MSP Chat

Oct 23, 2026

Episode 145: Anxiety to Advantage

Erick and Rich discuss 8bot, Pax8's MSP-ready answer to persistent agents like Meta Muse, as well as strategies MSPs can use to ensure they're running not just a busy business but a profitable one. Then they're joined by Sunny Kaila, CEO of IT By Design, for a tour from the front lines of AI adoption within MSPs and AI service offerings from MSPs. And finally, one last thing: A library break-in by a bookish (and hungry) California bear. Discussed in this episode: Bonus Post: Move Over, Meta. Pax8’s Got a Muse for MSPs. IT By Design Helps MSPs Eat the AI Elephant IT By Design AI Accelerators Su

Oct 16, 2026

Episode 144: Home Town Hero

Oct 12, 2026

Episode 143: Tech Trifecta

Coming to you live from TD SYNNEX's 2026 Inspire conference in Greenville, S.C., Erick and Rich discuss the distributor's both new and old identity as an outcome orchestrator, along with why your Q4 conversations with customers should focus on transitioning from technical services to strategic engagement in 2027. Then they're joined by Augie Staab, TD SYNNEX's Director of MSP Sales, and Meredith Payne, the company's VP of Digital Growth and Customer Success, for a look at why TD SYNNEX recently created both those roles and what they mean for its partners. And finally, one last thing: The most

Oct 6, 2026

Bonus Episode: Dark Side, Light Side

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 F

Oct 2, 2026

Episode 142: People, People, People

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 e

Sep 25, 2026

Episode 141: Sales Profanity

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 th

Sep 18, 2026

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

Sep 11, 2026

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 Us Ho

Sep 4, 2026

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 Services Top Down Outliers Blog - May 2026 Top Down Outliers Blog - June 2026 Top Down Outliers Blog - August 2026 The Top Down Outliers

Aug 28, 2026

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 a

Aug 21, 2026

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 Native David Schwartz blog post Pia ChatGPT webinar Couple initially told to pay cancellation fee for cab

Aug 14, 2026

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 Niagara New Jersey officers dress up as shrubs to catch distracted drivers on their ph

Aug 7, 2026

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 Community Dogs rid

Aug 4, 2026

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 sum

Jul 31, 2026

Episode 133: The Electric Co.

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 are willing to go to shave a few minutes from their daily commute. Discussed in this episode: When

Jul 24, 2026

Episode 132: The Word is No

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 finally, one last thing: The $1.5 trillion shock some subscribers got when AWS rounded their bill

Jul 17, 2026

Episode 131: Public Service

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 economy. And finally, one last thing: a helpful reminder that your local police department woul

Jul 10, 2026

Episode 130: VCAIISO

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 discovered the hard way that the long arm of the law extends into Waymos. Discussed in this episode: It

Jul 3, 2026

Episode 129: Hungry and Confused

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 there. Discussed in this episode: N-able Sheds Light on AI’s Shadows AI agents are breaking things a

Jun 26, 2026

Episode 128: Feel the Burn

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 in this episode: Rewst Answers the Automation Divide With AI-Native Capabilities as MSP Task Vo