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E45 - You Have An AI Policy. Your Vendors Have A Free Account.
Aug 30, 2026
Unknown duration
E44 - The Guy You Fired Still Has The Keys
Aug 23, 2026
Unknown duration
E43 - Your Bookkeeper Is Using AI On Your Books. Did You Approve It?
Aug 15, 2026
Unknown duration
E42 - AI Is Not Coming For Your Team. It Is Coming For The Worst Two Hours Of Their Day.
Aug 8, 2026
Unknown duration
E41: Stop Calling It ROI Unless It Hits the P&L
Aug 2, 2026
Unknown duration
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 8/30/26 | E45 - You Have An AI Policy. Your Vendors Have A Free Account. | You Have An AI Policy. Your Vendors Have A Free Account.An executive questioned one number in one ad. The marketing agency's answer stopped him cold: we got the numbers from you. Inside a shared marketing folder sat an accounting spreadsheet someone had dropped there by accident, and for two months the agency's AI had been reading the whole folder and building campaigns from it. The AI saw their real costs and priced an entire product suite at roughly a ten percent markup instead of their normal margin. One ad ran. Nobody lied. Nobody was hacked. Somebody dragged a folder, and an AI nobody approved made pricing decisions in public.Host Nick Dreyfus, VP of Business Development at i-NETT, argues that if your own house is in decent shape, your biggest AI risk is not your team. It is the vendors you trust most. You give your bookkeeper one hundred percent of your data. Your accountant, your marketing agency, your billing company, all of them are holding everything, and most businesses have never asked one question about what those vendors do with it in the age of AI.In this episode: the clean kitchen problem, why a spotless AI policy tells you nothing about your supply chain. The two question email to send every vendor Monday morning, free. The move almost nobody makes: putting vendor AI work inside your environment, behind your own security, and offsetting the license against their bill. Why we've got Copilot, we're totally good is not the finish line when twenty years of file permissions say otherwise. And the money nobody discusses: in client environments we have audited, do it yourself AI agents commonly cost three to five thousand dollars a month to run, usually because they are doing way too much thinking on a model that is too expensive for the task. Built right, the same agent often runs at a fraction of that.Questions answered: Which of my vendors are running my data through AI right now? What am I allowed to ask them? What does a real AI policy cover? Why do most AI projects show no return? What should an agent actually cost to run, and who is watching it after it ships?Start here, and it costs nothing. Send every vendor who touches your data two questions: are you using AI on any of our data, and if so, what guardrails and security do you have around it? Everything in this episode was preventable. All they did was not ask a couple of questions.Nick is not an attorney and this is not legal advice. Vendor obligations depend on your contracts, so bring them to your counsel.AI readiness: https://i-nett.ai | Managed services: https://i-nett.com | Technology Fund: https://nonprofit.i-nett.com | Book time: https://meetings-na2.hubspot.com/ndreyfus | [email protected] | (858) 337-2866Tags: AI policy, shadow AI, vendor risk, AI agents, token costs, Copilot, AI readiness, managed IT, MSP, cybersecurity, CEO, CFO, small business, San Diego, The Digital Dilemma, Nick Dreyfus, i-NETT | — | ||||||
| 8/23/26 | E44 - The Guy You Fired Still Has The Keys | The Guy You Fired Still Has The KeysHe was not fired. He resigned on good terms, and there was a party. That is worse, because when somebody leaves happy, nobody is watching. His login stayed active, since disabling it was a five minute job on a list of four hundred things. That account still had access to the company bank account, and the password on it was sitting in a public credential dump. Nobody was hacked. Somebody just did not do the job.Host Nick Dreyfus, VP of Business Development at i-NETT, argues that nobody attacks your best system. They attack your cheapest one. And your cheapest one got there one of two ways: a job that never got done, or a budget set by someone who was never given the full picture. Confuse those two and you make the wrong call every time.In this episode: why your IT director spends the day resetting passwords, and what falls off the list when they do. Which layer of support is worth a senior salary and which two are not. Why the person who knows how bad it is has every reason not to tell you. The technology leader who did not know what business continuity meant, and the one to two week recovery nobody upstairs knew about. How attackers reached one of America's largest retailers through an air conditioning contractor running free consumer antivirus. What happens