Your biggest "Missed Money" event that still kills you?

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investingdad
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Your biggest "Missed Money" event that still kills you?

Post by investingdad »

Is there one opportunity that you had to make a tidy sum of money that you somehow managed to mess up and it still kills you years later?

I realize that investing in individual stocks is not consistent with the Boglehead philosophy, but I still maintain a small amount of money in a trading account that I use as play money.

So what's the one trade I made that I still bang my head over? This one:

- bought 760 shares of Western Refining in 2010 for $5 a share
- no dividend payout at that time
- sold all shares less than a year later for $7 a share

Not bad right?

Look it up today...trading for over $40 a share with over $1 per share yearly dividend.

Awesome. :annoyed
rjm_cali
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Re: Your biggest "Missed Money" event that still kills you?

Post by rjm_cali »

Missed money event that still bugs me ?

Investing in company pension funds for 20 years and never looking at what they were doing with my money (and my future)....
westcoast
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Re: Your biggest "Missed Money" event that still kills you?

Post by westcoast »

Not listening to my wife, she wanted to buy Netflix several years ago at $20 a share and Starbucks don't remember the price of it though. Now we don't buy individual stocks.
kaudrey
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Re: Your biggest "Missed Money" event that still kills you?

Post by kaudrey »

Not investing in Under Armour many years ago when our best friends suggested it (they have made a TON).
TareNeko
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Re: Your biggest "Missed Money" event that still kills you?

Post by TareNeko »

Becoming a boglehead too late...
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fungus_amungus
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Re: Your biggest "Missed Money" event that still kills you?

Post by fungus_amungus »

Bought 1000 shares of SIGA at a buck and change and didn't sell when it was at 15 something a share.
barnaclebob
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Re: Your biggest "Missed Money" event that still kills you?

Post by barnaclebob »

I really considered buying trip adviser when it had its split/IPO from expedia at $35/share. I had used the website before and will pretty much only use it when planning vacations. I rationalized that the market had accurately priced trip adviser into expedia...

But I would only have put 5k in so while i could have made a nice chunk of many it would have been far from life changing.

Briefly considered a few bitcoins after the first plunge when they were around $100.
Mike Scott
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Re: Your biggest "Missed Money" event that still kills you?

Post by Mike Scott »

We started saving early but I wish we had saved more then and that I had known more of what I know now. There were a couple of items bought with borrowed money 20 years ago that I would like to take back.
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Re: Your biggest "Missed Money" event that still kills you?

Post by mhc »

investingdad wrote:Is there one opportunity that you had to make a tidy sum of money that you somehow managed to mess up and it still kills you years later?
I have definitely made some bad decisions, but no regrets. I think I have too many other things going on in life to worry about past mistakes. I just chalk it up to the cost of learning.
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22twain
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Re: Your biggest "Missed Money" event that still kills you?

Post by 22twain »

I received an inheritance in late 2008, right when the market was starting to plunge. I put it all in CDs for safety.

My mistake was waiting two years to put it in the market, instead of doing it when the first round of CDs matured in spring/summer 2009. :annoyed
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StealthWealth
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Re: Your biggest "Missed Money" event that still kills you?

Post by StealthWealth »

I was doing my PhD in a computational intensive area and we had a ton of very powerful servers. There were times when they were not fully utilized and I considered leveraging the idle servers for bitcoin mining. This was in 2010 and there would have been absolutely zero cost to doing so (electricity paid for by the University!). I have no idea what it could have generated but I imagine it would have been a tidy sum. It is probably good that I didn't do it because I could envision a scenario where there might have been some repercussions for leveraging publicly funded infrastructure to generate wealth for an individual. It definitely doesn't kill me, but I did find myself wondering the other day what it would be worth.
bloom2708
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Re: Your biggest "Missed Money" event that still kills you?

Post by bloom2708 »

Not saving more in our 401k in the "early years". We did the "6% to receive a 3% match"for the first 5-6 years after college. We could have/should have saved more when our expense were low and we had no kids.

