FREE NEWSLETTER

Philip Stein

    Forum Posts

    Cash Ain’t Trash

    18 replies

    AUTHOR: Philip Stein on 12/26/2025
    FIRST: Winston Smith on 12/26/2025   |   RECENT: David J. Kupstas on 12/27/2025

    How Big Is Your Umbrella, Follow-Up

    4 replies

    AUTHOR: Philip Stein on 5/1/2025
    FIRST: Ben Rodriguez on 5/2/2025   |   RECENT: Philip Stein on 5/3/2025

    How Big is Your Umbrella?

    16 replies

    AUTHOR: Philip Stein on 4/11/2025
    FIRST: Edmund Marsh on 4/11/2025   |   RECENT: baldscreen on 4/13/2025

    Meet Marcus

    8 replies

    AUTHOR: Philip Stein on 6/23/2024
    FIRST: David Powell on 6/23/2024   |   RECENT: Bottom Feeder on 6/29/2024

    Comments

    • The HumbleDollar up/down arrows remind me of the Like/Don’t Like buttons on social media web pages. The latter, I presume, feed algorithms that determine ad pricing and content feeds. Since HD does not allow advertising (thank goodness), or feed different content to different readers, I have to question the value of up/down arrows. Were some of the features of social media web pages simply copied to HD when the website was being developed? The whole purpose of HD, as I understand it, is to promote commentary so readers can shares ideas, information, and experiences. Just clicking an up or down arrow doesn’t add much to the conversation. I do have one question: How did you earn the sobriquet “DrLefty?” Are you left-handed?

      Post: The “Mean Girls”/Junior High Bullies at HumbleDollar

      Link to comment from January 10, 2026

    • I suspect that the tale of the anonymous investor who enjoyed a $70 million dollar profit from S&P 500 call options will lead a number of people to conclude that buying call options on the S&P 500 is the path to riches. But that investor was extraordinarily lucky. Consider what the media is not offering: stories about the much larger number of people who invested in S&P 500 call options and lost money. No one is interested in those stories. As Nassim Taleb warned us: don’t be “Fooled by Randomness.” Also, we know that correlation does not imply causation. Yet, Taylor Hamm seems convinced that paying $25 for a spell was responsible for her good fortune. I’ll guess that she’ll be buying many more spells in the future.

      Post: Money Moments

      Link to comment from December 27, 2025

    • One of those opportunities for spontaneous giving might include the tip jar at take-out eateries.

      Post: Cash Ain’t Trash

      Link to comment from December 27, 2025

    • Dan, thanks for mentioning the need to have smaller denominations available. If you only stockpile large denomination bills, you might find it difficult to purchase simple items in, say, a convenience store.

      Post: Cash Ain’t Trash

      Link to comment from December 26, 2025

    • I recently finished re-reading William Bernstein’s Four Pillars of Investing. Your strategy is consistent with the advice Bernstein offers in his book. I’d say you’ve done well and should continue to do so.

      Post: Your Portfolio, Your Business

      Link to comment from October 4, 2025

    • Like all HumbleDollar readers, I’m heartbroken after learning of Jonathan’s passing. I feel like Socrates’ students must have felt after their master drank his fateful cup of hemlock. My teacher, my guiding light is gone. I shall not see another like him in my lifetime. Rest in peace, Jonathan.

      Post: Farewell Friends

      Link to comment from September 22, 2025

    • Bogdan, welcome to the HumbleDollar site! A few questions for you: How did you meet Jonathan? What were the circumstances by which Jonathan chose you as moderator of the site? What is your day job? Do you have an independent accounting practice, or are you employed by a large firm? In addition to CPA, do you have any plans to become a financial advisor?