inside an IT company when margins get squeezed, and which tool quietly gets swapped. And a company that paid zero ransom and still lost two months, hundreds of thousands of documents, and a quarter of its revenue.Questions answered: How do I know if my IT team is telling me everything? What should I ask before approving another technology budget? Are we running anything that stops getting security updates this year? What happens when someone leaves, and who verifies it? If we were encrypted tonight, how many days until we operate again?Start here, and it costs nothing. Tell whoever runs your technology that nothing they report will be held against them, and mean it. Ask what happens when somebody leaves, then compare enabled accounts against headcount. Then ask your leadership which three customers would leave if you went dark for six weeks, and what those three are worth as a share of profit. That number is your real security budget.The full list of fifteen questions, plus every source cited, is at thedigitaldilemma.riverside.comNick is not an attorney and this is not legal advice. Breach disclosure duties vary by state and industry. Insurance policies differ, so read yours and get your broker's answer in writing.AI readiness: https://i-nett.ai | Managed services: https://i-nett.com | Technology Fund: https://nonprofit.i-nett.com | Book time: https://meetings-na2.hubspot.com/ndreyfus | [email protected] | (858) 337-286600:00 He was not fired, and that is worse 03:45 Why the five minute job never gets done 08:00 The word that scared me 09:15 The air conditioning guy 13:30 Why the cheap thing exists 16:30 What happens when margins get thin 19:00 Two months down, zero ransom paid 24:30 The seven questions 30:30 The ones with the least 32:00 What to do MondayTags: cybersecurity, offboarding, business continuity, ransomware, Server 2012 end of life, cyber insurance, managed IT, MSP, CEO, CFO, small business, San Diego, The Digital Dilemma, Nick Dreyfus, i-NETT | — | ||||||
| 8/15/26 | E43 - Your Bookkeeper Is Using AI On Your Books. Did You Approve It? | Your Marketing Agency Is Running Your Client List Through AIThe meeting ended. The guests dropped off. The team kept talking about costs and relationships. The AI note taker was still in the room, and it emailed the transcript to everyone on that call.Nobody was hacked. Nobody broke a policy, because there was not one. And there was no undo.Host Nick Dreyfus, VP of Business Development at i-NETT, argues your company already has an AI program. You did not approve it, you did not budget for it, and you cannot see it. Half of it is your team. The bigger half is everyone outside your building who already has your data.In this episode:The one document almost no company has, and why "everybody knows the rule" falls apart when it mattersWhy shadow AI is a procurement failure, not a discipline problemTwo risks everyone mashes together: a vendor reusing your work, and your data landing where you cannot see itThe free version is free because you are the paymentWhy an AI tool wired into your CRM is an authorized skeleton keyThe four questions to ask any vendor touching your data, and what to do when they get vagueWhy Uber burned its 2026 AI budget in four months with nobody misusing anythingWhy we are at 1998, and why committing to one model now is a bet you do not have to makeThis episode answers:Which of my vendors is running AI on my company's information?Do I need employees to sign something naming approved AI tools?Can a vendor reuse the work they did for me and sell it to my competitor?How does a small company push back on a much larger vendor?Who should pay when a vendor wants to use AI on my account?Start here, and it costs nothing. List every outside party that touches your information. Send one email asking whether they use AI on your account, which tools, what tier, and whether your material trains anything. Ask for it in writing. The answers, including the vague ones, tell you where you stand.Nick is not an attorney and this is not legal advice. Have your counsel review any policy or vendor document before anyone signs it.AI readiness assessment: https://i-nett.ai Managed services and cybersecurity: https://i-nett.com Community Technology Fund: https://nonprofit.i-nett.com Book a time with Nick: https://meetings-na2.hubspot.com/ndreyfus [email protected] | (858) 337-2866Chapters: 00:00 The note taker that stayed in the room 01:40 We deploy AI for a living 03:20 The paperwork almost nobody has 08:30 The part nobody talks about 09:40 Your work walking out the door 12:00 You are the payment 14:30 The skeleton key in your CRM 16:30 The four questions to ask every vendor 20:30 Uber burned a year of budget in four months 22:30 What to do this week for nothing 25:00 The decision that had to happen firstTags: shadow AI, third party risk, vendor management, AI governance, AI usage policy, data privacy, cybersecurity, managed IT services, MSP, small business, San Diego, intellectual property, data leakage, vendor agreements, The Digital Dilemma, Nick Dreyfus, i-NETT | — | ||||||
