Hey All - No need to get too personal about the specifics, but generally what is the biggest financial regret you have faced in your life?
For me, it was selling Microstrategy & Nvdia before the 200% bull run. I still made a profit, but nowhere near what I could have. My second biggest financial regret was not going all in at the bottom in 2022 for Bitcoin because I lost my job.
The way I make peace with this is the lesson to always have deep conviction towards your investments and not be too quick to take profits at every turn. Hopefully, I'm not learning the wrong lesson, but I missed out on some life-changing money on the NVDIA/Microstrategy stock I had.
People have covered a lot of ground with equities and their BTC journeys. To add something a little different, I would say the following:
1- Not prioritizing location - I spent a lot of time in different cities where your financial/economic development lag and you can only take remote jobs to make up the difference. However, you miss out on all of the convos that get people hired/help people fund their companies.
2- While this is a financial failing, I feel somewhat of a moral vindication that I haven't raised institutional venture capital, however that's easily one of the ways you can quickly build personal wealth if you play it right.
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Not prioritizing location
This is great. The most important financial decisions might not be directly financial.
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Yeah, who you choose to surround yourself with really matters - and where you are
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You are the average of the 5 people you spend most time with
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Right, the location piece is key. For example, where my day job is - you can't rise above a certain level without being in office. In addition, cost of living can make or break one over years upon years of paying high rent or mortgage.
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I have a few.
  1. post financial crisis I had an opportunity to buy a new build home that a developer in financial trouble was trying to unload. It was 550k and needed probably another 50k to finish what he left undone. It would have been a stretch at the time but I could have afforded it. That home is probably worth 2M now.
  2. I lost 50k trying to import goods from India at the advice of one of my business partners. We would have been way better off investing the time and money into our own business rather that this side project
  3. I bought Bitcoin at $1k but I only bought 0.1BTC at the time and didn’t buy again until the parabolic move up in 2017. If I had a bit more conviction l could have a few more coins now.
  4. I sold my business 2 years too late. It got devastated by Covid lockdowns. If I had sold it a couple years earlier, which I was considering, I would have gotten a couple hundred thousand more for my equity than I did.
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Timing is everything
I know it sounds like random luck but the success of a business or financial endeavor is determined by forces outside of your control
Your examples made me think of my own history and my friends and family
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For sure. There is a lot of luck and randomness in business. You can push luck in your favour by being active and good at what you do but sometimes it is right place right time.
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I didn’t buy enough bitcoin and MSTR in 2020. My allocation was too conservative
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I'm intrigued about what goods, if you can please specify, did you import from India?
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24 sats \ 1 reply \ @grayruby 9 Jun
Kitchen products.
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Whirlpool
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Yeah, sometimes a stretch at the time, in a few years will be a breeze. As for your point #3, I think conviction takes time to build - and that is how I was.
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197 sats \ 3 replies \ @antic 8 Jun
Selling bitcoin at $400. Day trading Bitcoin. Sending money to ASIC scams (butterfly labs, etc) pre-production that never landed. Not taking out as much debt as possible when rates were zero.
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"Not taking out as much debt as possible when rates were zero" - a very good point. I'm allergic to debt but yeah I should have done that.
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13 sats \ 0 replies \ @antic 8 Jun
Likewise. I’m just now finding that it makes sense to take reasonable amounts of calculated, low-APR debt in order to invest more in my own higher APY fund.
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Yea, I think listening to Dave Ramsey's advice for years kept me much more poor than I otherwise would be. For example 0-1% interest rates I should have been loading up - but listening to Dave at the time he made it sound like a 7 deadly sin. He is right on a few things financial related, but the vast majority he is completely off on.
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211 sats \ 1 reply \ @siggy47 8 Jun
Ignoring 2012 advice from fellow libertarians to buy some bitcoin.
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I was playing video games back then. Big regret!
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Noticed BTC at 3000 and was about to pull the trigger, but I chickened out .... I guess that fully qualifies as the worst decision of my life
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I am sure I have many regrets but this one is killing me at the moment.
Trying to get sats passively and help my friend earn “passive income” I convince him to go 50% on buying two hosted miners with compass mining. It went great.
My friend wanted to expand immediately going from 2 miners up to 20. To make this happen I took out a 150k unsecured business loan. The apr is 17% we agreed to go 50% on everything.
After getting the loan compass mining ran into issues and miners were delayed almost 12 to 15 months on full deployment of the 18 miners.
My friend got Covid and almost died. Thus he couldn’t hold up his end of the bargain making loan payments and paying the mining bill. All the burden fell on me and and I panicked.
Trying to supplement his monthly contributions with the BTC we earned by mining and buying I got suckered into a yield scam thanks to telegram. To date about 90k is trapped with them probably never to be recovered.
Then the halving hit and the revenues are slashed. Actively unloading miners to lower the power cost. So far unloaded 9.
All this and didn’t get to save a single sat by mining.
Painful stuff but I’m still optimistic we can turn this around!! Worst case scenario I’ll have to liquidate some assets I really don’t want to in order to pay off the terrible business loan. And my friend’s health is getting much better! He may even start contributing again.
