Evolved Radio

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 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 the brain filters ads. He recommends MSPs differentiate through human-led communication, storytelling, and documenting real problems in plain business language, often via simple, authentic video rather than polished production.  They discuss parasocial relationships, decision-making biases, AI-driven search/answers, and why personal brand should dominate corporate brand (about 95/5) to build trust and demand over time.  Links mentioned: opsleader.co; vosa.co/erik; @erikbolz. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP. 00:00 MSPs Becoming Line Items 00:15 Meet Erik Bowles 01:44 From Engineer to Brand Strategist 03:28 Outcomes Over Product Demos 04:42 Behavioral Psychology Roots 06:21 Brand as a Result 08:37 Pax8 Experience Differentiator 10:29 Why Template Marketing Fails 12:35 Neuroscience of Attention Filters 16:04 Talk Human Not Geek 18:37 Document Dont Create Content 19:45 Define Sally Your Real Persona 20:35 Authenticity Beats Perfect Video 23:15 Communication Presence and Zoom Fatigue 25:31 Stage Presence Basics 26:25 Reps Over Perfection 27:28 Authentic Content Wins 27:52 Capture Client Call Gold 29:57 Differentiating MSPs 31:13 Emotion Drives Decisions 33:05 AI Search Changes Buying 35:04 Parasocial Trust Building 43:16 Personal Brand First 46:14 Human Led Marketing Era 47:50 Where To Find Erik 48:52 Just Do It Anyway 49:34 Handling Online Hate 50:15 Wrap Up And Thanks (00:00) - MSPs Becoming Line Items (00:15) - Meet Eric Bowles (01:44) - From Engineer to Brand Strategist (03:28) - Outcomes Over Product Demos (04:42) - Behavioral Psychology Roots (06:21) - Brand as a Result (08:37) - Pax8 Experience Differentiator (10:29) - Why Template Marketing Fails (12:35) - Neuroscience of Attention Filters (16:04) - Talk Human Not Geek (18:37) - Document Dont Create Content (19:45) - Define Sally Your Real Persona (20:35) - Authenticity Beats Perfect Video (23:15) - Communication Presence and Zoom Fatigue (25:31) - Stage Presence Basics (26:25) - Reps Over Perfection (27:28) - Authentic Content Wins (27:52) - Capture Client Call Gold (29:57) - Differentiating MSPs (31:13) - Emotion Drives Decisions (33:05) - AI Search Changes Buying (35:04) - Parasocial Trust Building (43:16) - Personal Brand First (46:14) - Human Led Marketing Era (47:50) - Where To Find Eric (48:52) - Just Do It Anyway (49:34) - Handling Online Hate (50:15) - Wrap Up And Thanks

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 whether RMM is a “zombie product,” the ongoing role of PSA/ticketing as a system of record, and managing complexity through separate modules and staff literacy in Python/RPA. Aarin explains build-vs-buy decisions driven by ROI and fit, cites automated triage/dispatch with ~98% accuracy and shifting token costs, argues AI should augment rather than replace humans, and emphasizes documentation, playbooks, and focusing on operational “bad” anomalies. They also cover client tolerance for AI, limiting client-facing AI after hallucinated ticket notes, skepticism about voice AI, and concerns about AI economics and subsidies. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP. (00:00) - Automation First Mindset (01:10) - Aaron Origin Story (05:04) - From Scripts to Platforms (05:41) - Beyond the RMM Beehive (08:35) - Is RMM a Zombie (12:14) - Managing Complexity Safely (14:33) - Build vs Buy ROI (19:39) - Token Costs and Pair Coding (23:49) - AI Security Reality Check (27:34) - Scaling with Playbooks (30:12) - Hunt the Bad Stuff (30:59) - Blueprints Before Automation (32:46) - Ticket Volume and Vision (33:32) - Saying No as Integrator (35:44) - Healthy Disagreement Dynamics (37:08) - Client Facing vs Backend AI (40:05) - AI Hallucinations and Guardrails (43:05) - Voice AI and Live Answer (46:06) - Costs and Subsidized AI Era (49:26) - Outcome First and RPA Focus (51:36) - Wrap Up and Thanks

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 operations like accounts receivable/payable, collecting and making payments, payroll, and other non-revenue tasks that often fall on owner-operators (especially in sub-$1M MSPs). Victor describes AI agents, including voice AI for overdue invoice calls, and emphasizes human-in-the-loop controls, segmenting which customers are contacted, and escalation to a human to protect relationships while improving efficiency and owner quality of life. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP. 00:00 Meet Victor Lopez 01:20 From Law to Flexpoint 02:02 ConnectWise Deal Spark 02:57 Why PSA Billing Exists 05:35 AI Beyond Tickets 08:13 Operational AI Wins 14:09 Agentic AI for AR 16:50 Join Opsleader 17:26 Controls and Oversight 22:09 Voice Agents Calling Clients 28:27 Owner Time and Quality 32:20 Wrap Up and Takeaways

