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Best of 2020 Podcast Episodes Roundup

“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.

Ep250: Stephen Kalayjian – The Key to Success in Trading Is to Have Discipline

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).

Key takeaways

• Discipline is the key to success
• It’s better to admit you are wrong; than to lose all your money
• Know when to continue or quit a specific investment

Ep248: Karen Foo – Risk Management Is the Key to Success in Forex

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.

Key takeaways

• Risk management is the key to long-term success
• Seek out mentors who are experts in what you want to learn
• Write out your investment plan before investing
• Do your research, ask more questions than you answer

Ep279: James Jani – You May Gain the Right Skills From the Wrong Path

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.

Key takeaways

• Be brave to follow your purpose in life, no matter what.
• The skills you gain from every experience combine to help you create value in the future.

Ep249: Chris Mayer – Build a List of 5 Quality Companies and Enter at the Next Market Fall

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.

Key takeaways

• Buy the best companies, even if they are expensive
• Build your stock buy list and wait for significant market falls to buy them
• Consider the long-term returns instead of being seduced by today’s cheap stocks

Ep192: Sampath Mallidi – Your Startup Should Always Have Paying Customers

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.

Key takeaways

• A deal is never done until the money is in the bank
• Cash flow, not cash, is King
• Don’t let failure get to you. Bounce back fast, and figure out how to move forward.

Ep232: Ranveer Brar – Deepen Your Relationship with What You Love and Be a Good Businessman

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.

Key takeaways

• Don’t do something just because it worked for others; find what works for you
• Balance your passion with the need to create a profitable business model
• Deal with problems head-on rather than denying and avoiding them

Ep235: Rand Fishkin – Don’t Be Afraid to Stand up Against the Growth-at-All-Cost Venture Capital Model

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.

Key takeaways

• Find your niche and focus on it, do not get distracted
• Structure and incentives matter more than almost everything else when it comes to business success
• Just because investors want growth at all costs doesn’t mean it’s the right path
• Listen to different opinions but do what’s right for you

Ep255: Morgan Housel – A Successful Value Investor Focuses on Why a Stock Is Cheap

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.

Key takeaways

• Separate research on risk from research on the return
• Don’t blindly follow any investment book or guru, even Warren Buffett
• Cheap stocks are usually cheap for a reason, and they can get cheaper

Ep191: Cedric Dahl – You’re Going to Fail Countless Times, Don’t Dwell on the Failures

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.

Key takeaways

• Risk management is the key to long-term success
• When pressure, stress, and the impostor syndrome kick in, step back and take care of yourself
• Luck, whether you want to admit it or not, plays a role in life and investing
• Suit up and show up. You can’t get better if you don’t practice, and you can’t practice if you don’t start.
• Pursuing your big dream will be hard at first; challenges will be many, but you’ve got to stay in the game to succeed. Have the courage to stick with it.

Ep245: Mark Moss – Diversify Your Profits to Protect Your Wealth

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.

Key takeaways

• Diversify by holding various asset classes
• For newbie and seasoned investors alike, make sure that you understand how real estate investing works and have a strategy
• Some of the most dramatic investment stories often come from real estate, and even the most experienced investors experience loss

Ep239: E.B. Tucker – Go With Your Gut and Consider Starting Small

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.

Key takeaways

• Do your research, ask lots of questions
• Follow your gut and intuition, not your ego
• Take calculated risks and always assess whatever you will invest in so you don’t lose everything

Ep289: Jim O’Shaughnessy – Have the Discipline to Stick With Your Investment Process

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.

Key takeaways

• Set your investment system and follow it
• Consider entering and exiting investment positions in a step-by-step manner

Ep234: John Lee Dumas – Avoid the Sunk Cost Fallacy by Testing Your Idea in the Market

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.

