Silliest Investment Mistakes?

[aristotelian]

DELL stock. Thought it was too big to fail because everyone needs computers. My Roth IRA is lagging my wife's by about $70k now mostly due to poor stock picks in my youth.

[zarci]

Last year I saw a beautiful buying opportunity on an ETF of which the price at the time was way below the NAV. So I plunged ahead and purchased then and there. After the transaction I realised the ETF was priced in GBP on the brokerage platform, and the NAV to which I was comparing it was listed in USD...

All in all this fund was part of my plan, and I didn't really lose anything significant in the transaction. I was very happy it was a small transaction though.

[dziuniek]

I am not saying who but read about someone buying pfizer total landscaping instead of the pharma co, haha.

[Taylor Larimore]

Bogleheads:

My worst mistake was trying to be a market-timer in the early 90s.

At that time, I regularly visited the Miami Public Library to read their monthly market-timing newsletters (about 15) and books that advocated market-timing which was very popular in those days. One of the books I wish I had never read was "The Donoghue Strategies" written by a financial advisor. It convinced me that I had found "nirvana" and I started market-timing our commission-free Vanguard investments. I was so enthusiastic that I decided to share my new investing method. Accordingly, I began writing a market-timing newsletter which I sent to friends each month.

This is the worst investing mistake I ever made and the one I regret the most.

Best wishes.
Taylor

Jack Bogle's Words of Wisdom: "After nearly 50 years in this business, I do not know of anybody who has done market timing successfully and consistently. I don't even know anybody who knows anybody who has done it successfully and consistently."

[S4C5]

My decision to sell all of my commodity stocks and small cap value funds and liquidate my entire post-tax portfolio into cash in October and use that cash to write put options for gold funds with December expirations hasn't really worked out well.

Talk about zigging when you should have zagged. I couldn't have played that any more poorly.

However, with the current greed in small caps/value, and fear in gold, maybe it will end up working out. Selling greed and buying fear is usually a good idea, but I don't know if one month is going to be enough time to recover from this.

[Monsterflockster]

Living in the Silicon Valley my wife was laid off while pregnant in 2009 (when the housing bubble crashed). We weren’t in the best area of town and decided to sell and walk away. That was a million dollar mistake.

Lost a lot of money and took a bit of time but we were lucky to have ended up well.

[TSR]

I made a very serious, non-silly mistake in purchasing a house during the housing crisis in 2008. But as for "silly" mistakes it was probably the amount of time spent with a Northwest Mutual "financial advisor" (insurance salesperson) before realizing what was happening. I was just out of law school and had my first "real" job, and the NWM people were all over our firm. I drove up to meet with the (nice, well spoken, attractive) young woman at least three times before I realized what was going on. I asked her point-blank how she made money, and her answer that she received a commission on the sale of the insurance product seemed candid to me so she must be legit! I even gave her the name of another colleague to contact. When I realized that this was not a good thing for me to be involved in, I had to call him and say, "Hey, I gave your name to someone. Just tell her you don't want to meet." He did not appreciate this very much. Glad I did not buy whole-life insurance, but I still feel pretty dumb for all the time I spent swallowing that.

[Sand101]

I am not saying who but read about someone buying pfizer total landscaping instead of the pharma co, haha.

Considering PFE has been a terrible investment the last 20 years it may have been a happy accident!

[fizxman]

In September of 2011, I bought a 1/4 oz gold coin and 5 oz silver bar for what amounted to be about $2,100/oz and $47/oz respectively. Today gold is about $1,800/oz and silver is about $23/oz.

In May of 2018, I bought $500 worth of crypto which is now worth about $434.

[S4C5]

In September of 2011, I bought a 1/4 oz gold coin and 5 oz silver bar for what amounted to be about $2,100/oz and $47/oz respectively. Today gold is about $1,800/oz and silver is about $23/oz.

In May of 2018, I bought $500 worth of crypto which is now worth about $434.

Your worst investment is losing $66 on bitcoin? Dang.