I couple years back I bought 6% of a commercial real estate building. I could have bought in for a much higher percentage. The lease is amazing and the beer business in the building is growing like gang busters. Should have put more in. Hindsight.
FinancialDave
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Re: Your biggest "Missed Money" event that still kills you?

Post by FinancialDave »

Erhan wrote:Becoming a boglehead too late...
The above is certainly true, but not buying into Microsoft at a now adjusted price of 7 CENTS, is one that still haunts me - only because I wanted to get into the IPO but could not and when it came out, it jumped up and didn't look back, so I just took it off my radar.

:oops:
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VictoriaF
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Re: Your biggest "Missed Money" event that still kills you?

Post by VictoriaF »

Non, Je Ne Regrette Rien,

Victoria
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DonCamillo
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Re: Your biggest "Missed Money" event that still kills you?

Post by DonCamillo »

VictoriaF wrote:Non, Je Ne Regrette Rien,

Victoria
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Grt2bOutdoors
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Re: Your biggest "Missed Money" event that still kills you?

Post by Grt2bOutdoors »

The Williams Companies traded at 88 cents a share in 2004 after having been accused of rigging the California power markets (electricity) - the company had then and still has one of the largest natural gas pipelines in the country along with numerous midstream processing plans and terminals nationwide. Today, the stock is trading at $47 with a $2 dividend projected to increase in excess of 6% per year. :oops:

Apple Computer traded at $14 pre-split in late 2004 - today it trades at the equivalent price of $1,400. :oops:

Unlucky once, is bad enough - twice? :oops: :oops: :oops:
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bradshaw1965
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Re: Your biggest "Missed Money" event that still kills you?

Post by bradshaw1965 »

Not really a deep regret, but I sold off a decent bit of Apple stock before the big climb because I wanted to get out of individual stocks. Still think it was the right move, because it might have stoked the fires of the perception of my ability to pick stocks.
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Re: Your biggest "Missed Money" event that still kills you?

Post by bnes »

I bought NetFlix shortly after IPO. I sold the shares between bubbles at barely over $100.
Last edited by bnes on Mon Aug 18, 2014 12:32 pm, edited 1 time in total.
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prudent
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Re: Your biggest "Missed Money" event that still kills you?

Post by prudent »

I quit looking back at missed opportunities because my brain kept messing with me.

- Look, prudent, THIS situation is JUST like that other one!
- And you messed it up that time
- So don't do what you did before

I have to look at each decision with a fresh eye or I pollute my thinking by comparing to past situations.
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Re: Your biggest "Missed Money" event that still kills you?

Post by bnes »

I bought a house that was a fixer prior to sale.

The selling Realtor had handled renovations, hiring all the contractors. Two contractors told him of rot and termites. The Realtor told the floor contractor to put in new baseboards to cover up the rot. The Realtor told another contractor to work without permits to speed the job. I have both assertions in writing.

My mistake was not contacting an attorney. Instead I worked through the Realty Association, filing an ethics complaint. They said that the Realtor was not an expert in home renovation and thus not competent to understand the implications of the above. Thus it was ethical as far as they were concerned. And that by taking the case to them, I could not take it anywhere else.
leonard
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Re: Your biggest "Missed Money" event that still kills you?

Post by leonard »

Naw. Realized a long time ago that I can't predict the future.
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1210sda
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Re: Your biggest "Missed Money" event that still kills you?

Post by 1210sda »

"Your biggest 'Missed Money' event that still kills you?"

None !!

Various missed money events in my youth....but NONE that still kill me. :wink:

1210
Gecko10x
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Re: Your biggest "Missed Money" event that still kills you?

Post by Gecko10x »

I owned and sold 93 shares of Apple @ $15/share ... back around 2003?... which was before a 2:1 and a 7:1 split. :oops:
jeff1949
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Re: Your biggest "Missed Money" event that still kills you?

