Author Topic: am I ready? (concentrated real estate and bitcoin and health concerns)  (Read 944 times)

Plotorganic

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Hope you all don't mind analyzing my "plan." I think I am FI, but there's some unique aspects that make it less clear.

I am 43, married, stay at home wife, 2 small kids, working, earning about 500k in a senior corporate position.

1. net worth: I own real estate which passively produces 150k of income a year, its variability is i expect a worse but not catastrophic year as down to 120 from maybe higher expenses repairs or bad tenants etc). I made a gamble on bitcoin years ago and now have about a 3mm value. I also have another 700k of bonds and 700k of stocks in index funds. I have 1.8m in retirement accounts basically 80/20 stocks/bonds. So that's 120-150k of real estate income, and a 4.4mm taxable pool to access from until age 60, when i guess the retirement accounts open up.

2. budget: I live in a high but not highest cost urban environment. We pay 20k a kid in private school, 20k a kid in 529 contributions with goal to fully fund private university. high quality marketplace healthcare for family is like 30k a year, and maybe another 15k of out of pocket max expenses? our housing costs about 60k a year, so thats 185k a year basically out the door, sl lets say living expenses take is up to 240k a year, or 20k a month.

3. FI-ness: so lets say the 120k comes from real estate, and the other 120k comes from the 4.4mm taxable assets, that's about 120k right there, so technically, 4% rule applies, and the retirement accounts grow, but I estimated my taxes will be about 30-40k a year, so that needs to be grossed up to 240-280k a year of withdrawals / income needs.

I don't need you guys to tell me to sell bitcoin - i do not want to pay a seven figure tax bill on it just to rebalance into a stock fund. I have sold covered call options against 2/3 of that bitcoin exposure, that generates about a year's worth of living expenses, but caps bitcoin returns at about another 50% from here, so I am at least risk managing that situation.

I also have expected healthcare needs, like personal immune issues, and some ongoing healthcare my children need, that will definitely exceed any expected deductible. We also expect to probably need to (or intend to) help financially my in laws and my parents, as we both come from humble means and our respective sets pf parents unfortunately do not have nest eggs.

I am definitely experiencing "one more year" (or 3 more specifically) because in that time, I definitely can rebalance bitcoin on the margins, have 1-3 more years of expenses paid for such that i continue substantial saving and reinvesting, and can keep padding those tax deferred accounts, and my estimate, is that in 1 year, I'll secure that marginal buffer meaningfully, and after 3 years I will be able to meaningful impact either more rebalancing out of bitcoin, or simply contribute more to traditional non bitcoin investments.

What do y'all think? I imagine the FIRE perspective is "why are you even wasting our time, yes youre ready, and/or reconsider your expenses/budget" whereas when I look at traditional conservative boomer financial advisor perspectives, they would probably have me working for a few more years at least.
« Last Edit: May 29, 2025, 09:28:55 AM by Plotorganic »

seattlecyclone

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I don't need you guys to tell me to sell bitcoin - i do not want to pay a seven figure tax bill on it just to rebalance into a stock fund.

With your $500k work income plus $150k real estate income I expect you're already real close to the top capital gains bracket, if not already there. Spreading the Bitcoin sales out over a few more years of your working career therefore doesn't seem like it will meaningfully change the tax burden compared to if you just sell it all now.

Another option might be to give some of that Bitcoin to your parents and in-laws, they sell it in their lower tax bracket, and buy some more stable investments for their own retirement. Since you're planning to help support their retirement anyway this could be an efficient way to do that. The main concern would be whether you can trust them to make the money last over whatever time period you intend, rather than blowing through it and asking for more a few years later.

A final option I encourage people to consider when they have such highly appreciated assets is to put a portion into a donor advised fund to pay for charitable giving in the future. If you have any charitable intentions at all, it's more advantageous to you to do this donation while you still have that $500k salary and high tax bracket to deduct against, than after you retire.

