Enrich Your Future 37 & 38: The Calendar Is a Crook & Hot Funds Are a Trap episode artwork

EPISODE · Jul 7, 2025 · 18 MIN

Enrich Your Future 37 & 38: The Calendar Is a Crook & Hot Funds Are a Trap

from My Worst Investment Ever Podcast

In this episode of Enrich Your Future, Andrew and Larry Swedroe discuss Larry’s new book, Enrich Your Future: The Keys to Successful Investing. In this series, they discuss Chapter 37: Sell in May and Go Away: Financial Astrology and Chapter 38: Chasing Spectacular Fund Performance.LEARNING: Calendars don’t drive returns. Winners ignore hot funds. “For you to believe in a strategy, there should be some economically logical reason for it to persist, so you can be confident it isn’t just some random outcome.”Larry Swedroe In this episode of Enrich Your Future, Andrew and Larry Swedroe discuss Larry’s new book, Enrich Your Future: The Keys to Successful Investing. The book is a collection of stories that Larry has developed over 30 years as the head of financial and economic research at Buckingham Wealth Partners to help investors. You can learn more about Larry’s Worst Investment Ever story on Ep645: Beware of Idiosyncratic Risks.Larry deeply understands the world of academic research and investing, especially risk. Today, Andrew and Larry discuss Chapter 37: Sell in May and Go Away: Financial Astrology and Chapter 38: Chasing Spectacular Fund Performance.Chapter 37: Sell in May and Go Away: Financial AstrologyIn chapter 37, Larry explains why the idea of selling stocks in May and switching to cash, then buying back in November, is not a sound strategy.What financial advisers insist on repeating, in Larry’s view, is: “Sell in May, go to cash, and reinvest in November.” It makes sense and is even logical. And, as the adage has it, numbers don’t lie. Figures, backed by reliable data, show that stocks gain more from November through April (a 5.7% average premium) than from May through October (a 2.6% average premium). So why not time the market?Busting the mythLarry dismantles this advice, revealing that the ‘Sell in May’ strategy, despite its apparent logic, is a myth. He points out that stocks still outperform cash even during the May to October period, with stocks beating T-bills by 2.6% annually.Selling stocks prematurely leads to missed gains, and the strategy of switching investments underperforms a simple buy-and-hold approach. In fact, a ‘Sell in May’ strategy yielded an average annual return of 8.3% from 1926 to 2023, while simply holding the S&P 500 returned 10.2%—a significant 1.9% yearly gap.Larry adds that Taxes and fees make the strategy worse. Trading converts long-term gains (lower tax) into short-term gains (higher tax). Transaction costs always pile up.Additionally, this strategy is rarely effective. Before 2022, the last “win” was 2011. A single outlier (2022’s bear market) does not make a strategy worthwhile.The fatal flawAccording to Larry, one of the fundamental rules of finance is that expected return and risk are positively correlated. So if stocks actually do worse than cash between May and October, they’d need to be less risky for these six months, which is absurd because volatility doesn’t take summer vacations.Why do people believe in this flawed strategy?Larry notes four reasons why people still believe in this flawed investment strategy:Recency bias: Media hypes the strategy after rare wins (like 2022).Pattern-seeking: Humans confuse coincidence with cause.“Free lunch” fantasy: Active investors crave simple shortcuts.The proper investment to followLarry’s advice is to:Ignore the noise. Calendars don’t drive returns.Stay invested. Missing just 10 best days in 30 years slashes returns by 50%.Focus on what matters: Diversification, low costs, and tax efficiency.Bottom line: The “Sell in May” strategy is a form of financial astrology. It confuses seasonal patterns with strategy. The market’s not a magic 8-ball. Stop gambling on folklore—and start compounding.Chapter 38: Chasing Spectacular Fund PerformanceIn chapter 38, Larry explains why chasing spectacular performance is not a prudent investment strategy.He starts the article by highlighting that 2020 was a phenomenal year for hot funds. During that year, 18 US stock funds posted gains of over 100%, attracting $19 billion in investor dollars in pursuit of recent performance. Their prior records seemed unstoppable—17 of 18 had reigned supreme over markets for three straight years.The brutal realityA landmark Morningstar study by Jeffrey Ptak looked into equity funds that gained more than 100% in a calendar year. He found that of the 123 stock funds that gained at least 100% between 1990 and 2016, just 24 made money in the three years following their phenomenal return.More adversely, the average fund subsequently lost around 17% each year. Ptak also found that funds that failed in the years before their big gain were far more likely to earn more money during the years after that big year, compared to money that had been profitable during the period preceding their big gain.Why do hot funds implode?There are a few reasons why hot funds could implode. One is overvalued bets. For instance, the 2020 superstars held stocks trading at 3x the valuation of the Nasdaq 100. Another reason is the reversion to the mean. Extreme returns are statistical outliers, not a result of skill. Lastly, the crowd effect. Inflows surge after gains, forcing managers to buy at high prices.The index fund quietly winsLarry observes that while speculators chased fireworks, Fidelity’s Total Market Index (FSKAX) returned 20.8% in 2020, beating 80% of active funds in its category. It did this with a 0.01% fee, 1/100th the cost of typical active funds.In conclusion, Larry reminds investors that the race to spectacular returns is a marathon, not a sprint. Winners ignore the fireworks.Further readingJeffrey Ptak, “What Happens After Fund Managers Crush It?” The Evidence Based Investor, January 18, 2001.Did you miss out on the previous chapters? Check them out:Part I: How Markets Work: How Security Prices are Determined and Why It’s So Difficult to OutperformEnrich Your Future 01: The Determinants of the Risk and Return of Stocks and BondsEnrich Your Future 02: How Markets Set PricesEnrich Your Future 03: Persistence of Performance: Athletes Versus Investment ManagersEnrich Your Future 04: Why Is Persistent Outperformance So Hard to Find?Enrich Your Future 05: Great Companies Do Not Make High-Return InvestmentsEnrich Your Future 06: Market Efficiency and the Case of Pete RoseEnrich Your Future 07: The Value of Security AnalysisEnrich Your Future 08: High Economic Growth Doesn’t Always Mean High Stock Market ReturnEnrich Your Future 09: The Fed Model and the Money IllusionPart II: Strategic Portfolio DecisionsEnrich Your Future 10: You Won’t Beat the Market Even the Best Funds Don’tEnrich Your Future 11: Long-Term Outperformance Is Not Always Evidence of...