Post by jeff1949 »

Not being able to sell my stock in Enron when I wanted to. I was having trouble changing brokers and needed a signature guarantee to do it so that I could save a bunch on selling fees. Ended up putting it off and lost a potential $120k before they went bankrupt. Ugh. Thanks for reminding me. :(

I don't have any individual stocks now........just VG Index Funds.

:moneybag
Tom_T
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Re: Your biggest "Missed Money" event that still kills you?

Post by Tom_T »

Gecko10x wrote:I owned and sold 93 shares of Apple @ $15/share ... back around 2003?... which was before a 2:1 and a 7:1 split. :oops:
I feel your pain. In 1983, when I was in graduate school, we had to write reports on Apple. The stock price was around $60; split-adjusted, around $8. I had thought about buying some shares. A couple of years later, it had dropped to a split-adjusted price of $2. Of course, everyone knew that Apple was falling apart and had no future. :)

Then there were the early years of Microsoft and Dell and Yahoo, but I don't want to think about it.

P.S. The Internet tells me that a $10,000 investment in Apple in 2004 is now worth $450,000. And that's just ten years ago.

H.G. Wells, could you please deliver a time machine to me?
poker27
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Re: Your biggest "Missed Money" event that still kills you?

Post by poker27 »

I will list a non BH one and a BH one.

During the 2009 panic, a coworker invested in Sirius while there were talks of BK. he invested 2k when the stock was around .10. I decided to gamble a few bucks and threw a few hundred at the stock. Well I wish I have gameled more, a lot more

Same during the financial crisis, my income is closely tied to the economy (I'm in sales), and changed roles in 2008. I dropped my contribution % to something around 3-5%, I believe. I did buy a few blue chip stocks which gave me a nice return, but wish I would have taken advantage of tax free. This was obviously pre BH.
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Re: Your biggest "Missed Money" event that still kills you?

Post by Jack FFR1846 »

In 1975, I was offered cars to buy. Each was $2500. 67 big block 4 speed corvette, 63 1/2 ford lightweight and a superbird. I also sold my 50k mile 90 BMW M3 in 1997 for $15k, nust before they went up in value.
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Bacchus01
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Re: Your biggest "Missed Money" event that still kills you?

Post by Bacchus01 »

Not selling my stock options when the stock was at $72 in Dec 2008. By March of 2009 it was $3.50. It has since recovered to $40, but I left that company in 2010. That cost me mid 6-figures.

Conversely, in early 2009 I had a brief idea to move all my 401K into company stock at $3.50. Had I done that, the 401K balance today would be nearly 8X what it is today.

Buying $180,000 of company stock at a discount at the IPO for $18/share. It opened at around $20/share and I thought I did well. I decided to hold out for a year to avoid short term gains. It dropped to $12.50 at one point and I felt like a fool at $18. I eventually sold it at about month 13 for $21.50/share. Still did quite well, but would have actually done just as well with less angst had I just put it in S&P 500 mutual fund. I also would not have cashed out and paid any LTCG taxes either.

Had I done these 3 things above, I would like have a portfolio of $3.6M. Instead it is just $1.5M.

Do I lost sleep over any of these? Nope. Can't change it. And I'm living better than 99% of the world's population.
IlliniDave
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Re: Your biggest "Missed Money" event that still kills you?

Post by IlliniDave »

No one thing, but I do wish I'd been more knowledgeable and started investing with my first job in HS, through college, and more aggressively in my early professional years. Time is the key to it all.
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Ged
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Re: Your biggest "Missed Money" event that still kills you?

Post by Ged »

Not buying Intel stock in 1973. I was a hobbyist at the time messing with the first home computers.
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InvestorNewb
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Re: Your biggest "Missed Money" event that still kills you?

Post by InvestorNewb »

Not starting in 2009.
My Portfolio: VTI [US], VXUS [Int'l], VNQ [REIT], VCN [Canada] (largest to smallest)
levendis
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Re: Your biggest "Missed Money" event that still kills you?

