In 2023, I released about 160 My Worst Investment Ever podcast episodes, and this is a list of some of my and my listeners' favorites. I have also created a free “Top 27 from 2023” playlist where you can listen to and view this curated list for free. Just go to My Worst Investment Ever dot com and click the button that says, “Top 27 from 2023.” Since starting this podcast, I have published 760 episodes and look forward to continuing this journey in 2024! I welcome you on my journey “to help 1,000,000 people reduce risk in their lives.”

27. Ep738: Neil Johnson – Take the Profit When You Can

BIO: Neil Johnson is a renowned finance expert with over 30 years of experience in investment banking, merchant banking, and research analysis in Canadian and UK capital markets. He is the Executive Director and CEO of Duke Royalty, a $300 million alternative finance investment company listed on the London Stock Exchange.

STORY: Neil invested in an internet company building website templates when the internet started. The company filed to go public, but the financiers kept delaying the process and never went public. Six months later, the company went to zero. Neil lost his entire investment.

LEARNING: Take the profit when you can. Take some money out and play with the rest. Do your due diligence.

“Try not to be overly greedy. There’s something about leaving a little on the table for someone else.”

26. Ep658: Jeroen Blokland – Know the Actual Business Outlook Before Investing

BIO: Jeroen Blokland is a multi-asset investor with a long-term track record. He worked at Dutch investment bank, Robeco for almost 20 and now runs his independent investment research company, True Insights. Find him on Twitter.

STORY: Jeroen’s first investment was in a Dutch company selling PCs. He barely did any research or due diligence. The company reported a loss of $27 million in the same year Jeroen invested. It later went bankrupt, leaving him with a massive loss.

LEARNING: Know the actual outlook of a company before investing. Diversify your portfolio.

“90% of the investing population doesn’t know the actual outlook of a company.”

25. Ep674: Jesse Felder – Don’t Rationalize a Lousy Trade

BIO: Jesse Felder started his career at Bear Stearns and co-founded a multi-billion-dollar hedge fund firm. He left Wall Street to focus on The Felder Report and hosts the Superinvestors podcast. Find him on Twitter.

STORY: Jesse found a “cigar butt” stock that was cheap and performed extraordinarily well in just a few months after he took a sizable position. A friend convinced him to hold the stock long-term instead of short-term as planned. Government legislation affected the business, and Jesse lost about 50% of his investment.

LEARNING: Don’t rationalize a bad trade; get out. Be very careful when you’re in a situation where the government is supporting an industry.

“When you’re in a situation that’s not working out as you would hope, rather than dig the hole deeper, move on and find something different.”

24. Ep668: Jason Hsu – The Market Can Be Crazy for Longer than You Have the Conviction

BIO: Jason Hsu is the founder, chairman, and CIO of Rayliant Global Advisors, a global investment management group with over US$15+ billion in assets under management as of June 30, 2022. Find him on Twitter.

STORY: Jason bet against the GameStop short squeeze and learned that John Maynard Keynes’ saying that “markets can remain irrational longer than you can remain solvent” still holds true.

LEARNING: The market can be crazy for longer than you have the conviction to stay invested. Apply position constraints and diversify.

“In the short run, the market can really stay crazy for longer than you have the money to stay on. And if you forget that, the market will remind you in as painful of a way as possible.”

23. Ep646: Praveen Kumar Rajbhar – Don’t Fall in Love with Your Own Ideas

BIO: Praveen Kumar Rajbhar is an entrepreneur, founder, and CEO SkillingYou, an employability Skills Focused EdTech startup in rural India. Find him on Twitter.

STORY: When Praveen started his first startup, he spent money to hire many people, buy a lot of gadgets, and rent a huge office space. The business collapsed in less than two years.

LEARNING: Get the right mentor to guide you on how to make your startup a success. You don’t need a big team to be successful. Get on-time and accurate financial statements every month.

“Having the right mentor will help you create a great company.”

22. Ep731: Robin Wigglesworth – You Can’t Outsmart the Markets

BIO: Robin Wigglesworth is the editor of Alphaville, the FT’s financial blog. From Oslo, Norway, he leads a team of writers who dig into anything deeply nerdy or delightful that they spot. Find him on Twitter.

STORY: Robin invested in an ETF in Norway, a consumer durables company, and a fertilizer company after the 2008 financial crisis. These companies did incredibly well. Unfortunately, Robin reacted to short-term headlines when the European crisis started erupting and sold out.

LEARNING: You can’t outsmart the markets. Always let your winners ride.

“Always let your winners ride.”

21. Ep695: Jack Farley – Don’t Play in Markets You Don’t Know

BIO: Jack Farley is the host of the Forward Guidance podcast. He is interested in all things liquidity, macro, and central banking. Find him on Twitter.

STORY: Jack bought a lot of put options on the markets and individual stocks, notably Tesla, in February 2020 when the market was bearish. When the market crashed in March 2020, Jack made so much money (on paper). But, soon, the market started going up, and his position dropped to zero.

LEARNING: Don’t view the market as a place to create wealth; view it as a place to grow it. Don’t confuse being lucky with being an intelligent investor.

“When you get a windfall, realize those gains, and at the very least, trim the position down.”

20. Ep739: William Cohan – Get the Numbers Right Before You Invest

BIO: For nearly two decades William D. Cohan was a Wall Street investment banker and is now a New York Times bestselling author of seven non-fiction narratives, including Power Failure. Find him on Twitter.