On the bright side I used the mining business to offset my tax burden due to business loan interest being a business tax expense write off.
Learned a lot about trying to run this business from tracking income, doing monthly reports, and understanding capital management (which I did terrible on) All skills I learned during this rough time may prove useful in the future!
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Ouch, yeah I know a few people that got caught up in that compass situation.
In the end, you seem optimistic, and that is much better to still be kicking yourself. As long as you take these strong lessons and life skills going forward - you will be well-positioned.
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250 sats \ 0 replies \ @gmd 9 Jun
ouch! onward and upward...
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I didn't stick with Bitcoin, back in 2015, when I first started getting interested.
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Yea, I definitely didn't get in that early. My excuse then was I couldn't rub two sats together. Fortunately, you are off 0 now.
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I'm not beating myself up over. Live and learn
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174 sats \ 1 reply \ @pk 8 Jun
Not buying enough Apple stock in 2001
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I also severely underestimated Apple's upside.
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210 sats \ 1 reply \ @freetx 8 Jun
I've been lucky / blessed. However around 2004 I became convinced the stock market was overheated and a financial reckoning was coming so I moved heavily into gold / silver / commodities (I was a big listener to Jim Rogers at the time). I didn't appreciate how long the fiat system could continue to patch itself up, nor that structurally the stock market would just "melt upwards".
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This one hits close to me, but primarily because in my corner often was Peter Schiff and other gold bugs. From 2012 to 2019 he would always claim the sky was falling and the market was going to crash, and it never did. In that time range gold/silver went up, but at a small fraction of what the stock market went up at. The way I look at this lesson, is to be careful who you listen to cause things can get fixed over for a very long time. Furthermore, the government can always kick the can down the road by QE.
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Buying unnecessary things.
Getting obsessed with a new hobby every 3 years, spending money on the enthusiast-category items of said hobby and losing interest in this hobby a year later.
Rinse and repeat.
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Innocent hobbies for me historically were airsoft, paintball, and slot cars. None of these hobbies were cheap and I don't even touch them anymore.
Another destructive hobby was going to the casino, or going to the sportsbook with friends and drinking/betting on sports in the afternoon and this one has been the most expensive - and a huge waste of time.
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You can always come back to those hobbies.
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I spent all my bitcoin buying drugs on silk road in 2013.
I should have saved more but I didn’t understand the concept of wallets and 12 words at the time.
Coinbase suspended my account in 2015 for being a high volume trader. If they didn’t kick me off my net worth would be at least 10x more today
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134 sats \ 1 reply \ @cristaiji 8 Jun
I've got a few.
I had an opportunity to buy cheap property in 2001 in a growing university town. The Victorian terraced housing did something like a 5x over the next 15 years or so.
Then i lacked the courage of my convictions in 2013 when i first heard about Bitcoin from the Keiser Report on RT. I decided it was too complicated and too tricky running Bitcoin Core so I didn't stick with it. 🤦‍♂️
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Pulling the trigger is easier said than done. I definitely need to do more of this in my life, and stop playing things so safe.
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Compared to everything else this is quite irrelevant in the grand scheme of things but I did buy so much unnecessary stuff. Useless stuff in my life, we all have too much of it. Marie Kondo was right about this one.
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60 sats \ 0 replies \ @Lux 8 Jun
paying taxes
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23 sats \ 0 replies \ @quark 8 Jun
I guess like everyone here would say: not buying enough Bitcoin.
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10 sats \ 0 replies \ @TomK 8 Jun
Didn't really listen when a very good friend of mine was shilling btc to me 13 years ago (actually I made fun of him). As of my job I still had enough confidence in the MSM to know it better: mafia-coin, it's going to zero, the gov won't allow it etc etc
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56 sats \ 1 reply \ @ek 8 Jun
I lost €50 at the age of 16 and I thought I’m never going to financially recover from this
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hahaha, I bought a bag of Cheetos with a gold Sacagawea coin when I was 6 years old lol.
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34 sats \ 1 reply \ @beorange 9 Jun
Reading about bitcoin and playing with a wallet early on, but not paying too much attention to it for many years. By not thinking too deeply about what was in front of my eyes, I missed a great opportunity.
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yea, I was the perfect age to get into it from a tech-understanding standpoint. I was young and dumb personally back in 2012/2013 focusing on the wrong priorities.
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I actually have none. Not to say that all my money decisions have worked out, but I have always made decisions based on the best available information I could find at that point in time. So, knowing me, I would have made those extraneous decisions again if I were to turn back time.
Well, I’m sure I won’t regret shitposting here on SN. So that’s a win.
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Hell yea, live life with no regrets!!!
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  • Selling BTC on 2017
  • Selling TSLA on 2019
  • Started late saving and investing
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My Tesla one was listening to a financial podcast where they were more fundamentalist with how they traded close to lower P/E ratios. They said it was way overvalued in 2016/2017/2018. What a mistake. lol
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I sold NVDA early
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Not buying or researching Bitcoin when I first heard about it in 2013.
