to develop Mizo, an AI-powered help desk automation platform. We discuss the realities of AI adoption in the MSP industry, why AI agents can sometimes outperform humans in quality and consistency, and why Canadian companies have such an outsized impact in the global MSP software ecosystem. We're talking MSP innovation, Canadian tech pride, and the real-world impact of agentic AI in service operations. Let's get started! This episode is brought to you by Opsleader Pr

Dec 22, 2025

ERP128 - Critical Thinking, Career Change, and Identity

Today, my guest is Adam Dickinson, whose journey took him from planning a career in medicine, to becoming a Mandarin-speaking intelligence analyst with the FBI for 15 years, covering everything from cyber issues to counterintelligence and even terrorism. In this episode, we dig into what led Adam to the FBI, the unexpected turns in his career, and how pivotal moments—both personal and professional—prompted deeper reflection on identity, growth, and purpose. We discuss how he's translated those experiences into his new chapter as a business owner, and talk about the importance of intuition, cri

Oct 27, 2025

ERP127 - Navigating the AI hype cycle

Today's episode questions whether AI is delivering on all those big promises. There's been a lot of talk in the industry recently—everything from the "doom cycle of AI" to conflicting opinions on what AI is actually capable of right now. Are we in the trough of disillusionment? Are we overselling the tech? Or are we undervaluing the real impact it's having behind the scenes? To help break this down, I'm joined by two great guests: Michael Evers, CEO at Thread and Mark Alayev, co-founder and Chief of Magic at Thread. We dig into real-world examples, why so many AI projects are considered "failu

Aug 14, 2025

ERP126-How to Build Better Teams and Avoid the Peter Principle Trap

Welcome back to the Evolved Radio Podcast! Today, I've got a really fun and insightful episode lined up for you. Dustin Puryear and I are diving into the "Peter Principle." that all-too-familiar scenario where someone keeps getting promoted for being good at your job, but eventually land in a role where you're suddenly feeling out of your depth. We chat about the common traps people fall into on the career ladder, why owners and managers struggle to let go, and how the difference between delegation, abdication, and micromanagement shapes the success of your team. Plus, we'll dig into practical

Jun 27, 2025

ERP125 - Growing Your MSP with Co-Managed IT

Today I'm excited to bring you a really insightful conversation with Brian Largent. Brian brings nearly two decades of experience running an MSP that specializes in co-managed IT services, particularly in complex and regulated industries like healthcare and manufacturing. In this episode, Brian and I get into the nitty-gritty of co-managed IT. What it means, why it's not just for large enterprises, and how his team lives and breathes this model for clients, unexpectedly in rural markets. We dive into the real challenges and opportunities of working alongside internal IT teams, what makes for a

Jun 4, 2025

ERP124 - Security as a Utility

Welcome back to the Evolved Radio Podcast! In today's episode, I'm joined by Anup Ghosh with Threatmate. Anup and I deep dive into one of the MSP industry's hottest—and sometimes most confusing—topics: cybersecurity. But instead of focusing on the aftermath of a security incident (what they call "right of the boom"), we shift the conversation to proactive measures—what it really means to operate "left of the boom." We unpack the concept of security as a utility, discuss how to utilize NIST and CIS frameworks, and explore fear-based selling. This episode is packed with insights that will help y