[Johm221122]

Didn't invest as much as I could in my 401k with unlimited 100% match. I was just starting out and didn't want all my money locked up. I bought savings bonds with about 33% of my savings. I turned down about $4,000 a year for 2 years of free money. But in hindsight those savings bonds over 20 years now have always made me feel safe. Knowing you have to just walk in a bank with them and have instant access to money is priceless when your just starting to save

[fizxman]

In September of 2011, I bought a 1/4 oz gold coin and 5 oz silver bar for what amounted to be about $2,100/oz and $47/oz respectively. Today gold is about $1,800/oz and silver is about $23/oz.

In May of 2018, I bought $500 worth of crypto which is now worth about $434.

Your worst investment is losing $66 on bitcoin? Dang.

Didn't say worst, said silliest. And it wasn't Bitcoin. I bought $100 of Bytecoin which is now worthless. The remaining $400 was in Ethereum, which has gone up a little bit. They were silly for the same reason as the gold & silver purchases; I didn't know it at the time but I bought all of them when they were practically at their highest and I got caught up in the fever.

My worst investment was not investing until I was 30. Missing out on five years or so may have cost me thousands over a lifetime. The good things are (a) I'll never know how much and (b) the Great Recession was part of those five years.

[james22]

I bought VGPMX in both my IRA and Roth IRA. It used to be called Vanguard Precious Metals and Mining Fund. Now it is Vanguard Global Capital Cycles Fund.

Vanguard screwed me and every other investor in the fund by changing the investment strategy. Naturally gold has been on a tear ever since Vanguard did this.

My mistake was thinking that Vanguard would stay the course with the fund. Silly me.

+1

And they've just done the same with their Energy fund.

[Top99%]

I bought into the "trees really can grow all the way to the sun" mantra during the tech bubble and didn't sell my vested Nortel stock options which at the time represented 80% of our net worth. Those went to worth $0 at about 5:01 PM on October 17th 2000... I then followed that brilliant decision with some individual stock purchases which also worked out poorly.

[Croissant]

I bought VGPMX in both my IRA and Roth IRA. It used to be called Vanguard Precious Metals and Mining Fund. Now it is Vanguard Global Capital Cycles Fund.

Vanguard screwed me and every other investor in the fund by changing the investment strategy. Naturally gold has been on a tear ever since Vanguard did this.

My mistake was thinking that Vanguard would stay the course with the fund. Silly me.

+1

And they've just done the same with their Energy fund.

curious does Vanguard need the approval of the fund holders to change strategy? was this strategy change communicated to all of you before hand?

[Iowa David]

I opened a Roth IRA early in my career and made regular contributions, however, did not realize it was invested in a CD. It took me at least 5-7 years before I understood that a Roth wasn’t the actual investment.

[chenzi]

Sold Amazon stock at $600-700 -
used that entire money to close out my 2% carloan of $70K, and the for 200K downpayment for my SFH

[StevieG72]

Analysis paralysis, waited too long to start investing with Vanguard.

[L82GAME]

Cashing out a 401k in my twenties to fund three months of travel and relocating to the southwest. I should have saved the cash and left the 401k intact.

[RyeBourbon]

Bought a tech stock IPO in 1999 at $13. Rode it all the way up over $110 and thought about selling it to buy a sports car, but thought I'd hold on a little longer until it started plunging. No point in selling now, hang on, it will come back. It was delisted in 2002, worthless. Never got that car...

Maybe not the silliest, or worst decision, but probably the most interesting...

[heyyou]

With my entire inheritance, I bought into limited partnership (LP) real estate deals that were suggested after I asked my tax guy for investing advice. He likely received a referral fee from the seller, as the tax guy did not do anything without getting a fee. The LPs all failed in an Arizona real estate crash--no residual value. I had no idea about how leverage was higher risk when all that was shown at the meetings was the higher returns from successful LPs.

[SnowBog]

I can't compare with most of these posts, so I'll share a "technical" silliness...

I no longer remember the specifics, but somehow this year after Fidelity enabled fractional trading on its mobile app, I somehow managed to create a sell transaction for what I thought should have been all of my ESPP shares that just landed.

I was surprised when I logged in a few days later to see I still owned a few cents worth of the stock, which shows as 0.001 shares. However, any attempt to sell this 0.001 share is rejected as it shows I'm trying to sell more than I own...

Eventually called into support to learn that "somehow" the transition processed in such a way I was left with < 0.001 shares. But their system doesn't allow any operations for anything smaller than 0.001 shares. Even if I try to sell "all shares", it's rejected...