| 8/8/26 | E42 - AI Is Not Coming For Your Team. It Is Coming For The Worst Two Hours Of Their Day. | One in eight things it tells you is made up, and it says every one of them with the same confidence. You would fire that employee. So why did you hand it your invoicing?AI is not coming for your team. It is coming for the worst two hours of their day. But it is not an employee, and treating it like one is how companies end up with a pile of spend and nothing on the P&L.Host Nick Dreyfus, VP of Business Development at i-NETT, argues the replacement narrative is wrong and the real risk is the opposite one. Not that AI takes the job, but that nobody is checking its work.In this episode:The one in eight test: apply your hiring standard to a system that is confidently wrong, and your deployment plan writes itselfThe invoice that hit ten thousand percent: what a 5% price increase becomes with no guardrails, and why your client catches it before you doWhy MIT found roughly 95% of AI deployments show no return, and why it is not the technology's faultWhat an agentic engineer does all day, for a CEO with no interest in becoming technicalThe rule that changes everything: do not let AI think, let it chooseWhy five hours saved in accounting is worth almost nothing, and five hours saved in sales takes a 90 day close to 45This episode answers:Is AI going to replace my employees?Why do most AI projects fail to produce any ROI?What is an AI agent, and who should be building ours?Do we hire AI engineers or bring in a partner?What AI is already running in my company that I do not know about?You have three choices and one is not real. Do nothing, which is not neutral, because your team is already using AI on personal accounts. Build your own agentic engineering team. Or bring in a partner who has one.Start here. Ask your team what AI they use and what they put into it. Then ask who would catch it if it got something wrong. If nobody has an answer, you found your starting point.Free AI usage policy template you can hand your team Monday: https://i-nett.ai/ai-usage-policy A starting point, not legal advice. Have your attorney review it.Book a time with Nick: https://meetings-na2.hubspot.com/ndreyfus Our position on AI: https://i-nett.ai Managed services and cybersecurity: https://i-nett.com Community Technology Fund: https://nonprofit.i-nett.com LinkedIn: https://www.linkedin.com/in/nicholas-dreyfus/ [email protected] | (858) 337-2866Chapters: 00:00 The employee who makes things up one in eight times 03:00 Why confidence is the danger, not error 08:00 The invoice that hit ten thousand percent 13:00 Why 95% of AI deployments fail 18:00 What an agentic engineer actually does 23:00 Not all saved hours are worth the same 28:00 Your three choices, and one is not realYour team focuses on growth. Our team makes that happen. New episodes weekly.Educational only. Not legal or financial advice. Statistics cited are third party research and results vary.#AI #AIAgents #ArtificialIntelligence #SmallBusiness #CEO #BusinessStrategy #ManagedServices #MSP #AIStrategy #DigitalDilemma | — | ||||||
| 8/2/26 | E41: Stop Calling It ROI Unless It Hits the P&L | 98% of executives say their AI investment is paying off. MIT found that 95% of AI pilots cannot prove any return at all. Both numbers are real.Today we show you where the money actually goes.Tesla sells a feature called Full Self-Driving Capability. On their own website, in the same paragraph, they tell you "the currently enabled features do not make the vehicle autonomous." Nobody lied. The name just did the work. "Artificial intelligence" is doing the exact same thing to your budget.Host Nick Dreyfus breaks down why most companies cannot answer the one question that matters: did the AI you bought ever hit your P&L?No hype, no vendor spin, no Silicon Valley bias.In this episode:Why AI is not artificially intelligent, it is a prediction engine, and why that distinction explains every hallucination and every failed pilotWhy "we saved 10 hours a week" is not a financial result, and the exact math a CFO should run before believing itWhy not all saved hours are worth the same: free up accounting and you get accounting, free up sales and you get pipelineThe one sentence to put in your approval document before you spend a dollar on any AI projectThe two questions to ask any AI vendor before you sign anythingA free exercise you can run with your team Monday morning that costs nothing and tells you more than any vendor demoThis episode answers:Is AI actually artificial intelligence, or something else entirely?Why do 95% of AI pilots fail to show measurable ROI?When should a business kill an AI project instead of doubling down?What belongs on a CFO's dashboard for AI spend?The line to remember: you