MSP Chat

In this special bonus episode of MSP Chat, sponsored by Kaseya, Erick and Rich discuss AI’s role in declining member satisfaction with partner programs (it’s smaller than you might think) and three ways to ensure you talk to your clients about AI before someone else does. Then they’re joined by Paul Burke, the Kaseya VP of engineering in charge of the company’s AI-powered digital workforce, for a deeply informed conversation about AI, deterministic reasoning, and the “integration tax” many MSPs are paying today and shouldn’t be. And finally, one last thing: Just in time for the tail end o...

Erick and Rich discuss Fusion, the new security platform from Sophos, and what it says about the meaning of platform in the security market today as well as three things every MSP can do to ensure their business improves every quarter. Then they’re joined by Yaron Baitch of managed services suite vendor IgnitHQ for a conversation about what it means to build a truly AI-native MSP tool stack in the age of AI. And finally, one last thing: the dangerous lengths to which residents of a city in Greece are willing to go to shave a few minutes from th...

Erick and Rich discuss data from ConnectWise’s Service Leadership unit offering preliminary evidence that AI automation software for MSPs is having a productivity and profitability impact on early adopters, as well as suggestions for being smarter and more strategic about when to say yes to clients and when not to. Then Erick’s joined by Juan Fernandez of MSP as a Service to learn more about how that company’s solution is helping newcomers get managed service practices up and running quickly. And finally, one last thing: The $1.5 trillion shock some subscribers got when AWS rounded their bill way, way up...

Live from Ingram Micro’s 2026 Trust X Alliance Unplugged event in (fabulous, trust them) Buffalo, N.Y., Erick and Rich discuss the role community and trust play in adapting to AI transformation and strategies for easing employee anxieties about what AI means for their job. Then Rich is joined by Bill Brandel, Ingram’s EVP and president, North America, for a conversation about how Ingram’s helping partners navigate ever-shifting price changes and supply shortages while preparing for success in the AI economy. And finally, one last thing: a helpful reminder that your local police department would prefer that you NOT br...

Erick and Rich discuss why service desk automation startup Squash believes there’s a close connection between AI automation for MSPs and governance and why they’re probably correct, as well as three steps MSPs can take to ready tomorrow’s generation of leaders today. Then they’re joined by Arve Kjoelen for a timely conversation about the security implications for MSPs and their customers posed by leading-edge LLMs like Mythos and GPT-5.6. And finally, one last thing: how two joy-riding teens discovered the hard way that the long arm of the law extends into Waymos.

Discussed in this epis...

Erick and Rich discuss N-able’s Shadow AI Visibility solution and the larger opportunity it represents for MSPs to add AI services, plus why and how to build a multi-quarter AI and security roadmap for your clients today. Then they’re joined by James Farrow, CEO of Cyft, for an insider’s take on the present and future of AI productivity tooling for MSPs. And finally, one last thing: why the absolute worst time for a pizza delivery robot to arrive at someone’s home is when a SWAT team is already there.
 
Discussed in this episode:
N-able Sh...

Erick and Rich discuss Rewst’s effort to democratize automation for everyone who works at MSPs and their agents too, plus three ways to address customer satisfaction issues before they ruin client relationships. Then Rich is joined by Rewst CRO Charlie Tomeo for a look at Rewst’s perspective on the present and future of automation for MSPs. And finally, one last thing: how an Australian air conditioning mechanic set a new Guinness record by yelling a single word louder than a jet aircraft.
 
Discussed in this episode:
Rewst Answers the Automation Divide With AI-Native Capabilities as MSP T...

Erick and Rich discuss ConnectWise’s new AI-native platform, the fate of its earlier Asio platform, and why today’s most successful MSPs solve business problems, not technology problems. Then they’re joined by Tony Anscombe of ESET for an insightful conversation about ESET’s 2026 SMB Cyber Readiness Index. And finally, one last thing: how a single recent incident proves both that a memory stick could save your life and that dogs are more dangerous than you think.
 
Discussed in this episode:
ConnectWise Unveils the Industry’s First Predictive Intelligence Platform to Lead the Era of Predictive IT
ESE...

