MSP Chat

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 episode: From Anthropic: Building a new enterprise AI services company with Blackstone, Hellman & Friedman, and Goldman Sachs [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.anthropic.com%2Fnews%2Fenterprise-ai-services-company&data=05%7C02%7Criley%40channelmastered.com%7C7079ca20bda044069ca208deabb5c11d%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639136994279159643%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=X2neGw5ESCuAt2yJDXdhTwpbINqqTh%2BZs1FJJ0GKz2I%3D&reserved=0] Robot passenger causes flight delay in California [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.upi.com%2FOdd_News%2F2026%2F05%2F04%2FSouthwest-Airlines-Oakland-California-Elite-Event-Robotics-Bebop%2F1581777911612%2F&data=05%7C02%7Criley%40channelmastered.com%7C7079ca20bda044069ca208deabb5c11d%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639136994279193065%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=fnzTZpXNsnnuOLU1auI654nE53OSxTNTeAuSjayJulU%3D&reserved=0]  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.

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 April Fool’s Day gag that turned into a hit product for chronic doom scrollers.  Discussed in this episode:https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.kaseya.com%2Fresource%2F2026-kaseya-state-of-the-msp-report-insights%2F&data=05%7C02%7Criley%40channelmastered.com%7Cb1cf6754e149458cc55008dea7a5cda0%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639132527734077326%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=iwh0aJYfvYS%2Bhro%2BmHBUH6UoFHgVnLb8S%2BiQEG%2BVb2k%3D&reserved=0 2026 Kaseya State of the MSP Report [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.kaseya.com%2Fresource%2F2026-kaseya-state-of-the-msp-report-insights%2F&data=05%7C02%7Criley%40channelmastered.com%7Cb1cf6754e149458cc55008dea7a5cda0%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639132527734077326%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=iwh0aJYfvYS%2Bhro%2BmHBUH6UoFHgVnLb8S%2BiQEG%2BVb2k%3D&reserved=0] On-demand webinar: The MSP playbook: Insights from the 2026 State of MSP Report [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.kaseya.com%2Fresource%2Fwhat-the-2026-state-of-the-msp-report-reveals%2F&data=05%7C02%7Criley%40channelmastered.com%7Cb1cf6754e149458cc55008dea7a5cda0%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639132527734100558%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=lHRKgY5%2B5aJ4LpV1%2F6TA5i%2F7RkXz%2FvPmLQhzcF%2BXJrw%3D&reserved=0]https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.creativebloq.com%2Fdesign%2Fbranding%2Fwho-won-april-fools-in-2026&data=05%7C02%7Criley%40channelmastered.com%7Cb1cf6754e149458cc55008dea7a5cda0%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639132527734118130%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=kEM10Ms27Wfjds3%2BRYFFfsTW8b4OORWH%2BXXEnrE6ehA%3D&reserved=0 Which brand won April Fools in 2026? [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.creativebloq.com%2Fdesign%2Fbranding%2Fwho-won-april-fools-in-2026&data=05%7C02%7Criley%40channelmastered.com%7Cb1cf6754e149458cc55008dea7a5cda0%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639132527734118130%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=kEM10Ms27Wfjds3%2BRYFFfsTW8b4OORWH%2BXXEnrE6ehA%3D&reserved=0]  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.

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:https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3DAgs61Po98y0&data=05%7C02%7Criley%40channelmastered.com%7C680d4188a15140a2089108dea6529113%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639131070714590305%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=mQtOeZIH7kuTFn0I19GCMsKNbI6RgseJiE32rcADHbo%3D&reserved=0 MSP Chat Episode 88: From the Server Room to the Boardroom [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3DAgs61Po98y0&data=05%7C02%7Criley%40channelmastered.com%7C680d4188a15140a2089108dea6529113%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639131070714590305%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=mQtOeZIH7kuTFn0I19GCMsKNbI6RgseJiE32rcADHbo%3D&reserved=0]https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.globenewswire.com%2Fnews-release%2F2026%2F04%2F08%2F3270206%2F0%2Fen%2FCynomi-Redefines-How-MSPs-Scale-Cybersecurity-Services-and-Growth-with-the-Launch-of-New-CISO-Intelligence-AI-Agents.html&data=05%7C02%7Criley%40channelmastered.com%7C680d4188a15140a2089108dea6529113%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639131070714645084%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=BzG%2F9ba02Fdm4M3vjp19HxCE7m93kHZmVvAkncaklTA%3D&reserved=0 Cynomi Redefines How MSPs Scale Cybersecurity Services and Growth with the Launch of New CISO Intelligence AI Agents [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.globenewswire.com%2Fnews-release%2F2026%2F04%2F08%2F3270206%2F0%2Fen%2FCynomi-Redefines-How-MSPs-Scale-Cybersecurity-Services-and-Growth-with-the-Launch-of-New-CISO-Intelligence-AI-Agents.html&data=05%7C02%7Criley%40channelmastered.com%7C680d4188a15140a2089108dea6529113%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639131070714645084%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=BzG%2F9ba02Fdm4M3vjp19HxCE7m93kHZmVvAkncaklTA%3D&reserved=0] Police arrest man who replaced US$34,000 worth of Lego pieces with pasta [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.ctvnews.ca%2Fworld%2Farticle%2Fpolice-arrest-man-who-replaced-us34000-worth-of-lego-pieces-with-pasta%2F&data=05%7C02%7Criley%40channelmastered.com%7C680d4188a15140a2089108dea6529113%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639131070714682955%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=g5UaTXe3JN9ySJTTLuErpOMFDS5g33KSQ6NU2IDJ5z4%3D&reserved=0]  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.