cannot have AI thinking, you can have AI flagging. The humans do the thinking. The machine handles what is repetitious and flags what is out of the ordinary. Companies that respect that line are the ones whose numbers eventually show up.Book a time with Nick: https://meetings-na2.hubspot.com/ndreyfusLearn more:Managed services and cybersecurity: https://i-nett.comOur position on AI: https://i-nett.aiCommunity Technology Fund: https://nonprofit.i-nett.comConnect with Nick Dreyfus:LinkedIn: https://www.linkedin.com/in/nicholas-dreyfus/[email protected] | (858) 337-2866Chapters:00:00 Two numbers that cannot both be true02:30 What AI actually is, and is not07:00 Why saved hours are not a return13:00 Where to point AI first18:30 When to kill an AI project22:30 Two questions before you sign25:30 The Monday morning testYour team focuses on growth. Our team makes that happen.New episodes weekly.Educational only. Not financial or investment advice. Results vary by environment.#AI #ROI #CFO #SmallBusiness #ArtificialIntelligence #ManagedServices #MSP #BusinessStrategy #DigitalDilemma #AIStrategy | — | ||||||
| 7/28/26 | E40 - OpenAI’s Models Hacked Hugging Face. How Many Businesses Are Next? | An advanced OpenAI model was placed inside a restricted cybersecurity test. It found a way out, reached the internet, and compromised Hugging Face infrastructure while pursuing answers to the test.It was not told to attack Hugging Face.It was told to complete an objective.That distinction should get the attention of every CEO and CFO.In Episode 40 of The Digital Dilemma, Nick Dreyfus explains why this incident is not a science-fiction story about an evil machine. It is a business warning about speed, persistence, access, and what happens when a powerful system pursues a goal without enough boundaries.The next generation of cyberattacks will not need to get everything right on the first attempt. AI can test one path, fail, change its approach, and try again. One firewall, one antivirus product, or one green backup checkbox is no longer a business-continuity strategy.Nick connects the OpenAI and Hugging Face incident to the 2010 Flash Crash and Knight Capital's $460 million automated trading failure. He also shares firsthand stories from the field:• A respected IT provider reported successful backups, but the latest recoverable copy was more than six months old.• A manufacturer automated a process, shipped approximately 100,000 affected products, stopped taking new orders, and spent nearly seven months recovering.• Mid-sized companies believed enterprise equipment made them secure while unsupported servers and excessive permissions left openings attackers could exploit.This episode is built for leaders running companies where payroll, production, billing, accounting, sales, and customer relationships all depend on technology.CHAPTERS00:00 It was a matter of time01:35 What OpenAI says happened04:30 Why the model's objective matters06:20 The Flash Crash and Knight Capital lesson08:45 What i-NETT finds after an attack11:05 A green backup checkbox is not recovery14:10 How one automated mistake reached 100,000 products16:45 Why security is the last place to buy the cheapest checkbox19:10 Why a good MSP may still be unprepared for AI21:15 The new AI responsibility inside every business22:45 Why cyber insurance is not the strategy24:20 Three questions every CEO and CFO should ask this week26:20 The leadership decision that cannot waitTHE THREE QUESTIONS1. What are we protecting, and where are our unsupported systems or excessive permissions?2. Can you prove that our recovery works, and how long would it actually take?3. What authority are we giving AI, what data can it access, and who is watching it?Policy without testing is hope.Security without monitoring is hope.Backups without recovery are hope.Hope is not a business-continuity plan.Learn how i-NETT approaches responsible AI adoption:https://i-nett.aiExplore strategic managed IT, cybersecurity, and business continuity:https://i-nett.comConnect with Nick Dreyfus on LinkedIn for practical conversations about AI, cybersecurity, managed services, and the decisions facing business leaders right now.Follow The Digital Dilemma on Apple Podcasts, Spotify, or wherever you listen to podcasts. If this episode makes you think differently, share it with a CEO or CFO who needs to hear it. | — | ||||||
| 7/20/26 | AI project failurebusiness impact+4 | — | MITThe GenAI Divide: State of AI in Business 2025 | — | AI projectsbusiness ROI+5 | — | 21m 22s | ||
| 7/3/26 | cybersecurityAI attacks+4 | — | Fortune 500Lloyd's of London | — | AI attackscybersecurity+7 | — | 17m 28s | ||
| 6/7/26 | cybersecurityAI+3 | — | i-NETT | — | cybersecurityAI attacks+3 | — | 16m 21s | ||
| 5/30/26 | AI toolsdata privacy+4 | — | ChatGPTClaude+5 | — | AI toolsdata security+6 | — | 20m 52s | ||
