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PODCAST

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

technology

All Episodes

68:16

Episode 118: That Newfangled Thing

MSP Chat ·

2026/04/03

Erick and Rich discuss Treeline, a new kind of venture capital-backed MSP with interesting implications for the competitive landscape, as well as tips for driving more business with clients by clarifying your value proposition. Then they’re joined by Michael Crean of SonicWall for a look at the interesting and sobering results of the company’s 2026 Cyber Protect Report. And finally, one last thing: The most European robbery ever, and its amusing aftermath. Discussed in this episode:Treeline Raises

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71:59

Episode 117: Embrace the Cookie Cutter

MSP Chat ·

2026/03/30

Live from the 2026 RSA Conference in San Francisco, Erick and Rich discuss the puzzling lack of interest in AI governance among MSPs and a go-giver lead generation concept proven to work by Erick himself. Then they’re joined by Jeff Loehr and Joe Rojas of MSP consultancy Start Grow Manage for a fun and fact-filled conversation about lead generation, sales meeting success, employee motivation, and operational efficiency. And finally, one last thing: You know spring has finally arrived when they’re

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90:50

Episode 116: Accidental F-Bomb

MSP Chat ·

2026/03/20

Erick and Rich discuss MSP-as-a-Service, a new outsourcing option for newcomers to managed services and existing MSPs who need more time to go all-in on building an AI practice, plus three practical steps any MSP can take to ensure they’re dedicating time to growth, margin protection, and leadership instead of fighting fires all day. Then they’re joined by ex-MSP and current thought leader Alex Stanton for an insightful conversation about what MSP rollups, cyber resilience, and AI herald for the

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54:33

Episode 115: Stick the Landing

MSP Chat ·

2026/03/16

Erick and Rich talk about why Slide’s Series B funding round, the MSP Well initiative, and GTIA’s 2026 Community and Councils Forum all underscore why community is more important than ever in the channel. Then Erick explains why reviewing client profitability on anything other than a company-by-company basis is guesswork, and Rich speaks with GTIA research czar Carolyn April about the 2026 State of the Channel Report. And finally, one last thing: the chicken-wing flavored, protein-packed espresso

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96:46

Episode 114: Haves and Have Nots

MSP Chat ·

2026/03/06

Erick and Rich discuss recent evidence about security awareness and alert fatigue that show why outsourced, AI-based automation must play a critical part in how MSPs protect their clients, as well as practical ways to enforce proper security with your clients rather than rely on the good intentions of their employees. Then they’re joined by Robin Ody of Omdia for an in-depth conversation about the analyst firm’s 2026 MSP Trends and Predictions Report. And finally, TWO last things: an illustration of

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86:23

Episode 113: Chatbot Doom Loop

MSP Chat ·

2026/03/02

Erick and Rich discuss the right and wrong way to think about automating customer relationships with AI, as well as the connection between scalable service delivery and attractive exit prices. Then they’re joined by ScalePad CEO Chris Day for a deep dive into some of the surprising findings in that company’s recent MSP Trends report. And finally, one last thing: prepping for your performance review with an AI-powered version of the boss. Discussed in this episode:MSPs Need to Accelerate AI

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67:50

Episode 112: No Seagulling

MSP Chat ·

2026/02/20

Erick and Rich discuss the reasons MSPs need to be implementing AI automation tools and the risk limits they should consider when doing so, as well as concrete strategies for growing profits and exit value by simplifying your tool stack and customer base. Then they’re joined by Pinar Ormeci of Lexful to discuss that company’s ambitious new AI-native system of record for MSPs. And finally, one last thing: A boxing ring TKO in which the “T” stands for toupee rather than technical. Discussed in this

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65:50

Episode 111: The Wave is Here

MSP Chat ·

2026/02/13

Erick and Rich discuss why the channel’s AI maturity is stuck in a three-year rut according to IDC and what MSPs can do about it, plus strategies for converting focus and discipline into accelerated growth. Then they’re joined by the managing director of partner programs for Google Cloud, Phil Larson, for an insider’s take on opportunities for MSPs in cloud and AI. And finally, one last thing: how a real-life Jimmy Neutron produced nuclear fusion in his home lab. Discussed in this episode:AI is a

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74:12

Episode 110: Buying Into Florida

MSP Chat ·

2026/02/06

Erick and Rich discuss Lexful’s ambitions to build the ultimate AI-native data repository for MSPs, as well as proven strategies for updating your managed services prices between renewals. Then they’re joined by M&A expert Abraham Garver of FOCUS Investment Banking for an insider’s take on today’s exit environment for MSPs and the rise of “mega mega” MSPs with nine-figure top lines. And finally, one last thing: A Seattle Seahawks fan who’s even more excited about this weekend’s Super Bowl than

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72:19

Episode 109: Inherited Chaos

MSP Chat ·

2026/01/30

Erick and Rich discuss the impact that security and AI maturity are having on MSP valuations and three concrete techniques for increasing valuations by increasing EBITDA. Then they’re joined by Michael Assraf, CEO and founder of Flamingo, to explore that company’s unconventional open-source approach to MSP tooling. And finally, one last thing: A data-based look at the most overused buzzwords in email, and a confession by Erick and Rich that they use most of them. Discussed in this episode:Flamingo

