What was your costliest investment mistake?

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fetch5482
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What was your costliest investment mistake?

Post by fetch5482 »

Almost everyone would have made some investment mistakes in their life. Some would have gone with an expensive "expert" to manage his portfolio, some would have chosen a bad AA, etc.
What was your most expensive investment mistake?

For me: My biggest mistake was to sit on cash for almost 12 years of my working life. I did not know how to invest, and kept most money in online savings accounts earning a paltry interest rate. I started the bogleheads approach to investing just last year (at age 32). Better late than never, I guess :-)
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rob
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Re: What was your costliest investment mistake?

Post by rob »

Cashing out a retirement plan in late 20's and spending it on crap...... I shudder to think what it would be worth now (employer made 90% of the contributions so it was free money as well).
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Raybo
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Re: What was your costliest investment mistake?

Post by Raybo »

Letting a stock trader trade in my account. He margined me into a stock that lost enough that I got a margin call. It cost me $40K to get out of that position.
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Toons
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Re: What was your costliest investment mistake?

Post by Toons »

Drinking Budweiser for a couple decades instead of Investing in Anheuser-Busch :happy
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Flobes
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Re: What was your costliest investment mistake?

Post by Flobes »

Deja vu. 107 posts: What was your dumbest financial decision?
http://www.bogleheads.org/forum/viewtop ... 2&t=134130
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Re: What was your costliest investment mistake?

Post by HongKonger »

Paying monthly into a managed retirement fund for a decade only to discover that after 10 years it was worth less than if I had put the cash under my bed. I tried to cancel it and get what funds I could out. I was only allowed to take what would remain after the managers fees for the remaining 25 years of the policy. I got roughly 30% of my money back while the balance is slowly year by year being taken to zero. This was my sole serious retirement savings for that entire decade.

I could still cry just thinking about it.
jeff1949
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Re: What was your costliest investment mistake?

Post by jeff1949 »

Sticking with Enron as it went down. I do not invest in individual stocks anymore in case you are curious. :oops:
Onion
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Re: What was your costliest investment mistake?

Post by Onion »

I've had several investment mistakes involving selling too soon. I rarely sell too late. My last mistake? Making a few grand on Green Mountain Coffee when I could have sat it out for a year and made a bundle.
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Re: What was your costliest investment mistake?

Post by c078342 »

Being too heavily weighted toward stable value fund and not in equities for much too long in the early years of our 401k plans.
awval999
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Re: What was your costliest investment mistake?

Post by awval999 »

Selling DIS at $32.xx.

To be fair I learned a life lesson about the risks of individual stocks---that they are swingy and undiversified---and it really didn't cost me much (unless you count leaving lots of money on the table).

I learned not only do you have to buy at a good price, but you have to sell at a good price. And it doesn't matter if you are good at one unless you are good at the other.
Quickfoot
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Re: What was your costliest investment mistake?

Post by Quickfoot »

Not investing in my 401K in my twenties despite making very good money. The employer didn't offer a match and I decided I'd allow myself my twenties to establish myself. One divorce and four extremely costly custody battles later I lost everything I established and still had nothing in my 401k. On the plus side I didn't make investing mistakes as by the time I started investing I had discovered index funds and good investing practices and am still only in my early thirties.
Last edited by Quickfoot on Tue Jan 13, 2015 2:17 pm, edited 1 time in total.
Stonebr
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Re: What was your costliest investment mistake?

Post by Stonebr »

Getting locked into two real estate limited partnerships early in my investing life. Fortunately they were in an IRA so I could avoid complexities of tax reporting -- these were not leveraged RE investments so they were specifically structured for the IRA market by a big insurance company. These LPs went illiquid in about 1990 and didn't finally pay out until the late 90s. I think I broke even (before considering inflation). Losing two decades of compounding on some of my earliest investments was costly and painful. OUCH.
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Steadfast
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Re: What was your costliest investment mistake?

Post by Steadfast »

My biggest investing mistake was not investing more, earlier. I was in my mid-thirties before I fully understood the miracle of compounding returns. I could have reached the exponential section of the return curve a lot earlier than I will.

My costliest investing mistake was buying tax-inefficient asset classes (long-term treasuries and REITs) in a taxable account before I fully understood tax-efficient asset location, which at the time I viewed incorrectly as some advanced investing concept that I could safely ignore until later. I had to sell these assets at a loss, only to have to repurchase them in an IRA, to fix my mistake.