Want analysis for the episodes below?Free for Pro Submit a request, we'll have your selected episodes analyzed within an hour. Free, at no cost to you, for Pro users. | |||||||||
| 5/23/26 | AI adoptionleadership+3 | — | AICEO+1 | — | AIleadership+5 | — | 19m 28s | ||
| 5/19/26 | AI usageprompt engineering+3 | — | i-NETT | — | AIprompts+5 | — | 20m 36s | ||
| 5/12/26 | productivityAI implementation+4 | — | — | — | productivityAI+5 | — | 26m 10s | ||
| 5/4/26 | AI security risksshadow AI+3 | — | ChatGPTGoogle Gemini+3 | — | AIsecurity risks+5 | — | 21m 32s | ||
| 4/25/26 | AI and employmentjob displacement+3 | Al Bryant | RapidShift AICisco+2 | — | AIjob replacement+6 | — | 27m 47s | ||
| 4/18/26 | Shadow AIcybersecurity+4 | — | IBMAmazon | — | Shadow AIcybersecurity threat+4 | — | 21m 04s | ||
| 4/11/26 | AI strategybusiness competition+3 | — | Gen Zi-NETT | — | AI toolsbusiness owners+3 | — | 9m 48s | ||
| 4/4/26 | AI adoptionleadership communication+3 | — | i-NETTApple Podcasts+2 | — | AI rolloutcommunication failure+3 | — | 9m 35s | ||
| 3/6/26 | AI and creativityhuman originality+5 | — | — | — | AIcreativity+6 | — | 8m 34s | ||
| 2/6/26 | AI governancedata privacy+4 | — | organizationsAI+4 | — | AI governanceshadow IT+6 | — | 11m 40s | ||
| 1/26/26 | AI adoptionboard strategy+3 | — | — | — | AIboardroom+5 | — | 7m 30s | ||
| 1/22/26 | AI readinessleadership+4 | — | — | — | AI readinessleadership+5 | — | 10m 28s | ||
| 11/4/25 | AI policycybersecurity+3 | — | — | — | AI policybusiness+7 | — | 10m 51s | ||
| 6/24/25 | Why Smart CEOs Are Simplifying Their Networks Before It’s Too Late | SummaryIn this episode of The Digital Dilemma, Nick Dreyfus discusses the hidden profit drain caused by overly complex computer networks. He outlines the signs of a tangled network and provides six essential questions for business owners to assess their IT infrastructure. Dreyfus emphasizes the importance of simplifying networks to enhance efficiency, reduce downtime, and improve overall business performance. He also shares strategies for cloud migration and regular maintenance to ensure a reliable and agile IT environment.TakeawaysNetwork complexity can lead to significant revenue loss.Assessing the number of devices is crucial for reliability.Integration of systems can save time and resources.Over-reliance on a single IT guru can create vulnerabilities.Frequent updates should not cause unexpected outages.Streamlining office setups can accelerate growth.Cloud migration enhances security and operational agility.Regular maintenance is essential to prevent crises.Simplicity in IT leads to increased reliability.Business leaders must engage in IT discussions for effective management.TitlesCutting Through Network ComplexityThe Hidden Costs of IT ComplexitySound bites"How many separate devices do we rely on?""Cloud migration boosts security and agility.""Regular maintenance prevents crises."Chapters00:00 Understanding Network Complexity09:43 Assessing Network Efficiency19:24 Strategies for Simplifying IT InfrastructureKeywordsnetwork complexity, IT infrastructure, cloud migration, business efficiency, technology solutions Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 6/11/25 | The Hidden Cost of Free AI Tools: What You’re Really Giving Away | 🎙️ Show Summary – Episode Title: The Free AI Trap: What You’re Really Trading for ConvenienceIn this episode of The Digital Dilemma, Nick Dreyfus uncovers the hidden costs behind the AI tools that promise everything — for free. From ChatGPT to Canva AI and Google Gemini, millions of users are relying on free platforms to drive productivity. But what are we giving up in exchange?Nick explores how "free" AI tools may be mining your data, jeopardizing your intellectual property, and setting you up for long-term dependency. He breaks down the fine print in those overlooked Terms of Service, shares real-world examples of unexpected risks, and offers a practical AI privacy checklist to keep you protected.Whether you're a small business owner, educator, entrepreneur, or just someone who loves using tech — this episode is your wake-up call to audit your AI stack before it’s too late.🎧 Topics covered:How AI platforms use your data behind the scenesWhat terms like “training models” really mean for your IPThe risks of building workflows on free toolsSimple steps to protect your business and creativityA listener challenge to take action this week✅ Take the challenge:Audit your AI tools and see what you’re really trading.📩 Share your story or feedback with Nick at [your email] or DM on LinkedIn.Don’t forget to subscribe, rate, and share this episode with a colleague who needs to hear it. Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
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Chart history for The Digital Dilemma
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| Market | Genre | Peak | Current | Trend |
|---|---|---|---|---|
| United States | — | #151 | #151 | — |
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