MSP Chat

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 as Chief Executive OfficerMerch commemorating drunk Virginia raccoon raises over $250,000 for animal shelterSNL’s drunk raccoon sketchTrashed panda merch Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

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:News Flash: Networks and Endpoints Still ExistCisco 360 Partner Program Empowers Partners to Drive Profitability in an AI EraCisco Simplifies Security for Managed Service Providers, Accelerating Their Hybrid Mesh Firewall Deployments and Business GrowthDrone drops crab legs, steak and weed into South Carolina prison: “Folks were planning an early holiday Old Bay crab boil” Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

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. Discussed in this episode:Veeam Data Platform v13 Launches and Redefines the Standard for Cyber Resilience, Advanced Data Protection, Security and Identity Controls, and AI-Powered IntelligenceA New Era for Accelerating Safe AI at Scale: Veeam to Acquire Securiti AI; Unifies Data Resilience with DSPM, Privacy and AI TrustRaccoon goes on drunken rampage in Virginia liquor store and passes out on bathroom floor Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

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 AgeEpisode 20: Cracking the Code on MSP RelationshipsEpisode 27: Why M&A is Still OK for MSPsEpisode 59: End Game of End GamesEpisode 62: Rough is EnoughEpisode 66: It Takes a Community to Secure an End UserEpisode 71: Don’t Buy VoldemortEpisode 74: No Timmies AllowedEpisode 76: Human to HumanEpisode 77: 75 Days of UptimeEpisode 88: From the Server Room to the BoardroomEpisode 95: Kirk Versus Picard Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

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 parrot in South Korea who resembles humans not only in its ability to speak but in its love for coffee too. Discussed in this episode:Top Down Ventures Announces Release of its Industry-first Research Report: The State of MSP Capital in the Age of AICoffee-stealing parrot captured at South Korean cafeSome guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

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 guide. Discussed in this episode:MSP Chat Episode 35: Achieving Media MasteryFrom The Business of Tech: Datto Sues Slide: An Exclusive Investigative Report‘I try to make them feel as ignorant as possible’: German museum’s ‘grumpy guide’ is surprise hit Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

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 Parking Championship. Discussed in this episode:zofiQ Takes on the Hyperautomation Big BoysYes, There’s a Parallel Parking Championship, and I Was a ContenderSome guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

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) IntroductionSecuring the Agentic AI Control Plane: Announcing the MCP Security Resource CenterSome guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss whether or not we’re in an AI bubble and how much MSPs should be worried if we are, before exploring strategies for increasing profitability and client retention by selling outcomes instead of tools. Then they’re joined by the co-founders of Titan, a venture capital-backed A.I. software company/MSP rollup that’s building something totally new in the history of managed services. And finally, one last thing: Beware the surf-jacking otter of Santa Cruz, Calif. Discussed in this episode:Are we in an AI bubble?Move Over, Private Equity. Venture Capital is Investing in MSPs Too.Shield Technology Partners Is Building Something Totally New in Managed ServicesSurfboard-stealing otter attacks resume at California beach Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss the opportunity in cybersecurity for MSPs and the skills gap contributing to it, plus three strategies for coping with competition, client budget constraints, and profitability pressures. Then they moderate a panel discussion on operational excellence recorded live and onstage during the recent Kaseya DattoCon event in Miami. And finally, one last thing: why Cypress has as many cats as people. Discussed in this episode:Forrester Research: Global Cybersecurity Spending To Exceed $300B By 2029CompTIA: State of Cybersecurity 2025Cyprus has a cat problem: One feline for every resident Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss what Kaseya buying INKY says about the strategies stand-alone security vendors must embrace to remain competitive in the future, and why stand-alone MSPs competing with rollups should employ those strategies too. Then they’re joined by legendary MSP guru and Kaseya Chief Community Officer Gary Pica for an insightful exploration of the past, present, and future of managed services. And finally, one last thing: why the only bad time to in a Nobel Prize is in the middle of a digital detox. Discussed in this episode:Kaseya Acquires Leading AI-Powered Email Security Provider INKYNobel committee unable to reach prize winner who is ‘living his best life’ hiking off grid Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich talk about some flaws in that now famous MIT study suggesting that 95% of AI pilots end in failure, as well as three techniques for setting the right AI expectations with your clients. Then they're joined by TD SYNNEX executives Ed Morales and Tracy Holtz for wide-ranging conversations about AI and cloud computing recorded live at the recent TD SYNNEX Inspire conference. And finally, one last thing: who police in San Bruno, California gave the ticket to when a self-driving car made an illegal turn. Discussed in this episode:MIT report: 95% of generative AI pilots at companies are failingMusic by Ed MoralesCalifornia police pull over a self-driving Waymo for an illegal U-turn, but they can’t ticket Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss Microsoft’s newfound interest in SMBs and their MSP partners as a source of cloud growth, plus three tips for avoiding client onboarding chaos. Then Rich is joined by Michael George and Dee Zepf of Syncro for a conversation about Microsoft’s large and expanding role in the world of SMB technology and what it means both for managed service providers and vendors like Syncro. And finally, one last thing: proof from a BBC nature documentary that dolphins like getting stoned as much as humans do. Discussed in this episode:Microsoft blog post: Addressing multi-tenant management challenges for MSPs with Microsoft Intune and partner innovationsDolphins ‘deliberately get high’ on puffer fish nerve toxins by carefully chewing and passing them around Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss Syncro CEO Michael George’s take on why Microsoft is destined to dominate the managed services landscape and what that means for MSPs and vendors alike, as well as techniques for protecting your clients from deepfake phishing attacks and other AI-powered cyberthreats. Then Rich is joined by Art Gross, CEO of Breach Secure Now, to discuss his new book, From Prompt to Profit: The MSP Playbook for AI-Driven Client Success. And finally, one last thing: A new AI-based podcast service that spells certain doom for Erick, Rich, and MSP Chat. Discussed in this episode:From Prompt to Profit: The MSP Playbook for AI-Driven Client Success5,000 Podcasts. 3,000 Episodes a Week. $1 Cost Per Episode — Behind an AI Start Up’s Plan Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss DarcyIQ and Titan, two companies whose rapid progress in AI for managed services underscores why MSPs need to take AI seriously ASAP, plus three tips for scaling your business without adding headcount. Then they’re joined by Arlin Sorensen of ConnectWise to discuss why MSPs need to think now about the legacy they’ll eventually leave behind, and start planning for that someday today. And finally, one last thing: a few easy ways to become a Guinness World Records holder. Discussed in this episode:General Catalyst’s Latest AI Bet Is in ITNew AI Platform DarcyIQ Automates Deal Flow and Accelerates Win Rates for B2B Services CompaniesIT Nation Evolve peer groupsSignup form for Arlin’s private daily morning email list that covers faith, family, and businessFor information on Arlin’s success to significance peer groups and legacy planning, email arlin@arlinsorensen.comGuinness World Records turns 70 - and highlights some unclaimed records

