In this episode of Money Lessons, Andy closes the series on equity by turning to the hardest part of owning stocks: holding on.

He explains why volatility is the price investors pay for the equity risk premium, and why the market's steepest falls and sharpest recoveries tend to arrive back to back — which is what makes market timing a losing game.

He looks at the evidence that the more investors trade, the less they tend to keep, and at how modern trading apps are built to encourage the very activity that erodes long-run returns.

In this episode of Money Lessons, Andy makes the long-run case for owning stocks — why, over a lifetime, equities have rewarded the patient owner.

He unpacks the equity risk premium, the extra return stocks have paid over bonds and cash since 1928, and shows how compounding turns that yearly edge into life-changing wealth.

Andy closes with direct advice for young investors — start early, invest steadily, and give compounding the decades it needs to build the wealth a last-minute scramble never can. It's a lesson about patience, access, and the quiet power of starting now.

In this episode of Money Lessons, Andy widens the map beyond American markets to make the case for owning international stocks.

He explains home-country bias — the natural pull to invest only in the companies of your own country — and points out that more than a third of the world's stock market value sits outside the United States.

Andy walks through the two practical ways an ordinary investor can own foreign companies: broad international index funds and ETFs, and American Depositary Receipts, or ADRs, for a single overseas company.

In this episode of Money Lessons, Andy answers a question he has been holding since last year: if your stock trades are free, how does a broker make its money?

He explains payment for order flow — the arrangement where your broker sells your order to a wholesale market maker that fills it and pays for the privilege. Andy walks through why your everyday orders are so valuable, where the real conflict of interest hides, and what the 2020 Robinhood settlement revealed about the true cost of "free."

The takeaway: free isn't free — and the cost that matters most is the one that tempts you to trade too often.

In this episode of Money Lessons, Andy explains the exchange-traded fund — the ETF — the vehicle most people now use to own a whole index in a single trade.

He traces it back to the first one, State Street's SPDR, launched in 1993 to track the S&P 500, and shows how an ETF differs from the index mutual fund Jack Bogle created in 1976: one trades all day on an exchange like a stock, the other prices just once, after the close.

Andy pulls back the curtain on the creation-and-redemption process — the quiet arrangement with large firms that does the real index buying and keeps an ETF's price tied to the value of the stocks it holds. The takeaway: an ETF lets you trade like a stock, but the soundest way to own one is to hold it like a long-term investor.

In this episode of Money Lessons, Andy tackles a phrase we lean on without ever defining it: "the market."

He explains what a stock market index is, where the Dow, the S&P 500, and the Nasdaq-100 come from, and how each one measures the market differently — the Dow by share price, the others by company size.

He unpacks the Dow's hidden divisor and the outsized power of a denominator, shows how a handful of giant companies can carry an entire index, and explains why SpaceX's arrival on the Nasdaq means millions of index-fund holders are about to own a stock they never picked. The lesson: an index is a set of choices, and a fund that tracks one hands you all of them.

In this episode of Money Lessons, Andy uses the 2021 GameStop saga to reveal the hidden machinery that runs underneath every stock trade. He explains how a struggling video-game retailer became the most heavily bet-against stock on Wall Street, why ordinary investors banded together to buy it, and how its price rocketed from about $17 to around $483 in a matter of weeks. Then he answers the question that left millions of people furious: why did Robinhood suddenly stop letting them buy? The culprit turns out to be the market's plumbing — the two-day settlement delay, the clearinghouse that guarantees every trade, and the collateral deposit that exploded into the billions when prices swung wildly.

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.

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.

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.

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.

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.