Post by levendis »

I almost bought a $100 or so of bitcoins back when they were going for about a dollar each...
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kenyan
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Re: Your biggest "Missed Money" event that still kills you?

Post by kenyan »

Nothing, really. I'm not going to pretend that I was contemplating sinking my life savings into Apple/Netflix/bitcoins/whatever and didn't, so I don't consider those to somehow be missed opportunities. I've had people recommend various stocks that did nothing, and I'm sure that most of those who are bemoaning the recommendations they didn't follow up on also received plenty of other recommendations that didn't turn out so rosy; those just don't stick in the memory quite as vividly.

Sure, there are a couple of shoulda coulda decisions in my past, but those are cheap lessons at this point, and I haven't made any terrible mistakes. Hopefully I can continue to say the same for decades to come.
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Re: Your biggest "Missed Money" event that still kills you?

Post by Ron »

In the early 70's, there was a plot of land (<2.5 acres) that had a vacated (falling down) farmhouse on it that was to be sold for around $5k (today's inflated rate would be just under $30k). While I didn't see any value in the home, I did see possible future value in the land due to its location.

I had just received my military discharge (draft), working in a low paying job (today's inflated income of around $37k/year) and had a wife/child to support. My wife could not work at the time due to our disabled son's needs, so we were really just "surviving" at the time. Regardless of my foresight, there was no way that I/we could ever afford to buy the land - regardless of the price.

It seemed my hunch was correct. Within ten years, the large plot of land across the boulevard (then, a farmer's field) was sold to what turned out to be the region's largest hospital, and the area's biggest employer.

The plot of land I was interested in was sold and a commercial building (which now contains doctor's offices) was developed to support the services of the hospital.

According to current tax assessment records, the land (not including the building), has a current taxable value of just over $900k.

While the situation didn't "kill me" (I'm still kicking :happy ), every once in awhile I think of what could have been. In reality, even if I could have afforded the property, I'm sure I would have sold it rather than held it to today, at today's inflated price. Regardless of the gain, it still is a lost opportunity.

Oh well...

- Ron
fsrph
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Re: Your biggest "Missed Money" event that still kills you?

Post by fsrph »

Not taking money off the table during the Internet bubble. Internet stocks were going up $50+ some days. Let it ride, why not? Lesson learned.

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Re: Your biggest "Missed Money" event that still kills you?

Post by 111 »

I once quit a job to go back to school and then 3 months later they downsized and offered people like 20K + money to go back to school to people willing to quit. Of course, I had no way of knowing that was going to happen so it doesn't really kill me.
linenfort
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Re: Your biggest "Missed Money" event that still kills you?

Post by linenfort »

A pre-nup. ;-)

Also, I wish I had bought more Tesla. It doesn't "kill" me, but it's definitely in woulda/coulda/shoulda territory.
Crow Hunter
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Re: Your biggest "Missed Money" event that still kills you?

Post by Crow Hunter »

#1 Not buying gold and silver coins back around 2003-04 time frame.

I have always wanted some (from my D&D playing days) but I decided not to buy them because the price had gone up a little and I would just wait until the price went down some.... :oops:

#2 Listening to Dave Ramsey in 2007-2008 and only putting 15% of our income into retirement and using the rest to pay down debt.

Prior to that point I had been maxing out my and my wife's 401k. So I paid more in taxes AND didn't buy anywhere near as much "on sale" stock funds. I didn't have much choice in 2007 due to moving to a new job but I could have maxed out in 2008 for both mine and my wife's accounts. :oops:

#3 Recently inheriting 1,323 shares of AT&T stock and selling them as soon as I moved them to Vanguard only to see the price rise nearly $1/share. That cured me of wanting to buy/sell individual stocks.

#4 Having someone offer to buy a plot of timberland in Feb of last year (that I didn't even have for sale) and holding out for $10,000 more instead of just taking the cash and putting it into a taxable account.

