MSP Chat
A look at the strategies, services, and success tips IT providers need to make it big in managed services from two of the industry’s most experienced MSP authorities, Erick Simpson and Rich Freeman of Channel Mastered
Episodes
February 6, 2026 • 74 mins
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 Seahaw...
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January 30, 2026 • 72 mins
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 ...
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January 23, 2026 • 79 mins
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 mi...
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January 16, 2026 • 58 mins
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 M...
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January 9, 2026 • 79 mins
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 phishin...
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January 2, 2026 • 63 mins
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 ...
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December 19, 2025 • 78 mins
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, on...
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December 12, 2025 • 61 mins
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 sto...
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December 5, 2025 • 64 mins
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 ...
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November 28, 2025 • 30 mins
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...
Discussed in this episode:
Episode 5: Navigating...
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November 21, 2025 • 60 mins
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 in...
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November 14, 2025 • 48 mins
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 fo...
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November 10, 2025 • 68 mins
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 wi...
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October 31, 2025 • 67 mins
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 ...
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October 24, 2025 • 53 mins
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: Be...
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October 17, 2025 • 84 mins
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 th...
Discussed in th...
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October 10, 2025 • 53 mins
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:...
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October 3, 2025 • 76 mins
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...
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September 30, 2025 • 63 mins
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 f...
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September 22, 2025 • 76 mins
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 Clie...
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