Coming to you live from Pax8 Beyond in Salt Lake City, Erick and Rich discuss the many ways Pax8 is trying to accelerate the path from managed service provider to managed intelligence provider, plus three things you can do to reduce recurring issues that consume resources, frustrate clients, and suppress profitability. Then they have two interviews for you, one with Rex Frank, Pax8’s VP of Academy, about making the journey from MSP to MIP and another with Elliott Hyman, CEO of Lyra Technology Group, about what being an MIP looks like in today’s market. And finally, one last thin...

Erick and Rich discuss why the rapid emergence of usage-based AI pricing schemes is going to make “token economics” and AI spend management essential skills for MSPs as well as the importance of giving everyone inside an MSP an understanding of big picture business performance. Then they’re joined by John Harden to discuss client-facing AI service opportunities and how his new app Lemhi aims to help MSPs seize them. And finally, one last thing: The most (phones) and least (dentures with two teeth) common items in Uber’s lost and found.
 
Discussed in this episode:
AI Model Spe...

Erick and Rich discuss Veeam’s bold attempt to invent a whole new kind of data-focused platform for the age of AI, as well as why and how to earn your way to more and better client referrals. Then they’re joined by Danny Jenkins, CEO of ThreatLocker, for a thoughtful conversation about why AI security risks make left-of-boom, zero-trust security more important than ever. And finally, one last thing: evidence that those “triple washed” bags of lettuce aren’t always triple washed.
 
Discussed in this episode:
S**t Happens in AI. Veeam Says It Has the Answer.

Coming to you live from Nerdio’s NerdioCon event in sunny Palm Springs, CA, Erick and Rich discuss why Anthropic’s new AI services venture for midsize businesses is the latest reason MSPs need to get moving on an AI strategy, as well as techniques for building a strategic, sticky AI roadmap for your customers. Then they’re joined by Nerdio President Joseph Landes for his take on underappreciated MSP opportunities in Microsoft 365, Azure Virtual Desktop, Windows 365, and Microsoft Copilot. And finally, one last thing: How Bebop the robot inadvertently delayed a flight to San Diego. 

Discussed in this ep...

In this special bonus episode of MSP Chat, sponsored by Datto, Erick and Rich discuss why cyber resilience services continue to be a source of revenue and growth for MSPs and what that says about how they should construct their service portfolio and refine their tool stack, as well as why client proposals are sales tools, not technical documents. Then they’re joined by Dan Tomaszewski, Kaseya’s EVP of channel, for a deep dive into some especially interesting findings in the 2026 Kaseya State of the MSP Report, and what MSPs should do in response. And finally, one last thing: An A...

Live from the Kaseya Connect 2026 conference in Las Vegas, Erick and Rich discuss Kaseya’s giant AI platform rollout and strategies for turning your renewal process into a retention machine. Then they’re joined by Cynomi CEO David Primor for an insider’s take on the future of CISO services in the agentic AI era. And finally, one last thing: Who comes out ahead when a thief exchanges pasta for Legos? 

Discussed in this episode:
MSP Chat Episode 88: From the Server Room to the Boardroom
Cynomi Redefines How MSPs Scale Cybersecurity Services and Growth with the Launch...

Erick and Rich discuss why agentic AI makes business resilience versus just cyber resilience a necessity for end users and a strategic relationship builder for MSPs, as well as why and how MSPs can boost net revenue retention with their clients. Then they’re joined by Avihay Nathan of Palo Alto Networks for an insider’s take on both the challenges and opportunities of agentic AI security. And finally, one last thing: Ever wished there was a way on long drives to heed the call of nature without pulling off the road? Problem solved! 

Discussed in this episode:
...

Erick and Rich discuss what Anthropic’s Mythos Preview model and Project Glasswing initiative portend for the future of security in managed services as well as how to turn your service desk into a powerful extension of your sales organization. Then, live from the Channel Partners Conference & Expo in Las Vegas, they’re joined by Robert DeMarzo of conference host Informa for an insider’s take on in-person events in the age of AI as well as Peter Kujawa of ConnectWise for a conversation about the latest MSP benchmark data. And finally, one last thing: Why a pro soccer club in Dus...

