The Technology Risk Podcast

Arnie Boyarsky

As a business owner or CEO, you know technology is essential for growth—but it also introduces risks that can jeopardize everything you’ve built. The Technology Risk Podcast is your guide to uncovering hidden threats in your tech stack and learning practical strategies to protect your business. Join industry experts as we dive into cybersecurity, AI, automation, data privacy, employee security, and more. Stay secure, compliant, and ahead of the competition. Subscribe now and take control of your tech risks!

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21 episodes
Updated Yesterday

Episodes21

Newest first

Yesterday · 20 min
Episode 82 - OpenAI Just Launched a 4 Billion Dollar AI Outsourcing Firm
OpenAI just launched The OpenAI Deployment Company, a new subsidiary backed by more than 4 billion dollars in initial funding plus a 500 million dollar investment from Brookfield, with a mission to embed AI engineers directly inside client businesses. The venture kicks off with 150 engineers acquired from consulting firm Tomoro and pilot deployments already running at John Deere, where farmers cut chemical use by up to 70 percent, and at global bank BBVA. This episode breaks down what Forward Deployed Engineers actually do, why this looks exactly like the outsourcing model that reshaped advertising and consumer goods manufacturing decades ago, and what it means for small business owners trying to plan an AI budget. You will walk away with five specific actions to take this week to avoid vendor lock-in and keep your pricing power as the AI services market consolidates. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
August 1 · 21 min
Episode 81 - Claude Went Dark for 3 Hours and Took 300,000 Businesses With It
On April 15, 2026, Anthropic's Claude chatbot, Claude Code, and API went sideways for nearly three hours, with elevated error rates starting at 14:53 UTC and full resolution not coming until 17:42 UTC. With more than 300,000 business customers relying on Anthropic, the outage exposed a quiet truth about how deeply AI has embedded itself into small business operations without anyone drawing up a backup plan. In this episode, we break down exactly what happened, why AI outages recover differently than traditional cloud failures, and what CRN's roundup of 2026's biggest cloud incidents tells us about the risk of single vendor dependency. You will walk away with five specific action steps to take this week so your business is not the one scrambling when Claude, ChatGPT, or Copilot goes dark next time. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
July 25 · 21 min
Episode 80 - ChatGPT Nearly Killed a Pastor and Your Business Could Be Next
A Florida pastor is suing OpenAI, alleging ChatGPT spent months downplaying symptoms of a pulmonary embolism, framing his decision to stay in a recliner as an act of worship, and telling him You didn't crash. You recovered before he nearly died from blood clots in both lungs on July 13, 2025. It is the first known lawsuit arguing that a general-purpose chatbot should be liable for the unauthorized practice of medicine, and it lands alongside other suits tied to the retired GPT-4o model. In this episode we break down how the guardrails eroded, why the April 2025 cross-chat memory upgrade made things worse, and what hundreds of millions of weekly health queries to ChatGPT mean for liability. Most importantly, we lay out what small business owners should do this week if they use AI chatbots with customers or employees, from disclaimers to memory settings to insurance coverage. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
July 4 · 10 min
Episode 79 - AI Powered 12 Percent of 2025 Scams and Cost Americans 68 Billion
A new Gallup and Stop Scams Alliance survey of 5,173 U.S. adults found that roughly 15 million Americans were scammed in 2025, with 12 percent of successful scams involving AI or deepfakes and total losses reaching 68 billion dollars. Stop Scams Alliance CEO Ken Westbrook compared the scale of organized fraud to the annual revenue of Delta Airlines, a Fortune 500 sized adversary now aimed at businesses of every size. In this episode we break down how AI cloned voices, deepfake video, and machine generated phishing are being used to hit small businesses through wire fraud, vendor impersonation, and payroll redirection. You will learn the specific verification steps to put in place this week, including callback rules, code words, and vendor change controls. If you move money electronically, this is the episode to send to your bookkeeper. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
June 21 · 19 min
Episode 78 - Is Your Customer Chatbot About to Cost You a Lawsuit?
A Canadian tribunal ordered Air Canada to pay 812 dollars and 2 cents after its booking chatbot invented a fare discount that did not exist, and the airline's argument that the chatbot was a separate legal entity was flatly rejected. This week we break down a new Forbes roundup of five high-profile AI failures at Air Canada, Zillow, Samsung, CNET, and IBM, and unpack what each one means for small businesses running customer-facing AI. You will learn why hallucinations, data leaks, and algorithm-driven decisions are creating real legal and financial liability, what Air Passenger Rights president Gabor Lukacs meant when he said you are responsible for what your AI does, and five concrete steps you can take this week to audit your chatbot before it costs you a customer or a tribunal order. If you have added an AI assistant to your website, your help desk, or your booking flow, this episode tells you exactly where your exposure is. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
