My Worst Investment Ever Podcast

My Worst Investment Ever Podcast

Welcome to My Worst Investment Ever podcast hosted by Your Worst Podcast Host, Andrew Stotz, where you will hear stories of loss to keep you winning. In our community, we know that to win in investing you must take the risk, but to win big, you’ve got to reduce it. Your Worst Podcast Host, Andrew Stotz, Ph.D., CFA, is also the CEO of A. Stotz Investment Research and A. Stotz Academy, which helps people create, grow, measure, and protect their wealth. To find more stories like this, previous episodes, and resources to help you reduce your risk, visit https://myworstinvestmentever.com/

Episodes

May 7, 2025 5 mins

I once worked with a family business run by two brothers and a sister. The sister was a dreamer, pushing niche markets and creative ideas. Her CEO brother was all about landing big accounts to keep cash flowing. Every strategy meeting turned into a shouting match. Nothing got decided, and the business was stuck.

I pulled the creative sister aside and asked, “Do you want to be CEO?” She laughed, “No way.” That honesty was a game-chan...

  • Mark as Played

    BIO: Jeff Holman, founder of Intellectual Strategies, is revolutionizing legal support for startups and scaling businesses. His Fractional Legal Team model provides expert legal guidance without the cost of a full-time team.

    STORY: Jeff started a cold plunge and sauna business during the pandemic. The company looked great, but he had employee issues, which affected its success. Soon, tens of other studios, brands, and franchises wer...

    Mark as Played

    I met a family business owner in the Philippines who was proud of his “stable” company. Two percent net profit, year after year. Sounds okay, right? Until I showed him the math: because his margin was deeply below average, he’d missed out on $1.2 million in potential profit over three years.

    That “stability” was a slow bleed, draining his business while he didn’t even notice. Are you losing money you can’t see? That’s what this epis...

    Mark as Played

    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 31: The Uncertainty of Investing.

    LEARNING: Equity investing is always about uncertainty.

     

    “Most investors think of investing as much more like risk and forget there’s a lot of uncertainty. That’s a problem because ...

    Mark as Played

    I want to tell you about a midsize business owner drowning in consultants. He kept hiring them, one after another, each promising to turn things around. They’d show up, drop off a fancy report, and disappear. Meanwhile, his profit stayed flat, his team was overwhelmed, and he barely slept.

    One night, he was alone in his office, staring at a payroll he wasn’t sure he could cover. That’s when it hit him. He told me, “I realized it’s o...

    Mark as Played

    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 30: The Economically Irrational Investor Preference for Dividend-Paying Stocks.

    LEARNING: The dividend policy is irrelevant to stock returns.

     

    “Stock prices tend to rise in the month before they pay the dividend, be...
    Mark as Played

    I, Coffee: The Capitalist Miracle Behind Your Morning Cup

    I am the cup of coffee warming your hands right now. A simple drink with a story no government could brew. My journey from a cherry on a tree to your morning ritual is a testament to freedom, ambition, and human ingenuity.

    I exist not because of a single plan by a government or business but because of countless decisions, risks, and exchanges made by individuals and c...

    Mark as Played

    BIO: Collin Plume, a precious metals expert and serial entrepreneur, helps investors maximize returns with minimal risk.

    STORY: Collin inherited some money from his grandmother at 18. When two of his college friends came to him with the idea of creating a TV show, but on the internet, he cut them a check that was way too much than what he should have. The business didn’t work.

    LEARNING: If you’re going to make a mistake in something,...

  • Mark as Played

    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 28: Buy, Hold, or Sell and the Endowment Effect and Chapter 29: The Drivers of Investor Behavior.

    LEARNING: Smart people are humble and able to admit when they have made a mistake.

     

    “As humans, we make all kinds of ...

    Mark as Played

    BIO: Stu Heinecke is the author of How to Get a Meeting with Anyone, named one of the top 64 sales books of all time and the #1 sales book ever written on prospecting.

    STORY: Stu discusses his updated book edition, which caused a worldwide stir when the first edition was released in 2016. He talks about how to get a meeting with anyone.

