PODCAST · technology
Tech Deep Dive
by ITBroker.com
Almost $5 trillion dollars are spent on Information Technology (IT) annually. Cut through the hype and learn about the real needs, and problems that IT solves for your enterprise. Join us as we dive deep into case studies with providers and learn how IT can make your business better.
Episodes
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What AI Is Doing in Your Company (That You Don’t Know About)
Steve Wilson built his own AI assistant the careful way. He gave it its own Google account and read only access to his calendar, and told it not to talk to strangers. His company's CISO had a pen testing team go after it, and 4 days later the assistant reported that it had compressed his source...
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Playbook: Cybersecurity Truths
Before you compare a single vendor, a lot of the decision is already made. The systems you run today rule some platforms out, and the choices you make now decide whether a requirement three years from now means adding a license or replacing something the business runs on. In this Playbook, Max...
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Playbook: CSPs
Buying Microsoft 365, Google Workspace, or Azure direct feels like the simpler choice, until you need support or get locked out of your own tenant. In this Playbook, Max Clark breaks down what a Cloud Solution Provider (a CSP) actually does between you and the platform: faster support and...
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Did You Choose Cloud for the Wrong Reason?
A customer walked in sure they wanted colocation. The quote in their head was $10,000 a month. Once Jeremy Pease's team modeled the real requirements, staffing, connectivity, compliance, the number came back at $80,000. Jeremy Pease is CEO of Aptum, a hybrid multi cloud managed service provider.…
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Playbook: Buy on Purpose
You didn't choose your cloud provider. You inherited it, from whoever picked the safe option first and called it a decision. In this Playbook, Max Clark, CEO of ITBroker.com, names what that habit actually costs: three decades of consensus defaults, from the dot com era stack to LAMP to AWS's US...
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How to Tell If Anyone Is Actually Managing Your Technology Spend
A 270 line wireless account doesn't look like it has much room for savings. It had $4,000 a month sitting unnoticed, almost $40,000 a year, nobody had looked closely enough to catch it. Tommi Ellis is Channel Director at Intratem, a telecom and technology expense management company built on...
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How to Tell If Your MDR Provider Will Actually Stop an Attack
You're paying an MDR provider to protect you. Most of them will alert you and wait for someone else to act. This conversation names the one question that tells you which one you actually bought. Know the answer before it's 2am and someone's waiting on you to decide. You signed a contract for...
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Playbook: Cloud Cost Ownership
A VP spent weeks building a plan to cut an eight figure cloud bill. He walked into one meeting with engineering. Three words killed it: not my KPI. The bill lands on whoever gets handed the mandate to cut it, but the authority to actually change it sits with someone else entirely, usually...
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Playbook: Finding the Truth When Everyone Is Lying
Every vendor stretches the truth somewhere in your sales process, and most buyers respond to all of it the same way, forgiving everything or torching a good deal over nothing. In this Playbook, Max Clark sorts vendor lies into three categories, a harmless stretch, one rep's invented promise, and…
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Are Your Security Tools Actually Protecting You?
Your security tool says you're protected. So does your BAA, your SOC 2 report, and the maturity score you handed your board. None of that means any of them are telling the truth. Zach Stewart is a hands on CISO who spends his days doing exactly what this show is about: buying technology in a…
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How Do You Know Your Security Tools Are Actually Working?
Your website is no longer read only by people. Tony Lauro opens this episode with a client whose sequential order numbers let a competitor read their daily volume through a public API. No breach. No alert. Just a number counting up in plain sight. The same blind spot shows up when a product drop...
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Playbook: Buying MDR Without Getting Burned
Six months before the largest retail breach in U.S. history, Target's threat detection system worked exactly as it was supposed to. It caught the attack. It fired five separate alerts. Then nothing happened, because the system could watch, but it couldn't act. That gap between detecting a threat...
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Are You Buying Teams Voice in the Wrong Order?
Most Teams Voice buying decisions start with carrier pricing. This conversation argues that's backwards. Before comparing price per seat, you need to know who's actually running the infrastructure, what you're locking yourself into, and which risks stay invisible until after deployment. Eric…
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Did You Make a Security Exception for AI?