Key takeaways

• Don’t let failures stop you from doing what you love; it’s ok to pivot and persist
• FOCUS means Follow One Course Until Success
• Listen to your audience to find out what they want and build your business around that
• Before you create something, get proof of concept by getting a few people to buy
• Timing is essential; just because your offer doesn’t work the first time doesn’t mean that it’s a bad offer

Ep231: Neil Patel – Fail Your Way to Success by Practicing the 3Es: Experiment, Experiment, Experiment

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 web hosting that could have made millions of dollars and what went wrong.

Key takeaways

• Ideas are worthless without the right resources and people to implement them
• Experiment with your business idea as early as possible to learn from your mistakes

Ep253: Patrice Washington – Prepare for the Worst and Don’t Get Caught up in the Pretty

Patrice Washington is the host of The Redefining Wealth Podcast and was named by Success Magazine as one of 12 Inspiring Black Voices in Personal Development. Her website Patrice Washington teaches people the value of chasing purpose instead of wealth. I like to follow her on Twitter, Facebook, and Instagram, and enjoy her YouTube videos

Patrice talked about how she let her employees convince her to focus on unnecessary and expensive overheads that caused her to lose her entire life savings.

Key takeaways

• How you run your business in your worst month defines you
• Understand the motive behind the feedback you receive

Ep278: Daniel St-Jean – Decide on Your Investing System and Follow It

Daniel St-Jean is a professional real estate investor and entrepreneur with around 62 properties worth over $25 million. Visit The REITE Club to find out how he did it.

Daniel shared his riveting real estate story about how deviating from his rules for the sake of others nearly ruined his business.

Key takeaways

• Set your investment system and follow it
• Don’t mix business with charity

Ep178: Dante Vitoria – When an FBI Agent Tells You to Go to Breakfast, Do It

Dante Vitoria runs Vitoria Group, which has broad experience working with companies of various sizes to fulfill its client’s financial needs.

Dante shared how he used almost all his money on his first stock investment. I’m sure first-time investors can learn a lot from this episode!

Key takeaways

• Diversify by holding a collection of stocks
• Research if the company you want to invest in is legitimate
• Always have an exit plan

Ep228: Wim Steemers – Overcome Behavioral Biases with the Help of a Good Team

Wim Steemers is a fund manager at AL Capital and spends his free time as the Founder and CIO of Rosevalley Funds, where he builds portfolios based on behavioral finance.

Wim shared how he was super impressed by a laser machine that restored his sight in a matter of 15 minutes. His excitement saw him buy shares in the laser machine company without any information about it. He lost his entire investment.

Key takeaways

• Never buy a company just because you love its products
• Things that are too good to be true often are
• Do thorough research before you decide whether to buy or sell a stock

Ep179: Peter Sainsbury – Use a Journal to Stay Self-aware When Making a Contrarian Investment

Peter Sainsbury is an investor in resource stocks and a commodity futures trader. He uses his website Materials Risk to share his observations of the world of markets, economics and investing. He is the author of Commodities: 50 Things You Really Need to Know.

Peter talked about how his decision to go against the norm by making a contrarian investment from which he lost all the money he had invested in gold.

Key takeaways

• Diversify by holding various asset classes
• Get out of a bad position as soon as you can

Ep243: Rob Angel – When You Feel Overpowered by Emotion Listen to Your Intuition

Rob Angel is a speaker, author, and entrepreneur. He is the creator of the phenomenally successful and iconic board game Pictionary®. Learn how he turned a simple idea into the bestselling board game globally on his website Rob Angel. Don’t miss his recently published Game Changer, which has an Amazon rating of an incredible 4.9 out of 5.

Rob shared how a trusted friend scammed him by enticing him into an investment that he knew was too good to be true.

