HeyJaredMSP 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
- Indexed episodes, last 90 days
- 14
- Latest publication
- Sep 25, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 3, 2026
Latest episodes
Episode 141: Sales Profanity (opens the original)
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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 D
Episode 140: Working Out (opens the original)
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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
Episode 139: Smokejumping (opens the original)
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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
Episode 138: Kill the Meeting! (opens the original)
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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
Episode 137: Digital Twins Gone Rogue (opens the original)
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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 t
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