“Hello, fellow risk-takers, and welcome to My Worst Investment Ever,” that’s how I start every one of the 300+ My Worst Investment Ever Podcast episodes I have recorded. Below are some of the highlights from the 170 people I interviewed in 2020.
One of the things that makes the investors, businessmen and women, and experts who come on the show extraordinary is their willingness to share their worst investment with the world. Most people I ask to go on the show say, “No, thank you.”
The good news for you is that you don’t have to experience their loss. Listen and absorb the lessons they teach. Whether you’re an experienced investor or just starting your investment journey, these podcasts can give you a different investment perspective and expand your knowledge.
To get straight to the lessons, just click here and download my one-page cheat sheet.
Stephen Kalayjian is a Chief Market Strategist and co-founder of Ticker Tocker. He has decades of experience trading stocks, futures, currencies and has traded nearly 2 billion shares.
Steve shared how, in his youth, he used his hard-earned money to buy 550 calls and assumed that stocks only went higher (they don’t).
Karen Foo is a motivational speaker, financial trainer, and author. She has ranked #1 in a Singapore nationwide Forex trading competition. You can find her on her YouTube channel.
Karen shared how she lost her savings when she invested in forex and unit trusts without guidance and research.
James Jani is a YouTube Expert and Vlogger, who creates thought-provoking documentaries on YouTube about Business, Money, and Life.
James shared his story of investing years of his life into acting without success, only to realize later acting wasn’t what he wanted to do for the rest of his life.
Chris Mayer is the co-founder and portfolio manager of the Woodlock House Family Capital fund. He has authored four books, including 100 Baggers: Stocks that Return 100-to-1 and How to Find Them, ranked 4.6 out of 5 on Amazon with 290 reviews. You can follow him on Twitter.
Chris’s worst investment story happened when he bought cheap companies while disregarding what those businesses could offer in the long-term.
Sampath Mallidi is the Founder and CEO of Intandemly, an account-based sales platform that helps organizations simplify their sales pipeline.
Sampath shared that he and his then-boss spent all their money, shifting their company’s strategy because they anticipated funding. The money never came.
Ranveer Brar is one of India’s top chefs, a celebrity, a Masterchef India judge, author, restaurateur, food film producer, and benefactor. He shares his passion for food on his website and his excellent YouTube channel. Follow him on Facebook, Twitter, and Instagram.
Ranveer shared how he left his executive chef position in India to join a restaurant startup in the US. His big mistake was going with the flow of other people’s plans.
Rand Fishkin is CEO & co-founder of SparkToro, and author of Lost and Founder: A Painfully Honest Field Guide to the Startup World. The book has an impressive 4.7 out of 5 Amazon rating; I enjoyed how Rand personally narrated the book’s Audible format. He previously co-founded and ran the SEO optimization company, Moz.
Rand’s worst investment was when he received venture capital for Moz and focused on expanding its other marketing services while stopping what was working for the company.
Morgan Housel is an award-winning financial writer and a partner at The Collaborative Fund. Don’t miss his recently published, The Psychology of Money: Timeless lessons on wealth, greed, and happiness, which has received more than 3,000 ratings on Amazon which average an impressive 4.7 out of 5 ratings. Follow him on Twitter.
Morgan shared his story of how he blindly followed the advice of the father of value investing, Benjamin Graham, to buy stocks that were trading at less than book value.
Cedric Dahl was CEO of Buttercoin, one of the first Bitcoin marketplaces in the US. He writes the Internet Money newsletter covering the most critical events in the weird world of Internet Money. Find him on YouTube, where he has recently been posting Cedric Dahl Friend Call, and Twitter. Finally, consider joining his “1000x Group,” where Cedric and community members share projects and ideas that they believe have the potential for 1000x+ returns.
Cedric shared how he and his friend Bennett raised money for a Bitcoin startup and how it went downhill and was ultimately knocked out by the rise of Coinbase.
Mark Moss is a full-time investor with more than 25 years’ experience and has invested in businesses, real estate, stocks, gold, and cryptocurrencies. He created his website, Signal Profits, to help struggling traders. Follow Mark on his YouTube channel or Twitter to gain further investment knowledge (I watch everyone he puts out).
Mark talked about the time he kept placing all his efforts solely on his real estate investments even though the market was crashing.
E.B. Tucker is a board director and major shareholder of Metalla Royalty & Streaming, a gold royalty company. He’s been active in capital markets for over two decades and authored Why gold? Why Now? The War Against Your Wealth and How to Win It has received a 4.6 out of 5 with more than 500 reviews.
EB shared how he started as a sales VP for what he thought was a good company, which he then got his friends to invest in. Unfortunately, the company turned out to be a scam.
Jim O’Shaughnessy is the Chairman and Co-Chief Investment Officer of O’Shaughnessy Asset Management (OSAM). He is the author of various books, with What Works on Wall Street, Fourth Edition: The Classic Guide to the Best-Performing Investment Strategies of All Time being one of my all-time favorite finance books.
Jim ignored his investment model and sold his puts (the right to sell at a fixed price, a contract that investors enter when they think the market will fall) just before the market crashed instead of holding onto them at least one more day as his model told him.
John Lee Dumas (JLD) is the host of Entrepreneurs on Fire, an award-winning podcast where he interviews the world’s most inspiring entrepreneurs. Check out his fantastic book, The Common Path to Uncommon Success: A Roadmap to Financial Freedom and Fulfillment, which is launching now.
JLD walked us through his first investment in a penny stock and the course offering he created back when Entrepreneurs on Fire was in its first year.
Niel Patel is a New York Times bestselling author, one of the top influencers on the web, and is recognized as a top 100 entrepreneur under 30. You can find more about him on his website. I love to watch his YouTube videos, his Facebook, and his Twitter. Most importantly, I purchased a subscription to his Ubersuggest.
Neil shared his vision for...