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79:18

Episode 108: You Got Chocolate in My Peanut Butter

MSP Chat ·

2026/01/23

Erick and Rich discuss what ConnectWise buying zofiQ says about the future of AI automation and tool stacks for MSPs and how to make sales excellence as important a part of your culture as technical excellence. Then they’re joined by two top executives from Thread for an inside look at AI-powered service desk automation from a leading vendor in the field. And finally, one last thing: an incident involving a Waymo in Phoenix that might inspire you to delay your first ride in a self-driving

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58:52

Episode 107: S’mores for the Channel

MSP Chat ·

2026/01/16

Erick and Rich discuss the easily overlooked opportunity for MSPs in AI prep work like implementing infrastructure and how MSPs can prepare themselves operationally to meet rising end user demand for AI services and solutions. Then they’re joined by Dave Sobel of The Business of Tech podcast to discuss his recent acquisition of an MSP community and education resource, and what it says about the current and future needs of smaller MSPs at a time when larger ones are commanding more attention. And

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79:09

Episode 106: The AI Sh*t’s Getting Real

MSP Chat ·

2026/01/09

Erick and Rich discuss why the rise of AI-native “systems of action” poses a potential threat to the future of PSA solutions, as well as strategies for building an effective, valuation-boosting MSP leadership team. Then they’re joined by Kevin Lancaster, CEO of BetterTracker and Channel Program, for a must-hear conversation about what AI means for the long-term competitiveness of smaller MSPs. And finally, one last thing: a phishing attack involving actual fish, or aquatic creatures

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63:30

Episode 105: Slop!

MSP Chat ·

2026/01/02

Erick and Rich discuss overcoming the gap between employer enthusiasm toward AI and employee mistrust, plus strategies MSPs can use for transitioning from IT provider to business consultant. Then they’re joined by Jason Ulacio of informer to explore the thinking behind Microsoft’s Intune for MSP program and the opportunity that initiative presents MSPs. And finally, one last thing: guess what the Merriam-Webster dictionary’s world of the year for 2025 was. Discussed in this episode:AI’s potential

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78:58

Episode 104: AI Dog Years

MSP Chat ·

2025/12/19

Erick and Rich discuss what MSPs should make of AI-native, venture-funded MSP rollup Shield Technology Partners working side-by-side with OpenAI and hiring a C-level Palantir executive as its new CEO, as well as how and why to design your MSP for exit readiness even if you’re not selling today. Then they’re joined by ConnectWise CEO Manny Rivelo to explore AI’s long-term implications for MSPs and ConnectWise itself. And finally, one last thing: Just in time for holiday gift giving, there’s now drunk

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61:46

Episode 103: Controlled Chaos

MSP Chat ·

2025/12/12

Erick and Rich talk about strategies for changing endpoint and network management from increasingly commoditized services to profit engines, as well as three strategies for accelerating MSP growth in AI, cloud, and remote productivity. Then they’re joined by Cisco execs Tim Coogan and Elisabeth De Dobbeleer to discuss the new Cisco 360 partner program and the channel analysis behind it. And finally, one last thing: A jail break story about a failed attempt to break IN to a South Carolina prison with

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64:51

Episode 102: Cyber Wargames

MSP Chat ·

2025/12/05

Erick and Rich discuss Veeam’s addition of AI data to its data protection mission and what that says more broadly about challenges and opportunities in security for MSPs, as well as concrete tactics for retaining good clients and filtering out bad ones in 2026. Then they’re joined by Corey Nachreiner of WatchGuard for a conversation about AI in security generally and agentic AI in security specifically, as well as an early look at predictions in security for the new year. And finally, one last

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30:05

Episode 101: Trading Fours

MSP Chat ·

2025/11/28

Just in time for Thanksgiving, Erick and Rich celebrate 100 episodes of MSP Chat by trading thoughts on the show’s most thought-provoking, headline-grabbing, memory-making conversations. Then, just for fun, they share their favorite “One Last Thing” segments of the podcast in a conversation featuring return appearances by Charizard the Cheeto and Wally the emotional support alligator. Discussed in this episode:Episode 5: Navigating the Managed Services Landscape in the Cloud AgeEpisode 20: Cracking

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60:10

Episode 100: Caffeine Foul

MSP Chat ·

2025/11/21

Or is it caffeine fowl? You decide after listening to Erick and Rich discuss why venture capital funds are flooding into makers of AI software for SMBs and MSPs, plus tips on the most effective ways for MSPs to get lead generation mileage out of brief local speaking opportunities. Then they’re joined by Jennifer Anaya, SVP of global marketing at Ingram Micro, and Cheryl Rang, Ingram’s VP of technology solutions, for back-to-back interviews about the power of community, the opportunity for partners

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48:09

Episode 99: Hugs for Customers

MSP Chat ·

2025/11/14

Erick and Rich talk about the refreshing candor with which ConnectWise acknowledged past mistakes at its IT Nation Connect event and whether or not MSPs will buy into its plans to do better going forward, as well as tips for getting attention and coverage from reporters like Rich. Then they’re joined by Slide co-founders Austin McChord and Michael Fass for an inside look at that company’s next-generation data protection solution for MSPs and, yes, its pending lawsuit with Kaseya. And finally, one

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