Off the Stack is the podcast where technology leaders get real about what actually matters to small businesses. Host Marc Umstead, founder of Plus 1 Technology, sits down with CIOs, cybersecurity experts, AI practitioners, and founders to break down the tech decisions small business owners face every day.
No vendor pitches. No jargon. Just straight answers on the stuff that keeps you up at night: cybersecurity threats, AI adoption, compliance, hiring IT help, cloud costs, and where to spend your next technology dollar.
Automation Before AI: Fixing the Process First with Wesley Hartman
Wesley Hartman spent 15 years as technology director at an accounting firm before launching Automata, where he builds automations for accounting firms. Marc and Wesley talk about why you have to find the nail before you buy the hammer, how generative AI fits as one piece of a larger automated system, and why most firm problems can be solved with proven, cheaper technology. They also cover planning for exceptions, the risk of undocumented “Billy’s Best Software” tools, how junior staff will learn now that AI does the grunt work, and why your 2027 plan should start with fixing what’s broken in 2026.
Connect with us:
Marc Umstead: https://www.linkedin.com/in/marcumstead/ (https://www.linkedin.com/in/marcumstead/)
Plus 1 Technology: https://plus1technology.com (https://plus1technology.com)
Wesley Hartman: https://www.linkedin.com/in/wesley-hartman/ (https://www.linkedin.com/in/wesley-hartman/)
Automata: https://automatapracdev.com/ (https://automatapracdev.com/)
14 Oct 2026
Copilot Will Find the Files You Forgot You Shared (with Derek Morgan, Cloud Harbor Consulting)
Turn on Microsoft Copilot and your employees can suddenly ask, “What does everyone in the company make?” If your file permissions are a mess, they’ll get an answer.
Marc sits down with Derek Morgan, founder of Cloud Harbor Consulting and a former Marine, who specializes in Microsoft 365 security and Copilot readiness for small and midsize businesses. Derek explains why AI doesn’t create your security problems, it exposes the ones that have been quietly compounding for years: permission sprawl, orphaned SharePoint sites, and the confidential files employees never knew they could open.
They also get into why identity is now the number one way attackers get in, the forgotten account of a former employee that becomes a threat actor’s front door, and the free assessment already included in your Copilot license that most companies never run.
Connect with Derek: linkedin.com/in/derek-morgan-14370775 | cloudharborconsulting.cloud
Connect with Marc: https://www.linkedin.com/in/marcumstead | plus1technology.com
New episodes weekly. Follow the show so they land in your library automatically.
Topics or guest ideas? Visit plus1technology.com.
11 Sept 2026
Brian Ventura, SPM: How Often Should Your IT Provider Check In?
Some businesses hear from their IT provider every week. Others hear from them once a year, if that. Brian Ventura, CEO and CTO of SPM, an MSP headquartered in Los Angeles with staff across the country, joins Marc Umstead to talk about what the right cadence actually looks like and why technology maturity matters more than headcount.
Brian covers what belongs in a real business review, from service metrics to hardware refresh budgets, and makes the case for having a plain conversation about the business instead of reading a report out loud. He also shares how SPM opens the AI discussion: give the client a free, boilerplate AI usage policy, since their employees are already using AI whether leadership knows it or not, then start asking what they want to automate.
Plus the shadow AI problem, what almost every new client turns out to be missing in their security stack, and why SPM will walk away from a prospect that refuses to enforce MFA.
Connect with Brian Ventura: https://www.linkedin.com/in/bventura27/SPM: https://www.softpointmedia.com/
Connect with us:
Marc Umstead on LinkedIn: https://www.linkedin.com/in/marcumstead/ (https://www.linkedin.com/in/marcumstead/)
Website: plus1technology.com
Email: mumstead@plus1technology.com (mailto:mumstead@plus1technology.com)
Phone: 610-792-5660
Off the Stack brings technology leaders on to talk about the decisions small business owners actually have to make. Smarter IT. Simpler Processes. Stronger Results.
20 Aug 2026
You're Probably Paying for Security You Never Turned On | Kevin & Jordan Stock
Most small businesses treat IT like something you deal with once it breaks. Kevin and Jordan Stock think you should be setting it up the same week you call the power company.
Kevin and Jordan run RCR Technology Group, a fast-growing MSP in Findlay, Ohio, working with insurance agencies, financial institutions, and small municipalities. They sat down with Marc Umstead to talk about what actually goes wrong as a business grows past 10, 25, and 50 employees. The admin passwords that only live in one person's head. The zero trust policies your longest-tenured employees hate. The client who emails an engineer directly instead of opening a ticket, then wonders where the white glove service went.
They also get into the Microsoft 365 licenses businesses buy and never configure, why replacing hardware before it dies cuts your ticket count, and the pattern they see over and over: a concern gets raised, gets called too expensive, gets tabled, and shows up 16 months later as a week of downtime.
If you've ever told yourself you'll worry about IT later, start here.
