MSP AI Strategy: Beyond Shiny Object Syndrome | EP178

Most MSP owners swear they started a company for freedom, but all they really did was buy themselves a grueling, high-stress job. If stepping away from your desk for two weeks causes a client revolt, you don't own an asset—you own an expensive prison. Whether you intend to cash out to private equity in five years or casually run a boutique shop for thirty, ignoring documentation, delegating zero tickets, and letting clients demand only your personal cell number guarantees your business is dead in the water the second life forces you out of the driver’s seat.In this episode, Eric and Justin dismantle the comfortable myth of the "lifestyle business" versus actual enterprise value. Drawing inspiration from Dwight Manfredi’s transition from muscle to mob boss in Tulsa King, the guys break down the brutal operational adjustments required at each stage of growth: the solopreneur surviving on tight contracts and documentation, the 5-to-20 person shop breaking client codependency, and the 20+ seat MSP navigating private equity scrutiny and corporate governance. You'll learn how to remove yourself as the single point of failure, run backwards math on your next hire, and build a business that someone else would actually pay real money to buy.Connect with the Hosts: Justin Esgar: https://www.linkedin.com/in/justinesgar/ Eric Anthony: https://www.linkedin.com/in/esanthony/Join the Community & Follow All Things/MSP: Website: https://allthingsmsp.com YouTube: https://www.youtube.com/@AllThingsMSP LinkedIn: https://www.linkedin.com/company/allthingsmsp/ Facebook Group: https://www.facebook.com/groups/allthingsmspSpecial Thanks to Our Sponsors: Check out our community sponsors and exclusive partner offerings at https://allthingsmsp.com/sponsors: Blumira: https://blumira.com Material Security: https://material.security Choice Cyber Solutions: https://choicecybersolutions.com Compliance Scorecard: https://compliancescorecard.com EasyDMARC: https://easydmarc.com Gozynta: https://gozynta.com OITVoIP: https://oit.co SCOUTz: https://scoutz.com

Your clients are practically throwing money at ChatGPT and Claude subscriptions, but the second you ask them to turn on multi-factor authentication, it triggers a 19-email corporate meltdown. Only 42% of MSP clients reportedly enforce MFA on critical systems—meaning less than half of them have the deadbolt turned, yet they are demanding you integrate autonomous bots into their business workflows. In this episode of All Things/MSP, Justin Esgar and Eric Anthony dive into the ridiculous contradiction MSP operators face every single week: the tension between explosive AI enthusiasm and basic cybersecurity hygiene. Security has traditionally been treated as "negative dollars"—it feels like an expensive, annoying tax with zero visible ROI until catastrophe hits. Meanwhile, AI is seen as "positive dollars," promising immediate revenue and magic productivity boosts. Eric and Justin dissect what happens when clients view cybersecurity pitches like snake oil, how third-party AI liability lands squarely on your shoulders whether you manage it or not, and the very real debate over whether it’s time to raise your baseline security standard and fire clients who refuse to comply. Plus, what happens when autonomous AI agents start asking for access to your password manager? Big thanks to our sponsors who keep the lights on and make this show possible:Blumira: https://www.blumira.comChoice Cyber Solutions: https://choicecybersolutions.comCompliance Scorecard: https://compliancescorecard.comEasyDMARC: https://easydmarc.comGozynta: https://gozynta.comMaterial Security: https://material.securityOITVoIP: https://oit.coSCOUTz: https://scoutzsecurity.ioCheck out all our sponsors at: https://allthingsmsp.com/sponsorsHost Profiles:Justin Esgar: https://www.linkedin.com/in/justinesgar/Eric Anthony: https://www.linkedin.com/in/esanthony/Join the Community & Follow All Things/MSP:Website: https://allthingsmsp.comFacebook Group: https://www.facebook.com/groups/allthingsmspLinkedIn: https://www.linkedin.com/company/allthingsmsp/YouTube: https://www.youtube.com/@AllThingsMSPListen to the Podcast:Apple Podcasts: https://podcasts.apple.com/us/podcast/all-things-msp/id1679331639Spotify: https://open.spotify.com/show/4gXXVZ9RuVppd4k4hN1jp1