The rep thinks there's a way they could clean this up, but would require manual operation override. But I feel bad making them spend likely hundreds of dollars to fix something that is literally worth a few cents. Plus, I like the novelty of having an "impossible" < 0.001 shares, presumably the result of a "bug" in their new [at the time] fractional trading service, which can't be fixed (at least not by me or reps), so it can never be sold.

[pseudoiterative]

One of my first investments was in a Vanguard fund for Australian property. I chose it because it had gotten high returns in the previous few years, and also because in Australia we're generally obsessed with real estate. I invested through a vanguard managed fund paying additional fees instead of an ETF because I thought opening an actual brokerage account was too complicated. I kept the money invested for a bit over a year and then started trying to withdraw it to market-time a profit. The only way to get vanguard to execute a sell was to send them a fax, and when I'd send them a fax they'd reject it because my signature on the fax didn't look like the copy of my signature they had on record. I had to try about three times on three different days. I was even enough of a goose to try to market-time the day the withdrawal would be processed, which made the process even more shambolic.

Home country bias? Check. Non-diversified risk for sector concentration and country concentration? Check. Picking a sector to invest in because it's trendy? Check. Picking in investment based on past performance, with no understanding of expected future performance or fundamentals? Check. Investing with unnecessarily high expenses? Check. Exposure to fax machines? Check. Market timing? Check.

[Stinky]

One of my first investments was in a Vanguard fund for Australian property. I chose it because it had gotten high returns in the previous few years, and also because in Australia we're generally obsessed with real estate. I invested through a vanguard managed fund paying additional fees instead of an ETF because I thought opening an actual brokerage account was too complicated. I kept the money invested for a bit over a year and then started trying to withdraw it to market-time a profit. The only way to get vanguard to execute a sell was to send them a fax, and when I'd send them a fax they'd reject it because my signature on the fax didn't look like the copy of my signature they had on record. I had to try about three times on three different days. I was even enough of a goose to try to market-time the day the withdrawal would be processed, which made the process even more shambolic.

Home country bias? Check. Non-diversified risk for sector concentration and country concentration? Check. Picking a sector to invest in because it's trendy? Check. Picking in investment based on past performance, with no understanding of expected future performance or fundamentals? Check. Investing with unnecessarily high expenses? Check. Exposure to fax machines? Check. Market timing? Check.

Your transaction definitely checked all of the boxes.

I hope that you've found some way to sell your shares of the fund. And I hope that you made a profit when you sold.

[neglogic]

I bought about $2000 worth of Lucent stock in 1997. Finally donated it to charity a few years ago - it was worth less than $100 at that point.

Lesson learned.

[highercall]

Anyone remember CMGI?
Lost some money there. After I learned my lesson with CMGI I made sure I sold all my other individual stocks and moved to 100% mutual funds - I had some really silly companies at the turn of the century that I dumped:
- This company called NetFlix (how long could a mail-order CD business continue?)
- Another company called Amazon (how long would an online bookstore last? Just books - really?).
- There was another one called Starbuck (who is going to pay $5 for a 50 cent cup of coffee? Build a business off this? really?)
- And then there was another one I held called Apple (I bought because I loved the "Mac" but when they released the "Newton" I questioned how well they could bring new products to market).

Glad I sold them all

On the other hand I somehow timed my exit from Lucent correctly. I suppose that is the internet story I should tell. Sold at $120 before they sunk to $7. And the only reason I did it was because my spouse wanted to put in an inground swimming pool. If she didn't want the pool I would have lost the money.

Anyone remember CMGI? Ha yes very much so. Another one of those teaching moments that I continue to forget.

[Harry Livermore]

which made the process even more shambolic.

Your transaction definitely checked all of the boxes.

I hope that you've found some way to sell your shares of the fund. And I hope that you made a profit when you sold.

But you get extra credit for the use of the word "shambolic!"

Cheers

[burritoLover]

Early on, I had some high dividend tilts thinking that if the market drops and go sideways, I would still have that dividend return as if it was like a bond interest payment - not realizing how dividends are irrelevant.