Anthropic built Claude Code. Anthropic still couldn't stop its own source code from leaking straight into a competing product. If a coding tool is running behind your VPN right now with full access, this conversation names what that's already costing you. Thomas Cooper is AI Product Lead at...
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Playbook: The Hidden Bomb in your Contracts
The clause that matters most in your vendor contract is usually the one everyone skips. It sits there looking harmless until a patent troll shows up. By then you cannot renegotiate it. In 2025, patent trolls filed more than half of all U.S. patent lawsuits. In high tech, it was over 90%. More…
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Should You Re-Sign After Your Technology Vendor Gets Acquired?
A week before this recording, Lumen agreed to buy Alkira for $475 million. Alkira was one of two leading independent network as a service companies left in the enterprise market. With this deal, there's basically one. Today's guest runs it. Ali Shaikh is the CEO of Graphiant. He was there for the...
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Who Made Sure Your Security Tools Actually Work?
Dave Chronister has been doing penetration testing and incident response since 2007 — back when Fortune 500 CIOs called it a novel concept. In the years since, he's walked into breached environments where the EDR was running, the MDR was installed, the SOC 2 audit had passed, and none of it...
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Playbook: AI Layoffs
You've read the post. A CEO goes on LinkedIn. Hard decision. I own this. Because of AI, we'll come out leaner, faster, stronger. Max Clark has written one of these. He's also been on the receiving end of one. In this Playbook, he breaks down what that post actually says — and what it's designed…
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Did Your AI Agents Move Faster Than Your Security?
You bought the platform. You renewed the contract. And 80% of your breach risk is coming from the one thing the platform wasn't built to catch. Craig Patterson spent years inside the channel ecosystem that sits between what security vendors ship and what enterprise buyers actually receive — and...
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You Bought the Stack. You're Using Half of It.
The average enterprise uses 44% of the Microsoft stack it's paying for. Denis O'Shea measured it: the same 120 point assessment, run across hundreds of organizations, and the number doesn't move. The other 56% sits licensed and idle while the same teams buy third party tools to cover gaps…
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Playbook: MSPs
MSPs sell their book. The vendors they're authorized on. The platforms they're certified on. The products they have margin on. The infrastructure they're about to recommend for your business is shaped by all of that before you walk in the room. This Playbook covers what that actually means for…
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Nobody Owns Your Cloud Bill
Nobody in the building owns the cloud bill. Not IT, not finance, not engineering — and when a CEO finally gets desperate enough to set a hard ceiling, like getting spend below 9% of revenue or the business isn't viable, that's when everyone finds out the EDP they already signed made the target...
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You’re Scaling on Infrastructure You Don’t Control
You're making infrastructure decisions on a system you can't see. It's fast, stable, and invisible. That's the problem. Underneath it, global capacity is planned years in advance, routes are shaped by geopolitics, and resilience depends on infrastructure you don't control. Max Clark sits down…
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Playbook: Be Careful With Your SOC2 Controls
SOC 2 doesn't mean a company is secure. And a control that passes your audit today could become a problem the next time you change security vendors. In this Playbook, Max Clark, CEO of ITBroker.com, explains why SOC 2 compliance isn't proof of security and the mistake companies make when defining...
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You’re Paying for the Same Network Twice
You’re paying for your network in ways you don’t see. Most teams don’t catch it until the bill shows up. Traffic leaves the cloud for inspection, then gets sent back in. Every step adds cost. Most teams never map the full path, so it goes unnoticed. Max Clark sits down with Doug Houghton from...
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AI Is Exposing Bad Network Decisions
Most enterprise networks weren’t designed for what they’re carrying today. The problem isn’t traffic—it’s the decisions underneath it. Those decisions weren’t made for today’s reality. They were made years ago—then inherited, layered on, and never fully revisited. Over time, that turns into...
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The Market Is Built For Sellers
The IT market is built for sellers. After 200+ episodes of Tech Deep Dive, one pattern kept showing up. The technology wasn't the hard part. The decision was. What got approved. What finance pushed back on. What vendors didn't say. What broke after the contract was signed. This is where the focus...
