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
AAR64 - The Personal Finance Time Machine [not-audio_url] [/not-audio_url]

Duration: 1:00:20
What advice would you give your 22-year-old self if you found a DeLorean in your driveway? In this episode of At Any Rate, Evan and Andrew look back at their early 20s to unpack what actually matters when transitioning f…
AI, Space, and Defense: Separating Hype from True Moats [not-audio_url] [/not-audio_url]

Duration: 1:08:05
Wall Street loves a good sci-fi narrative. Between artificial intelligence, private space exploration, and next-generation defense tech, it is incredibly easy to get swept up in the stories these companies sell. But stor…
The Psychology of Position Sizing [not-audio_url] [/not-audio_url]

Duration: 42:47
Every investor lives with two competing internal voices: the hyper-optimist who wants to go all-in on an exciting growth story, and the hyper-skeptic who gets paralyzed by uncertainty or cut positions at the first sign o…
AAR63 - The Bottom Hits - What Most People Miss in Their Finances [not-audio_url] [/not-audio_url]

Duration: 55:59
We all know the "top hits" of personal finance, but what about the silent wealth killers? In this episode of At Any Rate, Evan and Andrew break down six common financial traps that are incredibly easy to fall into, regar…
Accidental Indexing: Why Owning Too Many Stocks Destroys Returns [not-audio_url] [/not-audio_url]

Duration: 43:36
Most retail investors spend endless hours hunting for the next breakout stock, only to ruin their returns by spreading their capital across dozens of minor positions. Buying too many stocks creates an "accidental index f…
AAR62 - Homeownership Progress Update [not-audio_url] [/not-audio_url]

Duration: 45:48
It has officially been one year since Evan and his wife purchased their first home at 27 years old. In this solo episode of At Any Rate, Evan takes a transparent look at how the finances, lifestyle changes, and hidden ex…
Why Your Brain is Sabotaging Your Portfolio [not-audio_url] [/not-audio_url]

Duration: 57:01
The stock market isn't just a platform for building wealth; it is a real-time stress test of human psychology. When headlines scream panic and portfolios bleed red, our innate cognitive biases trigger emotional reflexes…
The AI CAPEX Illusion with Thomas Chua [not-audio_url] [/not-audio_url]

Duration: 51:31
Tech giants are dropping hundreds of billions on AI infrastructure, but the market is punishing some players and rewarding others for the exact same strategy. In this episode, Thomas Chua from Steady Compounding reveals…
AAR61 - Drafting Our Finances [not-audio_url] [/not-audio_url]

Duration: 59:43
In this episode of At Any Rate, Evan and Andrew run a high-stakes "Fantasy Financial Draft." Alternating picks back and forth, they compete to build the ultimate personal finance strategy across six key categories: safe…