(00:00) Meet Kevin and Jordan Stock, RCR Technology Group
(00:38) Why insurance, financial institutions, and municipalities
(01:31) Selling to clients who already understand their own risk
(02:07) What growing headcount does to your attack surface
(03:26) The "Tim has all the passwords" problem
(04:51) Rolling out zero trust to the employees who were there first
(05:29) Tickets versus emailing your engineer directly
(07:01) When everyone in the company is a decision maker
(08:36) At what size does a business need a real IT strategy
(09:16) IT is a utility, treat it like one
(10:04) The counterargument, and how to know it's time
(11:42) Are businesses actually using Microsoft 365
(13:49) Buying E3 and E5 licenses you never turn on
(14:27) Intune and managing laptops that leave the office
(15:31) Where clients see real returns: AI and backups
(17:02) Lifecycle management and riding it till the wheels fall off
(19:43) The decision that burns clients most often
(21:15) Technology accelerates whatever direction you're already headed
(22:45) How to reach Kevin and Jordan
CONNECT WITH RCR TECHNOLOGY GROUP
Website: https://rcrtg.com
Kevin Stock: https://www.linkedin.com/in/kevin-stock-aa1038a3/
Jordan Stock: https://www.linkedin.com/in/jordan-stock-6a1b3189/
CONNECT WITH PLUS 1 TECHNOLOGY
Website: https://plus1technology.com
Marc Umstead: https://www.linkedin.com/in/marcumstead/
Off the Stack is a podcast where technology leaders talk about what small and mid-sized businesses actually deal with. No vendor pitches, no jargon. Follow the show so you catch the next episode.
30 Jul 2026
Is Your Team Secretly Feeding Company Data to AI?
If you have 20 employees, 17 of them are probably already pasting company data into AI tools. And you don't know it.
Marc sits down with Matt Hutter of Iconium Networks, an MSP serving accounting firms, law firms, manufacturers, and nonprofits in Northeast Ohio for nearly 20 years. What starts as a conversation about where accounting firm technology is headed turns into a warning every small business owner needs to hear about ungoverned AI use, remote hiring blind spots, and the assumptions that get companies burned.
Matt shares the story of a remote hire whose "slow computer" turned out to be borrowed Wi-Fi from the apartment next door, why a $3,000 gaming PC isn't a safe work machine, and the one habit that keeps business owners ahead of technology changes instead of behind them.
🔗 LINKSPlus 1 Technology: https://plus1technology.comMarc Umstead on LinkedIn: https://www.linkedin.com/in/marcumstead/Iconium Networks: https://iconiumnetworks.comMatt Hutter on LinkedIn: https://www.linkedin.com/in/matthutter/
New episodes weekly. Follow the show so they land in your library automatically.
24 Jul 2026
The Most Preventable IT Disaster? A Bad Contract
Every business owner has a vendor horror story. The slow callbacks, the surprise invoices, the multi-year contract you can't get out of.
In this episode of Off the Stack, Marc Umstead sits down with Benji Sawyer of Sawyer Solutions to talk about the most preventable IT disaster there is: signing a bad contract with the wrong provider. Benji shares the one whose stated goal was to lock clients in and do as little as possible without getting sued, and how to make sure you never end up there.
They get into how to vet an IT provider before you sign, the questions that actually matter when you're interviewing one, the work most MSPs quietly aren't doing on your Microsoft 365, and why the right partner should be making your business better instead of just keeping the lights on.
In this episode:
Why a bad contract is the most preventable IT disaster there is
How to do your due diligence, and how to use AI to read the fine print
The Microsoft 365 work most providers skip
The one question every owner should ask when interviewing an MSP
Why the human side of support is a real security issue
Connect with Benji Sawyer: https://www.linkedin.com/in/benji-sawyer-b966333/ (https://www.linkedin.com/in/benji-sawyer-b966333/)
Sawyer Solutions: https://sawyersolutionsllc.com/ (https://sawyersolutionsllc.com/)
Connect with Marc Umstead: https://www.linkedin.com/in/marcumstead/ (https://www.linkedin.com/in/marcumstead/)
Plus 1 Technology: https://plus1technology.com/ (https://plus1technology.com/)
15 Jul 2026
Your IT Provider Says You're Covered. Are You?
Your IT provider says the backups are running, the patches are current, and you're compliant. How do you know?
Marc sits down with Mark Balovnev, CEO of Cyrisma, a cyber risk and compliance platform used by thousands of MSPs, to talk about the question most business owners never ask: who's verifying the work? Mark has a rare vantage point. His platform is the tool many IT providers use to prove what they're doing, which means he's seen what happens when nobody checks.
They get into why compliance matters even when no regulator is knocking, what a second set of eyes on your IT actually looks like, and the questions any business owner can ask their provider this week, no technical background required.
Marc runs an MSP himself, so this isn't a hit piece on IT providers. It's the opposite: good providers welcome verification. The ones who don't are telling you something.
Learn more about Cyrisma at cyrisma.com.
Connect with Plus 1 Technology here plus1technology.com.
Connect with Marc Umstead here: https://www.linkedin.com/in/marcumstead/
Connect with Mark Balovnev here:
https://www.linkedin.com/in/mbalovnev/
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