personal investments

what’s the biggest return you’ve scored on a personal investment - return multiple / IRR?

highest return i had by better on black in roulette

ive though about that, going all in on black. if i lose i still have a paycheck to live off and 30+ years to rebuild. if i win, i’d do some crazy stuff.

I haven’t had any homeruns in my PA. My performance has been steady and consistent across the board. I’d have to say I did pretty well on my house even considering the current housing market. Then again, I don’t really look at my house as an investment.

I inherited 250 shares of Worldcomm when I was 18 (2001-2002). I watched it go from ~$60/share to ~$1/Share. I was in high school and didn’t understand capital markets very well, but once the news hit about the accounting scandal, I got out asap and got $150 or so for my 250 shares. As angry as this made me watching what was suppose to be my college tuition turn into nothing, it is what drove me to a financial service career.

in high school i made 200% on sun microsystems in about 4 months. i haven’t done much personal investing since then (24 years old now), but I’ve made about $10/share on oil in the past 2.5 months…

About 10 years ago, I dabbled in some day trading. Hee hee hee. Good thing I was too cheap to lose much in absolute terms, but in percentage losses I had some doozies that I can only look back at and laugh. I should note that this was before I got into finance. My favorite trade story had to do with The Globe, which was an Internet host site, sort of like Geocities. (Too bad The Globe people didn’t come up with Facebook, huh?) Anyway, I bought into The Globe at about $60 per share, and immediately it tanked down to about $35 to $40. It sat there for a while and I was depressed and I stopped checking it - classic ebullience cycle from Level III curriculum. A couple months pass and I check my account one day and I see that The Globe is up on breaking news to about $65 per share, or a $30 or so gain in one day. I sell it first and then I check out what the news is… are you ready for this? They had announced a stock split. I mean, holy moly. I haven’t been in finance / markets long, but - apart from the true tulipmania of centuries back - was there ever anything as crazy as Internet stocks in the late 90s?

I used bloomberg to plot a chart of the nasdaq’s historical PE ratio for fun at work today…it peaked at around 150x…Insane!!

i bought amzn when it was 65 and sold it when it reached 85. i bought ati at 12 and sold it at 18 when AMD bought it out. i bought VMW on opening days and sold it at 85, but bought back at 80 and sold some of it at 60. i bought V on opening day and still have it now. I think i’m just gambling my money away on scottrade… its better than going to casino where i lost 95% of the time.

i have a split adjusted basis in aapl of $14. but i also remember averaging into yhoo at $100 (the first leg of that position).

I read a little snippet in Forbes a couple of years ago about a would-be miniscule mining company in Australia - in twelve months I made just over 1100% return, though it has since dropped back to about 850% - I haven’t sold it yet but I do wish I had put more than $500 on it!!

I bought a couple thousand shares of a small biotech company called Urogen (now defunked) around $1 at the end of 1999 based on a hot tip from my boss. By March of 2000 it touched $20 and I managed to sell most of my position above $17 on its way back down to 0. So 1600% return in 4 months = 4800% annualized.

I’ve traded options from time to time with not a lot of capital, less than 1.5K, but I had some good success while I was doing it. My best trades all came from Mastercard. Maybe because they were always sandbagging their earnings or something they have had some tremendous gains after earnings reports. I bought several out of the money calls at different strikes up until $190. MA was trading @~155 I think and the next day MA traded all the way up to 195. Luckily I was in class most of the day and had told myself not to look at the market until it had closed (I have a bad habit of selling just too early). I got up early the next day and watched MA trade @200 in the premarket. You would have thought I was 9 and it was Xmas morning. On my highest % return I believe I made off with close to 1900% from the 190 calls. Unfortunately I only owned about 5 of those calls and then there is the fact that I made a dumbass trade on Amazon (hate the stock now) and nearly wiped out all of my profit but learned my lesson. All in all I tripled my little ugrad options account and with my profit I bought a new tv and a trip to Mexico. I’ve learned that 90% of people who try to trade options lose their money and really have no clue what they are doing, I got lucky. It is cool to see how much money you can truly make from options. Could have bought Google 510 calls before its earnings report for $5 and then sold them the next day for $3000 when Google was trading @540 after a $90 jump. I won’t even mention BearStearns although someone made a fortune with 55,000 put contracts. Probably bought for 300K and sold for ~ 150M

The challenge with options is that your chance of losing 100% of your investment is much higher than with stocks and bonds. That’s why options can give you some spectacular payoffs in compensation. However, taking small amounts of capital and buying out of the money options might not be so bad, since it’s hard to price the tail risk and you’re more likely to make money there. Options are highly risky if you think of your investment cost as “how much you paid for the premium”. If you think of the option in terms of the price of the notional amount controlled, it’s not so risky, but that presumes that when you buy an option, you simultaneously commit the remainder of notional amount to some risk free asset. Doing that lowers those spectacular returns quite a bit.

Autonomy Corp. Turned out to be as cheap as it looked. Still own it.

+3,000% return since 2005

I just bought some warrants on the TSX that have the following risk/return parameters: underlying has to appreciate by 22% per year just to break even (intrinsic value only) every 1% of additional return boosts the return on the warrant by 300% (intrinsic value only) This is one of those investments where it’s “heads I lose a little, tails I lose a little… but if the quarter happens to land on the edge then I make mugabillions”

Last year I pulled 135% on my portfolio as a whole. AAPL @ $87 pre-iphone launch was a home run. I have always wanted to get some little micro stock and have it *explode* but just don’t have the the balls to mess with that stuff…

Day 1 of Mastercard IPO($44), sold few months ago at $293.

I was up as much as 55% on my trading portfolio this year through mid-June when I made a stupid bet going long consumer discretionary, technology, and financials in anticipation of a bear market bounce. Gave back about half my gains.