Erick and Rich talk about the growing need for virtual Chief AI Officers and what it means for an MSP to be one, plus tips on selling cybersecurity services without actually selling. Then they’re joined by Joel Abramson and Mark Scott of Top Down Ventures for a venture capital investor’s take on today’s managed services market. And finally, one last thing: the gritty tale of a woman who spent three weeks digging in the dirt for an engagement ring diamond, and found one. Discussed in this episode:The Challenges to Ensuring Information Is Secure, Compliant and Ready for AI, a report by OpenText and Ponemon InstituteTop Down VenturesThe Top Down LinkedIn NewsletterTop Down Horizons eventA New York woman dug for 3 weeks to find her own engagement ring diamond

Erick and Rich discuss the present-day opportunity for MSPs in cloud FinOps and the emerging need for AI FinOps, plus some proven advice for managing service desk capacity for maximum efficiency and minimum employee churn. Then Rich is joined by Kaseya CEO Rania Succar for an in-depth look at her thoughts on AI solutions for SMBs, MCP interfaces, community, culture, and more. And finally, one last thing: the munchies doom loop of eating THC-laden pizza at a pizzeria. Discussed in this episode:Kaseya Wants to Sell AI Through MSPs As Well As To ThemPizzeria mishap left at least 85 people intoxicated with THC after infused oil used for dough

Erick and Rich discuss the multiple issues (and yes, AI is one of them) leading more MSPs to consider joining forces with a rollup rather than go it alone, plus three criteria MSPs should apply when evaluating vendor partner programs. Then they’re joined by Canalys analyst Jay McBain for an insight-packed look at the massive opportunity for MSPs in AI, and why getting in on it early is so important. And finally, one last thing: Why you should probably do a little research online before agreeing to meet with a diplomat from Westarctica. Discussed in this episode:The New Rules of Partner Programs are Still TBD10 Tips for Modern MSPs to Evaluate Vendor Channel ProgramsMan posed as an ambassador and ran a fake embassy, Indian police say

Erick and Rich discuss early examples of how MSPs are re-tooling their workforce for the age of agentic AI as well as effective, empathetic techniques for addressing underperforming staff members. Then they’re joined by Chris Black, technical advisor at Xurrent, for a look at that company’s “right of observability” product strategy, and what it says about evolving MSP tool requirements as they grow and mature. And finally, one last thing: An opportunity for friends of a Danish zoo to show their support by feeding their pets to a lynx. Discussed in this episode:Building the Workforce of the AI FutureHow a “People Company” is Going AIThere’s No ServiceNow for MSPs. Xurrent Aims to Close That Gap.A zoo in Denmark asked patrons to donate their pets. Not as attractions, but for food

Erick and Rich discuss why LLMs, chatbots, and MCP could combine to revolutionize the way technicians interact with RMM, PSA, and other line-of-business systems, as well as how delivering business resilience rather mere uptime can be a ticket to sticky, profitable client relationships. Then they’re joined by Ryan Morris, who serves MSP Chat parent company Channel Mastered as chief channel program strategist, for an insightful expert look at why and how partner programs are changing in response to a newly complex channel ecosystem. And finally, one last thing we can summarize in three simple words: Radioactive. Wasp. Nest.  Discussed in this episode:Is Your Next Help Desk Tech Named Claude?Slide is Living in the MCP FutureRadioactive wasp nest found at site where US once made nuclear bombs