All Things MSP

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/sponsors

Guest Links: Dave Sobel LinkedIn: https://www.linkedin.com/in/davesobel/ Business of Tech Podcast: https://businessof.tech  Free 68-Point MSP Checklist: https://freemspchecklist.com

Host 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 VoIP


Hosts & 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.com
All Things MSP Facebook Group: https://www.facebook.com/groups/allthingsmsp
All 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/sponsorsBlumira
Choice Cyber Solutions
Compliance Scorecard
EasyDMARC
Gozynta
Material Security
Sync365

Hosts:Justin Esgar: https://www.linkedin.com/in/justinesgar/
Eric Anthony: https://www.linkedin.com/in/esanthony/
 All Things/MSP Community: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
 

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:Blumira
Choice Cyber Solutions
Compliance Scorecard
EasyDMARC
Gozynta
Material Security
Sync365
Sponsor Links Here: https://allthingsmsp.com/sponsors

Find 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.com
Facebook Group: https://facebook.com/groups/allthingsmsp
LinkedIn 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.com
EasyDMARC: https://easydmarc.com
Choice Cyber Solutions: https://allthingsmsp.com/sponsors
Gozynta: https://allthingsmsp.com/sponsors
Material Security: https://allthingsmsp.com/sponsors
Sync365: https://allthingsmsp.com/sponsors
 

Connect with Guest Brad Powell:ThreatCaptain Website: https://threatcaptain.com
Email: [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.com
All Things/MSP Facebook Group: https://www.facebook.com/groups/allthingsmsp
All Things/MSP LinkedIn: https://www.linkedin.com/company/allthingsmsp/
All Things/MSP YouTube: https://www.youtube.com/@AllThingsMSP
 

In this episode of All Things MSP, hosts Justin Esgar and Eric Anthony dive into one of the most pressing topics facing Managed Service Providers today: AI adoption and governance. Unlike past technology waves where MSPs introduced new tools to clients, AI has caught the attention of end-users first. Clients are already experimenting with tools like ChatGPT and Claude—often uploading sensitive company data, PHI, or PII using personal accounts without IT oversight or corporate governance policies. Justin and Eric break down why MSPs must move past treating AI as just another "shiny object" and step up as trusted advisors. They discuss the critical three-stage operational framework MSPs need to establish: Discover & Document (knowing what tools staff are using), Govern & Secure (setting acceptable use policies and guardrails to prevent data leakage), and Deploy & Enable (providing secure enterprise tools and training employees). The conversation highlights why technology should come last. Success lies in prioritizing People and Process before deploying Technology. MSPs that fail to guide their clients through AI policy and risk mitigation risk losing accounts to more mature providers who do. Tune in to discover how to move your MSP from basic IT delivery to high-value advisory services in the age of AI. 
Connect with the HostsJustin Esgar: https://www.linkedin.com/in/justinesgar/
Eric Anthony: https://www.linkedin.com/in/esanthony/

Join the All Things MSP CommunityWebsite: https://allthingsmsp.com
Facebook Group: https://www.facebook.com/groups/allthingsmsp
LinkedIn: https://www.linkedin.com/company/allthingsmsp/
YouTube: https://www.youtube.com/@AllThingsMSP

Special Thanks to Our Sponsors

Learn more about our premier sponsors and special partner offers at https://allthingsmsp.com/sponsorsBlumira
Choice Cyber Solutions
Compliance Scorecard
EasyDMARC
Gozynta
Material Security
Sync365 License

In this episode of the All Things MSP podcast, founder and co-host Eric Anthony sits down with MJ Patent, Chief Marketing Officer at Logically—one of the nation's leading managed security service providers (MSSPs)—and a key member of CompTIA’s Data Advisory Council. Recorded live at ChannelCon in San Diego, MJ shares an insider look into how Logically approached artificial intelligence from the inside out. Rather than treating AI as a quick tool for cost-cutting or headcount reduction, Logically adopted an "AI-first" leadership mindset designed to amplify employee capabilities, elevate client value, and transform business operations. MJ breaks down the vital groundwork required before deploying AI tools like Microsoft Copilot or custom tenants like Logic AI. From conducting shadow AI assessments to establishing firm internal policies, training, and ongoing change management, she highlights why technology alone is never enough for successful adoption. Furthermore, drawing from her work on the Data Council, MJ dives deep into the non-negotiable role of clean data. She explains why AI is only as good as the underlying data, offering actionable advice on establishing a single source of truth, removing legacy rot, and configuring data sets securely. Special Thanks to Our Sponsors:Blumira: https://blumira.com
Choice Cyber Solutions: https://choicecybersolutions.com
Compliance Scorecard: https://compliancescorecard.com
EasyDMARC: https://easydmarc.com
Gozynta: https://gozynta.com
Material Security: https://material.security
Sync365: https://sync365license.com
Learn more about all our show sponsors: https://allthingsmsp.com/sponsors

Connect with Our Guest:MJ Patent on LinkedIn: https://www.linkedin.com/in/mjpatent/
Logically Website: https://www.logically.com
 Connect with Hosts & All Things MSP:Justin Esgar on LinkedIn: https://www.linkedin.com/in/justinesgar/
Eric Anthony on LinkedIn: https://www.linkedin.com/in/esanthony/
All Things MSP 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
 