In this special bonus episode of MSP Chat, sponsored by Datto, Erick and Rich talk about why there’s still plenty of growth potential in backup and security for MSPs and why their clients need help in both areas now more than ever, as well as why speed is the ultimate competitive advantage for MSPs and how to cultivate it. Then they’re joined by Kaseya’s Adam Marget for a look at why cyber resilience solutions should be part of every MSP's service offerings and why every end user needs cyber resilience. And finally, one last thing: When those cute i...

Erick and Rich discuss why anyone using or selling LLM tokens badly needs FinOps help, as well as why an MSP’s onboarding process determines how long new clients stay, how much they spend, and how profitable they become. Then they’re joined by Rev.io’s Evan Rice for a conversation about why MSPs are the logical candidate to own the agentic layer at SMBs, and how they can go about doing it. And finally, one last thing: We’ve had it with these &*$%-ing bees on this &*$%-ing plane. 

Discussed in this episode:

Balancing AI innova...

Erick and Rich discuss Treeline, a new kind of venture capital-backed MSP with interesting implications for the competitive landscape, as well as tips for driving more business with clients by clarifying your value proposition. Then they’re joined by Michael Crean of SonicWall for a look at the interesting and sobering results of the company’s 2026 Cyber Protect Report. And finally, one last thing: The most European robbery ever, and its amusing aftermath. 

Discussed in this episode:
Treeline Raises $25 Million to Reinvent IT ServicesSonic
Wall Reframes Annual Research Around SMB Protection Outcomes, Reveals the Seven Deadly Sins...

Live from the 2026 RSA Conference in San Francisco, Erick and Rich discuss the puzzling lack of interest in AI governance among MSPs and a go-giver lead generation concept proven to work by Erick himself. Then they’re joined by Jeff Loehr and Joe Rojas of MSP consultancy Start Grow Manage for a fun and fact-filled conversation about lead generation, sales meeting success, employee motivation, and operational efficiency. And finally, one last thing: You know spring has finally arrived when they’re burning socks in Annapolis. 

Discussed in this episode:

Closing the AI Governance Gap
Start Grow...

Erick and Rich discuss MSP-as-a-Service, a new outsourcing option for newcomers to managed services and existing MSPs who need more time to go all-in on building an AI practice, plus three practical steps any MSP can take to ensure they’re dedicating time to growth, margin protection, and leadership instead of fighting fires all day. Then they’re joined by ex-MSP and current thought leader Alex Stanton for an insightful conversation about what MSP rollups, cyber resilience, and AI herald for the future of managed services. And finally, one last thing: the crazy price paid at auction for a Flamin’ Hot Ch...

Erick and Rich talk about why Slide’s Series B funding round, the MSP Well initiative, and GTIA’s 2026 Community and Councils Forum all underscore why community is more important than ever in the channel. Then Erick explains why reviewing client profitability on anything other than a company-by-company basis is guesswork, and Rich speaks with GTIA research czar Carolyn April about the 2026 State of the Channel Report. And finally, one last thing: the chicken-wing flavored, protein-packed espresso martini you never knew you wanted. 

Discussed in this episode:

Slide Raises $70 Million Series B Led by General Catalyst to Ex...

Erick and Rich discuss recent evidence about security awareness and alert fatigue that show why outsourced, AI-based automation must play a critical part in how MSPs protect their clients, as well as practical ways to enforce proper security with your clients rather than rely on the good intentions of their employees. Then they’re joined by Robin Ody of Omdia for an in-depth conversation about the analyst firm’s 2026 MSP Trends and Predictions Report. And finally, TWO last things: an illustration of the wrong way to incorporate voice AI in the call center and a follow-up on Erick’s suggestion last w...

Erick and Rich discuss the right and wrong way to think about automating customer relationships with AI, as well as the connection between scalable service delivery and attractive exit prices. Then they’re joined by ScalePad CEO Chris Day for a deep dive into some of the surprising findings in that company’s recent MSP Trends report. And finally, one last thing: prepping for your performance review with an AI-powered version of the boss. 

Discussed in this episode:

MSPs Need to Accelerate AI Evolution. Distributors Say They Can Help.Scale
Pad MSP Trends Report 2026
Uber...