NOW PLAYING

Enrich Your Future 37 & 38: The Calendar Is a Crook & Hot Funds Are a Trap

0:00 18:32

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

That Hoarder: Overcome Compulsive Hoarding That Hoarder Hoarding disorder is stigmatised and people who hoard feel vast amounts of shame. This podcast began life as an audio diary, an anonymous outlet for somebody with this weird condition. That Hoarder speaks about her experiences living with compulsive hoarding, she interviews therapists, academics, researchers, children of hoarders, professional organisers and influencers, and she shares insight and tips for others with the problem. Listened to by people who hoard as well as those who love them and those who work with them, Overcome Compulsive Hoarding with That Hoarder aims to shatter the stigma, share the truth and speak openly and honestly to improve lives. The Small Business Startup School – Business Notes | Financial Literacy | Retail Psychology – For Professionals & Entrepreneurs The Small Business Startup School Inc. Starting or buying a small business? While personal circumstances may vary, business patterns remain timeless. On The Small Business Startup School, we explore strategies, insights, and practical solutions to help entrepreneurs confidently navigate their journey.Hosted by Ola Williams—a retail entrepreneur, fintech founder, and financial coach with over two decades of experience—this podcast marries financial awareness and retail psychology with optimism to deliver actionable takeaways.Join us to learn, grow, and connect as we uncover the keys to business success.Let’s continue to learn together and be encouraged to keep on connecting! DIOSA. Carolina Sanper This podcast is a sacred space created by Carolina Sanper where you connect with your inner wisdom and embody your magnetic feminine power.It is the realization that the mystical realm is where you plant the seeds of your desired reality.It is a portal to your true essence: awareness, presence, and receiving with ease. Welcome home, DIOSA. 🖤 XXX Tech by SOVRYN Dr. Brian Sovryn The crossroads between technology, sensuality, and metaphysics - and the longest running anarchist podcast in the world! Brought to you by Dr. Brian Sovryn.

Frequently Asked Questions

How long is this episode of My Worst Investment Ever Podcast?

This episode is 18 minutes long.

When was this My Worst Investment Ever Podcast episode published?

This episode was published on July 7, 2025.

What is this episode about?

In this episode of Enrich Your Future, Andrew and Larry Swedroe discuss Larry’s new book, Enrich Your Future: The Keys to Successful Investing. In this series, they discuss Chapter 37: Sell in May and Go Away: Financial Astrology and Chapter 38:...

Is there a transcript available for this episode?

Yes, a full transcript is available for this episode. You can read the complete transcript on the episode page.

Can I download this My Worst Investment Ever Podcast episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.
URL copied to clipboard!