MSP Chat

MSP Chat

byMSP Chat

Technology

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(40 episodes)

Episode 138
Episode 138: Kill the Meeting!
Erick and Rich discuss CORE, a new offering from Integris that combines traditional monitoring and management with AI services, as well as four ways MSPs can waste less time on meetings. Then they’re joined by Mark Scott and Joel Abramson of Top Down Ventures for a venture capital perspective on investing and M&A in managed services today. And finally, one last thing: Even ChatGPT loves Snickers bars. Discussed in this episode:Managed BPO Is the New Managed ServicesTop Down Outliers Blog - May 2026Top Down Outliers Blog - June 2026Top Down Out...
Published: Sep 4, 2026Duration: 1h 21m 43s
Episode 137
Episode 137: Digital Twins Gone Rogue
Erick and Rich discuss the MSP opportunity in “digital workers” and the potential drawbacks worth considering before diving in, as well as techniques for making your business faster and more effective by granting decision making authority at every level. Then they’re joined by Ryan Walsh of Pax8 for an in-depth exploration of that company’s recently published white paper on The Agentic Workforce Economy. And finally, one last thing: how an Italian scamster created the eight—and worst—wonder of the world. Discussed in this episode:Pax8 Report: AI Breaking Historic Link Between Revenue Growth and Headcount for...
Published: Aug 28, 2026Duration: 1h 22m 34s
Episode 136
Episode 136: When SaaS Goes Surfing
Erick and Rich discuss Syncro’s big bet on Claude, ChatGPT, and other chatbots becoming the MSP’s RMM/PSA interface of choice plus three tips for ensuring every interaction with clients builds rather than erodes trust. Then they’re joined by David Schwartz, CEO of Pia, for an AI-native vendor’s point of view on the SaaSpocalypse, AI pricing, vibe coding, and more. And finally, one last thing: Two unbelievably bad examples of billing department idiocy. Discussed in this episode:Syncro Goes NativeDavid Schwartz blog postPia ChatGPT webinarCouple initially told to pay ca...
Published: Aug 21, 2026Duration: 1h 21m 25s
Episode 135: Ding Dang Right
Erick and Rich discuss the thorny challenges MSPs face on AI pricing as well as strategies for never, ever sending clients an invoice that surprises them. Then they’re joined by Hexi Xiao, CEO of Bumblebee, for an experience- and expertise-based conversation about why AI agents are powerful and why they’re also not the cure-all answer to every business pain. And finally, one last thing: Why the next shrub you drive past may be surveilling you. Discussed in this episode:MSPs Are Drifting Toward an AI Pricing NiagaraNew Jersey officers dress up as shrubs to ca...
Published: Aug 14, 2026Duration: 1h 4m 3s
Episode 134
Episode 134: All Are Welcome
Live from GTIA’s 2026 ChannelCon event in San Diego, Erick and Rich discuss the importance of GTIA’s new regulatory and standards initiatives, as well as why MSPs should stay focused on the fundamentals despite constant technological change. Then they’re joined by GTIA’s Dan Wensley and MJ Shoer for their take on GTIA’s unique role in the channel and where the association plans to train its considerable resources going forward. And finally, one last thing: dogs that hang ten. Discussed in this episode:GTIA Advances Trusted AI, Strengthens Self-Governance, and Expands Global CommunityDogs ride w...
Published: Aug 7, 2026Duration: 59m 18s
Bonus Episode: Air Traffic Control
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...
Published: Aug 4, 2026Duration: 57m 45s
Episode 133
Episode 133: The Electric Co.
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...
Published: Jul 31, 2026Duration: 1h 11m 11s
Episode 132
Episode 132: The Word is No
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...
Published: Jul 24, 2026Duration: 1h 3m 41s
Episode 128
Episode 131: Public Service
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...
Published: Jul 17, 2026Duration: 43m 18s
Episode 130
Episode 130: VCAIISO
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...
Published: Jul 10, 2026Duration: 1h 3m 8s
Episode 129
Episode 129: Hungry and Confused
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...
Published: Jul 3, 2026Duration: 1h 18m 23s
Episode 128
Episode 128: Feel the Burn
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...
Published: Jun 26, 2026Duration: 1h 9m 52s
Episode 127
Episode 127: Too Many Lamborghinis
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 ITESE...
Published: Jun 19, 2026Duration: 55m 29s
Episode 126
Episode 126: 1-0 Count
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...
Published: Jun 12, 2026Duration: 1h 40m 12s
Episode 125
Episode 125: Impostor Syndrome
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...
Published: Jun 5, 2026Duration: 1h 31m 17s
Episode 124
Episode124: Fighting the Terminator
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.<br...
Published: May 29, 2026Duration: 1h 2m 53s
Episode 123
Episode 123: More Cowbell
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...
Published: May 8, 2026Duration: 47m 11s
Bonus Episode: Delicious Feeling
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...
Published: May 5, 2026Duration: 1h 3m 12s
Episode 122
Episode 122: Place Your Bets
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 BoardroomCynomi Redefines How MSPs Scale Cybersecurity Services and Growth with the Launch...
Published: May 1, 2026Duration: 1h 5m 4s
Episode 121
Episode 121: FOMO Pressure
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:...
Published: Apr 24, 2026Duration: 1h 23m 55s