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 interviews about the power of community, the opportunity for partners in AI and security, and much more. And finally, one last thing: a story about a parrot in South Korea who resembles humans not only in its ability to speak but in its love for coffee too. 

Discussed in this episode:
Top Down Ventures Announces Release of its Industry-first Research Report: The State of MSP Capital in the Age of AI
Coffee-stealing parrot captured at South Korean cafe

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.

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 for MSPs and, yes, its pending lawsuit with Kaseya. And finally, one last thing: A Düsseldorf museum tour that for just €7 extra comes with an authentically grumpy German guide. 

Discussed in this episode:

MSP Chat Episode 35: Achieving Media Mastery
From The Business of Tech: Datto Sues Slide: An Exclusive Investigative Report
‘I try to make them feel as ignorant as possible’: German museum’s ‘grumpy guide’ is surprise hit 

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.

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 with Lee Silverstone of service desk automation vendor zofiQ. And finally, one last thing: Forget about the World Series. The winner-take-all contest to watch is the Parallel Parking Championship. 

Discussed in this episode:
zofiQ Takes on the Hyperautomation Big Boy
sYes, There’s a Parallel Parking Championship, and I Was a Contender

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.

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 waiting for. 

Discussed in this episode:

Security Risks of Agentic AI: A Model Context Protocol (MCP) Introduction
Securing the Agentic AI Control Plane: Announcing the MCP Security Resource Center

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.

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: Beware the surf-jacking otter of Santa Cruz, Calif. 

Discussed in this episode:
Are we in an AI bubble?
Move Over, Private Equity. Venture Capital is Investing in MSPs Too.
Shield Technology Partners Is Building Something Totally New in Managed Services
Surfboard-stealing otter attacks resume at California beach 

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.

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 this episode:
Forrester Research: Global Cybersecurity Spending To Exceed $300B By 2029Comp
TIA: State of Cybersecurity 2025
Cyprus has a cat problem: One feline for every 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.

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: why the only bad time to in a Nobel Prize is in the middle of a digital detox. 

Discussed in this episode:
Kaseya Acquires Leading AI-Powered Email Security Provider INKY
Nobel committee unable to reach prize winner who is ‘living his best life’ hiking off grid 

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.

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 Bruno, California gave the ticket to when a self-driving car made an illegal turn. 

Discussed in this episode:
MIT report: 95% of generative AI pilots at companies are failing
Music by Ed Morales
California police pull over a self-driving Waymo for an illegal U-turn, but they can’t 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.

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 from a BBC nature documentary that dolphins like getting stoned as much as humans do. 

Discussed in this episode:
Microsoft blog post: Addressing multi-tenant management challenges for MSPs with Microsoft Intune and partner innovations
Dolphins ‘deliberately get high’ on puffer fish nerve toxins by carefully chewing and passing them around 

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.

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 Client Success. And finally, one last thing: A new AI-based podcast service that spells certain doom for Erick, Rich, and MSP Chat. 

Discussed in this episode:

From Prompt to Profit: The MSP Playbook for AI-Driven Client Success
5,000 Podcasts. 3,000 Episodes a Week. $1 Cost Per Episode — Behind an AI Start Up’s Plan 

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.

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 thing: a few easy ways to become a Guinness World Records holder. 

Discussed in this episode:
General Catalyst’s Latest AI Bet Is in IT
New AI Platform Darcy
IQ Automates Deal Flow and Accelerates Win Rates for B2B Services Companies
IT Nation Evolve peer groups
Show more...