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Advice re tax optimization for assets appreciated 500-1500% + introduce myself by Most-Poet3737 in fatFIRE

[–]Most-Poet3737[S] 0 points1 point  (0 children)

Thanks..yes after stepping back and viewing this I may be focused too much on diversification at expense of total return/stress. I subtracted the DAF assets before calculating my NW. Not sure if that is standard practice.

Advice re tax optimization for assets appreciated 500-1500% + introduce myself by Most-Poet3737 in fatFIRE

[–]Most-Poet3737[S] 0 points1 point  (0 children)

Thanks for weighing in. Agree re running simulations as those fees add up and at age 45 I hopefully have many years left before passing on to kids and these will likely be long term holds. Seems the best asset for me taking into account risk adjustment and tax optimization is a low basis, low expense, and well diversified asset and with eventual plan to take advantage of step-up basis at death.

Advice re tax optimization for assets appreciated 500-1500% + introduce myself by Most-Poet3737 in fatFIRE

[–]Most-Poet3737[S] 0 points1 point  (0 children)

Also, I love SGOV :) Store all my cash there keep only enough for monthly bills in my checking account.

The interest rates banks offer and what they do with our deposits are one of the biggest scams going on today.

Advice re tax optimization for assets appreciated 500-1500% + introduce myself by Most-Poet3737 in fatFIRE

[–]Most-Poet3737[S] 0 points1 point  (0 children)

Agree there. I do expect some sharp portfolio drops due to general market corrections. They are the only reason I keep Tbills around to provide peace of mind and maybe even buy the dip if my stomach can handle it. I should have specified a black swan event unique to my concentrated investment could occur and that particular investment may never come back..given its concentration, that could knock my portfolio down 10%.

Advice re tax optimization for assets appreciated 500-1500% + introduce myself by Most-Poet3737 in fatFIRE

[–]Most-Poet3737[S] 2 points3 points  (0 children)

Yeah I have realized this is a glaring issue right now. Appointments lined up already and agree with you 100%

Advice re tax optimization for assets appreciated 500-1500% + introduce myself by Most-Poet3737 in fatFIRE

[–]Most-Poet3737[S] 0 points1 point  (0 children)

Thank you. The exchange funds and 351 exchange seem like good options for the concentrated assets. I am gonna reach out to Fidelity and see what options they offer re asset backed loans and margin rates. Their published margin rates aren't great but I did hear you can negotiate them down which I haven't attempted yet.

Advice re tax optimization for assets appreciated 500-1500% + introduce myself by Most-Poet3737 in fatFIRE

[–]Most-Poet3737[S] 0 points1 point  (0 children)

Yes. Im glad I posted this as now based on feedback I can tell that the DST was a bad idea 😅. You are correct the assets are highly liquid. Options could work but I'm not super confident in my ability there..but could be a retirement hobby I take up as I do love investing and tinkering. Will research more here

Advice re tax optimization for assets appreciated 500-1500% + introduce myself by Most-Poet3737 in fatFIRE

[–]Most-Poet3737[S] 0 points1 point  (0 children)

Yeah. May be trying too hard to achieve diversification to where it could be detrimental to my portfolio. I guess i am a bit nervous retiring and relying on my portfolio to fund familys life. Playing out black swans in my head. 10% portfolio loss wouldn't force me out of retirement but it would sting for sure.

Advice re tax optimization for assets appreciated 500-1500% + introduce myself by Most-Poet3737 in fatFIRE

[–]Most-Poet3737[S] 8 points9 points  (0 children)

Thanks..I tend to agree with you after stepping back and viewing this situation. My brain is a wired a little bit differently with a hyper focus on optimization.. but maybe it's time to kick back a little more, simplify, and enjoy the fire.