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What’s your biggest “what if” when it comes to finances?

Posted on 4/30/26 at 9:40 pm
Posted by DrrTiger
Gulf of America
Member since Nov 2023
2537 posts
Posted on 4/30/26 at 9:40 pm
I bought about $60,000 of Nvidia in a Roth IRA back in 2018. Admittedly, it wasn’t a “buy and hold” position for me at the time. I was just looking to make a little money after it dipped. I sold it a few months later.

Had I held it, it would be worth about $3 million in a tax free account today.
Posted by Rize
Spring Texas
Member since Sep 2011
19349 posts
Posted on 4/30/26 at 9:53 pm to
Financial advisor told me to sell some of my company stock because we had 6500 shares and options between the wife and I. No options were over $50 ish most high $20’s to $40 range. Sold 1000 to 1500 shares at $150 then wife got let go and we lost anything that wasn’t vested. Then it shot up to around $900 and split 4 ways

That and I should have sold game coin when I had 700k to 800k in that shite

Hopefully I have another 7 figure one coming up in 28 or 29 and need to play my cards right this time.
This post was edited on 4/30/26 at 9:55 pm
Posted by FAT SEXY
California
Member since Jun 2020
2097 posts
Posted on 4/30/26 at 10:05 pm to
I try to steer clear of the what ifs because that ish will drive you crazy
Posted by Tiger Prawn
Member since Dec 2016
25790 posts
Posted on 4/30/26 at 10:05 pm to
My buddy tried to get me to buy Bitcoin when it was like $20-30. I laughed at his fake money nonsense

He didn’t hold long enough to become a crypto millionaire like Wiki Tiger, but he invested a couple hundred bucks and ended up selling for enough profit to put a pretty hefty down payment on a house.
Posted by Rendevoustavern
Member since May 2018
1910 posts
Posted on 4/30/26 at 10:05 pm to
Parents neighbor went bankrupt in 08-09, 1,250 acres of prime hunting grounds of I-10 in Kendall Ct, Tx. Turned down our first right of refusal.

It sold in 2020 for 18.75m. The guy that bought it, a friend of mine, put about 1.5m into the property and made over $16m.


Posted by Everyday Is Saturday
Member since Dec 2025
1399 posts
Posted on 4/30/26 at 10:28 pm to
Never (almost, to be honest) do I ‘what if.’ Try to stick to objective, timeline for money and risk appetite. Once decision is taken, moving forward.

But I would be lying if I stopped there. I lived near Silicon Valley during dot com boom. Sold piece of real estate that made us a lot of money at the time (that was near early in career). Not too long ago, I looked it up. Multiple millions in value today, and not quite as high as your Nvidia regret.

So, you win!
This post was edited on 4/30/26 at 10:40 pm
Posted by JackDempsey
Lake Charles
Member since May 2023
855 posts
Posted on 5/1/26 at 6:09 am to
I have several. One that bothers me the most was not buying the Facebook ipo, which was around $38 a share. I thought about it and decided not to invest in it. I still don't use Facebook but I sure wish I had invested in their stock.
Posted by ForeverLSU5
Member since Mar 2019
2249 posts
Posted on 5/1/26 at 7:25 am to
Not selling Gamecoin at the peak lol
This post was edited on 5/1/26 at 7:29 am
Posted by MrLSU
Yellowstone, Val d'isere
Member since Jan 2004
29713 posts
Posted on 5/1/26 at 12:08 pm to
quote:


My buddy tried to get me to buy Bitcoin when it was like $20-30. I laughed at his fake money nonsense


I had the same thing happen to me with Bitcoin but have been rapidly expanding my holdings in MegPrime based on what I'm seeing so far. It is the only crypto holding next to ETH that I'm holding.
Posted by dstone12
Texan
Member since Jan 2007
40298 posts
Posted on 5/1/26 at 12:23 pm to
I bought a thousand LWLG at 1.21 and sold them at 2.16.

Had a chance to buy more at 4.20. THought it would head back down to 3.90.
Posted by Skee
Fayetteville
Member since Dec 2025
28 posts
Posted on 5/1/26 at 12:41 pm to
Not investing more into vintage Pokémon cards during the pandemic. I knew the vintage sets were heavily undervalued.
Posted by RedlandsTiger
Greenwell Springs, LA
Member since Jan 2008
3188 posts
Posted on 5/1/26 at 1:38 pm to
quote:

The guy that bought it, a friend of mine, put about 1.5m into the property and made over $16m.


You have to have money, to make money. (And be risk tolerant.)
This post was edited on 5/1/26 at 1:39 pm
Posted by Whatafrekinchessiebr
somewhere down river
Member since Nov 2013
1711 posts
Posted on 5/1/26 at 9:12 pm to
What if I bought gold @ 400oz instead of weed circa 2003.
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