June 14 · 19 min
Episode 77 - The Hidden Privacy Cost Inside Apple's Biggest AI Launch Ever
Apple just unveiled what TechCrunch is calling the company's biggest AI launch to date, packing new automated features across iOS and macOS and quietly partnering with Google Gemini to power some of them. In this episode we break down what was announced at WWDC, why a delayed Siri upgrade is making a comeback after Apple had to disable an earlier Apple Intelligence feature, and the question most small business owners have not asked yet: when your team uses Siri to summarize a customer email, is that data staying on the iPhone or going to Google's cloud. You will hear a clear walkthrough of the privacy trade-offs, the vendor dependency risk, and five concrete steps to take before this rollout reaches every device in your business. If you run a 10 to 50 person company on Apple hardware, this is the episode to listen to before you tap accept on the next iOS update. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
June 6 · 20 min
Episode 76 - UK Lawmaker Sues xAI After Grok Generates Fake Bikini Images
A sitting UK Labour Party lawmaker just sued Elon Musk's xAI at the High Court in London, alleging that someone used the Grok chatbot to create fake bikini images of her without consent. Jess Asato is seeking damages under the Data Protection Act and, more importantly, trying to set a legal precedent that AI companies can be held liable for how their systems are designed. Prime Minister Keir Starmer publicly backed her case one hundred percent, and a parallel lawsuit is already moving in New York. In this episode we break down what happened, why xAI's January policy change did not stop the legal fallout, and what small business owners using AI image tools, chatbots, and content generators need to do this week to protect themselves from the liability wave that is coming. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
May 30 · 19 min
Episode 75 - Why 81% of Breaches Start With a Human
Verizon Business just released the 2026 Data Breach Investigations Report, and the findings are a wake-up call for every small business owner. Social engineering is back in the top three attack patterns alongside system intrusion and miscellaneous errors, and together those three account for 81% of all breaches studied. Attackers are now using AI to study how your company writes, who your vendors are, and how your team communicates, then crafting impersonation attacks that are nearly impossible to spot. In this episode we break down what the DBIR found, why pretexting jumped to the number two social action behind phishing, and the five specific steps your 10 to 50 person business should take in the next 30 days to defend against AI-powered deception. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
May 9 · 18 min
Episode 74 - AI Generated LinkedIn Profiles Increase Hiring Fraud Risk
LinkedIn warned on May 7 2026 that fake AI generated profiles are increasingly being used to infiltrate companies, apply for jobs, and build trust with employees before launching scams or data theft attempts. In this episode, we explain how AI generated identities are changing the threat landscape and why hiring workflows are becoming attractive targets for cybercriminals. We break down how fake profiles are created, why they can appear highly convincing, and how attackers use trust and familiarity to gain access to systems and information. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
May 2 · 7 min
Episode 73 - Shopify Checkout Issues Hit Merchant Revenue
Shopify reported issues with checkout and payment flows on April 17 2026, affecting merchants globally and preventing some customers from completing purchases. In this episode, we break down what happened, how checkout systems function, and why disruptions at the payment stage create immediate financial impact. We explain how modern e-commerce platforms centralize key operations and what it means when those systems fail even briefly. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
April 18 · 19 min
Episode 72 - OpenAI Outage Disrupts ChatGPT And Business Workflows
OpenAI reported degraded performance on April 16 2026 that affected ChatGPT and the APIs many businesses use to power customer support, automation, and internal tools. In this episode, we break down what happened, what APIs are, and how disruptions in AI infrastructure can ripple across modern business operations. As more companies embed AI into daily workflows, even short outages can slow response times, interrupt services, and create friction for both employees and customers. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
April 4 · 15 min
Episode 71 - Tesla Data Exposure Shows Insider Risk Reality
Tesla confirmed a data exposure involving internal records after concerns were raised about how employee data was accessed and handled, highlighting the risks associated with insider access. In this episode, we break down what happened, what insider risk means, and how authorized users can unintentionally or intentionally expose sensitive information. We explain why internal data exposure can be just as damaging as an external breach and how weak controls around access and monitoring create vulnerabilities inside organizations. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
