3320: My Worst Money Mistakes by ESI on Lessons Learned from Financial Missteps

Summary

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Podcast Summary: Optimal Finance Daily

Episode 3320: My Worst Money Mistakes by ESI on Lessons Learned from Financial Missteps
Host: Diania Merriam
Date: October 17, 2025

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Overview

This episode delves into the rarely discussed but all-too-relatable topic of personal finance missteps. Diania Merriam narrates a candid post from ESI of esimoney.com, laying out his biggest money mistakes in a humorous, self-aware, and highly educational fashion. Diania supplements the story with her own thoughts on learning from financial errors without shame. Listeners are taken on an honest journey that underscores: everyone makes mistakes with money, what matters most is the lessons learned and how to move forward.

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Key Discussion Points & Insights

1. The Value of Admitting Money Mistakes

• ESI reflects on why sharing financial missteps is as important as touting financial wins.

• Candor and humility in the personal finance space can provide powerful learning opportunities for others.

  Quote [01:36]

  “You might think I’m a financial genius who has always had everything money related figured out. That’s far from true.”
  — ESI (read by Diania)

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2. List of Major Money Mistakes

A. Waiting to Save [02:10]

• ESI enjoyed newfound post-grad income without budgeting or saving, describing years spent living the “high life.”

• Lost approximately five prime investing years to instant gratification.

• Emphasizes the massive compounding opportunity cost, estimating “this delay probably cost me somewhere close to a million dollars, certainly hundreds of thousands.”

  Quote [02:57]

  “Given that time is the best way to maximize your investment return, and that I lost five years of compounding, this delay probably cost me... close to a million dollars.” — ESI

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B. Trying to Invest in Individual Stocks [03:20]

• Early overconfidence in stock-picking abilities, influenced by popular books and ego.

• Underperformed versus the market.

• Followed with high-fee mutual fund investments, further stunting gains before ultimately discovering low-cost Vanguard index funds.

  Quote [03:49]

  “It’s like watching a train wreck in slow motion. I didn’t lose a fortune, thank goodness, but I certainly underperformed in my stock choices.” — ESI

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C. Not Buying More Real Estate When It Was Cheap [04:20]

• ESI recognizes being too rigid (demanding only 10%+ returns) on investment properties, missing out on otherwise solid 9% returns.

• By being overly conservative, he ended up with fewer properties, less passive income, and a later retirement than possible.

  Quote [04:40]

  “If I had loosened up a bit... I’d probably have twice as many properties as I do now... I’d be earning well over $100,000 a year and would have retired at least a few years earlier.” — ESI

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D. Putting Money in an Uninsured Bank [05:00]

• As a teenager, ESI deposited savings in an uninsured bank out of family tradition.
• The bank failed, resulting in years-long uncertainty and a partial loss of savings (“I got around 80% of my money back”).
• Important lesson about risk and the necessity of FDIC insurance.

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E. Investing in Multi-Level Marketing (MLM) [05:49]

• ESI and spouse joined an MLM early in their marriage (“five years worth of laundry detergent in our basement”).

• Spent too much time for too little return; cited as emotionally and financially draining, though monetary losses weren’t catastrophic.

  Quote [06:25]

  “It was brutal going through it.” — ESI

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3. The Bigger Picture: Mistakes Are Not the End

• Acknowledges there were probably more stumbles, but these “have to be the highlights.”

• Despite these errors, things still worked out, pointing to the resilience possible in personal finance journeys.

  Quote [06:48]

  “It’s amazing that even with all these stumbles, things turned out well for us.” — ESI

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Diania Merriam’s Reflections & Takeaways

On Shame and Forgiveness [08:37]:

• Diania comments on the common shame associated with money blunders.

• Advocates for self-compassion and a growth mindset.

• Emphasizes that money is “a completely impersonal tool,” and that financial mistakes are uniquely recoverable.

  Quote [08:51]

  “I have literally never met anyone who didn’t make financial mistakes. And you can always make more money, but you’ll never get back this time you’re spending feeling bad about yourself.” — Diania Merriam

On Perspective [09:12]:

• Suggests reframing mistakes as learning steps instead of sources of regret.
• Encourages enjoyment in the process of learning from finance failures, instead of dwelling in shame.

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Notable Quotes (with Timestamps)

• “You might think I’m a financial genius... That’s far from true.” — ESI (01:36)
• “Given that time is the best way to maximize your investment return, and that I lost five years of compounding, this delay probably cost me... close to a million dollars.” — ESI (02:57)
• “It’s like watching a train wreck in slow motion. I didn’t lose a fortune, thank goodness, but I certainly underperformed in my stock choices.” — ESI (03:49)
• “If I had loosened up a bit... I’d probably have twice as many properties...” — ESI (04:40)
• “It was brutal going through it.” — ESI (06:25)
• “It’s amazing that even with all these stumbles, things turned out well for us.” — ESI (06:48)
• “I have literally never met anyone who didn’t make financial mistakes...” — Diania Merriam (08:51)

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Timestamps for Major Segments

• 01:36 — Introduction to ESI’s confessions
• 02:10 — Waiting to Save
• 03:20 — Stock-Picking Mistakes
• 04:20 — Real Estate Regrets
• 05:00 — Lessons from Bank Failure
• 05:49 — MLM Experience
• 08:37 — Diania’s Perspective on Money Mistakes

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Final Thoughts

Grounded in real, relatable missteps, this episode stands out for its honest, approachable guidance. Both ESI and Diania stress that almost everyone makes some financial errors, but these need not be paralyzing or shameful. Instead, with humor and humility, they become critical learning experiences—reminders that financial success is possible even after multiple blunders. The heartfelt commentary makes this episode essential listening for anyone feeling embarrassed or stuck about their past money decisions.

