re: What is your biggest financial regret/missed opportunity ?

This is painful to talk about.

I’ve never talked about it to anyone before but I’ll tell it here.

… deep breath

On the morning of November 2, 2021 I bought calls on AVIS car rental company after they had reported earnings. I bought the 2 weeks out $180 strike. The day before earnings the stock closed at $171.46. Pretty risky, more than my usual. There was slight “pop” after earnings but it kinda faded in the first 45 minutes the market was open. After I put the trade on, I told myself that this was a shortsighted, greedy trade and so I sold calls at the $185 strike — turning my original position into a vertical call spread- limiting my possible losses while capping any gains - which I considered unlikely.

Hours after I made the trade, the stock squeezed and ran all the way up to $545. All I could do was sit and watch as commas were getting added to what had been my original position.

That was hard on me… f*ed me up for awhile.

Yeah the Crains are good people especially ole Alb

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Guy in 2011 told me to buy bitcoin. I thought, “sounds dumb.”

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2017 here and still regret it.

I should have held more real estate but I was afraid if the short term destruction of renters.

Lots of individual stock sells. One stands out: Intuitive Surgical. Spring 2006.
I held over $100k with more on margin. There was a dip and a margin call.
I was just done with margin trading and earnings call plays and sold.
I sold at $13/sh (, for decent gains). So let’s estimate that was around 7700 shares.
At the current $480/sh it would be worth over $3.7M.

This isn’t, “I could have bought XYX in 2006.” It was a gut check that I failed when I could have retired early. Oh well.

I had a friend at LSU tell me about Bitcoin in 2009-2010 and purchased 10 coins for about $1 per coin. Forgot about them, threw laptop away 3-4 years later and did not save the hard drive info.

Even with prices taking lately, this simple mistake cost me $770,000

I almost bought a couple of Lakeview lots side-by-side right after Katrina for literal pennies on the dollar.

Bought a shotgun double in Algiers Point tho and that ended up being a good decision. Still own it, too. But the point is that I could've afforded to get all 3 properties at once.

Just plain old nickel and diming crap.

Once you’re in you late 30s and 40s, you’re going to realize the missed financial opportunity of being smarter with your money, regardless of how much you made in your first 15-20 years of adult working.

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Passed on buying a lot at Rosemary Beach when there was nothing there but sand

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Not me but a guy I know had a chance to buy 10 lots on Ono Island in the 80's for 90k total. He said he didn't have the money at the time so he bought his one lot and built a house.

Albert died a few years ago. He was only 58.