The Truth About Market Timing, Crashes, and Long-Term Investing with Ben Carlson

The Truth About Market Timing, Crashes, and Long-Term Investing with Ben Carlson

Author: Andrew Sather, Stephen Morris, and Evan Raidt June 8, 2026 Duration: 49:31
What’s the secret to investing? According to Ben Carlson (CFA, Ritholtz Wealth Management), the “secret” is that there isn’t one—building wealth is mostly about time, consistency, and letting compounding do the heavy lifting. In this conversation, Ben breaks down why the lottery-ticket approach and constant market timing are usually a losing game, even for smart people. We also dig into how the stock market and the economy don’t always move together, why macro data is hard to use in real time, and what history can teach us about surviving the worst-case scenarios (like the Great Depression). Ben shares a practical way to think about diversification, how to avoid extremes (including the Japan bubble example), and why having rules—an investing “policy statement”—can keep your emotions from wrecking your results. What You Will Learn Why the “secret to investing” is there is no secret—and why that’s good news The hidden trap of market timing: you have to be right twice Why the stock market and the economy can diverge What the Great Depression and Japan’s bubble teach about time horizon & diversification How rules and automation can protect you from emotional decisions Timestamps 00:14 — Ben Carlson, Ritholtz Wealth Management & his book Risk and Reward 00:57 — “What’s the secret to investing?”  02:26 — Market timing temptation 04:01 — “Worst market timer” story: investing at peaks and still compounding over time 05:03 — Cash as a “gateway drug” & the psychological toll of timing 07:15 — The Great Depression: the worst crash and what long-term returns still show 10:10 — Why studying market history matters 14:36 — Stock market vs economy 23:16 — Japan’s bubble & what it teaches about extremes and global diversification 38:15 — Rules, automation, and an “investment policy statement” to manage emotions Resources Mentioned The Value Spotlight Newsletter: ⁠https://einvestingforbeginners.com/value-spotlight-newsletter⁠/ Have questions or want your story featured? Email the show at ⁠newsletter@einvestingforbeginners.com⁠ or comment below. Your feedback shapes the podcast! Remember, invest with a margin of safety—emphasis on the safety. Have a great week, and we’ll talk to you next time. Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Today’s show is sponsored by: Download the Plynk app today to start building your investing confidence. https://plynkinvest.app.link/plynkifb2026 Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠SHOPIFY.COM/beginners⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to start selling with Shopify today.⁠ ⁠⁠⁠⁠⁠https://www.shopify.com/beginners⁠⁠⁠⁠  Upgrade your wardrobe with Quince to get high-quality, luxury essentials at a fraction of the cost by visiting ⁠https://quince.com/beginners⁠  Turn your passion into profit, connect directly with eager buyers, and grow your business by hosting live, interactive auctions at ⁠https://whatnot.com/sell⁠  Supercharge your productivity and automate your daily tasks by building custom AI agents in your all-in-one workspace at ⁠https://notion.com/investing⁠ The Perfect Jean makes insanely comfortable, great-fitting jeans you can wear all day—check them out at theperfectjean.nyc. Function Health helps you get ahead of your health with comprehensive lab testing and clear, actionable insights—learn more at functionhealth.com. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Interested in how your company sponsor the show? Reach us at  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠equity@einvestingforbeginners.com⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠SUBSCRIBE TO THE SHOW⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Amazon⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Tunein Learn more about your ad choices. Visit megaphone.fm/adchoices

Navigating the stock market can feel like deciphering a foreign language, but it doesn't have to. The Investing for Beginners Podcast-Your Path to Financial Freedom, hosted by Andrew Sather, Stephen Morris, and Evan Raidt, exists to translate that complexity into clear, actionable understanding. This isn't about get-rich-quick schemes; it's a practical guide built on foundational principles. Each episode breaks down how successful, long-term strategies actually work, focusing on core approaches like value investing and dividend growth investing. You'll also hear how elements of growth investing and trend following can fit into a thoughtful plan. The hosts delve into the psychological side of the market, discussing how to recognize and potentially benefit from the emotional swings that drive prices, rather than being driven by them. Tuning into this podcast provides a structured education in buying stocks with confidence, moving from uncertainty to a place where you can make your own informed decisions. It’s a steady resource for anyone building their financial literacy from the ground up, aiming to turn the intimidating world of investing into a manageable part of their journey toward greater independence.
Author: Language: English Episodes: 50

The Investing for Beginners Podcast - Your Path to Financial Freedom
Podcast Episodes
6 Warning Signs a Company Is Quietly Dying (Part 1) [not-audio_url] [/not-audio_url]

Duration: 47:24
Most investors think the biggest risk is buying the “wrong” company. But a sneakier risk is buying a company that used to be great—and not realizing the story has changed until the stock is down 70%. In this episode, And…
AAR57 - What Does Your Perfect Day Cost? [not-audio_url] [/not-audio_url]

Duration: 53:30
Money is pointless if it doesn’t help you live a better life. In this episode, Evan is joined by Andrew Sather to talk about what most people are really chasing when they chase money: peace and control. They start with a…
Tech Stocks Are Down—Is It “Tech Rot” or Just Noise? [not-audio_url] [/not-audio_url]

Duration: 47:50
Tech stocks dip and suddenly the media declares the bubble popped—“AI is over,” rates are killing growth, and data centers cost too much. Stephen and Andrew cut through the headlines and explain what’s actually going on:…
AAR56 - Engineering POV on Building Margin Into Personal Finance [not-audio_url] [/not-audio_url]

Duration: 43:15
Most personal finance advice gets treated like a checklist: hit the emergency fund number, hit the savings rate, and you “pass.” In this episode, Evan explains why that mindset breaks in the real world—and why you should…
What the Shiller P/E  (CAPE) Can and Can’t Tell You [not-audio_url] [/not-audio_url]

Duration: 47:55
A listener named Chris emailed in with a question a lot of investors are quietly thinking: if the CAPE ratio is around 40 and forecasts say future stock returns could be low, why keep investing at all—especially when CDs…
How to Read a 10-K in 20 Minutes (The Beginner Speedrun Checklist) [not-audio_url] [/not-audio_url]

Duration: 47:52
Most investors download a 10-K, scroll for a few minutes, and quit—because it feels like 100 pages of legal pain. In this episode, Andrew and Stephen break down a practical “speedrun” approach to get real value from a 10…
Why A Negative P/E Happens and What to Use Instead [not-audio_url] [/not-audio_url]

Duration: 40:13
Ever pulled up a stock and noticed the P/E is negative—then immediately wondered if the company is “cheap” or just a disaster? In this episode, Stephen and Andrew break down exactly why a P/E ratio “breaks” when earnings…