In this episode of Money Lessons, Andy explores information asymmetry—the gap between what some market participants know and what others know—and the rules that try to keep that gap from getting too wide.

He walks through the structural advantages built into the architecture of the market itself, the meaningful distinction between buy-side and sell-side analysts that financial pundits throw around without explanation, and the legal line that separates productive research from criminal insider trading.

Andy then unpacks Regulation Fair Disclosure—the SEC rule adopted in 2000 that ended the worst of selective disclosure to favored Wall Street clients. The closing message: the retail investor is structurally on the wrong side of many information gaps, and the most reliable response is to focus on what you can actually control.

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In this episode of Money Lessons, Andy explores one of the most misunderstood practices in financial markets — short selling. He traces the origins of the practice to Isaac Le Maire and the Dutch East India Company in 1609, walks through the mechanics of borrowing shares to sell them, and explains the asymmetric risk that makes short positions fundamentally different from owning a stock.

He brings the lesson to life with the spectacular 2008 Volkswagen short squeeze, when the German automaker briefly became the most valuable listed company in the world.

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In this episode of Money Lessons, Andy picks up where last week's IPO episode left off and walks through what changes once a company is publicly traded.

He explains the lockup period that follows every IPO — using Airbnb's May 17, 2021 lockup expiration and six-percent drop as the concrete example — then breaks down the SEC's three core disclosure filings (10-K, 10-Q, and 8-K) that drive the rhythm of public-company life.

Andy then tackles the real cost of all this — short-termism — citing Warren Buffett and Jamie Dimon's 2018 Wall Street Journal op-ed and drawing on his own experience to show how the quarterly cycle shapes corporate behavior at public and private companies alike.

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In this episode of Money Lessons, Andy walks through what happens when a company goes public — how a private business with a small group of owners becomes a publicly traded stock that anyone with a brokerage account can buy.

The episode covers the five reasons companies decide to go public, the underwriting process and the role of investment banks, the road show and how the offering price gets set, and what happens on the first day of trading — including why the price you and I pay is almost always different from the price the institutions paid the night before.

Using Airbnb's December 2020 IPO as a concrete example, Andy unpacks the "pop" between offering price and opening price, then revisits the three risks of stock ownership from two weeks ago to highlight how cognitive biases — particularly the urge to follow the crowd — make hot IPOs especially dangerous territory for everyday investors.

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In this episode of Money Lessons, Andy tackles one of the most foundational questions in investing: what is a stock actually worth? Returning to value-investing pioneer Benjamin Graham, Andy walks through the three primary lenses professional analysts use to estimate stock value—relative valuation, asset-based valuation, and cash-flow-based valuation—and shows how each one offers a different angle on the same question.

Using the dot-com bubble as a cautionary tale, Andy illustrates what happens when relative valuation becomes untethered and stock prices disconnect from underlying business fundamentals. The unifying principle: speculation can run for surprisingly long stretches, but eventually a business must generate cash, or its price will be revalued to reflect what's actually there.

In this episode of Money Lessons, Andy walks through the three categories of risk that dominate the experience of owning stock: firm-specific risk, market risk, and behavioral risk. He explains why a stock's daily movement is mostly driven by company news, but why the broad market overwhelms those differences when it moves sharply—answering the listener's natural "which is it?" question.

Using the 2008 financial crisis and the March 2020 pandemic crash as examples, Andy shows how fast and slow declines both punish panic-selling, just on different timelines. He closes with observation that most of the gap between what individual investors earn and what the market returns isn't about picking the wrong stocks—it's about behavior.

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In this episode of Money Lessons, Andy explores leverage and margin — what happens when investors borrow money to buy stocks. He traces the story from the unchecked margin trading of the 1920s that fueled the 1929 crash through the regulatory response that reshaped modern markets, including Regulation T and FINRA's maintenance margin requirements.

Andy walks through a margin call example to show how borrowed money amplifies both gains and losses, then closes with practical questions every investor should ask before borrowing to invest.

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In this episode of Money Lessons, Andy explores preferred stock — the hybrid security that sits between bonds and common stock in a company's capital structure. He traces its origins to the Railway Mania of 1840s Britain and the aftermath of the Panic of 1837 in America, where distressed railroads and canal companies invented a new class of shares to attract cautious investors.

Andy explains how preferred stock borrows features from both debt and equity, defines the critical distinction between cumulative and non-cumulative preferred shares, and shows where preferred shareholders stand in the priority hierarchy alongside bondholders and common shareholders.

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