MSP Chat

In this special bonus episode of MSP Chat, sponsored by Kaseya, Erick and Rich discuss the large ongoing risk posed by deepfakes and other sophisticated AI threats, as well as what MSPs need to do about them, plus how MSPs can and should help their clients protect clients from social engineering threats with more than just passwords. Then they’re joined by Kaseya’s Matt Sywulak for a deep dive into the email security threat landscape and the latest tools for mitigating those threats. And finally, one last thing: The world’s first inconvenience store.
 
Discussed in this episode:
Gartner Survey Finds 41% of CISOs Reported At Least One Social Engineering Incident Involving a Deepfake in the Past 12 Months
Coalition 2026 Cyber Claims Report
Gartner Forecasts the Market for Securing AI Will Reach $4.8 Billion in 2027
Seattle’s ‘Inconvenience Store’ features pre-tangled USB cords
 
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.

Coming to you live from the MSP Summit in Orlando, Erick and Rich discuss why Shield Technology Partners views cutting edge AI as a means to empower people rather than replace them and what MSPs can learn from that strategy, as well as why MSPs must make themselves “customer zero” for AI services before offering anything to clients. Then they’re joined by Omdia analyst Jay McBain for an expert tour through market conditions and AI opportunities for MSPs today, and the power of community in the channel. And finally, one last thing: Batman takes down an evildoer in real life.
 
Discussed in this episode:
Shield’s Secret Weapon Isn’t AI. It’s People.
Jay McBain linked in post on channel profits
Jay McBain linked in post on partner-led AI opportunity
Jay McBain linked in post on vendor incentive models
Jay McBain linked in post on GTIA buying ASCII Group
Pow! Man in Batman costume chases down suspected Norwich handbag thief
 
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 explain why MSPs and their clients are far less insured against AI-related damages than they think they are, as well as why “what should I charge?” is the wrong first question MSPs should ask about a new service. Then they’re joined by Jeff Gaines of AI-forward MSP Treeline for a front-line view of AI in managed services today. And finally, one last thing: proof that “who’s a good boy?” is sometimes not a rhetorical question about your dog.
 
Discussed in this episode:
Treeline is Different
Treeline’s Buying
Worst guard dog in the world exposed by Ring camera in San Diego — and the breed won’t surprise you
 
 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 Flamingo's hybrid flat-rate/token-based pricing scheme for managed services software and whether or not it’s how all MSP vendors will eventually bill, as well as three strategies for augmenting profits and stickiness with your best clients by going deep with them on business outcomes. Then they’re joined by James Mignacca and Larry Meador, two cyber software vendors who now also help run an initiative named MSP Well aimed at getting stressed-out IT entrepreneurs the mental health support they need. And finally, one last thing: Sometimes that awesome Airbnb listing really is too good to be true.
 
Discussed in this episode:
Somebody Had to Test Token Pricing for MSPs. Flamingo Volunteered.
MSP Well Offers a Helping Hand Out of the IT Pressure Cooker
MSP Well home page
988 Lifeline home page
Fake 10 Downing Street listing on Booking.com highlights security failures
 
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 how a new tool from Clairify illustrates why context quality beats context quantity when it comes to AI tools for MSPs and their clients, as well as three tips for making sure your services prices don’t exceed their fresh-by date. Then they’re joined by MSP and ransomware recovery specialist Oli Thordarson for a front-line view of today’s ransomware threatscape. And finally, one last thing: a new smart device that measures something … unflattering that your Oura ring isn’t tracking for you.
 
Discussed in this episode:
Clairify Builds a Chief of Staff for the Rest of Us
How often do you fart? This smart flatulence underwear can tell you that and more
 
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 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 Services
Top Down Outliers Blog - May 2026
Top Down Outliers Blog - June 2026
Top Down Outliers Blog - August 2026
The Top Down Outliers podcast
Snickers Hungr.AI
 
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 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 SMBs
Pax8 Research Finds Small Businesses All-in on AI with 2 in 3 Projecting Stronger Competitive Composure
Are Digital Workers the AI Strategy MSPs Have Been Looking For?
‘A sucker born every minute’: The man who duped tourists with a fake Greek amphitheater
 
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’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.

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.

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.