Evolved Radio

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 o...

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 sys...

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...

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 havin...

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 faile...

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...

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 ma...

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 Par...

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...

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 prof...

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 M...

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 professiona...

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 dow...

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 t...

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...

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...

Welcome back to another episdoe of the Evolved Radio Podcast! In this episode, I'm joined by Peter Melby and Ryan Barton with New Charter Technologies . Sure, AI is everywhere these days, but we cut through the hype to talk about how things actually changed when ChatGPT hit the scene and suddenly put powerful AI tools in the hands of everyone. Ryan shares how that breakthrough moment inspired him...

Today on the Evolved Radio Podcast, I'm joined by Paul Green , the author of " MSP Marketing Start Here ," for a deep dive into the world of LinkedIn social marketing. This episode is perfect for MSPs looking to streamline their marketing efforts. Paul shares insights from his book, emphasizing the importance of simplifying marketing strategies and focusing on building long-term relationships thro...

Welcome to another insightful episode of the Evolved Radio Podcast! Today, we dig into the timeless wisdom of "The 7 Habits of Highly Effective People." with Andrea Caldwell, VP of Coaching and consulting at Franklin Covey. Celebrating the book's 35th anniversary, Andrea sheds light on why Stephen Covey's principles have stood the test of time, attributing their longevity to the foundational truth...

In this episode of the Evolved Radio Podcast, I'm joined by Alex Markov from Strategy Overview . Alex and I continue the rethinking vCIO series. Alex is a long-time friend of the podcast, appearing in a very early episode of the pod (ERP031). I had him back to jam on vCIO again. We explore the importance of mature VCIO practices, the integration of AI and automation, and maintaining high standards...

Today on the Evolved Radio Podcast, we continue our series on Rethinking the vCIO role in MSPs. I'm joined by Jim Tarala from VCIO University to discuss the challenges and opportunities of the vCIO role. We'll explore the importance of role clarity, client segmentation, and tips for distinguishing between account managers and vCIOs. Jim shares valuable insights into the need for a strategic approa...

On this episode of Evolved Radio, we're continuing our rethinking vCIO series with Adam Walter from Humanize IT . Adam helps give a fresh perspective. Adam has years of experience as a director of security and as a vCIO in the corporate world. He has great insight on what it's like sitting on the other side of the table from a typical MSP. In this episode, Adam shares a compelling story from his c...

In today's episode, I'm joined by Alex Farling from Empath . In the last episode, Luis Giraldo and I were talking about vCIO. Alex was listening to the episode and took up my challenge to fight us in the comments. Alex has lots of opinions and experience in the vCIO field, having built one of the leading platforms for vCIO out there. Interestingly, even Alex says he hates the term vCIO and explain...

Today, I'm chatting with my old friend Luis Giraldo , Chief Experience Officer at Scalepad. Luis and I are discussing how most of our industry might be doing vCIO all wrong. vCIO has the Critical Objective of creating real client value by delivering services that lead to genuine business outcomes, but many struggle to make this a reality. We discuss why people hate the vCIO title and ideas about w...

Welcome to another episode of Evolved Radio Podcast! Today, we're talking Sales strategies and tactics with my guest, Megan Killion, chief consultant with MKC Agency. We start off by discussing finding strength in adversity. Megan shares her story about an incredibly challenging period in her life and what she learned. This was an unexpected rabbit hole we went down, but it's relevant since busine...