I consider myself lucky, despite these mistakes. I have avoided the horror stories and rip-offs others have posted.
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Admiral
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Re: What was your costliest investment mistake?

Post by Admiral »

A) Not ditching Morgan Stanley 20 years ago and moving to Vanguard (and Vanguard funds); and B) not discovering this forum a whole lot earlier. I also wish I had been more/better diversified in 2008. Things have come back but I can't help but think where I might be now had I made better investment choices in the 10 years leading up to the Recession.

You live and you learn. I did make some nice $ on CSCO, however. On the other hand I sold Google at $250. :oops: That's why I don't pick stocks anymore.
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fetch5482
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Re: What was your costliest investment mistake?

Post by fetch5482 »

Steadfast wrote:My biggest investing mistake was not investing more, earlier. I was in my mid-thirties before I fully understood the miracle of compounding returns. I could have reached the exponential section of the return curve a lot earlier than I will.

My costliest investing mistake was buying tax-inefficient asset classes (long-term treasuries and REITs) in a taxable account before I fully understood tax-efficient asset location, which at the time I viewed incorrectly as some advanced investing concept that I could safely ignore until later. I had to sell these assets at a loss, only to have to repurchase them in an IRA, to fix my mistake.

I consider myself lucky, despite these mistakes. I have avoided the horror stories and rip-offs others have posted.
Sounds like we are both in the same boat :-)
Same mistakes, same conclusion. After looking at the high-cost rides some of my friends were taken for by the so-called experts, I consider my mistake to be relatively less costly. Sure, I could have been a lot wealthier had I invested in 2004 when I started my first job out of college, but I could have also been sucked into these high-cost mistakes had I not known about Bogleheads then. All is well that ends well :-)
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Re: What was your costliest investment mistake?

Post by KlangFool »

Folks,

Trade / gamble on individual stock about 10+ years ago. Get caught in Telecom bubble. Wipe out 50% of my whole life savings at that time. I am still writing off the capital loss from that mistake. And, I do not have to worry about capital gain for a long long time.

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gardemanger
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Re: What was your costliest investment mistake?

Post by gardemanger »

Working for an employer that did not offer benefits, and not seeing to it that I had private disability insurance during that period, and then becoming disabled. This is the kind of mistake that can literally cost you everything.
greenfire
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Re: What was your costliest investment mistake?

Post by greenfire »

sigh. this wasn't investing, exactly, but I lost $400,000 on a universal life insurance policy. My dad had my brother and me buy this policy on my parents to help pay estate taxes. We paid $12,000 a year for 20+ years. When my dad died, I took over all of my mom's finances. My dad had 67 different accounts, plus several life insurance policies. My brother and I kept paying the annual bill for this policy. Every year they sent a statement which I didn't read the tiny print and just filed, being already overwhelmed with all of the other accounts that I was dealing with. At one point the policy had a cash value of over $250,000. Well, it turns out that as my mom got older (she is now 94) the premiums increased monthly. The paid up insurance covered the additional premiums. After a while I got a notice that the value of the policy was zero. I could continue to keep it if I paid some ungodly amount of money every month - and, if my mother lived to 95, I would get nothing any way. I just try to not think about this.
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Peter Foley
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Re: What was your costliest investment mistake?

Post by Peter Foley »

Investing in QQQ (NASDAC) in the year 2000 - thinking it was an "index fund".
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stemikger
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Re: What was your costliest investment mistake?

Post by stemikger »

Not so much a mistake but really just being unaware. I didn't start investing until around 30 and I was all over the place for several years. I didn't know the difference between a money market fund and an aggressive growth fund. At that time, we just so happened to have 10 funds in our 401K so I just put 10% in each of them. Hey it equaled 100%. I thought that was good enough for several years. LOL. Thinking back, I think I had a couple of bond funds, a couple of money market funds and probably the rest in all different types of equity funds. I still cringe thinking how clueless I was.

The second was investing in a very expensive whole life insurance policy which I kept for several years when I first got married. It was through my Father-in-Law who was an insurance agent at the time. Thanks for having out backs Dad! :x
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SquawkIdent
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Re: What was your costliest investment mistake?

Post by SquawkIdent »

Too many...