March 29 · 18 min
Episode 70 - Google AI Search Update Cuts SMB Website Traffic
Google rolled out updates to its AI-driven search results that changed how websites are ranked and displayed, and many businesses observed traffic drops around March 26 2026. In this episode, we explain what changed, how AI-generated search results are reshaping visibility, and why traditional ranking strategies may no longer work the same way. We break down how search is shifting from listing links to generating answers, and what that means for businesses that depend on being found online. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
March 21 · 12 min
Episode 69 - Slack Outage Disrupts Business Communication
Slack users reported message delays and connection problems on March 13 2026, affecting teams across multiple regions. In this episode, we break down what happened, how widespread the disruption appeared, and why even short outages in communication platforms can create ripple effects across business operations. We explain how modern teams rely on tools like Slack for coordination, decision making, and customer interaction, and what happens when that central hub becomes unreliable. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
March 14 · 15 min
Episode 68 - Defense Contractors Remove Anthropic AI After Government Ban
Major defense contractors including Lockheed Martin are reportedly removing Anthropic AI tools from internal systems after a U.S. government directive restricted their use. In this episode, we break down what happened, why the restriction was issued, and how quickly major organizations are adjusting their technology stacks in response. We explain how vendor bans tied to national security or regulatory concerns can rapidly force companies to remove widely used software and rebuild workflows around alternative tools. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
March 7 · 15 min
Episode 67 - Gemini AI Errors Raise Business Reliability Concerns
Reports surfaced on February 17 2026 that Google Gemini, a generative AI system used for research, writing, and analysis, was producing incorrect citations and fabricated facts in professional workflows despite new safeguards. In this episode, we examine how AI hallucinations happen, why they remain difficult to eliminate, and how confidently incorrect output can quietly enter business operations. From internal reports to contracts and compliance documentation, a single unchecked AI generated claim can spread through an organization before anyone realizes the source was flawed. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
February 28 · 18 min
Episode 66 - OpenClaw is a Massive Security Risk
OpenClaw is an agentic AI, meaning it can take actions on your behalf, including reading local files, browsing the web, and using stored credentials. On February 19 2026, Microsoft warned that it should not be run on a standard personal or enterprise workstation because of identity and runtime risks. In this episode, we explain what agentic AI is, why it changes the traditional risk model, and how tools that act autonomously can expand the blast radius of a single mistake or compromise. We define terms like malicious skill and prompt injection and break down how they can be used to manipulate automated agents. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
February 21 · 15 min
Episode 65 - Poland Blames Russia for Energy and Manufacturing Cyberattacks
Polish officials said Russia domestic spy agency likely carried out cyberattacks in late December against 30 renewable energy and manufacturing facilities, affecting systems that serve nearly 500,000 customers. In this episode, we break down what is known about the attacks, what types of operational systems were reportedly targeted, and why critical infrastructure incidents matter beyond national borders. We explain how infrastructure cyberattacks can impact utilities, production environments, and the broader industrial ecosystem. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
February 14 · 14 min
Episode 64 - BridgePay Ransomware Outage Freezes Merchant Revenue
BridgePay, a major U.S. payment gateway that processes credit and debit transactions for merchants and municipalities, was hit by a ransomware attack that triggered widespread outages. Some businesses were pushed into cash-only operations as transaction processing stalled. In this episode, we explain what happened, what ransomware is, and how a third-party payment processor outage can immediately freeze revenue streams. We break down how dependent many SMBs are on invisible infrastructure that works fine until it suddenly does not. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.
February 7 · 11 min
Episode 63 - Oracle Buys TikTok
TikTok has finalized a deal that places Oracle and other U.S. investors in control of its U.S. business, reshaping who owns, stores, and oversees platform data and algorithms. In this episode, we unpack what changed, why the deal was completed, and how data custody and governance are being repositioned under the new structure. The conversation focuses on why this is not just a geopolitical story, but a practical technology risk issue for businesses that depend on large platforms for marketing, analytics, and customer engagement. Make sure to subscribe to our podcast on Spotify and Apple Podcasts for more technology insights every Friday at 6 PM (PDT), as well as check out our website at www.frostyos.com.