Evolved Radio

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 maturity model built from cyber insurance requirements and CIS controls (favoring CIS for its pr...

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 the brain fil...

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.

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...

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 CP...

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...

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 yo...

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.

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 he...

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 li...

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 servic...

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!

...

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 logi...

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 in...

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...

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...

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 i...

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...

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...

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...

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.

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 approach when targeting different client segments and how MSPs can create value with vCIO services. Listen for more actionable strategies to refine your client interactions and elevate the services you provide.

This episode is...

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 career, highlighting the crucial role of curiosity in client interactions.

Whether you're an MSP owner, a vCIO, or someone looking to...

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 explains why. We also discuss "firing" clients, the critical role of communication in maintaining positive relationships, agendas, and the nuanced roles required in smaller MSPs.

This...

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 what we should call it instead.

We discuss some common pitfalls, like focusing too much on tools over processes.

Whether you're trying to...

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 business development means getting a lot of "No"s, which can be so uncomfortable for people that they never start.

Then Megan shares practical tactics on qualifying leads, understanding client needs, and...

Welcome to the Evolved Radio Podcast, In today's episode, I'm joined by industry expert Gerwai Todd CEO of Timezest and Pia. We delve into the transformative role of AI technology in ticket management, highlighting its ability to automate and streamline service desk operations. We chat about the role of dispatcher and how it can be done in different ways in MSPs. We also discuss how AI and RPA tools are not only enhancing efficiency but also creating new career opportunities within MSPs.

Join us for an insightful episode that explores how automation and AI are revolutionizing service...

Welcome to another episode of Evolved Radio Podcast! Today we have an insightful discussion lined up with cybersecurity expert Wes Spencer. We explore the critical need for governance and how cyber insurance is a catalyst for improved security practices in small businesses.

We also touch on the hype cycle in the cybersecurity industry and the need to move beyond a tool-centric focus.

We also discuss strategies for protecting our kids in the digital age, from screen time limits to open conversations about social media.

Finally, we chat about the influence of private equity...

In today's episode, my guest Steve Copeland and I are talking about a bunch of nerdy tech stuff, but also some serious business opportunities. We're covering 5G technology and how your MSP could potentially leverage the technology for a differentiated service offering. We chat about the AI and it's impact on the technology space and especially data privacy. We also chat about the cloud and why some companies are opting to on-prem their servers again.

Get ready for a fascinating discussion that will leave you thinking about how these advancements will shape our world!

This...

Today I'm speaking with Kory Kogan VP of content development at Franklin Covey. Kory and I dive deep into the world of project management. Kory shares invaluable insights on the practical skill of managing projects, whether they're official or unofficial. We'll explore how breaking down tasks and setting specific deadlines can reduce risks.

The discussion extends to the attributes of successful unofficial project managers, emphasizing that good organizational and people skills can often outweigh technical expertise. Kory provides actionable advice for those managing teams without formal authority, stressing the importance of high trust leadership behaviors such as...

Welcome to another exciting episode of the Evolved Radio Podcast! In today's episode I chat with industry veteran Rob Rae CVP @ Pax8. Together, we explore the dynamics of technology conferences, from choosing locations and handling logistics to balancing networking opportunities amidst distractions. Rob shares insights from his experience running the PAX8 Beyond event and delves into the impact of the COVID-19 pandemic on transitioning from live to virtual events and back.

The conversation also highlights the ever-changing landscape for managed service providers (MSPs), examining the shift from traditional distribution to a more marketplace-centered model and how this...

Welcome to Evolved Radio Podcast. Join us as Matt Linn, the COO of Thread, shares insights from his journey from account management to spearheading innovative chat solutions in the MSP space with Thread. We'll explore the dynamic integration of internal ticketing systems with platforms like Microsoft Teams, address the real-time benefits of chats for triggering workflows, and consider the pressing challenges and opportunities of evolving chat support models in the MSP industry. We'll also explore how AI will have a major role to play in chat support. Don't miss this engaging discussion on the critical role chat platforms play...