1. Ex wife
2. CMGI
3. SFE
4. Any PBHG Fund. I owned all of them at one time.
5. Trying to pick the hot fund of the year. You name it, I bought it.

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stoptothink
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Re: What was your costliest investment mistake?

Post by stoptothink »

At 24, losing most of my life savings (low six-figures) in real estate investing. At 29, my ex-wife, after having paid off her undergrad loans and putting her through dental school debt-free then losing half of the assets I accumulated while putting her through school.
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Artsdoctor
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Re: What was your costliest investment mistake?

Post by Artsdoctor »

It wasn't that "costly" because I was just starting out. But buying Fidelity Select funds with a load (was it 5%?) in the 1980s was one of the stupidest things I've done.

The other ridiculous thing that I did was buy individual tech stocks in the late 1990s because "everyone else was doing it" and "that time, it was different." It wasn't costly because I sold most before the crash, but it certainly ranks up there with one of the stupidest investment mistakes that I made. It was nothing more than gambling, in retrospect.
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Re: What was your costliest investment mistake?

Post by Gill »

Buying a house in haste in 2007 and quickly deciding we didn't like it, only to have it on the market until 2009, losing about $170,000 in the deal. I still kick myself for buying the place.
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subham
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Re: What was your costliest investment mistake?

Post by subham »

Not taking responsibility to educate myself early on and instead trusting "experts" to do it for me, only to see them wreck my financial car.
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Re: What was your costliest investment mistake?

Post by Twins Fan »

Getting married... and divorced... Getting married a second time... and divorced a second time!! :oops: :D

Investing wise though... not starting to even look into all this and start saving until I was 39! Luckily I found Bogleheads pretty much right off the bat and the BH style suited me.
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Re: What was your costliest investment mistake?

Post by wilpat »

In the .com crash in the early 60's I lost a little over $800,000. I owned a company that manufactured equipment for them and I paid all my bills on time, but toward the end they did not pay me for what I had shipped to them. I could cry and whine over it, but life is more important than that .
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Crimsontide
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Re: What was your costliest investment mistake?

Post by Crimsontide »

Walking in the door at A.G. Edwards in 1999, right before the "dot-com" crash. 5.75% front loads, diversifying among many different fund families, etc...
zbxb006
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Re: What was your costliest investment mistake?

Post by zbxb006 »

Buying WAMU on the decline thinking I couldn't possibly lose out - right before they went belly up. Then not buying Citi at $1 or WellsFargo at $8, worried that they might go under.

I no longer play around with individual stocks in my primary investment accounts and stick to a small 'play' account to satisfy my urge to splurge.
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Re: What was your costliest investment mistake?

Post by Rysto »

Several years ago my employer established a share purchase plan with a 50% match (the catch was the 1 year vesting period). I started the process of getting signed up but never filled the required paperwork, so I sat in limbo all that time. I easily didn't need the money (and already had my retirement contributions maxed), and I recently ran the numbers and I would have a good $70K by now if I had just gone with it.

(I finally got enrolled last year. So far I haven't made a cent, and I expect to leave the company now before any of the match vests. *sigh*)
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Re: What was your costliest investment mistake?

Post by mister_sparkle »

wilpat wrote:In the .com crash in the early 60's I lost a little over $800,000. I owned a company that manufactured equipment for them and I paid all my bills on time, but toward the end they did not pay me for what I had shipped to them. I could cry and whine over it, but life is more important than that .
Early '60s? .com crash? Tell me more. 8-)
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jfn111
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Re: What was your costliest investment mistake?

Post by jfn111 »

During the tech boom I bought RFMD in the single digits and watched it grow to the triple digits. Did I sell, heck no. :oops:
I rode it all the way back down. :annoyed
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Re: What was your costliest investment mistake?

Post by staythecourse »

Once I decided to start getting serious I read all the right books and started my asset allocation which is basically the same as it now changing a bit as my risk tolerance increased. Unfortunately, I also thought I would be REALLY smart by investing in a farmland fund abroad. I researched all of it and seemed legitimate. I put 15k into and was great for the first couple years. Then I get a letter after they missed their yearly distribution saying there was a bad season due to rain and had no good crops. Now they (the other investors) are trying to sell the land to recoup the losses to the investors. Who knows if that ever happens.

Luckily after I originally made the investment I realized how foolish I was to think I was smarter then anyone else. I just assumed I was never going to see that 15k and looks like I was right about that one! :(

Good luck.
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Re: What was your costliest investment mistake?