College degrees. I could have succeeded and saved a whole lot more time and money hustling without.
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Yea, My college degree hasn't served me at all. The only thing I did find value out of it, was the lifelong connections of the people I met.
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Ignoring Bitcoin when buddies were mining it in 2014, bought my first sats at the peak in 2021
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They must be near retirement haha
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Nope they sold it all. They should post here lol
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Don't buy a home in 2012
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Same with me, but in 2019/2020. Home prices are going parabolic around me still even in this environment. Sitting on the sidelines has not served me well.
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Not mining bitcoin in the beginning. I was in college, I could have easily done it.
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Same I was too busy drinking and partying. Big mistake!
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I was too busy studying
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For me it was not buying Moderna and Pfizer stocks before the corona virus bull run. I saw everything coming and yet didn't buy it. Like Bitcoin in 2017 I bought it almost at the top so I made a little bit of money but not at all what I could have done. My lesson: never follow moral or ethical principals too strongly. In a country when everyone will be against you just buy what people believe will be useful.
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Or one could also follow Nancy's Pelosi stock portfolio and outperform by degrees of magnitude! :D
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Especially when government money is involved
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Exactly, just go with the flow. Recently I read that in the 1920s during hyperinflation, highly graded Austrians from the military got reckt too because they followed moral and ethical principals too strongly. If they corrupted themselves a little bit like politicians they wouldn't have been reckt and they could even have made money.
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i bought a bunch of freddie mac and fannie mae stock in like 2015 thinking they were gonna get out of receivorship but did not happen nor will it ever happen. didnt lose a ton once i sold but the opportunity cost was fucking brutal in hindsight holding that government trash in lieu of other assets i could have bought.
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Freddie and Fannie stock - the ultimate shitcoin!
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it was shitcoins before shitcoins...and i fell right in to that stinky trap 😂
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13 sats \ 0 replies \ @Zk2u 10 Jun
Either paying taxes or paying a scalper £1050 for an RTX 3070 to. Also got scammed out of £500 of bitcoin when attempting to buy a GPU
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Reading about bitcoin multiple times, from around 2011 forward.
And thinking over the course of the years, multiple times, I should learn more about that. I should REALLY look into that.
And then actually not looking into it till much, much later. Thank goodness for the book The Bitcoin Standard.
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Lol never had much luck in markets, surprised I actually made it to bitcoin, but I guess it would be not going harder earlier on, wasting time on shitcoins, and not taking equity in two startups I worked at, that both sold for massive multiples, nothing as mad as NVIDIA or MSTR that's such a hard pill to swallow,
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Right, the second best time to go hard is now though!
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I don't say I have regret but that was just a bad decision. I did not like to invest in assts. Just accumulated a lot of money in my bank account. In 2021. Instarted investing in Bitcoin and now I feel that my money was sitting like junk in these bank accounts.
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I can relate
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Shitcoining in 2021/22. The money I lost would've bought me at least half a coin if I DCA'd instead.
Also, even though I was into anarchy and the cypherpunk movement etc. in the early 00s, the interest waned and I completely missed it when Bitcoin arrived.
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Someone advised me to buy bitcoin but I didn't buy it in 2012.
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13 sats \ 0 replies \ @travis 9 Jun
Prior to bitcoin: Buying a used car with a loan that we couldn't really afford. Trying to own horses when we couldn't really afford it.
After bitcoin: Not buying more bitcoin when it was lower in USD value.
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My biggest regret was letting Celsius hold onto half my life savings. I had a lot of reservations but my brother said it would be fine. I got 25% back from the bankruptcy court. Second biggest is putting the rest of my money in Bitcoin when it was $63k in 2021. I wish I DCA’d in.
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For me, it was buying dogecoin at around $.7, I was doing t for the first and last time.
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I spent 90% of my wealth on girls and booze. The other 10% I blew.
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The fun was unmatched I bet!
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It's all about priorities.
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Shitcoining so hard early on in my Journey remains one of my biggest regret. Thank God for books like the bitcoin standard which did help, philosophically speaking.
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As I get older I consume much less of that content. Looking back 10 years I cringe at some of the shitposting and degenerate things I was doing. Grateful to seek higher truths than what I see on Reddit/twitter.
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21 sats \ 1 reply \ @k00b 8 Jun
I don't really know even though I've probably made plenty of financial decisions worthy of regret. For some reason I reserve my regret for other things. Like, not finding my interest in programming sooner, or missing the days in design class where we went over color theory. I think I might not need to be rich as much as I need to be something else in some kind of Maslow-like upside down hierarchy.
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That's fair! Sometimes it isn't about money, but having the right purpose aligned!
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It's definitely not starting to investing in Bitcoin while I knew about it from as early as 2014
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The best time to plant the tree is 10 years ago, the second best time is today.
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I've been constantly planting trees more than 10 years now. But only trees.
As far as planting a bitcoin tree is concerned, just started regularly after 2020.
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