Moving clients beyond basic, commoditized IT support into a mature, strategic partnership is one of the toughest challenges facing Managed Service Providers today. In this episode of the All Things MSP Podcast, hosts Justin Esgar and Eric Anthony dive into the operational maturity curve, focusing specifically on how to handle new and existing clients who aren't yet sold on higher-level strategic offerings. Justin and Eric break down the critical steps of client discovery and onboarding. They discuss why so many traditional MSPs struggle with strategic business conversations, how to address risky client behaviors—such as unmanaged personal devices used by C-suite executives—and how to communicate cyber risk in plain business language rather than technical jargon. The conversation covers handling security incidents as pivotal moments for client buy-in, establishing clear operational tiers, and enforcing mandatory Business Review meetings (QBRs) to align technology with real business outcomes. Whether you are setting pricing thresholds for meeting frequencies or looking to elevate your service stack, this episode provides actionable insights to help push your MSP's operational maturity forward. A special thank you to our premier sponsors for supporting the show: Blumira, Choice Cyber Solutions, Compliance Scorecard, EasyDMARC, Gozynta, Material Security, and Sync365. Learn more about our partners at https://allthingsmsp.com/sponsors. Connect with the Hosts:
Justin Esgar: https://www.linkedin.com/in/justinesgar/
Eric Anthony: https://www.linkedin.com/in/esanthony/

Connect with All Things MSP:
Website: https://allthingsmsp.com
Facebook Group: https://www.facebook.com/groups/allthingsmsp
LinkedIn: https://www.linkedin.com/company/allthingsmsp/
YouTube: https://www.youtube.com/@AllThingsMSP

In this episode of the All Things MSP podcast, hosts Justin Esgar and Eric Anthony dive into one of the most critical topics facing managed service providers today: practical AI adoption for MSPs and their SMB clients. Recorded live on-site at GTIA ChannelCon in San Diego, Eric sits down with two leading MSP business owners, Ann Westerheim of Ekaru and Jeremy Treister of CMIT Solutions of Chicago, to explore how real-world IT service providers are implementing artificial intelligence internally to boost operational efficiency while safely guiding micro-SMB and Main Street clients through AI governance, security, and technology enablement.Ann Westerheim discusses how Ekaru uses AI tools and automation to handle complex distributor billing reconciliations and license management with custom internal workflows. She also shares effective strategies for helping non-technical Main Street businesses embrace AI productivity without compromising sensitive corporate data. Jeremy Treister shares how CMIT Solutions of Chicago approaches AI enablement through structured governance, acceptable use policies, and practical frameworks designed to combat shadow AI risks while helping small business clients maintain a strong competitive edge in their local markets. Together, they outline actionable strategies for MSPs to transition from simple software license reselling into high-value strategic AI advisors for their clients.Whether you are looking to streamline your internal MSP operations or establish safe AI guardrails for your small business customers, this episode provides essential insights for navigating the rapidly evolving artificial intelligence landscape.

Special thanks to our premier sponsors for supporting the All Things MSP community and making this show possible: Blumira, Choice Cyber Solutions, Compliance Scorecard, EasyDMARC, Gozynta, Material Security, and Sync365. Learn more about our valued sponsors and explore their IT security and automation solutions at https://allthingsmsp.com/sponsors.

Connect with Our Guest Experts:
Ann Westerheim (Ekaru) LinkedIn: https://www.linkedin.com/in/annwesterheim/ Website: https://www.ekaru.com
Jeremy Treister (CMIT Solutions of Chicago) LinkedIn: https://www.linkedin.com/in/jtreister/ Website: https://www.cmitsolutions.com
Connect with Our Podcast Hosts:
Justin Esgar: https://www.linkedin.com/in/justinesgar/
Eric Anthony: https://www.linkedin.com/in/esanthony/

Follow & Join the All Things MSP Community: Website: https://allthingsmsp.com YouTube Channel: https://www.youtube.com/@AllThingsMSP LinkedIn Page: https://www.linkedin.com/company/allthingsmsp/ Facebook Group: https://www.facebook.com/groups/allthingsmsp
Listen & Subscribe to the Podcast:
Apple Podcasts: https://podcasts.apple.com/us/podcast/all-things-msp/id1679331639
Spotify: https://open.spotify.com/show/4gXXVZ9RuVppd4k4hN1jp1

In this episode of the All Things MSP podcast, hosts Justin Esgar and Eric Anthony dive deep into what it truly means to achieve operational maturity as a Managed Service Provider. Challenging the common misconception that operational maturity is tied directly to annual revenue metrics, they break down the levels of technology maturity from reactive break-fix setups to fully proactive and strategic partnerships. Throughout the discussion, Justin and Eric explore the spectrum of MSP operations, discussing how internal SOPs, ticket triage, and AI integration dictate true maturity—regardless of whether you manage Apple endpoints or enterprise setups. Learn how to set baseline technology stacks for your clients, build consistent internal governance, and transition from basic reactive maintenance to providing outcome-oriented strategy that drives client value. Connect with the 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.com
Facebook Group: https://www.facebook.com/groups/allthingsmsp
LinkedIn: https://www.linkedin.com/company/allthingsmsp/
YouTube: https://www.youtube.com/@AllThingsMSP

Sponsors:A special thanks to our sponsors for making this show possible. Learn more about our partner programs here: https://allthingsmsp.com/sponsorsBlumira
Choice Cyber Solutions
Compliance Scorecard
EasyDMARC
Gozynta
Material Security
Sync365