MSP Chat

64:03

Bonus Episode: Dark Side, Light Side

MSP Chat ·

2026/10/06

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,

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67:42

Episode 142: People, People, People

MSP Chat ·

2026/10/02

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

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72:16

Episode 141: Sales Profanity

MSP Chat ·

2026/09/25

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

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83:54

Episode 140: Working Out

MSP Chat ·

2026/09/18

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

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61:25

Episode 139: Smokejumping

MSP Chat ·

2026/09/11

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

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81:43

Episode 138: Kill the Meeting!

MSP Chat ·

2026/09/04

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

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82:34

Episode 137: Digital Twins Gone Rogue

MSP Chat ·

2026/08/28

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

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81:25

Episode 136: When SaaS Goes Surfing

MSP Chat ·

2026/08/21

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

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64:03

Episode 135: Ding Dang Right

MSP Chat ·

2026/08/14

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

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59:18

Episode 134: All Are Welcome

MSP Chat ·

2026/08/07

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

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57:45

Bonus Episode: Air Traffic Control

MSP Chat ·

2026/08/04

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

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71:11

Episode 133: The Electric Co.

MSP Chat ·

2026/07/31

Erick and Rich discuss Fusion, the new security platform from Sophos, and what it says about the meaning of platform in the security market today as well as three things every MSP can do to ensure their business improves every quarter. Then they’re joined by Yaron Baitch of managed services suite vendor IgnitHQ for a conversation about what it means to build a truly AI-native MSP tool stack in the age of AI. And finally, one last thing: the dangerous lengths to which residents of a city in Greece

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63:41

Episode 132: The Word is No

MSP Chat ·

2026/07/24

Erick and Rich discuss data from ConnectWise’s Service Leadership unit offering preliminary evidence that AI automation software for MSPs is having a productivity and profitability impact on early adopters, as well as suggestions for being smarter and more strategic about when to say yes to clients and when not to. Then Erick’s joined by Juan Fernandez of MSP as a Service to learn more about how that company’s solution is helping newcomers get managed service practices up and running quickly. And

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43:18

Episode 131: Public Service

MSP Chat ·

2026/07/17

Live from Ingram Micro’s 2026 Trust X Alliance Unplugged event in (fabulous, trust them) Buffalo, N.Y., Erick and Rich discuss the role community and trust play in adapting to AI transformation and strategies for easing employee anxieties about what AI means for their job. Then Rich is joined by Bill Brandel, Ingram’s EVP and president, North America, for a conversation about how Ingram’s helping partners navigate ever-shifting price changes and supply shortages while preparing for success in the AI

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63:08

Episode 130: VCAIISO

MSP Chat ·

2026/07/10

Erick and Rich discuss why service desk automation startup Squash believes there’s a close connection between AI automation for MSPs and governance and why they’re probably correct, as well as three steps MSPs can take to ready tomorrow’s generation of leaders today. Then they’re joined by Arve Kjoelen for a timely conversation about the security implications for MSPs and their customers posed by leading-edge LLMs like Mythos and GPT-5.6. And finally, one last thing: how two joy-riding teens

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78:23

Episode 129: Hungry and Confused

MSP Chat ·

2026/07/03

Erick and Rich discuss N-able’s Shadow AI Visibility solution and the larger opportunity it represents for MSPs to add AI services, plus why and how to build a multi-quarter AI and security roadmap for your clients today. Then they’re joined by James Farrow, CEO of Cyft, for an insider’s take on the present and future of AI productivity tooling for MSPs. And finally, one last thing: why the absolute worst time for a pizza delivery robot to arrive at someone’s home is when a SWAT team is already

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69:52

Episode 128: Feel the Burn

MSP Chat ·

2026/06/26

Erick and Rich discuss Rewst’s effort to democratize automation for everyone who works at MSPs and their agents too, plus three ways to address customer satisfaction issues before they ruin client relationships. Then Rich is joined by Rewst CRO Charlie Tomeo for a look at Rewst’s perspective on the present and future of automation for MSPs. And finally, one last thing: how an Australian air conditioning mechanic set a new Guinness record by yelling a single word louder than a jet aircraft. Discussed

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55:29

Episode 127: Too Many Lamborghinis

MSP Chat ·

2026/06/19

Erick and Rich discuss ConnectWise’s new AI-native platform, the fate of its earlier Asio platform, and why today’s most successful MSPs solve business problems, not technology problems. Then they’re joined by Tony Anscombe of ESET for an insightful conversation about ESET’s 2026 SMB Cyber Readiness Index. And finally, one last thing: how a single recent incident proves both that a memory stick could save your life and that dogs are more dangerous than you think. Discussed in this

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100:12

Episode 126: 1-0 Count

MSP Chat ·

2026/06/12

Coming to you live from Pax8 Beyond in Salt Lake City, Erick and Rich discuss the many ways Pax8 is trying to accelerate the path from managed service provider to managed intelligence provider, plus three things you can do to reduce recurring issues that consume resources, frustrate clients, and suppress profitability. Then they have two interviews for you, one with Rex Frank, Pax8’s VP of Academy, about making the journey from MSP to MIP and another with Elliott Hyman, CEO of Lyra Technology Group,

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91:17

Episode 125: Impostor Syndrome

MSP Chat ·

2026/06/05

Erick and Rich discuss why the rapid emergence of usage-based AI pricing schemes is going to make “token economics” and AI spend management essential skills for MSPs as well as the importance of giving everyone inside an MSP an understanding of big picture business performance. Then they’re joined by John Harden to discuss client-facing AI service opportunities and how his new app Lemhi aims to help MSPs seize them. And finally, one last thing: The most (phones) and least (dentures with two teeth)

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