      Post: Quick Intro

      Link to comment from September 21, 2025

    • Much of the discussion below centers around the FICA tax. But, as William Dorner mentions, isn’t another necessary reform raising the retirement age? With advances in healthcare helping people live longer, 70 may be the new 65. For decades, demographers have been telling us that Social Security will be in trouble when the Baby Boom generation retires. Indeed, that has come to pass. Yet, numerous congresses have been content to kick the can down the road. Like other HumbleDollar readers, I’m disheartened by the failure of Congress to tackle the hard problems the nation faces. The cynic in me sees too many representatives more interested in reelection and ideology than passing tough, but necessary, legislation and taking the heat.

      Post: Does Social Security work?

      Link to comment from August 30, 2025

    • I have a rule for when it’s time for a new pair of shoes: I step in a puddle and my sock gets wet. Also, I’ve found that you can find nice T-shirts at the Goodwill Store for $2 or $3 each.

      Post: Frugality, Minimalism, and Aligning Values

      Link to comment from August 30, 2025

    • In my neighborhood, it’s easy to identify the households with too much accumulated stuff. They’re the ones who always park on the driveway or in the street because their car won’t fit in the garage.

      Post: Frugality, Minimalism, and Aligning Values

      Link to comment from August 30, 2025

    Articles

    Harmful Illusion

    Philip Stein   |  Jan 1, 2024

    MANY FOLKS EQUATE a stock market downturn with losing money. I often hear comments like, “I lost money yesterday. The stock market went down.”
    I believe this impression of loss is an illusion, one that can be detrimental to our financial health—because it blinds us to certain fundamental truths.
    1. Illusion of lost money. You only lose money if you sell shares at a loss. If you don’t sell amid a downturn,

    A Profitable Read

    Philip Stein   |  Oct 31, 2023

    I RECENTLY FINISHED reading the second edition of William Bernstein’s The Four Pillars of Investingtwice. This new edition is a significant rewrite of the first edition that was published in 2002. Even if you’ve read the first edition, reading the second edition is worth your time.
    Though I’ve read most of the books written by well-known investment luminaries familiar to HumbleDollar readers, there were still pearls of wisdom I gathered from this second edition.

    Old Money

    Philip Stein   |  Aug 7, 2023

    COMMENTARY ABOUT America’s wealth inequality seems to be everywhere. According to Wikipedia, as of 2021’s fourth quarter, Federal Reserve data indicate that the top 1% of households hold 32.3% of the country’s wealth.
    Meanwhile, Pew Research Center reports that the median wealth of the richest 20% of American families increased by an inflation-adjusted 45% between 1998 and 2007, while the median wealth of middle-income families rose just 16%.
    And then there’s the Federal Reserve Bank of St.

    No Right Answer

    Philip Stein   |  Jul 20, 2023

    DURING MY 30s, I worked for a defense contractor. The Berlin Wall fell in November 1989 and the Soviet Union imploded just over two years later. Many at work believed that the end of the Cold War would lead Congress to reduce defense spending. Sure enough, layoffs at my company commenced soon after.
    I was fortunate to avoid being laid off. I do recall, though, overhearing one coworker in his 50s who, after receiving a pink slip,

    Skill or Luck?

    Philip Stein   |  May 26, 2023

    NASSIM NICHOLAS TALEB has written a trilogy on the topic of chance: Fooled by Randomness, The Black Swan and Antifragile. I didn’t find these three books to be easy reading, plus Taleb has strong opinions, which may turn off some readers. Still, there’s a host of investment lessons to be culled from his works.
    Taleb argues that randomness plays a powerful role in financial markets and,

    Saved by Compounding

    Philip Stein   |  Apr 13, 2023

    IF I MADE A LIST of all the dumb things investors do, I likely committed them all. I chased performance, sold stocks in a bear market, invested in things I didn’t understand—you get the picture.
    Yet, despite the numerous setbacks I suffered before I matured as an investor, I was able to retire comfortably. How was that possible? My conclusion: compound growth. Indeed, I believe compounding is a surer way to wealth than picking market-beating investments.

    SHARE