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Why Companies Spend Millions on Data (And Still Get No Value)
Max Clark is joined by Ed Bailey, Field CISO at Cribl, to discuss why many companies invest heavily in collecting data but struggle to turn it into meaningful outcomes. They explore common mistakes in data strategy, the gap between tools and skills, and what organizations should consider before...
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From 400 Calls in Queue to Zero Hold Time
What happens when your contact center hits peak demand… and the queue explodes? In this episode, Max sits down with Michael Cibelli (PolyAI) to break down how one major brand went from 400+ callers waiting in queue to zero hold time—without wrecking customer experience. You’ll learn why…
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Why Contact Center AI Projects Fail After the Demo
The demo was perfect. Then deployment happened. If your contact center AI “worked” in a pilot but fell apart in production - this episode explains why. Max Clark sits down with Jim K. Tennant (VP, Channel Sales at Observe.AI) to unpack the real reasons contact center AI projects fail after...
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The Azure Bill That Ended Cloud
What if the real problem isn’t Azure… it’s putting the wrong workloads there? In this episode, Max Clark sits down with William Sellers, Solutions Architect at DartPoints, to dissect a real-world migration from the energy sector: an internal research app that went into Azure “to move fast,”…
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DSPM vs DLP: The Data Blind Spots Killing Your Cloud Security
If you’re betting on “the cloud is secure” and a few DLP rules to save you, you’re exposed. Most breaches aren’t a tool failure, they’re a visibility failure. You can’t protect data you can’t see. In this episode, Max Clark sits down with Sirena Ong from Secuvvy to break down Data Security…
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Inside the Network That Prevented Prison Riots
You know that moment when the alerts start flooding in, and your entire network goes dark? Systems down. Phones silent. Operations frozen. Now imagine that happening inside a prison. Six hundred of them. One outage away from chaos. In this conversation, Max Clark sits down with Oliver Maxwell…
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Why This School Ditched Cisco and Saved $250K
Ever feel trapped in the endless cycle of network refreshes, license renewals, and “surprise” upgrade costs? You’re not alone. One school faced the same uphill battle and decided to break free. The result? A $250K turnaround and a totally new way of thinking about IT infrastructure. In this...
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How Do You Convince the Board to Fund Security?
You know the risks. The board knows the budget. So how do you bridge the gap? For most IT and security leaders, convincing executives to prioritize security is the toughest job they face. In this episode, Max Clark sits down with Alejandro Ziegenhirt, Sr. Manager of InfoSec & DevOps at OfferUp…
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Is Your IT System Killing Your Leads?
Every minute you wait to respond, another lead dies. Missed calls, ignored forms, slow follow-ups, your IT system might be the silent killer behind your pipeline collapse. In this episode, Max Clark sits down with Kaitlynn Crossno, Sales Engineering Manager at Capacity, to uncover the hidden IT...
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The IT Gap That Can Shut You Down
Imagine signing the lease, hiring the staff, setting the date and then realizing you can’t even open your doors. That’s exactly what happened to a fast-growing healthcare provider. In this episode, Max Clark and Darcy Guidry, Regional Channel Director at Epic iO, expose the hidden IT gap that can...
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AI That Saves Agents: Not Replaces Them
Imagine your call volume doubles overnight, but your hiring budget is stuck at zero. Most contact centers would collapse. Heritage Federal Credit Union didn’t. In this episode, Max Clark sits down with Brent Wilford and Patrick Russell from Glia to unpack how Heritage: Navigated a messy merger...
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Backups Don’t Equal Recovery
They had backups. The storm didn’t care. When a major client demanded proof of uptime and recovery, a Florida-based marketing company realized their DR plan was just a plan, not a solution. In this episode, Max Clark sits down with Keith Lukes from UbiStor to break down how backup confidence can...
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Your Fleet Is a Lawsuit Waiting to Happen
How many moving lawsuits are driving around with your logo on them right now? Fleet liability is no longer just a risk—it’s a ticking time bomb for your business. Accidents, claims, inflated insurance premiums, distracted drivers… the dangers are real, and they’re hiding in plain sight. In this...