    LEARNING: Be audacious and try to get that meeting that seems impossible.

     

    Mark as Played

    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 27: Pascal’s Wager and the Making of Prudent Decisions.

    LEARNING: Use Pascal’s wager to avoid making devastating mistakes.

     

    “You have to think about the cost of being wrong versus giving up on that hope or the abili...

    Mark as Played

    BIO: Wes Schaeffer is The Business Fixer®. He sees the message you want to convey but can’t find the words and gives them to you because if you don’t toot your own horn, there is no music.

    STORY: Wes discusses the evolving landscape of business and marketing, emphasizing the importance of human connection, trust, and information.

    LEARNING: Future-proof your business with trust, strategy, and agility.

     

    Read more
    Mark as Played

    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 26: Dollar Cost Averaging.

    LEARNING: Invest all your money whenever you have it.

     

    “If you want to put the odds in your favor, which is the best we can do because we don’t have clear crystal balls, you should put all...

    Mark as Played

    BIO: Elvi Caperonis is a former Harvard University Analyst and Technical Program Manager at Amazon and LinkedIn’s top Voice and a career strategist who has mastered the art of storytelling to create a six-figure personal brand on LinkedIn.

    STORY: Elvi decided to be her own boss and started an e-commerce business for which she had no knowledge or passion. It turned out to be a nightmare that cost her $30,000.

    LEARNING: If you don’t ha...

    Mark as Played

    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 25: Battles are Won Before They Are Fought.

    LEARNING: Be well-prepared for potential disruptions in the market.

     

    “Many investors let emotions drive their decisions, and they end up buying high and selling low—t...

    Mark as Played

    BIO: Fabrizio has always wanted to fly jets and has had a career flying both private jets and for various airlines worldwide. He has shared the cockpit with pilots from over 65 nationalities, giving him a broader perspective on people and life.

    STORY: Fabrizio invested in a luxury car business in Italy but chose the wrong person to run the show, and because of this, he lost all his money and a very good friend.

    LEARNING: Do not mix b...

    Mark as Played

    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 24: Why Do Smart People Do Dumb Things?

    LEARNING: Past performance does not guarantee future results. Change the criteria you use to select managers.

     

    “There are only two things that are infinite, the universe ...

    Mark as Played

    BIO: James “Jimmy” Milliron is Co-Founder & President of National Brokerage Atlantic, specializing in Wealth Enhancement, Estate Planning, and Asset Protection.

    STORY: Jimmy wanted to invest $100,000 in Bitcoin, but when he couldn’t find an easy way to do it, he bought a car instead.

    LEARNING: Research and learn all you can about investment opportunities before investing.

     

    “Don’t be afraid ...
  • Mark as Played

    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 23: Framing the Problem.

    LEARNING: Understand how each indexed annuity feature works before buying one.

     

    “I would never buy an annuity that didn’t give me full inflation protection.”

    Mark as Played

    BIO: Mitch Russo is a serial entrepreneur who built and sold his first software company for eight figures, scaled a $25M business with Tony Robbins and Chet Holmes, and was twice nominated for Inc. Entrepreneur of the Year.

    STORY: Mitch bought several Amazon stores to make passive income, which he did for a while. Unfortunately, the lucky streak ended after Amazon significantly reduced the commissions it paid to its resellers, and G...

    Mark as Played

    Popular Podcasts

      Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

      24/7 News: The Latest

      The latest news in 4 minutes updated every hour, every day.

      Therapy Gecko

      An unlicensed lizard psychologist travels the universe talking to strangers about absolutely nothing. TO CALL THE GECKO: follow me on https://www.twitch.tv/lyleforever to get a notification for when I am taking calls. I am usually live Mondays, Wednesdays, and Fridays but lately a lot of other times too. I am a gecko.

      The Clay Travis and Buck Sexton Show

      The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.

      The Bobby Bones Show

      Listen to 'The Bobby Bones Show' by downloading the daily full replay.

    Advertise With Us
    Music, radio and podcasts, all free. Listen online or download the iHeart App.

    Connect

    © 2025 iHeartMedia, Inc.