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146

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Aug 2026

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About the show

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

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August 21, 2026Episode 1361 hr 21 min

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 Native David Schwartz blog post Pia ChatGPT webinar Couple initially told to pay cancellation fee for cable, internet after wildfire destroys home Woman dies, comes back to life, gets parking 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.

August 14, 20261 hr 4 min

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 Niagara New Jersey officers dress up as shrubs to catch distracted drivers on their phones 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.

August 7, 2026Episode 13459 min

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 Community Dogs ride waves at California’s World Dog Surfing Championships 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.

August 4, 202657 min

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 of summer, Snickers Ice Cream has a job opening for a Chief Online Chill Officer. Discussed in this episode: Don’t Blame AI for Sliding Partner Program Satisfaction Kaseya Unveils the First Agentic IT Management Platform – Turning Data into Autonomous Action Searching for Its First-Ever ‘Chief Online Chill Officer’ to Help Bring More Chill and Humor to the Internet 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.

July 31, 2026Episode 1331 hr 11 min

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 their daily commute. Discussed in this episode: When Is a Security Platform Not a Security Platform? I gnitHQ Dares to Dream Locals Keep Driving on This Buckled Bridge Because It’s Quicker Than the Detour 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.

July 24, 2026Episode 1321 hr 3 min

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. Discussed in this episode: Service Leadership Takes on Two MSP Mysteries MSP as a Service website Amazon Web Services customers receive bills for up to $1.5tn after global glitch 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.

July 17, 2026Episode 12843 min

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 bring your unused hand grenades to the station. Discussed in this episode: Ontario police: Do not bring grenades to police stations 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.

July 10, 2026Episode 1301 hr 3 min

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 episode: It’s Governance First, AI Second at Squash Police detain 2 teens after a joy ride in a Waymo in Northern California 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.

July 3, 2026Episode 1291 hr 18 min

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 Sheds Light on AI’s Shadows AI agents are breaking things and organisations know it. They are deploying more anyway. AvePoint Research Reveals AI Visibility Gaps Have Nearly Tripled as AI Agents Scale and Almost Half of Enterprise Employees Now Rely on Agents Daily or Weekly New Research Finds Workforce AI Policy Compliance Is an Enforcement Problem, Not an Awareness One DoorDash Delivery Robot Invades SWAT Scene, Won’t Leave as Cops Flashbang 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.

June 26, 2026Episode 1281 hr 9 min

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 Task Volume Surges 2.4x Man crowned world’s loudest person makes as much noise as a jet taking off 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.