[Harry Livermore]

I assumed this thread would get locked, but I am happy to see management appreciates a nice, lighthearted discussion.
I have made many silly mistakes, but I'll try to list out a couple, in no particular order:

I used to chase "hot" mutual funds... I would read about a particular superstar manager in Money, Smart Money, or Kiplingers, buy the fund, and (usually) watch it underperform.
I invested in a couple of Japan funds, back in the late 1990s, after the NIikkei had fallen quite a bit ("it's Japan, how can this not bounce back???"), stubbornly "stayed the course", and sold in the early 2010s. Perfect BAD market timing.
Over the years, I have tried my hand at all manner of commodities, in my "fun money" allocation. Natural gas, uranium, copper, oil, silver, gold. I have done OK with the PMs. The others have been a mixed bag, and seemingly just dumb luck, despite my careful "research" showing that the market was out of whack and the commodity in question was being misvalued. I did OK with copper. Nat gas was a disaster, mostly due to contango, and waiting until deep March for K-1s was just the icing on the cake.
I have occasionally used options, sometimes wisely, sometimes poorly. Once again, the "poor" result has come from thinking I know something that the market does not.

I'm not sure if those rank as "silliest" within the sample of the group, but those are the ones I have made that come to mind.
Cheers

[SmileyFace]

Anyone remember CMGI?
Lost some money there. After I learned my lesson with CMGI I made sure I sold all my other individual stocks and moved to 100% mutual funds - I had some really silly companies at the turn of the century that I dumped:
- This company called NetFlix (how long could a mail-order CD business continue?)
- Another company called Amazon (how long would an online bookstore last? Just books - really?).
- There was another one called Starbuck (who is going to pay $5 for a 50 cent cup of coffee? Build a business off this? really?)
- And then there was another one I held called Apple (I bought because I loved the "Mac" but when they released the "Newton" I questioned how well they could bring new products to market).

Glad I sold them all

On the other hand I somehow timed my exit from Lucent correctly. I suppose that is the internet story I should tell. Sold at $120 before they sunk to $7. And the only reason I did it was because my spouse wanted to put in an inground swimming pool. If she didn't want the pool I would have lost the money.

Anyone remember CMGI? Ha yes very much so. Another one of those teaching moments that I continue to forget.

Teaching moment indeed. I think of my CMGI investment when I see folks post that they are "all-in" for FAANG stocks - why wouldn't they be? They drive the new economy! Times are different than they used to be! and so-on. I had the "N" and the "A" in FAANG decades ago but I also learned my lesson with the others. The new stories and companies all just sounds too familiar for those that were the arrogant young whippersnappers at the turn of the century.

I too am glad the admins chose to keep this thread open. A reminder of our mistakes is a reminder not to make them again. It is very actionable!
Hard work, living below my means, and simple index investing became my new formula for success after CMGI.

[whoshighpitch]

Co-worker, who knows absolutely everything about everything, recently told me his investments didn't go up at all over the last DECADE. After talking to him a bit I realized his contributions were just going into a money market fund. He thought someone managed it and put his money into stocks or mutual funds, but nope, it just sat there for more than a decade in a money market fund as he missed out on the longest bull market in US history. I would feel bad if he wasn't such an arrogant know-it-all. I guess that wasn't a silly mistake that was a BRUTAL mistake.

[Stinky]

Co-worker, who knows absolutely everything about everything, recently told me his investments didn't go up at all over the last DECADE. After talking to him a bit I realized his contributions were just going into a money market fund. He thought someone managed it and put his money into stocks or mutual funds, but nope, it just sat there for more than a decade in a money market fund as he missed out on the longest bull market in US history. I would feel bad if he wasn't such an arrogant know-it-all. I guess that wasn't a silly mistake that was a BRUTAL mistake.

Did you tell the arrogant coworker that he’s basically earning nothing on his MM fund right now?

Or is he still blissfully unaware of the effect of his investment choice?

[Workinprogress]

How about WorldCom?

Back when I was very first starting to invest, my Edward Jones advisor suggested I own about $5K worth of them. (about 30% of my portfolio) A good chunk of change for someone bringing home $20K annually.

He failed to notify me and I knew not enough to watch, as it disappeared.

All in all, it was a cheap lesson that got me to educate myself and start doing my own investing work.

[Johnsson]

I had this in another post (yesterday) because I hadn't seen this one...

