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 engineering, whose time is already spoken for by other priorities. A FinOps platform will find you the free money, orphaned resources, idle instances, the stuff nobody has to defend. It won't touch the savings that…
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 a lie the whole company stands behind, and gives a different response for each. Then he turns the mirror on buyers, the shopped quote, the invented deadline, the fake executive sponsorship, because buyers run…
Your Security Tool Says You're Protected. Is It Lying?
Your security tool says you're protected. Most of the time nothing is lying to you on purpose. It's just reporting what it was configured to report, whether or not anyone ever checked if that setup was correct in the first place. Zach Stewart, CISO and Director of IT at Steno, spends this conversation walking through exactly where that gap hides, and it's not only the tool. There's the BAA that only protects you if you configured it correctly, and most companies never click the button. The SOC 2 stamp…
AI Agents Read Your Site in Under 1,000 Tokens. Most of What You Built Never Gets Seen.
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 gets sniped by bots in seconds, or when the large language models you're exposing to customers and employees get probed before anyone notices. Tony has spent 13 years inside Akamai's bot management and API…
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 and stopping it is where most MDR contracts fail their buyers. Max Clark recently evaluated a well known provider for ITBroker's own portfolio and found the same gap hiding under the brand name: full "Manage…
Your Teams Voice Contract Was Built 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 Burton runs National Channel at AudioCodes. He spent two decades selling dial tone on the carrier side before moving to the infrastructure side, the seat where most Teams Voice projects actually win or lose. This…
Your Developers Already Installed a Black Box Behind Your VPN.
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 Expedient, where he works daily with enterprises building AI governance after the fact, once a tool is already live and the CISO's original objection has already been overruled. This episode is what to check before…
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 than half their targets were companies under $25 million in revenue. They are not chasing Apple. They are chasing companies your size, because companies your size settle. The average defense cost runs around $4…
Your Vendor Got Acquired. Most Customers Realize the Risk Too Late.
Lumen just announced it's acquiring Alkira. If your network strategy runs through a vendor that just changed hands, or through one that might, this conversation covers what actually happens next. Ali Shakh, CEO of Graphiant, was part of the Viptela founding team when Cisco acquired them. He was in the room for that integration. Prices went up. Not by a little. The customers who got hurt were the ones who had no hedge and no questions ready. This episode is those questions, plus what most enterprise…
The EDR Was Running. The Ransomware Still Won.
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 mattered. This conversation covers the gap between what companies think they bought and what they actually have why tools become the program by default, why compliance audits and security programs are two…
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 to leave out. Not to indict the people who write them, but to hand you one question: whenever a company or a vendor tells you why they're doing something, who was that explanation written for? It's the same…
AI Agents Are Already Inside Your Company. Nobody’s Watching Them.
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 he's unusually direct about where those two things don't match. In this conversation: the Microsoft "free SIEM" that isn't free once you turn it on, the insider threat blind spot baked into nearly every…