# How Black Monday Broke the Stock Market Page: https://stenobird.com/podcast/trail-boss-radio-ai-tech-digital-independence-7780171/how-black-monday-broke-the-stock-market Text version: https://stenobird.com/podcast/trail-boss-radio-ai-tech-digital-independence-7780171/how-black-monday-broke-the-stock-market.md Podcast: [Trail-Boss Radio: AI, Tech & Digital Independence](https://stenobird.com/podcast/trail-boss-radio-ai-tech-digital-independence-7780171) Published: 2026-07-08T22:00:05+00:00 Episode link: https://johnsondanny866.podbean.com/e/how-black-monday-broke-the-stock-market/ Audio file: https://mcdn.podbean.com/mf/web/7hepzypn37pewkst/How_Black_Monday_Broke_the_Stock_Market.mp3 Processing state: not_requested JSON: https://stenobird.com/v1/public/podcasts/trail-boss-radio-ai-tech-digital-independence-7780171/episodes/how-black-monday-broke-the-stock-market Duration seconds: 1265 ## Resource How Black Monday Broke the Stock Market On October 19, 1987, the Dow Jones Industrial Average dropped over 22% in a single day β€” the largest one-day percentage crash in stock market history. Trail Boss Dan Johnson breaks down what happened on Black Monday, why it happened, and what it still teaches investors today about panic, program trading, and the danger of following the crowd instead of a plan. Questions this episode answers: What caused the Black Monday stock market crash of 1987? How much did the stock market drop on Black Monday? What is program trading and how did it contribute to the crash? What can investors learn from past market crashes? How do you protect a portfolio during a market downturn? History doesn't repeat, but it rhymes β€” and the same discipline that gets investors through a crash is what we're building live, one week at a time, in the $100 Experiment. Follow along and see the Trail Boss Baseball Portfolio System in action at unbridlednation.com/investing. Continue the Trail Boss Journey 🌐 Unbridled Nationhttps://UnbridledNation.com Explore practical lessons on ownership, entrepreneurship, technology, and lifelong learning. 🌐 Trail Boss Investinghttps://UnbridledNation.com/investing Follow the Trail Boss Investing Project as we simplify ETFs, REITs, dividend investing, portfolio construction, and long-term investing through open-source education. 🌐 Unbridled Tech Academyhttps://UnbridledTechAcademy.com Learn AI, websites, entrepreneurship, and digital business through a modern apprenticeship focused on learning how to think. 🌐 iLyft4Uhttps://iLyft4U.com Discover how today's work can help fund tomorrow's opportunities and build lasting ownership. πŸŽ™οΈ Subscribe to Trail Boss Radio and join the Trail Boss Open-Source Experiment as we explore investi… ## Actions - request_transcript: `POST https://stenobird.com/v1/public/podcasts/trail-boss-radio-ai-tech-digital-independence-7780171/episodes/how-black-monday-broke-the-stock-market/transcription-requests` β€” Idempotently request low-priority transcript generation for this episode. - read_markdown: `GET https://stenobird.com/podcast/trail-boss-radio-ai-tech-digital-independence-7780171/how-black-monday-broke-the-stock-market.md` β€” Read the agent-friendly Markdown representation of this episode resource. A page view does not enqueue transcription. Agents should invoke `request_transcript` explicitly when they need this episode processed. ## Transcript Full transcripts are not published on public pages unless there is a clear rights basis.