STORY: In 1990, William asked a trader to buy him 10 shares in Berkshire Hathaway, thinking a share was selling at $1,200, only to be told it was $12,000. He decided to keep two shares and sold the other eight. Had William invested $120,000 for the 10 shares in Berkshire Hathaway in 1990, they would be worth $7.4 million today.

LEARNING: Get the numbers right before you invest.

“I decided to write this book for people who wanted to know about how Wall Street works but were afraid to ask how things work.”

19. Ep655: Pim van Vliet – Just Because It’s Cheap Doesn’t Mean You Have to Buy It

BIO: Pim van Vliet is Head of Conservative Equities and Chief Quant Strategist at Dutch investment bank, Robeco. He is responsible for a wide range of global, regional, and sustainable low-volatility strategies. Find him on Twitter.

STORY: Pim wanted to make more money investing, so he decided to go all in on a cheap stock. He believed the price would eventually go up as it had done a few years back. Unfortunately, the company went bankrupt, and Pim lost 75% of his investment.

LEARNING: Don’t be overconfident and over-optimistic when investing. Just because it’s cheap doesn’t mean you have to buy it.

“I thought taking risks gives you a return. That’s not always the case. Taking more risk could give you a lower return.”

18. Ep708: Phil Bak – Be Slow to Jump Onto Bandwagons

BIO: Phil Bak is the CEO of Armada ETFs, a REIT-specialty asset manager that delivers customized solutions to REIT investors through ETFs, SMAs, and proprietary AI and machine learning REIT valuation models. Find him on Twitter.

STORY: Phil got into baseball cards when he was 14. Rookie Greg Jeffries became the hype one year and was poised to be the next big thing. Phil bought the hype, sold all his cards, and invested in Jeffries’ cards. He believed cards would be worth $40 to $50 a piece in just a few years. It never happened because Jeffries’ career didn’t pan out, and the entire baseball card bubble collapsed.

LEARNING: Be slow to jump onto bandwagons. Expect the unexpected, be prepared, and have a backup plan. Be diversified in as many different ways as possible.

“As long as you can recognize your mistake, learn and grow from it, then you understand that investing is a risky business. That will make you a smarter investor.”

17. Ep719: David Kass – Don’t Invest in a Company Unless the CEO Owns a Large Stake

BIO: Dr. David Kass received his Ph.D. in Business Economics from Harvard University and has published articles in corporate finance, industrial organization, and health economics. He teaches financial management at the University of Maryland and has been blogging about Warren Buffett for more than a decade.

STORY: In his early 20s, David invested $2,000 in a company paying out high dividends. Only after he invested did he realize that none of the senior executives in the company owned its shares. Soon enough, the stock went down to zero due to accounting fraud.

LEARNING: Only invest in a company if senior executives, especially the CEO, own a significant stake. The value of the CEO’s stock in his own company to his annual salary should be at least 3:1.

“Look carefully at proxy statements and make sure the CEO and other senior managers have skin in the game, that their interests are likely aligned with yours and have a large stake through their stock holdings.”

16. Ep667: Shreekkanth Viswanathan – Qualitative Strengths of a Company Matter Too

BIO: Shreekkanth (“Shree”) Viswanathan is the founder and portfolio manager of SVN Capital, a Chicago-based, concentrated, long-only, global equity-focused fund. Find him on Twitter.

STORY: Shree’s biggest mistake was an error of omission. That is, after studying a particular business, he decided not to invest in it for various reasons. The stock turned out to be a multi-bagger a couple of years later.

LEARNING: The qualitative strengths of a company are not always readily apparent in the financials. Get out and work in business; it will make you a better analyst and investor. Shree introduced me to a study of 64,000 companies from 1990 to 2020, which showed that 57% of these stocks underperformed one-month U.S. Treasury bills in compound returns. Also, the top-performing 2.4% of firms, or 1,500, accounted for all US$76trn net global stock market wealth creation over the same period. Here’s a link to the study.

“If you don’t know who you are, the market is an expensive place to find out.”

15. Ep746: James M. Dahle – Don’t Buy More Insurance Than You Need

BIO: James M. Dahle, MD, is a practicing emergency physician who took an interest in personal finance and founded The White Coat Investor in 2011 to help fellow docs get a fair shake on Wall Street. Find him on Twitter.

STORY: James got sold a whole life insurance policy in medical school. He invested in it, thinking it would be a good option, only to realize seven years later that it was not. When he pulled out of the policy, he lost 33% of the premiums he had paid.

LEARNING: You must understand anything you buy. Don’t buy more insurance than you need. Focus on one catastrophe-related insurance product that’s reasonable.

“Insurance is expensive, so don’t buy more than you need.”

14. Ep756: Peter Goldstein – Check Your Emotions at the Door

BIO: Peter Goldstein is a seasoned entrepreneur, capital markets expert, and investor with over 35 years of diverse international business experience. He is CEO of Exchange Listing LLC. Find him on Twitter.

STORY: He and four others put a significant amount of money into opening a facility selling cannabis in Long Beach, California. This was a time when cannabis was in great demand and was in the process of being legalized for recreational purposes. At the time, there were no clear regulations, making compliance with the ever-changing rules costly to the point where the business was not making any profits.

LEARNING: Check...