Post by garlandwhizzer »

Using margin to recoup losses as tech stocks collapsed in 2000 was my second biggest mistake. Being taken in on a real estate Ponzi scheme, losing 100%, qualifies as my biggest. Beware of smooth talking men in fine Italian suits letting you in on a great deal over an delicious meal at a nice restaurant. Mistakes serve an educational purpose however. I no longer look for home runs with every swing, just consistent singles and walks which do the job nicely in the long run. Pigs get fat. Hogs go to market.

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Re: What was your costliest investment mistake?

Post by grabiner »

Not learning about recharacterizations of Roth conversions in time.

I converted a large traditional IRA to a Roth IRA, splitting the conversion over two years to reduce taxes. Most of the conversion was done in May 2007, with a small part in January 2008. If I had known about the recharacterization rule in 2008, I would have recharacterized both conversions in October 2008, near the market bottom, and re-converted in January 2009; the tax savings would have been about $4000. Instead, I learned about recharacterization in 2009, and was only able to recharacterize the 2008 conversion in September 2009; the tax savings wound up being about $600.
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mister_sparkle
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Re: What was your costliest investment mistake?

Post by mister_sparkle »

I had a tiny sum from my first employers' 401(k) that I rolled over to First Chicago Bank (now Chase) and rolled it over into...a money market fund. I didn't know anything about investing, and that's what the First Chicago rep recommended. It was only a few thousand dollars, but I felt like a real idiot when I really got serious about retirement about 8 years later (1999) and realized that a money market was probably not the best choice of investment.

But for me, single worst "investment" decision was buying a house for $304K that I closed on on Halloween, 2007 ( :oops: ) with the intention of living with my then-girlfriend for a few years before we had kids and move out. She and I broke up a year later, my house plunged almost 50% in value, I ended up despising the area I lived in and some of my direct neighbors and I ended up renting it out for a few years before one of my tenants died, leaving the house in a very dirty, cluttered, damaged state, and I finally sold in 2014 when I realized the house was probably a ticking timebomb as far as maintenance/issues, after a 3-month sale process straight out of Kafka. Probably lost $140,000 on the whole deal.

But, spilled milk and all that. I bought another house, a fixer-upper, in a much better neighborhood in 2010, so I bought at a relative bottom there, and things have been smooth sailing since then, other than The Albatross.
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Re: What was your costliest investment mistake?

Post by nashirak »

My only mistake is starting (relatively) late in terms of taking in interest in how my 401k and other retirement planning is set up. I was 27 before I even had a 401k; up to that point and a little after I wasn't as financially responsible as I should have been. Thankfully I didn't end up in crazy debt or anything like that. I didn't find this website until 6 months ago (age 31) and really took an interest in total financial setup (investing, banking, budgeting, etc).
staythecourse
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Re: What was your costliest investment mistake?

Post by staythecourse »

garlandwhizzer wrote:I no longer look for home runs with every swing, just consistent singles and walks which do the job nicely in the long run. Pigs get fat. Hogs go to market.
I agree 100%.

Good luck.
"The stock market [fluctuation], therefore, is noise. A giant distraction from the business of investing.” | -Jack Bogle
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Ged
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Re: What was your costliest investment mistake?

Post by Ged »

Not following the trail to Vanguard sooner.

For most of my adult life I was underinvested, and carried too much cash. Luckily I was saving enough.
davegreen10
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Re: What was your costliest investment mistake?

Post by davegreen10 »

Delayed advancing my career while being a ski bum and a few other things along the way in between real jobs. My rationale was that I was taking my retirement a little bit at a time and I would just work a little longer. In reality, the expense of my human capital was ok but ignoring the power of compounding was ignorant. Working less then, requires much more than working the same amount later to make up compounding benefit that was squandered. I'm targeting 63 for retirement in 15 years, but always give thanks that I found this forum or that probably might not happen.
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wilpat
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Re: What was your costliest investment mistake?

Post by wilpat »

mister_sparkle wrote:
wilpat wrote:In the .com crash in the early 60's I lost a little over $800,000. I owned a company that manufactured equipment for them and I paid all my bills on time, but toward the end they did not pay me for what I had shipped to them. I could cry and whine over it, but life is more important than that .
Early '60s? .com crash? Tell me more. 8-)
Read this.

http://www.stockpickssystem.com/2000-st ... ket-crash/
Contrary to the belief of many, profit is not a four letter word!
bs010101
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Re: What was your costliest investment mistake?