Welcome back to the Evolved Radio Podcast. Today's episode features Dr. Heather Denniston, a former chiropractor turned wellness specialist who's here to share her insights into maintaining energy and focus during our workday—especially for those of us in the high-stress technology sector.

We dive into practical strategies for overcoming the infamous afternoon slump, as Heather recommends simple recharging techniques you can use. We also navigate the crucial role of setting clear boundaries to conserve energy and touch upon a client's innovative approach of using out-of-office emails to signal availability.

Heather's transition to wellness was fu...

Today, we welcome Joel Abramson, managing partner at TopDown.

In this episode, we will explore the ever-relevant topic of maximizing productivity in an increasingly remote and digital work environment. Joel shares his insights on the challenges that businesses face, such as the distractions of technology and the need for better tools to monitor productivity. Together, we delve into Produce 8, an innovative response to the plateaued productivity issues.

We'll also discuss how the pandemic has brought new concerns over employee productivity to the forefront for many CEOs. Joel illuminates the fine line between automation benefits and...

Welcome back to Evolved Radio Podcast, today we are diving into the groundbreaking revolutionary world of the AI. My guest today is, Jimmy Hatzell, a man who's not just fascinated by the capabilities of AI but also turned that fascination into a MSP focused AI startup. Together, we're going to explore the ins and outs of AI in the world of Managed Service Providers.

Jimmy and I reflect on how far the ecosystem has advanced in such a short period. We nerd out abit on the underlying technology behind generative AI, and how it's prompting millions of...

Joining us today is Michael Nelson, the co-founder of Scaled and owner of TLC Tech, an MSP in California. Michael's journey began with skepticism towards remote work, but through revolutionary changes and an open mind, he's since embraced a mainly remote workforce, reaping benefits in productivity, profitability, and employee happiness.

In this episode, we'll uncover the transformative impact of remote work for MSPs, the integration of overseas talent into local company cultures, and how these remote powerhouses can reinvigorate your organization. We'll also discuss the distinctions between staff augmentation and outsourcing, the importance of intentional onboarding, and...

Welcome to another episode of the Evolved Radio Podcast! In today's episode, I'm joined by Mike Psenka, CEO and Founder of Moovila, to delve into the world of project management, particularly in the MSP (Managed Service Provider) space. If you've ever wondered why projects just can't seem to get delivered on time and how you could make your project delivery process better, you're gonna love this one. We discuss the importance of understanding dependencies, the critical path, and how technology can streamline project management processes. Mike shares his insights on APMM (autonomous project monitoring and management) and its innovative...

In this episode, I'm joined by my long-time friend and marketing expert, Matt Rouse, co-founder of Hook SEO and author of "Will AI take my job?" Together, we delve into the world of small and medium-sized business (SMB) marketing and explore the fascinating role that artificial intelligence plays in this domain. From their personal experiences in the industry to the essential strategies and tactics that maximize digital advertising ROI, we cover it all. We also reveal their insights on leveraging AI tools to enhance SEO, advertising, and content creation. So, get ready to dive deep into the world of...

Welcome back to another episode of Evolved Radio Podcast! In today's episode, Todd is joined by Jake Gregorich, VP of Growth for Lyra Technology Group, to discuss some fascinating topics related to the challenges and strategies involved in exiting a business. Together, they dive into the concept of the "Death Valley" in the 1 to 5 Million range, where businesses face difficulties due to lack of buyer interest, low selling prices, and stalled organic growth. But fear not, because our experts are here to guide you with tactical and strategic approaches to overcome this hurdle.

They explore the importance...

Today on the podcast, I'm joined by Lucas Acosta, CEO of Foojee. Foojee is an MSP that focuses on supporting Mac environments. As a long-time Apple fanatic, I'm always interested in people working in the Apple ecosystem.

Lucas and I discussed how supporting Mac environments is like supporting a stable Windows environment. This provides more opportunities to provide value to the customer. We talk a bit about how Windows-focused MSPs should think about the Mac fleets they manage. We also talk about what Lucas attributes his company growth to.

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