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
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...
Mark as Played
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...
Mark as Played
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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September 15, 2025 • 65 mins
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 thin...
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September 5, 2025 • 86 mins
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 ...
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August 29, 2025 • 65 mins
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 e...
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August 22, 2025 • 64 mins
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...
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August 15, 2025 • 60 mins
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...
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August 8, 2025 • 64 mins
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 exper...
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August 4, 2025 • 98 mins
Live and side by side at GTIA’s ChannelCon event in Nashville, Erick and Rich discuss Pax8’s bold plan to re-invent marketplaces for the agentic AI era, and a roadmap MSPs can use to get started in AI services before it’s too late. Then they’re joined by back-to-back interview guests—Will Brooks from UKON and Eric Altamura from SPECTRA—to explore two of several emerging models for turning cyber insurance from a stressful headache i...
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July 25, 2025 • 73 mins
Erick and Rich discuss the pros and cons for MSPs of placing bets on today’s emerging crop of startup AI automation vendors and the best practice roadmap for helping clients make AI-driven business model shifts. Then they’re joined by Juan Fernandez, founder of MSP Owners Group, to discuss that recently launched company’s unique, private equity-free approach to building a PE-style MSP platform. And finally, one last thing: the seet...
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July 18, 2025 • 53 mins
Wondering about the future of managed services? Erick and Rich (who’s back after a multi-week absence) explain why new research from Barracuda suggests offering consultative security and AI services to midsize businesses is a big part of the answer. Then they share three specific tips for cross-selling and upselling services like that to your existing client base, before getting a big-picture perspective on AI, security, and more f...
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