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No Cyber Insurance. Still Got Paid.
What if you had no cyber insurance… and still walked away with the money? Most companies wouldn’t be so lucky. But one small manufacturer found themselves in the middle of a cybercrime event—and somehow, a loophole in the system worked in their favor. In this episode, Max Clark sits down with...
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A Child Died Dialing 911
It’s every parent’s worst nightmare—your child dials 911... and nothing happens. Most of us assume emergency services will be there when we need them. But what if your office phone, your cloud system, or your campus setup silently fails in a moment that counts? In this episode, Max Clark is…
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Microsoft Wants You Off Calling Plans
Microsoft doesn’t just allow you to leave Calling Plans—they’ve built tools to help you do it. That’s not a glitch in the strategy. It is the strategy. In this episode, Max Clark sits down with Steve Forcum, Director of Marketing at SIPPIO, to explore the future of voice inside Microsoft…
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The Cyberattack That Killed a Patient
Could one missed alert put lives at risk? Hospitals were once worried about downtime. Now they're facing something far worse: real-world consequences when cybersecurity fails. One ransomware attack shut down a hospital—and a patient died. It was a moment that changed how healthcare leaders view...
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They Got Breached Mid-Merger
What if the company you just bought came with a hidden cyber landmine? M&A is risky enough. But when cybersecurity gaps go unchecked during a merger, the consequences aren't just technical — they’re financial, operational, and reputational. And most leaders don’t see the breach coming until it’s...
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Why Your IT Puts Your Patients at Risk
A 20-year-old server. A forgotten backup plan. A single system crash. In healthcare, these aren’t just IT oversights — they’re threats to patient lives. From delayed treatments to data breaches, outdated tech can trigger a cascade of consequences no provider can afford. In this episode, Max Clark...
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How a Forgotten Laptop Became a Security Time Bomb
What happens when a three-year-old laptop, long forgotten, quietly reconnects to your network? It sounds like a harmless scenario—until it isn't. In today’s digital landscape, what we forget can hurt us. Join Max Clark and guest Alexey Goncharov of Cepheid as they dive into the overlooked blind...
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The Cyber Gap That Paralyzed a $2B Enterprise
3,000 apps. One entry point. Total compromise. In just hours, a $2B IT enterprise was paralyzed by ransomware, and what followed over the next 72 hours became a wake-up call for the entire industry. In this episode, Max Clark is joined by Brian Majowicz and Mac McClenathan of 11:11 Systems as…
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How 1,500 Franchises Dodged a $10M Tech Meltdown
What’s the true cost of IT chaos across a national franchise chain? Try lost transactions, reputation damage, and weeks of operational disruption. Now multiply that by 1500. In this deep-dive conversation, Max Clark is joined by Craig Collister, Sales Solutions Engineer at Spectrotel, to explore...
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SASE’s Hidden Loophole – Michael Ortega of CATO Networks Reveals the Biggest Threat to Businesses
Imagine logging in tomorrow and finding your entire network compromised. That’s exactly what happened to a company that relied on outdated security. In this episode of Tech Deep Dive, Max Clark sits down with Michael Ortega, VP of Sales Engineering at CATO Networks, to expose why legacy security…
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ABOUT THIS SHOW
Almost $5 trillion dollars are spent on Information Technology (IT) annually. Cut through the hype and learn about the real needs, and problems that IT solves for your enterprise. Join us as we dive deep into case studies with providers and learn how IT can make your business better.
HOSTED BY
ITBroker.com
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Frequently Asked Questions
How many episodes does Tech Deep Dive have?
Tech Deep Dive currently has 202 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Tech Deep Dive about?
Almost $5 trillion dollars are spent on Information Technology (IT) annually. Cut through the hype and learn about the real needs, and problems that IT solves for your enterprise. Join us as we dive deep into case studies with providers and learn how IT can make your business better.
How often does Tech Deep Dive release new episodes?
Tech Deep Dive publishes regularly with 202 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Tech Deep Dive?
You can listen to Tech Deep Dive on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Tech Deep Dive?
Tech Deep Dive is created and hosted by ITBroker.com.
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