Chasing late client payments is awkward, and spending three to five hours copy-pasting vendor screenshots into a slide deck only to have the client cancel an hour before the meeting is pure torture. Running an MSP means constantly getting stuck between uncomfortable debt collection and broken account management processes that bleed profit. In this episode live from the Pax8 Beyond floor, Justin and Eric ditch the polite industry fluff to address two massive operational headaches: getting paid on time and proving strategic value to clients without burning entire workdays. First up, Victor Lopez (CEO of FlexPoint) breaks down how AI agents are taking over the most dreaded task in an MSP’s back office: picking up the phone to track down overdue invoices. From southern-voiced AI phone calls to handling "the check is in the mail" objections, discover how automating AR outreach can bump collections by up to 5X simply by replacing awkward silence with consistent follow-up. Then, Ryan Sigouin (CRO of ScalePad) joins Eric to dismantle the classic "cut-and-paste QBR". Ryan explains why MSPs spend all their budget acquiring new clients while letting existing accounts bleed out the back door, and how turning warranty data and assessments into dynamic budgets and strategic roadmaps transforms your team into real trusted advisors that buyers and private equity firms actually value. A huge thank you to our sponsors who make this show possible:BlumiraChoice Cyber SolutionsCompliance ScorecardEasyDMARCGozyntaMaterial SecurityOITVoIPSCOUTzLearn more about all our sponsors: https://allthingsmsp.com/sponsorsConnect with your hosts:Justin Esgar: https://www.linkedin.com/in/justinesgar/Eric Anthony: https://www.linkedin.com/in/esanthony/Join the All Things/MSP Community:Website: https://allthingsmsp.comYouTube: https://www.youtube.com/@AllThingsMSPLinkedIn: https://www.linkedin.com/company/allthingsmsp/Facebook Group: https://www.facebook.com/groups/allthingsmsp

An advertisement claiming a 67-person IT firm was offered over $1 million for their ticket archive started circulating in MSP communities. While the offer turned out to be fake news from an unverified source, the underlying danger is dangerously real. MSPs are sitting on vast troves of client passwords, network diagrams, and confidential records—and both malicious actors and AI vendors are eyeing that data.In this episode, Eric and Justin dismantle the fake $1M offer and explore the serious ethical, legal, and security implications of ticket data harvesting. They discuss why MSPs are custodians - not owners - of client data, how HIPAA and compliance violations lurk in everyday PSA tickets, and the alarming risk of low-level techs having unchecked data export permissions. Plus, Justin shares a real-world story of Claude AI taking control of a browser to audit systems in seconds, emphasizing why MSPs must strictly enforce least-privileged access for both human employees and AI tools.Sponsors: Thank you to our premier sponsors for supporting the show:Choice Cyber Solutions: https://choicecybersolutions.com/partnersEasyDMARC: https://easydmarc.comBlumira: https://www.blumira.comGozynta: https://www.gozynta.comMaterial Security: https://material.securityOITVoIP: https://oit.coSCOUTz: https://scoutzsecurity.ioCompliance Scorecard: https://compliancescorecard.comCheck out all of our sponsors at https://allthingsmsp.com/sponsorsHosts:Justin Esgar: https://www.linkedin.com/in/justinesgar/Eric Anthony: https://www.linkedin.com/in/esanthony/Connect with All Things MSP:Website: https://allthingsmsp.comFacebook Group: https://www.facebook.com/groups/allthingsmspLinkedIn Page: https://www.linkedin.com/company/allthingsmsp/YouTube Channel: https://www.youtube.com/@AllThingsMSP

Most MSP owners are brilliant at solving technical nightmares, but when it comes to getting new clients or getting paid on time, it’s a total free-for-all. You're grinding away fixing networks and putting out fires, yet you're leaving thousands of dollars on the table because sales feels uncomfortable and billing is a monthly chore. Why are we still running critical business operations without the same discipline, processes, and automation we demand for our clients' IT infrastructures? In this episode, Justin and Eric break down two major pain points every MSP faces: getting customers and getting paid. Featuring insights straight from Pax8 Beyond, Justin sits down with Baxter Lanius (CEO of Alternative Payments) to discuss automating accounts receivable, eliminating credit card processing fees, and making cash flow predictable. Then, Christopher Smith (Founder of Empellor CRM) jumps in to tackle the fear behind MSP sales, why CRMs usually suck, and how building a repeatable revenue process removes the discomfort of lead generation. Eric wraps it up with a hard-hitting operational challenge to help you stop chasing invoices and start scaling like a real business. Special Thanks to Our Sponsors:Blumira: https://www.blumira.comChoice Cyber Solutions: https://www.choicecybersolutions.comCompliance Scorecard: https://compliancescorecard.comEasyDMARC: https://easydmarc.comGozynta: https://www.gozynta.comMaterial Security: https://material.securityOITVoIP: https://oit.coSCOUTz: https://scoutzsecurity.io Connect with Our Guests:Baxter Lanius (Alternative Payments): https://www.linkedin.com/in/baxterlaniusiv/Christopher Smith (Emplellor CRM): https://www.linkedin.com/in/christophersmith-crm-expert/ Connect with the Hosts:Justin Esgar: https://www.linkedin.com/in/justinesgar/Eric Anthony: https://www.linkedin.com/in/esanthony/Follow All Things MSP:Website: https://allthingsmsp.comFacebook Group: https://www.facebook.com/groups/allthingsmspLinkedIn Page: https://www.linkedin.com/company/allthingsmsp/YouTube Channel: https://www.youtube.com/@AllThingsMSP

