HeyJaredThe Technology Risk Podcast
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.
- Indexed episodes, last 90 days
- 7
- Latest publication
- Sep 5, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 4, 2026
Latest episodes
Episode 85 - EU Hits ChatGPT With Tougher Rules Your EU Customers Will See First (opens the original)
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The European Union just designated ChatGPT as a Very Large Online Platform under the Digital Services Act, making it the first AI chatbot to face this level of regulatory scrutiny. With more than 159 million EU users, OpenAI now has four months to meet new risk-management, transparency, and content-moderation obligations, and Reddit and Roblox got the same designation. This episode breaks down what changed, why the EU classified ChatGPT as a search engine to bring it under the DSA, and what smal
Episode 84 - Meta Sued After AI Picked Layoff Targets And Judge Wont Stop It (opens the original)
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Meta is being sued by employees who say the company used its own flawed AI system to pick who got laid off, and that the model discriminated against workers on medical and family leave. On July 17, 2026, a federal judge refused to block those layoffs from moving forward, meaning the workers lose their jobs now and litigate later. In this episode we break down what Reuters, Futurism, and other outlets are reporting, why this is one of the first real court tests of AI in employment decisions, and
Episode 83 - GitHub’s 8 Hour Outage Kills your Deployment Window (opens the original)
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On August 17, 2026, GitHub went dark for 7 hours and 47 minutes, freezing Issues, Pull Requests, APIs, Actions, and Copilot for developers around the world. GitHub's postmortem blames saturated load balancers in its Central US facility, an autoscaling policy that watched the wrong metric, and a latent retry bug in Visual Studio Code that amplified traffic to a single internal endpoint by roughly 10 times. In this episode we break down what actually broke, why the Copilot Token Service was the la
Episode 82 - OpenAI Just Launched a 4 Billion Dollar AI Outsourcing Firm (opens the original)
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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 De
Episode 81 - Claude Went Dark for 3 Hours and Took 300,000 Businesses With It (opens the original)
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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
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