My Worst Investment Ever Podcast

BIO: Laurie Barkman is a Certified Exit Planner, M&A Advisor, and founder of The Business Transition Sherpa®. STORY: Laurie explains why it's important to start planning your exit plan five to seven years before and what you need to do during that period. LEARNING: Don't wait until you're exiting to plan your exit. "Don't wait to do exit planning when you're exiting, it will be too late. Start...

BIO: Tony Martignetti is the evangelist for Planned Giving fundraising for small- and mid-size nonprofits. STORY: Two years into building his business, Tony convinced himself he could become the nation's thought leader on planned giving fundraising — not just for nonprofits, but for all Americans. He walked into a swanky Midtown Manhattan PR agency, got dazzled by a four-inch binder, and signed up...

BIO: David Siegel is a Silicon Valley entrepreneur who has founded more than a dozen companies. He has written five books on technology and business, was once a candidate for the dean of Stanford Business School, and is now an AI thought leader leading an AI startup he hopes will pave the way for the agentic economy. STORY: Nine months after David's last appearance on the podcast, the conversation...

BIO: Athena Brownson is a Denver realtor, investor, developer, and former professional skier whose resilience through chronic illness fuels her refined, strategic, and client-focused approach to real estate. STORY: Athena lost $130,000 in her first development project when a builder she considered a friend vanished with the upfront funds. Her trust and incomplete due diligence led to a total loss,...

BIO: Jon is the Founder and CEO of FranBridge Consulting, a 2-time Inc. 5000 company, and a leading franchise consultant. STORY: Jon believes franchising remains one of the most effective ways to build durable income, especially when investors focus on operational discipline and unit economics. He shares his top franchise categories for 2026. LEARNING: Look for businesses with repeat customers, op...

BIO: David Siegel is a Silicon Valley entrepreneur who has founded more than a dozen companies. He has written five books on technology and business, was once a candidate for the dean of Stanford Business School, and is now an AI thought leader leading an AI startup he hopes will pave the way for the agentic economy. STORY: David invested heavily in launching a longevity coaching business, believi...

BIO: Jon is the Founder and CEO of FranBridge Consulting, a 2-time Inc. 5000 company, and he is a top 1% franchise consultant. STORY: Jon co-founded a marketing and call-center business that appeared successful on the surface, growing to millions in revenue and dozens of employees. However, excessive customization and an inability to charge prices that matched rising costs meant the business never...

BIO: Edwin Endlich is the Chief Marketing Officer of Wysh and President of the National Alliance for Financial Literacy and Inclusion. STORY: Edwin’s worst investment was buying Tilray stock at $143 during the early hype of legal cannabis investing. Swept up in the excitement of a “new frontier,” he held on as the price crashed—eventually selling at around 30 cents and losing over 99% of his inves...

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 F...

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, t...

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 mill...

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...

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 pla...

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...

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 Qualit...

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 excit...

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 s...

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 i...

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...

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...

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 i...

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...

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 gree...

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 in...