Erick and Rich discuss the reasons MSPs need to be implementing AI automation tools and the risk limits they should consider when doing so, as well as concrete strategies for growing profits and exit value by simplifying your tool stack and customer base. Then they’re joined by Pinar Ormeci of Lexful to discuss that company’s ambitious new AI-native system of record for MSPs. And finally, one last thing: A boxing ring TKO in which the “T” stands for toupee rather than technical. 

Discussed in this episode:
Summary of Omdia’s 2026 MSP predictions
Lexful Goes God-Mode on...

Erick and Rich discuss why the channel’s AI maturity is stuck in a three-year rut according to IDC and what MSPs can do about it, plus strategies for converting focus and discipline into accelerated growth. Then they’re joined by the managing director of partner programs for Google Cloud, Phil Larson, for an insider’s take on opportunities for MSPs in cloud and AI. And finally, one last thing: how a real-life Jimmy Neutron produced nuclear fusion in his home lab. 

Discussed in this episode:
AI is a Growing Business Yet Risky Bet for Channel Partners
ID...

Erick and Rich discuss Lexful’s ambitions to build the ultimate AI-native data repository for MSPs, as well as proven strategies for updating your managed services prices between renewals. Then they’re joined by M&A expert Abraham Garver of FOCUS Investment Banking for an insider’s take on today’s exit environment for MSPs and the rise of “mega mega” MSPs with nine-figure top lines. And finally, one last thing: A Seattle Seahawks fan who’s even more excited about this weekend’s Super Bowl than Rich because a home team victory will result in his first haircut in over a decade. <...

Erick and Rich discuss the impact that security and AI maturity are having on MSP valuations and three concrete techniques for increasing valuations by increasing EBITDA. Then they’re joined by Michael Assraf, CEO and founder of Flamingo, to explore that company’s unconventional open-source approach to MSP tooling. And finally, one last thing: A data-based look at the most overused buzzwords in email, and a confession by Erick and Rich that they use most of them. 

Discussed in this episode:

Flamingo home page (including links to OpenMSP and OpenFrame)
Flamingo’s Unorthodox Plan to Turn MS...

Erick and Rich discuss what ConnectWise buying zofiQ says about the future of AI automation and tool stacks for MSPs and how to make sales excellence as important a part of your culture as technical excellence. Then they’re joined by two top executives from Thread for an inside look at AI-powered service desk automation from a leading vendor in the field. And finally, one last thing: an incident involving a Waymo in Phoenix that might inspire you to delay your first ride in a self-driving car. 

Discussed in this episode:
ConnectWise To Acquire zofiQ—Bringing AI-Powered Autom...

Erick and Rich discuss the easily overlooked opportunity for MSPs in AI prep work like implementing infrastructure and how MSPs can prepare themselves operationally to meet rising end user demand for AI services and solutions. Then they’re joined by Dave Sobel of The Business of Tech podcast to discuss his recent acquisition of an MSP community and education resource, and what it says about the current and future needs of smaller MSPs at a time when larger ones are commanding more attention. And finally, one last thing: How deepfake monkeys conquered St. Louis. 

Discussed in this episode:

Erick and Rich discuss why the rise of AI-native “systems of action” poses a potential threat to the future of PSA solutions, as well as strategies for building an effective, valuation-boosting MSP leadership team. Then they’re joined by Kevin Lancaster, CEO of BetterTracker and Channel Program, for a must-hear conversation about what AI means for the long-term competitiveness of smaller MSPs. And finally, one last thing: a phishing attack involving actual fish, or aquatic creatures anyway. 

Discussed in this episode:
AI “Systems of Action” Have Worrying Implications for PSA Vendors
By Kevin Lancaster: MSPs, the AI $hit is a...

Erick and Rich discuss overcoming the gap between employer enthusiasm toward AI and employee mistrust, plus strategies MSPs can use for transitioning from IT provider to business consultant. Then they’re joined by Jason Ulacio of informer to explore the thinking behind Microsoft’s Intune for MSP program and the opportunity that initiative presents MSPs. And finally, one last thing: guess what the Merriam-Webster dictionary’s world of the year for 2025 was. 

Discussed in this episode:
AI’s potential excites executives and investors, but general public remains skeptical, survey says
CEOs to Keep Spending on AI, Despite S...