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 operations and personal finances with a CPA, tax lawyer, financial planner, and business lawyer. The conversation covers deal structure tradeoffs (cash, time commitments, and total value), common earn-out/retention periods owners find miserable, valuation drivers like profitability, standardization, and running without the owner, typical multiples for small and mid-sized MSPs, and options for smaller firms such as selling a book of business or rare seller-financed sales to employees. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 explains her workflow moving from Lovable scaffolding to GitHub/VS Code with Copilot, plus experimenting with Bolt and tools like OpenClaw, emphasizing trust boundaries, least privilege, and treating agents like employees. They discuss prompt engineering using philosophical mental models, risks of unvetted "vibe-coded" SaaS, and advising MSPs to start with data readiness and education before deploying AI for clients. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP. 00:00 Meet Ashley Cooper 01:17 Lovable Gift Surprise 03:01 Early Builds and Lessons 05:25 Hackathon One Shot Apps 09:34 Finding Ideas to Build 11:00 Viral AI Side Projects 14:09 Keeping or Killing Projects 18:22 Local First Automation Wins 19:51 Beyond Lovable Toolchain 24:03 OpenClaw Risks and Power 30:49 AI As Employee 31:18 Stress And Bias 32:02 Context Anxiety 34:52 Prompt Writing Workflow 37:23 Mental Model Prompts 41:44 Deep Instruction Sources 47:20 SaaS Apocalypse Debate 49:53 MSP AI Readiness 53:47 Education And Governance 56:30 Closing Thoughts

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 walk away knowing how to spot your "butter zone" in leadership, and a new way to think about partnering with the tech vendors in your stack. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 your own AI-powered assistants, augmenting your IT workflows, or just want a better handle on demystifying "the network layer," this episode is packed with insights. Resources: John' Github Repo John's YouTube Channel --- This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 Hard challenge, ditching alcohol, and building sustainable routines that actually stick. We dig into the importance of accountability, how discipline can unlock true freedom, and why sometimes the smallest steps—like a daily walk—can have the biggest impact. If you've ever felt like you can't find the time, energy, or motivation to look after yourself, this episode is going to speak to you. We get honest about the trade-offs, the wins, and why choosing to invest in your well-being pays off in every other aspect of your life and business. So, whether you're listening on your lunch break, out for a walk, or just looking for that spark to get started—stick around. There's a lot of practical wisdom, some laughs, and maybe that nudge you've been needing to make a positive shift. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 delivery is profitable. We're going deep into why projects are causing financial headaches and customer churn, and, more importantly, what MSPs can actually do to fix it. Mike and I will talk through real-world challenges, practical fundamentals, and how AI and automation are changing the game for project delivery. Whether you're struggling with projects, worried about client retention, or just looking to level up your operational maturity, this episode is packed with actionable advice. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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, critical thinking, and balancing logic with your gut in decision-making. Whether you're grappling with change, rethinking your direction in business, or fascinated by journeys from federal service to entrepreneurship, there's something here for you. So, let's jump right in! -- This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 “failures,” and how the key to success just might be integrating AI into actual business workflows, rather than just handing people shiny new tools and hoping for the best. We also touch on the future of AI—not just software, but what happens when it starts interacting in real life. Robots, manufacturing, the evolving workforce—you name it. This is a fun, honest conversation about the messy middle we’re living through, and where we’re headed next with AI. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 advice around KPIs (you know I love talking dashboards), the most common mistake managers make when promoting team members, and even some hard-won lessons from the front lines—including what happens when someone has the courage to step down from a role that isn’t the right fit. Whether you’re thinking about your own career path, building a team, or just love some good management strategy, this episode is packed with practical takeaways you can start using today. Let’s jump in!

Today I’m excited to bring you a really insightful conversation with Brian Lagran. 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 successful partnership, and some lessons learned from both our journeys in the MSP space. Whether you’re an MSP looking to branch into co-managed services or looking to improve your co-managed offering, you’ll get a ton of actionable insights from this conversation. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 you strengthen your security posture before disaster strikes. So listen in to stay ahead of the next big threat. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 to roll up his sleeves and experiment with AI in real business scenarios. Peter talks about why New Charter decided to take a hands-on approach with AI, instead of just waiting around for vendors to figure it out. We talk honestly about what’s working, what isn’t, and why sometimes you just have to make your own path with new technology. If you want an inside look at how AI is impacting MSPs or you’re just curious about what’s really possible right now, tune in! We’ve got practical insights, plenty of candid takes, and even a few laughs along the way. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 through platforms like LinkedIn. He discusses practical steps like creating engaging content, leveraging LinkedIn's unique tools and features, and the power of setting up reliable marketing systems. Todd and Paul also explore the importance of connecting with ideal clients, the impact of video content, and why consistency is key to achieving success in the competitive MSP ecosystem. Use the insights to discover actionable tips that can transform your LinkedIn presence and take your marketing to the next level. Also there is a time limited ester egg at the end of the pod, so listen early and stick around till the end for that bonus. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

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 truths they encapsulate. We explore how these habits have shaped our personal and professional lives, emphasizing the significance of paradigms, proactive behavior, and continuous self-renewal. Whether you're familiar with Covey’s work or new to these concepts, this episode promises to offer valuable insights into creating a more intentional and effective life. So let’s go! This episode is brought to you by Evolved Management Training Courses. Online courses specifically crafted for MSP needs. A Service Manager BootCamp course, a project manager for MSPs course, an MSP Account Management course course, and an IT Documentation Done Right course.

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 in client services.  Enjoy the continued conversation in rethinking the vCIO series.