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: Business Resilience and the System of Speed [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.channelholic.news%2Fp%2Fbusiness-resilience-and-the-system&data=05%7C02%7Criley%40channelmastered.com%7Cacf810c220644313ed5808dea09cb1d7%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639124792013259864%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=lKemKfkVNu%2Bba3d%2BuUO%2Bcbce%2Bh3uqzANZYs3OpYNuOA%3D&reserved=0]https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.businesswire.com%2Fnews%2Fhome%2F20260421249893%2Fen%2FNew-Survey-Highlights-Gap-Between-Perceived-AI-Readiness-and-Tested-Disaster-Recovery-Capability&data=05%7C02%7Criley%40channelmastered.com%7Cacf810c220644313ed5808dea09cb1d7%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639124792013316551%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=d9HoBSyYYr%2FseoGs2trwXfJQGAwANppewXFsaiY%2Fejc%3D&reserved=0 New Survey Highlights Gap Between Perceived AI Readiness and Tested Disaster Recovery Capability [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.businesswire.com%2Fnews%2Fhome%2F20260421249893%2Fen%2FNew-Survey-Highlights-Gap-Between-Perceived-AI-Readiness-and-Tested-Disaster-Recovery-Capability&data=05%7C02%7Criley%40channelmastered.com%7Cacf810c220644313ed5808dea09cb1d7%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639124792013316551%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=d9HoBSyYYr%2FseoGs2trwXfJQGAwANppewXFsaiY%2Fejc%3D&reserved=0]Autonomous but Not Controlled: AI Agent Incidents Now Common in Enterprises [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fcloudsecurityalliance.org%2Fartifacts%2Fautonomous-but-not-controlled-ai-agent-incidents-now-common-in-enterprises&data=05%7C02%7Criley%40channelmastered.com%7Cacf810c220644313ed5808dea09cb1d7%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639124792013358105%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=DjVE4GoD%2BlDsMXxNPJH6SGM6AcVACGe7Fvwlhm9vHzc%3D&reserved=0]https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.channelholic.news%2Fp%2Fagentic-ais-scary-security-risks&data=05%7C02%7Criley%40channelmastered.com%7Cacf810c220644313ed5808dea09cb1d7%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639124792013396651%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=aF6GZAYxCoCrRCFJkbZnMnZwTvu1Arxk9U%2F5ujbj2Yw%3D&reserved=0 Agentic AI’s Scary Security Risks [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.channelholic.news%2Fp%2Fagentic-ais-scary-security-risks&data=05%7C02%7Criley%40channelmastered.com%7Cacf810c220644313ed5808dea09cb1d7%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639124792013396651%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=aF6GZAYxCoCrRCFJkbZnMnZwTvu1Arxk9U%2F5ujbj2Yw%3D&reserved=0]Chinese car company patents voice-activated 'in-vehicle toilet' [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.upi.com%2FOdd_News%2F2026%2F04%2F17%2FSeres-patent-in-car-toilet%2F8281776442128%2F&data=05%7C02%7Criley%40channelmastered.com%7Cacf810c220644313ed5808dea09cb1d7%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639124792013446456%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=5nHip6yqO4rxpVlf1vglPpwoicJxBnheE0RV5uMRGoo%3D&reserved=0]  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.

Episode 120: Master of Time and Space

Erick and Rich discuss what Anthropic’s Mythos Preview model and Project Glasswing initiative portend for the future of security in managed services as well as how to turn your service desk into a powerful extension of your sales organization. Then, live from the Channel Partners Conference & Expo in Las Vegas, they’re joined by Robert DeMarzo of conference host Informa for an insider’s take on in-person events in the age of AI as well as Peter Kujawa of ConnectWise for a conversation about the latest MSP benchmark data. And finally, one last thing: Why a pro soccer club in Dusseldorf replaced Coach Beginning with Coach End.  Discussed in this episode:By Richard Stiennon: Mythos Preview Is a Break-Glass Moment [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.instapaper.com%2Fread%2F2000905207&data=05%7C02%7Criley%40channelmastered.com%7C7f81818f33504516d4e708de9b390d8a%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639118866515222557%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=C94%2F7DEMDxv9NG18Wy7g4cZwsx0%2F%2BevBJuIi3SB%2BVUg%3D&reserved=0]https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fapnews.com%2Farticle%2Fmarkus-anfang-alexander-ende-fortuna-dusseldorf-701e431e07374abafee572fc77cc2112&data=05%7C02%7Criley%40channelmastered.com%7C7f81818f33504516d4e708de9b390d8a%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639118866515262542%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=dc2IkfzVGubEfjj9ezi72MreehGAE8ItEP8%2B%2BrhCuUI%3D&reserved=0 From beginning to end: Soccer team switches two coaches with opposite names [https://nam02.safelinks.protection.outlook.com/?url=https%3A%2F%2Fapnews.com%2Farticle%2Fmarkus-anfang-alexander-ende-fortuna-dusseldorf-701e431e07374abafee572fc77cc2112&data=05%7C02%7Criley%40channelmastered.com%7C7f81818f33504516d4e708de9b390d8a%7C33ab369697864944ad4c6a95f59ad055%7C0%7C0%7C639118866515262542%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=dc2IkfzVGubEfjj9ezi72MreehGAE8ItEP8%2B%2BrhCuUI%3D&reserved=0] 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.