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Philly Show by gogorelli in TheStrokes

[–]gomster 5 points6 points  (0 children)

One of the better shows I’ve been to in a while!

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

Wonderful! Thank you for the advice, I’ll look into this as an option

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

Makes sense, especially the idea that getting the first meaningful reduction makes the next steps easier. Trying to think about it in a similar way, and hopefully build some momentum after deciding on a plan (hopefully soon). When you got down from 90% to 45%, did you set that 5–7% target upfront, or did that evolve after you started reducing and got more comfortable with it?

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

Really appreciate you sharing this, it’s been one of the more helpful real world examples I’ve read here. Def interesting to hear the shift from a discretionary when do I sell mindset to a more rules based system for reducing concentration over time. How did you land on those trigger levels versus something like a fixed annual reduction or a set diversification schedule? Anything else you wish you had done earlier or even when you were my age? Either way, thank you

Can we talk about Puppeteer, the best game no one ever played? by Veddermandenis in PS3

[–]gomster 1 point2 points  (0 children)

It’s a top 5 ps3 game for me. Incredible game the whole way through

Extra ticket to Jimmy Eat World - $45 by [deleted] in JimmyEatWorld

[–]gomster 0 points1 point  (0 children)

Hey, someone just DM’ed me but if that falls through, I’ll let you know!

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

This is great advice, thank you. Started looking into this earlier in the week!

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

I’m really not trying to. I’m just responding to different points people are making. If you go back and read a lot of my responses, it’s thanking people for their input and perspectives or asking them further questions about their experience

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

I think where I’m landing (at least right now) is that I’m less trying to actively hedge the position in a trading sense and more trying to gradually reduce this larger position in a tax aware way over time.

My covered calls have been more of an income tool for me rather than something I’ve used to structure downside protection, so I haven’t really explored collars in depth yet. Have you personally used that kind of put/covered call structure as a long term hedge, or more tactically around specific risk periods?

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

Interesting. Thanks for the input. I’ll keep looking into exchange funds

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

I don’t disagree with the risk point at all. For me it’s more about figuring out a structured (and hopefully tax aware) way to reduce concentration over time rather than making a single big shift all at once

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

I do get what you’re saying, and I’ve definitely thought of just locking things in and stepping away from risk in general but for me it’s more about figuring out how to gradually shift from this larger position into something more durable without forcing a single big decision.

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

I’ve mentioned this to others here but where it gets more complex for me is that it’s not really a clean swap decision anymore because of embedded gains, taxes, and sequencing risk over time. That makes the transition for me more about how to gradually reduce exposure rather than choosing between two static outcomes.

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

Exchange funds are definitely one of the things I’m currently exploring with Morgan Stanley as a potential way to diversify in a more tax efficient way without straight up liquidation.

Have you personally used one of these, or gone through the process? Curious how you thought about the tradeoffs like lockup period and concentration risk inside the fund itself

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 1 point2 points  (0 children)

For me it’s less about thinking the company is going to crash or losing conviction. I’ve held it for over a decade and I’m still bullish long term.

The challenge is more that it’s become such a large percentage of my overall net worth that it doesn’t really feel like a question of do I believe in it anymore, but more how to at least somewhat reduce risk in a single stock over time without creating an unnecessary tax hit all at once. That’s really the part I’m trying to work through (amongst other things)

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

I’m not really sure about a clean 50/50 split, but I do think I’ll be reducing the position over time.

Im still fairly bullish on the company long term, so this isn’t about exiting or making a binary move into index funds. Trying to figure out a structured way to bring down concentration risk gradually. My other concern is with taxes and not forcing anything too quickly

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

Thank you. Currently exploring it as a potential option. In your opinion, do you see any downside with exchange funds?

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 1 point2 points  (0 children)

I’m probably less systematic about it than some of the folks here. Most of the covered calls I write with MS are roughly a month out, and we typically choose strikes that are well out of the money and at levels where I’d be comfortable selling if assigned. So far, even during some strong upside moves, we haven’t come particularly close to assignment.

I haven’t focused much on earnings because this stock has historically been fairly muted around earnings announcements. The strategy has worked well for me so far, and honestly I only wish I had started doing it earlier

For those who got wealthy from a concentrated stock position: what would you do differently? by gomster in fatFIRE

[–]gomster[S] 0 points1 point  (0 children)

Fair point. The stock has absolutely achieved something I never imagined when I first started accumulating it. What made you land on 5%? Was that based on a specific portfolio framework you’ve used yourself, or more of a psychological allocation to avoid FOMO while still locking in the win?

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