Key takeaways

• Don’t invest based on the excitement of the moment; step back and do your research
• Follow your gut and intuition, not your ego
• Get inspired and learn from those who have gone before you

Ep271: Oluwatosin Olaseinde – Africa’s Financial Literacy Queen Says Be Careful Who You Trust

Oluwatosin Olaseinde is a professional accountant and the Founder and CEO of Money Africa, an ed-tech platform that enhances financial literacy and investments leveraging technology. In 2019, she was selected as one of the top 100 women by The Leading Ladies Africa. Enjoy a daily dose of her powerful energy by following her on Instagram.

Oluwatosin was encouraged by a friend to invest in Bitcoin. When she called him to sell, he was nowhere to be found. It turned out he just took her money and never actually invested it in Bitcoin.

Key takeaways

• Financial literacy is critical whether you invest in a savings account, shares, Bitcoin, Cryptocurrency, etc.
• Always own your assets; never put them in someone else’s name
• Remember that even the best investors make mistakes, don’t beat yourself up over it
• Monitor your investments regularly

Ep270: Beverley Agbakoba-Onyejianya – You Need All Types to Build a Successful Business

Beverley Agbakoba-Onyejianya, a Sports & Entertainment lawyer and entrepreneur, is also the founder of the Lagos Tigers Football Club, the Little Tigers Football Foundation, and a social network for women called GFC.

Beverly talked about the value of exercising emotional intelligence when running a partnership and the time that she didn’t and paid the price.

Key takeaways

• Don’t let your emotions overpower logic and reason when making business decisions
• Don’t be in a rush; take your time to build a quality, sustainable business

Ep185: Jeffrey Hayzlett – Avoid Losing Your Business by Following Customer Behavior

Jeffrey Hayzlett is a global business celebrity, Hall of Fame speaker, Chairman, CEO of C-Suite Network, and best-selling author of The Hero Factor: How Great Leaders Transform Organizations and Create Winning Cultures. The book has an Amazon rating of 4.7 out of 5. I follow him on Twitter and Facebook.

Jeffrey talked about how he invested in a pheasant business, without the remotest idea of how the market worked or whether there was any demand for pheasant meat. One night a rainstorm ran him out of business before he even started.

Key takeaways

• Back up your never-done-before business idea with thorough market research
• Your passion is not enough; your business must fill a market need

Ep259: Gillian Perkins – Patience Is Critical to Growing Your Business

Gillian Perkins is the founder of Startup Society and the host of the Earn More, Work Less podcast, where she teaches people how to start and build profitable online businesses. I enjoy learning from her on her YouTube channel. I watch everyone she puts out (you will experience the attention she pays to the quality of her video and content – It has been an excellent example for me).

Gillian shared how she bought an online course that was too advanced for her startup business, and therefore she could not implement what she had learned.

Key takeaways

• Don’t commit too fast, do your research first
• But eventually, moving forward and acting is a crucial part of growing your business. You don’t have to have all your ducks in a row.
• Many people will offer you advice on how to run your business; you don’t have to follow every piece of advice you get. Choose what is right for you.

Ep267: John Pastor – Ask the Right Questions When Finding a Job

John Pastor has close to two decades of leadership experience in the business process industry in the Philippines. He is the Chief Operating Officer at GHL Systems Philippines, and you can find him on LinkedIn.

John shares how losing one job made him so desperate that he took the first job offer that came without giving it any thought. He ended up losing this job, too, in just a few months. I really admire John’s openness to share a difficult period for him and his family.

Key takeaways

• Take the time to find the right job for you
• Don’t be too hard on yourself when things don’t work out

Ep189: Ed Latimore – Well Begun is Half Done – Get Your Relationships Right from the Start

Ed Latimore is a former professional boxer and a veteran of the United States Army National Guard. He shares his life experiences on his blog, The Mind and Fist. Like me, you can also follow his daily musings on his Twitter.

Ed shared an emotional story of how he let heartbreak lead him into a disastrous relationship that left him even more broken.

Key takeaways

• Be very careful about the people you let into your life
• Don’t let the fear of the pain of a breakup hold you back from walking away from the wrong situation