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by MSP Chat
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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- 2 days ago1h 23m
Episode 140: Working Out
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 CookerMSP Well home page988 Lifeline home pageFake 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.
- 1 weeks ago1h 1m
Episode 139: Smokejumping
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 UsHow 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.
- 2 weeks ago1h 21m
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 Outliers Blog - August 2026The Top Down Outliers podcastSnickers 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.
- 3 weeks ago1h 22m
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 SMBsPax8 Research Finds Small Businesses All-in on AI with 2 in 3 Projecting Stronger Competitive ComposureAre 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.
- Aug 21, 20261h 21m
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 cancellation fee for cable, internet after wildfire destroys homeWoman 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.
- Aug 14, 20261h 4m
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 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.
- Aug 7, 202659 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 CommunityDogs 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.
- Aug 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 SatisfactionKaseya Unveils the First Agentic IT Management Platform – Turning Data into Autonomous ActionSearching for Its First-Ever ‘Chief Online Chill Officer’ to Help Bring More Chill and Humor to the InternetSome 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.
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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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