My Worst Investment Ever Podcast

BIO: Scott Alldridge is CEO of IP Services and President of the IT Process Institute, a bestselling author of the VisibleOps series, and a Certified Chief Information Security Officer.

STORY: Scott’s worst investment was a stake in a startup promising to deliver hot coffee by drone. Excited by the futuristic idea, he invested before the concept was proven—but the project quickly crashed when the FAA banned drone deliveries and a pro...

BIO: Thomas J. Powell, founder of The Powell Perspective™, is a seasoned entrepreneur, investor, and advocate for founders, bringing clarity, strategy, and resilience to leaders building at scale.

STORY: Thomas invested $3.6M in a friend’s cannabis company, where he ignored his own due diligence framework. Because he skipped key governance protections and didn’t document alignment or exit terms, the investment became frustrating, ha...

BIO: As Co-Founder & CEO of Mode Mobile, Dan Novaes is leading the transformation of how people interact with technology. His “Earn As You Go” software empowers millions of consumers to turn daily habits into passive income.

STORY: Dan decided to take the bold move of turning his treasury into a long-term crypto strategy. What started as $2 million in Bitcoin and Ethereum ballooned to $30 million, but the 2022 crash and business...

BIO: Dr. Gilbert  A. Guzmán is a business strategist and systems thinker. He is the founder of IntraQ AI, a SaaS solution designed to eliminate knowledge gaps within the workplace, and the author of Atomic Impact: Systems for Transformative Productivity.

STORY: In 2012, Gilbert  envisioned a portable charger vending system for airports, universities, and theaters—a “Redbox for power.” He over-engineered, over-researched, a...

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 conclude the lessons from the book.

LEARNING: Investing isn’t about chasing the next hot stock—it’s about building a resilient, well-diversified portfolio you can live with in good times and bad.

“Once you have enough, stop playin...

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 41: A Tale of Two Strategies and Chapter 42: How to Identify an Advisor You Can Trust.

LEARNING: Passive investing is still the winner. If something is worth doing, it’s worth paying someone to do it for you.

“A go...

BIO: Pieter Slegers is the founder of Compounding Quality Newsletter. Pieter worked for three years as a Belgian asset manager before focusing full-time on his investment newsletter, Compounding Quality, in July 2022. Compounding Quality has over 1 million followers across social media and nearly 500,000 email subscribers. The goal of the newsletter is to help other investors by focusing on Quality Investing.

STORY: At the age of 13...

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 40: The Big Rocks.

LEARNING: Passive investing will give you the freedom you need.

“Indexing and passive investing have the ‘disadvantage’ of being boring. I admit it. However, if anyone needs to get their exciteme...

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 39: Enough.

LEARNING: More wealth does not give you more happiness.

“Prudent investors don’t take more risk than they have the ability, willingness, or need to take. If you’ve already won the game, why are you stil...

BIO: Blair LaCorte is a dynamic executive with experience across entertainment, aviation, AI, aerospace, consulting, and more.

STORY: Blair shares three catastrophic investment failures and the life-altering lessons that rewired his approach to wealth.

LEARNING: Chase knowledge, not hype, and don’t let greed hijack logic. Invest with friends only if you’re willing to lose both.

“The worst inve...

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 sho...

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 36: Fashions and Investment Folly.

LEARNING: Do not be swayed by herd mentality.

“Markets can remain irrational longer than you can remain solvent. So do not bet against bubbles, because they can get bigger and big...

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 35: Mad Money.

LEARNING: Investors are naive, and Cramer is an entertainer, not a financial advisor who adds value.

“Do not confuse information with value-added information. If you know something because it wa...

BIO: Mike Koenigs is a serial entrepreneur with five successful exits, a 19-time bestselling author, and a top strategist for founders post-exit.

STORY: Mike invested big in a SaaS startup set up for success, but infighting brought it to its knees.

LEARNING: Character is bigger than charisma.

“If you’re a shareholder, your best exit is for a big company to come and buy what they believe is mon...

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 34: Bear Markets: A Necessary Evil.

LEARNING: Investors must view bear markets as necessary evils.

“If stocks didn’t experience the kind of bear markets that we have, investors would be very unhappy.”

BIO: Jeff Sarti, CEO of Morton Wealth, leads a firm managing over $3 billion in assets. With a mission to empower better investors, Jeff helps clients achieve their financial goals while supporting employees in their career growth.

STORY: Jeff bought a few dot-com companies, thinking it was smart and safe because he bought the big brands. All of the companies dropped 90%+.

LEARNING: Don’t let greed, FOMO, and a lack of imagination dr...

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 33: An Investor’s Worst Enemy.

LEARNING: You are your own worst enemy when it comes to investing.

“The right strategy is to avoid the loser’s game. Don’t try to pick individual stocks or time the market, just inves...

A retailer in Bangkok was staring down a cash crunch after COVID. He was ready to sign for a loan, convinced it was his only option.

Instead, we dug into his numbers and found $30,000 in unsold inventory gathering dust and $8,000 in overpayments to suppliers. That cash was enough to stabilize his business; no debt was needed. The money was there; he just couldn’t see it.

Download The Profit Gap for free at TheProfitBootCamp.com to se...

BIO: Oeystein Kalleklev is the outgoing CEO of Flex LNG and Avance Gas. He has prior experience as CFO of Knutsen NYK Offshore Tankers and Umoe Group and Chairman General Partner of MLP KNOT Offshore Partners.

STORY: Oeystein has been part of some terrible investments made by his employers. One invested $150 million to become the biggest shareholder of a mine in Guinea, which was lost due to a bad regime. During the great financial ...