Erick and Rich discuss what MSPs should make of AI-native, venture-funded MSP rollup Shield Technology Partners working side-by-side with OpenAI and hiring a C-level Palantir executive as its new CEO, as well as how and why to design your MSP for exit readiness even if you’re not selling today. Then they’re joined by ConnectWise CEO Manny Rivelo to explore AI’s long-term implications for MSPs and ConnectWise itself. And finally, one last thing: Just in time for holiday gift giving, there’s now drunk raccoon merch. 

Discussed in this episode:
Jim Siders joins Shield Technology Partners...

Erick and Rich talk about strategies for changing endpoint and network management from increasingly commoditized services to profit engines, as well as three strategies for accelerating MSP growth in AI, cloud, and remote productivity. Then they’re joined by Cisco execs Tim Coogan and Elisabeth De Dobbeleer to discuss the new Cisco 360 partner program and the channel analysis behind it. And finally, one last thing: A jail break story about a failed attempt to break IN to a South Carolina prison with a stash of steak, weed, crab legs, cigarettes, and Old Bay. 

Discussed in this episode:
New...

Erick and Rich discuss Veeam’s addition of AI data to its data protection mission and what that says more broadly about challenges and opportunities in security for MSPs, as well as concrete tactics for retaining good clients and filtering out bad ones in 2026. Then they’re joined by Corey Nachreiner of WatchGuard for a conversation about AI in security generally and agentic AI in security specifically, as well as an early look at predictions in security for the new year. And finally, one last thing: a raccoon that got drunk as a skunk in a liquor store. 

Discu...

Just in time for Thanksgiving, Erick and Rich celebrate 100 episodes of MSP Chat by trading thoughts on the show’s most thought-provoking, headline-grabbing, memory-making conversations. Then, just for fun, they share their favorite “One Last Thing” segments of the podcast in a conversation featuring return appearances by Charizard the Cheeto and Wally the emotional support alligator. 

Discussed in this episode:
Episode 5: Navigating the Managed Services Landscape in the Cloud Age
Episode 20: Cracking the Code on MSP Relationships
Episode 27: Why M&A is Still OK for MSPs
Episode 59: End Game of End Games

Or is it caffeine fowl? You decide after listening to Erick and Rich discuss why venture capital funds are flooding into makers of AI software for SMBs and MSPs, plus tips on the most effective ways for MSPs to get lead generation mileage out of brief local speaking opportunities. Then they’re joined by Jennifer Anaya, SVP of global marketing at Ingram Micro, and Cheryl Rang, Ingram’s VP of technology solutions, for back-to-back interviews about the power of community, the opportunity for partners in AI and security, and much more. And finally, one last thing: a story about a parr...

Erick and Rich talk about the refreshing candor with which ConnectWise acknowledged past mistakes at its IT Nation Connect event and whether or not MSPs will buy into its plans to do better going forward, as well as tips for getting attention and coverage from reporters like Rich. Then they’re joined by Slide co-founders Austin McChord and Michael Fass for an inside look at that company’s next-generation data protection solution for MSPs and, yes, its pending lawsuit with Kaseya. And finally, one last thing: A Düsseldorf museum tour that for just €7 extra comes with an authentically grumpy German...

Join Erick and Rich for a whirlwind visit to two tech conferences. First up is Ingram Micro’s ONE show, where they discuss the new definition of distribution in the age of AI as well as tactics for raising rates in response to rising costs without alienating your clients. Then, in a conversation recorded live at ConnectWise’s IT Nation 2025 conference, they bring you a conversation about the future of AI-powered service delivery with Lee Silverstone of service desk automation vendor zofiQ. And finally, one last thing: Forget about the World Series. The winner-take-all contest to watch is the Parallel Park...

Erick and Rich discuss the MCP protocol’s underappreciated security risks and how to handle clients at financial risk due to the ongoing federal government shutdown. Then they’re joined by Glenn Mathis, CEO of Integris, to discuss a giant MSP’s strategy for using AI internally, selling it to clients, avoiding commoditization, and more. And finally, one last thing: why haunted car washes are the Halloween thrill ride America’s been waiting for. 

Discussed in this episode:

Security Risks of Agentic AI: A Model Context Protocol (MCP) Introduction
Securing the Agentic AI Control Plane: Announcin...