Post by bs010101 »

LNUX. Fortunately I had just started working and didn't have very much money.
ramsfan
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Re: What was your costliest investment mistake?

Post by ramsfan »

Several...

Thinking publications like Money Magazine and Kiplinger's were there to help me....
This lead to the following mistakes:

Biggest mistake by far - In the late 1990's Believing that 100% equities, and specifically concentrating heavy in Tech was the only way to go. Got really crushed in that. Looking back, in additional to my myriad of individual tech stocks, almost all equity mutual funds were dominated by tech, and I worked for a tech company. No diversification. Had good run up, specatular crash down. ALL the press, water cooler talk, etc... was about tech stocks..... everything else was "dead", brick and mortar was a bad word. Manufacturing was going to be gone, etc...

Also, another good mistake Not understanding how uncorrelated assets can work to reduce risk and even improve returns in some cases. Also, in parallel, believing the Financial Porn industry that bonds were bad, and cash was even worse. The good news is once I learned this (from books recommended here), I was able to set an asset allocation, move into cash and bonds for first time, and then stick with that plan, rebalancing.

Feel absolutely phenomenal about where I am now, thanks in large part to the great group of people and expertise on this site.
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Re: What was your costliest investment mistake?

Post by maroon »

In 2007, I bought vacant land as an investment. Ouch. Fortunately, in 2011 I got a great deal on the foreclosed house next door. I'm possibly about even on the total investment.
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Re: What was your costliest investment mistake?

Post by member »

Wow wow, keep them coming please. I lost almost 30k and now I don't feel so bad anymore.
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wilpat
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Re: What was your costliest investment mistake?

Post by wilpat »

wilpat wrote:
mister_sparkle wrote:
wilpat wrote:In the .com crash in the early 60's I lost a little over $800,000. I owned a company that manufactured equipment for them and I paid all my bills on time, but toward the end they did not pay me for what I had shipped to them. I could cry and whine over it, but life is more important than that .
Early '60s? .com crash? Tell me more. 8-)
Read this.

http://www.stockpickssystem.com/2000-st ... ket-crash/
MY ERROR I meant early 2000's! I was only off by 40 some years! :happy
Contrary to the belief of many, profit is not a four letter word!
gator15
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Re: What was your costliest investment mistake?

Post by gator15 »

I may be making my costliest investment mistake right now. In 2009, I bought an investment property in a great area for a great price. It was a foreclosure and I've probably spent less than $700 in 5 years on the property. I'm lucky. I've had great tenants. The property has more than doubled in value and I could pocket six-figures today if I sold. My great tenants move out in May and I'm considering selling. The problem is the property cash flows well as the mortgage is cheap and the property is in a highly desirable area. Something tells me I'm going to kick myself in a few years if I don't sell this year while I can make a nice profit.
sambb
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Re: What was your costliest investment mistake?

Post by sambb »

costliest? Conservative asset allocation - but it allowed me to sleep at night. 100% equities would have been better. Easy to say at a market high.
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mister_sparkle
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Re: What was your costliest investment mistake?

Post by mister_sparkle »

wilpat wrote:
wilpat wrote:
mister_sparkle wrote:
wilpat wrote:In the .com crash in the early 60's I lost a little over $800,000. I owned a company that manufactured equipment for them and I paid all my bills on time, but toward the end they did not pay me for what I had shipped to them. I could cry and whine over it, but life is more important than that .
Early '60s? .com crash? Tell me more. 8-)
Read this.

http://www.stockpickssystem.com/2000-st ... ket-crash/
MY ERROR I meant early 2000's! I was only off by 40 some years! :happy
:mrgreen: I figured as much, I was just busting your chops.
N52570
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Re: What was your costliest investment mistake?

Post by N52570 »

member wrote:Wow wow, keep them coming please. I lost almost 30k and now I don't feel so bad anymore.
Well, I rode the tech bubble rocket up 7 figures and then rode it back back down 7 figures, barely crawling from the smoking hole alive.

A -72% decline in just 30 months! Now that's "staying the course", if I do say so myself! :D

Feel better? :D
"Nobody knows nothing"! Raymond
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