I have a bunch more. 8-)
Buckeye
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Re: Your biggest "Missed Money" event that still kills you?

Post by Buckeye »

About 7 years ago my wife said would we should by stock in this new eatery that had opened up nearby.

She loved the food!

I did my investigation and analysis and determined that we had already missed the easy money and that Chipotle stock wasn't going much higher anytime soon. :annoyed
Gill
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Re: Your biggest "Missed Money" event that still kills you?

Post by Gill »

Sold my house in Southwest Florida for $350,000. Not a bad profit, having paid $142,000 a number of years earlier. However, the purchaser sold it six years later for nearly one million.

Had the same experience with the next house. Bought it in 1995 for $255,000 and sold it for $308,000 three years later. Again, thought I had made a nice profit until I learned the buyer later sold it in 2005 at the peak of the Florida book for $800,000.

Can't dwell on these things... Guess I shouldn't have changed houses quite so often.
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technovelist
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Re: Your biggest "Missed Money" event that still kills you?

Post by technovelist »

Buying silver on the day of the top in 1980... on margin.
Well, actually, I didn't miss that opportunity: I "took advantage" of it. :oops:
But at least it cured me of using margin!
In theory, theory and practice are identical. In practice, they often differ.
gvsucavie03
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Re: Your biggest "Missed Money" event that still kills you?

Post by gvsucavie03 »

Hindsight is 20/20, but FWIW...

Spending too much in college and having to still be paying off loans 9 years later. We could be so much further along than we are now if we didn't start married life with close to $60,000 in debt on a starting teacher's salary.
kermit
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Re: Your biggest "Missed Money" event that still kills you?

Post by kermit »

I was offered to take a sign on bonus in cash or RSUs at a pre IPO company that eventually IPO'd. At the time let's say the company was worth x (internal valuations). At time of IPO it was valued at 17x. Can't complain too much as things have worked out very well but if I took the RSUs we'd be set for life.
island
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Re: Your biggest "Missed Money" event that still kills you?

Post by island »

Years ago DH bought a big chunk of Qualcomm stock, but we chickened out and sold it quickly. Then it took off like a rocket and would have been worth a ton if we kept it. Oh well c'est la vie, not something that kills us to think about.
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Re: Your biggest "Missed Money" event that still kills you?

Post by Alex Frakt »

I should have put it all on Buster Douglas at 35-1. I knew Tyson was ripe for a fall.

Seriously, what's the point of this?
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Toons
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Re: Your biggest "Missed Money" event that still kills you?

Post by Toons »

Can't really think of any missed money events. :happy
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SpaceCowboy
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Re: Your biggest "Missed Money" event that still kills you?

Post by SpaceCowboy »

Not joining the pre-IPO tech company that later IPO'd and then was bought for $40bn. Stayed at Megacorp and with my then girlfriend who has been my DW for 20+ years, so it worked out on the life side of things.
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Crimsontide
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Re: Your biggest "Missed Money" event that still kills you?

Post by Crimsontide »

There hasn't been anything yet that I haven't been able to get over. There is the whole sordid AG Edwards affair, but I just chalk that up to learning a life lesson...
chameleon
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Re: Your biggest "Missed Money" event that still kills you?

Post by chameleon »

Loading up on apple in 2004 wouldn't have made a lot of sense then unless you were a tech nostradamus. The only good product they had was the MAC book and I think the ipod was still in infancy stages. The iphone was still a good 3 years away. There's no way anyone could have predicted all this popularity as a certainty so you really can't view this as a "missed" opportunity.
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Re: Your biggest "Missed Money" event that still kills you?

Post by harrychan »

Two years ago I came across bitcoin and it caught my interest. I started researching on how to build a rig to mine bitcoin bit thought it was too much power for the house and gave up. I started looking into buying bitcoins but never followed through. Doesn't "kill me" per se but I have thought "what if" a few times.
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