Transcript

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Is optimal Finance Daily My Worst Money Mistakes by esi of esimoney.com Reading ESI Money, you might think I'm a financial genius who has always had everything money related figured out. That's far from true. I do write mostly about the positive sides of what I've done because 1 much of it has been positive and 2 I think people want to try and emulate what's worked well. That said, there are obviously learnings to be learned from failures. Not to mention the fact that I need to eat some humble pie now and then. So today I'm sharing with you the list of my worst money mistakes. Waiting to Save Once I got out of grad school, I did what many new MBA students do. I went on a shopping spree. I bought a new car, new clothes, and lived the high life with my friends. I had no budget and absolutely no savings. I was making a fortune after all. Or at least it was a fortune to me. Why did I need to save? If this was just a blip on the radar, it would have been fine. But it lasted for several years. Even after I was married, I didn't begin saving in earnest for a couple years. So all in all, I probably lost five good investing years, including my issues with the next mistake. That may not sound like much, but given that time is the best way to maximize your investment return, and that I lost five years of compounding this delay probably cost me somewhere close to a million dollars, certainly hundreds of thousands. You know my net worth. Imagine what it would be with five more years to grow. Ugh, I'm getting sick just thinking of it. Trying to invest in individual stocks Once I did begin investing, I knew that I was a much better stock picker than everyone else. Why I thought this exactly remains a mystery. It must have been because I had superior intelligence compared to the rest of the world. Oh, and I had more insight than trained money managers with millions of dollars and tons of staff at their disposal. Spurred on by books like Beating the Street, I just knew I could pick stocks better than most. I think you know where this is heading. It's like watching a train wreck in slow motion. I didn't lose a fortune, thank goodness, but I certainly underperformed in my stock choices. And once that didn't work, my next move was to mutual funds with high fees. I eventually found my way to Vanguard and their low cost index funds, but I certainly hindered my returns for many years, not buying more real estate when it was cheap. I've said previously that I was too tight on my financial projections when I bought my properties. If I had loosened up a bit and been willing to accept properties with a 9% return versus my 10% goal, I'd probably have twice as many properties as I do now and they'd be earning at least 8% total at the worst. In addition, they would likely have appreciated big time. I'd be earning well over $100,000 a year and would have retired at least a few years earlier. Putting Money in an Uninsured Bank When I was in high school, we had two banks in town. One was insured by the federal government and the other had so many assets that everyone knew it could never go bankrupt. I worked for $3.35 an hour and saved $3,000. I put it in the uninsured bank because that's where my family kept their money. Well, guess what happened? Yep, the state came in, closed down the bank and everything was frozen. It looked like we were going to get nothing back, but then the state started selling the bank's assets and over the course of two years I got around 80% of my money back. In the end, it appeared that the bank did not have enough assets to cover deposits. There were expenses that were incurred when the state started selling everything and didn't really need to close. Thank you State of Iowa for killing a bank that was doing fine. Anyway, I was thankful that I dodged a bullet mostly and decided not to invest again in an uninsured bank. Getting involved in a multi level marketing business or mlm. Anyone ever tried multi level marketing? My wife and I did when we were first married. I'll spare you the gory details, but it was what you would expect. Too much time, too little money, and five years worth of laundry detergent in our basement. We lost maybe a couple thousand dollars, so it wasn't a killer, but it.

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Recently a new friend of my wife's tried to get us to join her MLM business. Though it's been 20 years since our last one. I almost broke out in a rash at the thought of it. There have probably been more stupid moves I've made, but these certainly have to be the highlights. It's amazing that even with all these stumbles, things turned out well for us. You just listened to the post titled My Worst Money Mistakes by esi of esimoney.com Nobody wants to pay rent, but.

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I notice when people talk about money is the undertone of shame many have about financial mistakes. And I get it when I think about how much better off I would probably be if I wasn't so careless and financially illiterate in my 20s. It's really hard not to have regrets, but what about some self compassion? I have literally never met anyone who didn't make financial mistakes. And you can always make more money, but you'll never get back this time you're spending feeling bad about yourself. The thing about money is that it really is all figureoutable. I think this tool of money is one of the few things in life that you can completely screw up and still come out on top eventually. It's much harder to heal from a health scare, fix a broken relationship, go through a career change and waste time you'll never get back. But money? It is a completely impersonal tool. I think with a slight perspective shift you can actually enjoy the process of learning from money mistakes rather than drowning yourself in shame and regret. And that'll do it for today. Have a great day and start to your weekend. If you're listening in real time. And I'll be back here over the weekend where your optimal life awaits.