Running an MSP is ridiculous, especially when everyone is screaming that AI will make you a millionaire overnight while nobody shows you how to actually bill for it. In this episode, Justin Esgar and Eric Anthony sit down with industry analyst Dave Sobel (Business of Tech) to cut through the hype, vendor webinars, and sunshine-and-rainbows marketing around AI.  They dive deep into recent research revealing that a staggering 68% of MSP websites don't mention AI at all, effectively opting themselves out of future AI agent discovery and buyer searches. Dave breaks down why MSPs are getting stuck on individual productivity instead of re-engineering client workflows, how to capture high-margin consulting dollars instead of chasing basic MRR, and why human legal liability remains the ultimate guardrail regardless of what tool your team uses. Plus, they explore Carl Pultscik and Dave Sobel's new 68-point assessment checklist to help you evaluate client AI and compliance readiness without sounding like the "Department of No."  Special Thanks to Our Sponsors: Blumira: https://www.blumira.com   Choice Cyber Solutions: https://www.choicecybersolutions.com   Compliance Scorecard: https://compliancescorecard.com   EasyDMARC: https://easydmarc.com   Gozynta: https://www.gozynta.com   Material Security: https://material.security   OITVoIP: https://oit.co   SCOUTz: https://scoutzecurity.ioFind all our sponsors at: https://allthingsmsp.com/sponsorsGuest Links: Dave Sobel LinkedIn: https://www.linkedin.com/in/davesobel/ Business of Tech Podcast: https://businessof.tech  Free 68-Point MSP Checklist: https://freemspchecklist.comHost Links: Justin Esgar LinkedIn: https://www.linkedin.com/in/justinesgar/ Eric Anthony LinkedIn: https://www.linkedin.com/in/esanthony/All Things MSP Pages: Website: https://allthingsmsp.com Facebook Group: https://www.facebook.com/groups/allthingsmsp LinkedIn Company Page: https://www.linkedin.com/company/allthingsmsp/ YouTube Channel: https://www.youtube.com/@AllThingsMSP

Most MSP owners talk a big game about cybersecurity and compliance, yet operate their own businesses with zero formal governance. You try selling $10k/month agreements or pitching enterprise-level clients, but as soon as an RFP asks for a SOC 2 report, you’re instantly disqualified. Running an MSP while pretending governance doesn't apply to you is ridiculous. In this episode, Justin and Eric break down Justin’s actual $17,000 journey through SOC 2 compliance for Virtua Computers. They bypass the corporate marketing fluff to analyze the harsh financial realities, real-world ROI, and practical operational headaches of getting audited. Justin reveals how GRC software caught hidden personal email setups, Cloudflare domain errors, and untracked devices. The guys discuss using Dungeons & Dragons style tabletop exercises for incident response testing, handling exceptions during audits, and why passing the SOC 2 requirement immediately unlocks higher-margin, $100k+ enterprise contracts. If you’re trying to move up-market or sell compliance without eating your own dog food, this episode is a mandatory reality check. Sponsors: https://allthingsmsp.com/sponsorsBlumira Choice Cyber Solutions Compliance Scorecard EasyDMARC Gozynta Material Security Sync365 OIT VoIPHosts & Show Resources:Justin Esgar (Host): https://www.linkedin.com/in/justinesgar/Eric Anthony (Founder & Producer): https://www.linkedin.com/in/esanthony/All Things MSP Website: https://allthingsmsp.comAll Things MSP Facebook Group: https://www.facebook.com/groups/allthingsmspAll Things MSP LinkedIn: https://www.linkedin.com/company/allthingsmsp/All Things MSP YouTube: https://www.youtube.com/@AllThingsMSP