Bogleheads are all about planning for success. I didn't plan properly. While I understand no plan is perfect, I'm really feeling this one because it was so stupid.

I'm writing this as a cathartic outlet for my sins. DON'T BE LIKE ME!!!

I'm a recent Boglehead (from the last few years) who has decided on our AA and put together our 'PLAN' (IPS) and plotted a strategy using information from this forum and some of the recommended tools.

My specific sin is that I have been planning for retirement (post June 2021), not pre-retirement (now). Investing is a continuum where many of us attempt to take advantage of market ups and downs while keeping an eye on our plans with retirement being a change of direction, not a new 'trip' as I have been treating it.

I have been planning for Roth conversions starting next year. Where I missed the boat was not starting now, or maybe last year, or maybe the year before. We should also have been maxing out 401k/Roth accounts and have not been. I guess it was some kind of mental block. No excuse!!

Probably tomorrow I''ll be converting some stock I bought around the low point in March that has since doubled (and I expect to almost double again). If I had been planning to convert this year and converted AND bought the stock in March I would have saved ~$15K in 2020 taxes.

On one hand it's not a lot of money. On the other I have to work a lot longer to make that after-tax money than it would have taken to convert earlier in the year, so it hurts. A case of working harder, not smarter.

Thank you for reading my confession. Hopefully I learned something. For some reason losing money seems to help drive a lesson home.

Again, DON'T BE LIKE ME

[Luckywon]

Passed on about $80k of additional pretax contributions our Pension TPA said I could make when a Defined Benefit pension plan we had was being wound down.

If I made the contribution and then converted it to Roth I would have paid no more in taxes than I did by not making the pretax contribution. So I basically passed on a "free" Roth conversion of $80k

[RyeBourbon]

How about WorldCom?

Back when I was very first starting to invest, my Edward Jones advisor suggested I own about $5K worth of them. (about 30% of my portfolio) A good chunk of change for someone bringing home $20K annually.

He failed to notify me and I knew not enough to watch, as it disappeared.

All in all, it was a cheap lesson that got me to educate myself and start doing my own investing work.

I also had WCOM, but no one advised me, I did it all by myself.

[checkyourmath]

08/09/2018 08/07/2018 VCIT VANGUARD INTERMEDIATE TERM CORP BOND ETF
Sell – 365.9280 $83.89 $0.40 $30,697.30
08/09/2018 08/07/2018 VWOB VANGUARD EMERGING MKTS GOVT BOND INDEX ETF
Sell – 352.0000 $75.91 $0.35 $26,719.97
03/14/2017 03/09/2017 VCIT VANGUARD INTERMEDIATE TERM CORP BOND ETF
Sell – 200.0000 $85.08 $0.37 $17,014.63
10/19/2016 10/14/2016 BND VANGUARD TOTAL BOND MARKET ETF
Sell – 235.6490 $83.44 $0.43 $19,660.94

I lost $3,000 dollars selling bonds. It was a tough lesson I didn't realize that bonds can go into forbearance, the benefit of lowering interest rates, and knowing the Federal Reserve will buy them when they start to drop in price. I could have made around 15k if I would have just held on for the ride and waited for the Fed. It is my example of market timing. I don't know if the stock market can go into forbearance but there is always the Fed in case things go bad.

[columbia]

Holding VXX (VIX futures) for about 6 (?) months.

(I bought at $27 and sold at $34, but even dabbling in that sort of thing was dumb.)

[whoshighpitch]

Co-worker, who knows absolutely everything about everything, recently told me his investments didn't go up at all over the last DECADE. After talking to him a bit I realized his contributions were just going into a money market fund. He thought someone managed it and put his money into stocks or mutual funds, but nope, it just sat there for more than a decade in a money market fund as he missed out on the longest bull market in US history. I would feel bad if he wasn't such an arrogant know-it-all. I guess that wasn't a silly mistake that was a BRUTAL mistake.

Did you tell the arrogant coworker that he’s basically earning nothing on his MM fund right now?

Or is he still blissfully unaware of the effect of his investment choice?

I did tell him he needs to actually pick a fund or funds and buy shares but I left it there, and I'm guessing he never did it. I'm certainly not going out of my way to help him because like I said, he knows everything about everything! There has been several times when he's been a total jerk when he knew more about something than I did, so now he's gonna pay!

