709 why the market always goes up + how to buy the dip

In this episode, Nick dives into the story of Dumb Money, a trio of everyday investors who made millions during the chaos of 2020. From betting big on Crocs to shorting the market during peak panic, their social media-driven strategy paid off. But were they a one-hit wonder or did lightning strike twice?Nick & Glen’s book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.

Last April, Nick conducted an experiment by following the advice from a popular investing book. The journey began in Episode 616: The little book that beats the market (listen here: Apple | Spotify), where Nick reviewed the book’s philosophy and invested $2,000 into a retirement account based on its strategy. In today's episode, amid ongoing market chaos, Nick revisits that original approach, refreshes listeners' memories on the investing philosophy, and checks in on how the $2,000 retirement account has performed one year later.Nick & Glen’s book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.

This week, Nick chats with ex-hedge fund manager, options trader and educator Mark Yegge about how he uses covered calls and in-the-money leaps to generate regular income from the stock market. Mark shares the logic behind his “cash flow machine” strategy, how it compares to buy-and-hold investing, and why he believes it’s possible to earn 1–2% per week even when markets are down.Download Mark's free ebook, Regular Paychecks here: https://www.cashflowmachine.io/regularpaychecks-ytNick & Glen’s book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.

Desperate times call for desperate measures. The markets are as wonky as Donald Trump's hairline and when the crazy American president is causing chaos in the markets, I figured I’d do a fun episode today. I asked three popular Language Learning Models this question: “Of all the great buying opportunities in the markets today, what do you think are the best picks in terms of current valuation and long term potential upside?". Here are the answers of Google's Gemini, xAI’s Grok and the king of them all, ChatGPT.Nick & Glen's book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.

Do you love a good Black Friday sale? Some of your best stocks are 20-25% off right now. Are they value buys are bear traps in the waiting? Nick unpacks these 10 stocks.Nick’s latest book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.

Nvidia (ticker symbol NVDA) invests in companies just like the rest of us. In today’s episode, we unpack six of their most recent investment moves. What they’ve bought, what they’ve sold, and whether it’s worth taking a closer look for your own portfolio.Nick’s latest book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.

Ever watched a stock plunge 20, 30, or even 50% and assumed it was a lost cause? Well on today’s episode Nick breaks down six stocks that defied the odds and made historic comebacks from their 2022–2023 lows.Nick’s latest book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.

Founder-led companies such as Apple, Microsoft and Amazon often bring vision, innovation, and long-term focus. In this episode, Nick dives into four lesser-known stocks with strong founder involvement - HIMS, RKLB, TEM, CARG - and breaks down what makes them stand out (or stumble) in the market. Nick’s latest book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.

When markets are down, many investors freak out. But should they? In this episode, Nick breaks down why the stock market is designed to go up over time, why downturns are often buying opportunities, and how to use moving averages to find smart entry points.Nick’s latest book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.

Are the Mag 7 still magnificent, or is their best growth behind them? Nick dives into the latest numbers, breaks down whether these tech giants are overhyped or buy-the-dip opportunities and has a good ol rant about Elon Musk.Nick’s latest book 'The Quick Start-Guide to Investing' is available here:  https://amzn.to/3QNNrbvHave a question or topic for the show? Post it in our Facebook group.This podcast is produced and published by Oregon Trail Investor in the USA. All information is for entertainment purposes only. This brand is used under license. Hosted on Acast. See acast.com/privacy for more information.