Everyone is trying to sell AI solutions to MSPs promising faster ticket resolution and automated triage, but nobody is talking about the hidden financial trap underneath: token economics. In this episode, Eric and Justin pull back the curtain on how AI tokenization actually works, why "cheap" AI models can end up costing you significantly more, and how variable consumption costs threaten to blow up the predictable flat-rate pricing models MSPs have built their businesses on. Justin and Eric break down what a token actually represents in plain English (and why submitting your entire ticketing history for a simple printer issue is a massive waste of money). They dive into the reality of AI hallucinations—where you end up paying for the AI's mistakes, the corrections, and the final answer—and explore why local hardware solutions like Apple's M-series chips are pushing back against cloud consumption models. Whether you're trying to figure out how to manage token usage internally across your help desk or trying to prevent your clients from burning $50,000 a month asking ChatGPT for its "vibe score," this conversation offers an honest, operator-focused look at navigating the AI bubble without watching your margins shrink. Sponsors:Thank you to our sponsors for supporting the show! Learn more about them at https://allthingsmsp.com/sponsorsBlumiraChoice Cyber SolutionsCompliance ScorecardEasyDMARCGozyntaMaterial SecuritySync365Hosts:Justin Esgar: https://www.linkedin.com/in/justinesgar/Eric Anthony: https://www.linkedin.com/in/esanthony/ All Things/MSP Community:Website: https://allthingsmsp.comFacebook Group: https://www.facebook.com/groups/allthingsmspLinkedIn Company Page: https://www.linkedin.com/company/allthingsmsp/YouTube Channel: https://www.youtube.com/@AllThingsMSP 

SaaS vendors are aggressively raising prices, cutting reseller margins, and squeezing MSP profit margins to satisfy investor expectations. Between forced AI additions, changing reseller tiers, and minimal advance notice, running a profitable MSP feels like a constant battle against your own stack. In this episode, Eric and Justin dive straight into the absurdity of current vendor behavior, exploring whether it still makes sense to front licensing costs for clients or if MSPs should push clients to pay vendors directly. They break down the real-world operational risks of handling client billing, discuss the growing temptation to vibe code lightweight SaaS replacements, and map out practical strategies for passing costs down to clients before margins disappear completely.Thank you to our premier sponsors:BlumiraChoice Cyber SolutionsCompliance ScorecardEasyDMARCGozyntaMaterial SecuritySync365Sponsor Links Here: https://allthingsmsp.com/sponsorsFind out more about our hosts and join the community:Justin Esgar LinkedIn: https://www.linkedin.com/in/justinesgar/Eric Anthony LinkedIn: https://www.linkedin.com/in/esanthony/All Things MSP Website: https://allthingsmsp.comFacebook Group: https://facebook.com/groups/allthingsmspLinkedIn Page: https://www.linkedin.com/company/allthingsmsp/YouTube Channel: https://www.youtube.com/@AllThingsMSP

Running an MSP is weird. Most business owners aren’t driving to work thinking about cybersecurity; they care about their financial bottom line. Yet, so many MSP owners default to dumping technical jargon, feature lists, and fear-mongering FUD on prospects, only to wonder why deals stall. If you want to close higher-margin security business, you have to stop pitching tech and start pitching financial consequences. In this episode recorded live at GTIA ChannelCon, Eric Anthony sits down with Brad Powell, co-founder of ThreatCaptain, to break down how MSPs can transform complex cybersecurity chatter into clear, business-level financial discussions that decision-makers actually understand. They dive into ThreatCaptain’s Gen 4 platform release, how direct integrations with CRMs like HubSpot and ConnectWise keep sales data flowing cleanly, and why listening directly to community feedback is the real secret to building tools that actually make MSPs money. Back in the studio, Justin and Eric bring their usual candid, operator-first humor to discuss why moving past traditional fear-based selling is the only way forward for modern IT providers. Special thanks to our sponsors for supporting the show:Blumira: https://blumira.comEasyDMARC: https://easydmarc.comChoice Cyber Solutions: https://allthingsmsp.com/sponsorsGozynta: https://allthingsmsp.com/sponsorsMaterial Security: https://allthingsmsp.com/sponsorsSync365: https://allthingsmsp.com/sponsors Connect with Guest Brad Powell:ThreatCaptain Website: https://threatcaptain.comEmail: [email protected] Connect with Hosts & All Things/MSP:Justin Esgar (LinkedIn): https://www.linkedin.com/in/justinesgar/Eric Anthony (LinkedIn): https://www.linkedin.com/in/esanthony/ All Things/MSP Website: https://allthingsmsp.comAll Things/MSP Facebook Group: https://www.facebook.com/groups/allthingsmspAll Things/MSP LinkedIn: https://www.linkedin.com/company/allthingsmsp/All Things/MSP YouTube: https://www.youtube.com/@AllThingsMSP