What's your worst trade ... ever?

RaceBannon said:

Jay Buhner

Take it to the baseball board.

Please don't make me access my powers. Benny, you're on probation. Maybe even double secret probation. I can't confirm or deny, or it wouldn't be secret.

RedRocket said:

RaceBannon said:

Jay Buhner

Buhner was a good prospect, no question about it. But my baseball people loved Ken Phelps' bat. They kept saying Ken Phelps, Ken Phelps.

RedRocket said:

When buying the dip earlier this year I decided to get cute and hedge with some puts on the Russell. Was only a few thousand dollars but it went down the drain in a matter of weeks so felt like I just lit it on fire. That's what I get for betting against America.

@doogie says don't fight the Fed. you fought the Fed.

dnc said:

Bought my first house as a 25 year old bachelor in March, 2006. Way more house than I needed.

Was upside down in that thing for a long, long ass tim.

So much for "you can't lose with real estate."

RaceBannon said:

creepycoug said:

dnc said:

Bought my first house as a 25 year old bachelor in March, 2006. Way more house than I needed.

Was upside down in that thing for a long, long ass tim.

So much for "you can't lose with real estate."

I didn't run out of money I ran out of time

Sounds like @dnc was able to make the payments to get above water

Nothing is a sure thing past death and taxes

I think its insane to buy a house today but the market disagrees so far

Other than maybe if you're in already and you trade up with free money (<3% 30-year money). That's what I've been contemplating.

RaceBannon said:

dnc said:

RaceBannon said:

creepycoug said:

dnc said:

Bought my first house as a 25 year old bachelor in March, 2006. Way more house than I needed.

Was upside down in that thing for a long, long ass tim.

So much for "you can't lose with real estate."

I didn't run out of money I ran out of time

Sounds like @dnc was able to make the payments to get above water

Nothing is a sure thing past death and taxes

I think its insane to buy a house today but the market disagrees so far

Yeah I'm in much better shape now.

Had I not refinanced 5 years ago I'd be halfway through this damn mortgage.

Next worst decision I ever made was not getting a 15 year mortgage. Never again.

With mortgage rates no reason not to go 15 years

When I bought my second house, I was a smidge over my head, and in 2000 the rates were in the high 7s and low 8s. Several years into it, they moved down into the 5s and the refi parties began. I waited and one day our CFO, who knew I was looking, called me and said the mortgage guy we both used would do a 4.5% at 15. A 15 was a pipe dream up to that point, so I did the payment calculation, said "yep" and called him. Best thing I ever did. Had that house paid off by my early 40s.

As rates went below 4.5, the remaining balance didn't justify the upfront costs of a refi, so I just rode it out.

CuntWaffle said:

I bought like 20 king size snickers bars for 25 cents a piece in High School and was hoping to sell them for $1 a piece to people. I left them in my car that day during baseball practice and it was 80 degrees out. They all just got decimated, I was fucking pissed at the time and still kind of am.

It involves profit and loss. I'll allow it.

HoustonHusky said:

The rational side of me agrees wholeheartedly with the idea of paying your house off, not buying in this market, conservative mortgage, etc.

The sad part of me thinks that rational logic gets screwed...you print money year over year and asset prices go up. Those people get screwed, and the folks that ride that monetary wave up are the ones that own/lever-up to own assets.

We've all been saying in this money printer overtime era we're in, assets will be king.

Blu82 said:

creepycoug said:

Blu82 said:

I was part of a startup that went public in 2004.
ASAP after the IPO, I sold the stock as fast as legally possible.
This move cost me more than I can imagine over the past 16 years.
However, I have complete peace of mind and retired at 45.
Since I'm lead a fairly conservative lifestyle I'm able to spend my time and money changing the lives of others.
Essentially, I traded for lifestyle.

Comment on this if you like. I'm always curious about such things.
All opinions presented respectfully are always appreciated.

Listen, you're not going to get second guessing from me. If selling after the 180 day lock up would have put me in retirement, I'd have done the same thing.

Glad to know you're doing something worthwhile with your time as well.

After a certain point money is nothing other than a way to keep score.
Just wasn't a game I'm interested in playing.

Me either. As a slow strategy guy who has indulged his children, I still work. I could stop now in my early 50s, but I'm not quite where I want to be for that yet, and not really ready to do it in other respects as well.