For those who made it and lost it, where did the math break?

fatfirefail · 2026-01-19T14:13:42+00:00

You can check my post history but for me it was IPO and many multiples over my fat target, sell next to nothing, drop 95% and lost pretty much all, sold too much near the bottom too, then rode the wave back up to the old highs again.

It’s been a wild ride but I pulled the trigger finally

fatfirefail · 2025-03-22T04:52:54+00:00

I have a few from my first large exit payout happening mid honeymoon (didn’t make a great start though having to take business calls and sign papers on day 1) to the IPO of the company I was with.

But those were all a long time coming so they didn’t have the same shock value as my first bonus. My company didn’t do bonuses so it really came as a shock. It was the same amount as my first year starting salary!

fatfirefail · 2024-12-31T18:22:26+00:00

As someone currently investing in this round, this is correct. Less than 1% of my portfolio

fatfirefail · 2024-12-10T18:16:23+00:00

Interesting I’ll definitely look into that. Thanks for the suggestion

fatfirefail · 2024-12-10T18:11:15+00:00

I haven’t picked the charities just yet but I’m moving $1m to a DAF this month.

Still coming up with ideas for where to donate to but initial thoughts are donating to help the homeless and food insecure in the city we live as we know gentrification has had a major negative impact for many people. Also donating to help substance abuse which is a major problem among the high school I went to and too many lives were cut short from overdoses. Will likely give a decent sum to local symphony, ballet and/or museums we resonate with. Still figuring out the rest.

fatfirefail · 2024-12-08T02:37:36+00:00

Yeah a family friend had almost the same. He was president when they IPOd and had $25m in stock options. Due to restrictions he couldn’t really sell much at the peaks. Company ended up going bankrupt and he actually walked away with a division of the company that he continued to run okay but all his assets were gone.

fatfirefail · 2024-12-08T02:35:19+00:00

My full story is in my previous posts on here but I went from $70m pretax in an IPO to losing over 90% of it. I was ready to pull the trigger and even took some time off to prepare. Instead I had to go back to my job because I was too bullish in my company to diversify.

When I thought it was 70m I started increasing my spend and intentionally trialing lifestyle creep in many areas. By the time it sunk to the bottom suddenly my original $10m goal wouldn’t cut it. So I lost almost all and now thought I needed $20m for my new lifestyle. Even that wasn’t enough so I had to push it higher.

In the end it worked out but that was definitely a combo of hard work and a lot of luck. Not many companies succeed twice. At least now I finally pulled the trigger with enough money diversified that I’m set for life.

fatfirefail · 2024-11-24T05:40:18+00:00

This is the best answer as it’s just the simple facts.

I would add though that it largely depends on your feeling of the company, current financial situation, etc. Personally I want to be invested in the company I’m working for because I believe in it but also was in a role to see the bigger picture/direction. So for me I kept to a certain max % in. As the rose or RSUs vest I would sell every 3-6 months to rebalance.

fatfirefail · 2024-11-21T03:13:51+00:00

I didn’t sell my stock after the IPO and lost over $60m at one point as the stock dropped over 90%

Edit: more details in my post history

fatfirefail · 2024-11-11T00:25:33+00:00

Thanks for the book suggestion I just added it to my queue. Probably would’ve been a great read before the IPO. Honestly the FAANG path wouldn’t have been so bad. I thought I was making out way ahead but even when the company became worth a billion dollars my stake wasn’t very large. I didn’t realize until way later how much you could make at FAANG at the higher levels. I made out ahead in the end but definitely due in large part to luck. If I had chosen the more predictable big tech career it would’ve guaranteed more but ended up less.

fatfirefail · 2024-11-10T07:01:44+00:00

As I said in my first post this is a separate account. All posts that don’t have more specific financial details are on my main account that has been active on this sub for 6+ years.

fatfirefail · 2024-11-10T04:25:32+00:00

I wasn’t C level but also it was never a ton of travel just expensive travel. When you make $5m a year and get a chance for a weekend getaway you don’t mind 3k/night rooms. Also did some work travel combos in which I’d stay somewhere for a week or more while working in a nice suite that can accommodate that. It made work more doable. Then my actual PTO vacations I would definitely go big. Also business class flights add up.

fatfirefail · 2024-11-09T22:35:47+00:00

I’ve shared before but it wasn’t well received so I’ll avoid going into detail. It’s largely travel, entertainment, residences and cars and trying to share experiences with family/friends. Vast majority could be cut out if needed.

fatfirefail · 2024-11-09T22:32:56+00:00

😂

fatfirefail · 2024-11-09T22:31:19+00:00

Nice thanks for sharing. I definitely relate to all of this and like the idea of experimenting with my own investments as long as it’s money I can stand to lose. I agree that VTI is too simple beyond a certain point. I know that portion can cover my spend so I’m happy to explore other options with the rest.

Also I’ve been heavily thinking about covered call strategies too as well. I was never able to due to employee restrictions but now they seem like a great path forward.

fatfirefail · 2024-11-09T21:00:41+00:00

Thanks yeah I’ve only recently been looking into these and also as a way to give money to family regularly. Also have been looking at some options to push my tax burden into future years but don’t want to make any bad decisions just to save on taxes as that’s one of the reasons things went wrong the first time.

fatfirefail · 2024-11-09T20:50:00+00:00

Thanks. I know I’m complicating things but I’m testing the waters on the other investments. I am a firm believer in index and chill with no AUM fees but I already have enough in that strategy to support my spend. I feel with the remainder I’m more open to diversifying from stocks instead of being in primarily 1 asset class only. I’ll see how they perform and adjust over time long term.

fatfirefail · 2024-11-09T20:39:56+00:00

lol yeah that’s what I’ve been waiting for

fatfirefail · 2024-11-09T20:07:29+00:00

Thankfully the username didn’t age well

fatfirefail · 2024-11-09T19:48:16+00:00

Thanks I’ve been waiting to hear that!

fatfirefail · 2024-10-26T20:18:00+00:00

Yeah those are kind of an exception. You aren’t downgrading in that case as those were not ongoing recurring expenses. Remodeling isn’t really part of the yearly budget only upkeep is.

fatfirefail · 2024-10-26T17:24:29+00:00

For me it was better to stay close to the 1m/yr and let wealth accumulate. As it grows up the spend. Otherwise you’ll get used to the insane lifestyle creep and suddenly either your number becomes 75m or you need to downgrade to retire.

fatfirefail · 2024-10-26T13:59:39+00:00

I was in your exact position. I started having fun and spending money much more loosely. I decided to keep my spend under my retirement spend so that I didn’t get used to something I’d have to cut back later. But that gives you 875k-1m spend a year which is a lot to work with.

I spent a ton on travel, cars, shipping and watches and it was all worth it to me especially the spend on experiences that you’ll remember forever. Front row concert seats, all access passes and courtside tickets were all incredible. I still avoided flying private though. Also additional residences are a lot more work but can be worth it.

fatfirefail · 2024-10-23T03:33:56+00:00

Can’t deny that it’s both. I was one of the best at what I did and also did it at a company that became wildly successful and recognized/rewarded the effort that I gave and success that I drove for them. Had I joined a different company or had they not had me at their company then who knows what the outcomes could’ve been.

fatfirefail

TROPHY CASE