[Harry Livermore]

Holding VXX (VIX futures) for about 6 (?) months.

(I bought at $27 and sold at $34, but even dabbling in that sort of thing was dumb.)

Yes, I should have put that on my list as well. When I start thinking how smart I am, looking at the VIX and thinking, "This can't be right! I'm going to be contrarian!" and bet wrong, almost every time.
Luckily it's small money and not very often... I would probably get more entertainment value out of a weekend in Vegas though
Cheers

[anoop]

Sitting on cash since early 2008. And still sitting on cash and conjuring up convoluted reasons why I should invest around ethics and morals.

[atdharris]

Selling Apple in 2008 ("no one will buy an expensive phone during a deep recession" - but got back in in 2013); selling Amazon at $200 ("they'll never find a way to turn a profit" - got back in at $700). At least I learned my lesson when I bought Facebook at $22/share in 2013 and held on till today. Trading mistakes are largely why and how I found bogleheads. I ended up with big gains in those companies and still hold them, but what could have been had I held in the interim...

[FelixTheCat]

Not investing in Bogle's S&P 500 fund since it's inception.

[hagridshut]

Buying a small amount of individual stocks about 20 years ago, hoping that they would double in value within 2-3 years, which would fund the purchase of an expensive replacement notebook computer.

I ended up losing half the $ when it came time to cash out, and buying a much less expensive computer than I wanted as a consequence The amount lost was ultimately small in the grand scheme of things, but the experience was a valuable lesson in appropriate allocation for a short time horizon.

[Cheez-It Guy]

Buying anything other than VTSAX early on. I have too many funds and it will take years to disentangle.

[lazynovice]

Thinking I would never care enough to TLH in my taxable account and not turning specific ID on my first taxable account. I was able to change it for purchases going forward but not those I had made before I changed my mind. Not sure this one cost me anything. Maybe a few hundred dollars in taxes.

Trying to replicate total stock market in my employer account by choosing 75% S&P 500 and 25% extended market and reversing the two and not noticing until I rebalanced the next quarter. I decided I was not going to do the math to see how much this one cost me. It was either going to be immaterial or make me angry.

[DigitalJanitor]

Sold my 200 shares of AAPL in 1986, when I didn't even need the money.

[abuss368]

Bogleheads:

My worst mistake was trying to be a market-timer in the early 90s.

At that time, I regularly visited the Miami Public Library to read their monthly market-timing newsletters (about 15) and books that advocated market-timing which was very popular in those days. One of the books I wish I had never read was "The Donoghue Strategies" written by a financial advisor. It convinced me that I had found "nirvana" and I started market-timing our commission-free Vanguard investments. I was so enthusiastic that I decided to share my new investing method. Accordingly, I began writing a market-timing newsletter which I sent to friends each month.

This is the worst investing mistake I ever made and the one I regret the most.

Best wishes.
Taylor

Jack Bogle's Words of Wisdom: "After nearly 50 years in this business, I do not know of anybody who has done market timing successfully and consistently. I don't even know anybody who knows anybody who has done it successfully and consistently."

Thank you for sharing Taylor! Many years ago when we traded individual stocks, we subscribed to many newsletters from The Bull Market Report. It was a costly mistake. Sure, we had winners and we had losers.

We read Jack Bogle’s books and the rest is history.

[Buckrodgerz]

77 years old here - my "investing mistakes list" is long. But here are some the doozies:
1. Bought minority shares in a private entity that I did not understand.
2. Bought minority shares in a private entity that I did understand but did not have voting control.
3. Sold stock in a down market.
4. Invested (until age 65) without a written Investment Policy (IP).
5. Hired "Financial Advisors" that gave little advice but sold (brokered) "products." (do it on my own now - Vanguard).
6. Bought tax disadvantaged investments in a taxable account.
6. Bought mutual funds well before a dividend paying date instead of after the dividend was paid.
7. Paid too high of fees and loads for mutual funds. (My average now is 0.13% with Vanguard, no loads and no 12-b fees).

Live and learn.

[NewMoneyMustBeSmart]

Upon further review, this thread is actionable as a general discussion.

Makes sense. I learned in University Philosophy 101 that inaction is indeed action. And these learnings may drive me to inaction!