MustacheAndaHalf

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It's hard to avoid talking about the majority of your net worth, and it being in Bitcoin.  I sold my $GBTC call options and shares in Jan 2022, and haven't owned Bitcoin since.  In late 2023 / early 2024, Bitcoin approval sent the price surging, but it fell afterwards.  In late 2024 until now, the election of a crypto-friendly President sent Bitcoin surging.  I'm avoiding Bitcoin now because I don't think those events will repeat, and are the main recent drivers of its price.

You mention $150k real estate income, marked conservatively down to $120k for bad years or repairs.  Don't taxes alone cost almost $30k?  Meaning, you have $120k after taxes in a good year, and may need to reduce that further to account for repairs and bad years.

Bitcoin's bad years can be dramatic, like -76% in 2022 or -82% in 2018.  Consider a cash reserve to pay expenses during bad Bitcoin years - like a "Bitcoin emergency fund".

Telecaster

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12321

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Can I ask where you are selling covered calls directly on the bitcoin? Or is it a derivative like GBTC/IBIT?

I am in a similar boat, have looked into taking a loan against the Bitcoin to diversify and put off the tax bill.

yachi

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I don't need you guys to tell me to sell bitcoin - i do not want to pay a seven figure tax bill on it just to rebalance into a stock fund. I have sold covered call options against 2/3 of that bitcoin exposure, that generates about a year's worth of living expenses, but caps bitcoin returns at about another 50% from here, so I am at least risk managing that situation.

Sure, you could just wait for it to crash and then you can sell it without the tax bill.

maizefolk

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It's worth calculating what your annual spend would be without child related expenses. At least $40,000k/year of your spending is specifically child related and is only going to last 15-20 years rather than for the rest of your life. You don't need permanent cashflow or 25x expenses in investments to support expenses that are going to last less than two decades.

Related, your children won't be young forever. Three years more working is giving up a lot of hours and time with your kids in their pre-teenage years.

Is your real estate mortgaged? If so, how long until the mortgages are paid off, at which point your cashflow would presumably increase?

3. FI-ness: so lets say the 120k comes from real estate, and the other 120k comes from the 4.4mm taxable assets, that's about 120k right there, so technically, 4% rule applies, and the retirement accounts grow, but I estimated my taxes will be about 30-40k a year, so that needs to be grossed up to 240-280k a year of withdrawals / income needs.

4.4M in taxable assets would support $176k/year in spending using a 4% withdrawal rate.

Plotorganic

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Can I ask where you are selling covered calls directly on the bitcoin? Or is it a derivative like GBTC/IBIT?

I am in a similar boat, have looked into taking a loan against the Bitcoin to diversify and put off the tax bill.

IBIT. The options markets on this one are unbelievably liquid with tons of strikes and maturities. Somę of the other etf’s have poorer visible bid ask, but if you work limit orders and try to interpolate for the similar maturity and strike on ibit to get a better sense of mid, I’ve found I get filled not far off.

Coinbase buying Deribit is inevitably going to bring real bitcoin options to the US market, but that’s gonna take a while. Feel free to ping me if you want to brainstorm, I have a decent amount of options experience.
« Last Edit: June 01, 2025, 07:30:58 PM by Plotorganic »

Plotorganic

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Thanks a lot - these are very useful thoughts, as I understand it, a lot of retirement planning ends up being over conservative by every parameter and model context, and this one I actually haven’t considered *that* much, besides the expanded waterfall of access to retirement accounts.

The issue of living off of the bitcoin and real estate and *some* legacy bond/equity assets, is that the path dependency / sequencing of returns matters before I make it to the ability to efficiently draw from retirement assets. 2/3 od the bitcoin esposure “hedged” with sold calls actually has a decent amount of protection for portfolio value for the first 10-20% of declines, but anyhow yes the trope is it can go down 75% etc.

I know going into a traditional American investing platform discussion board and bringing up the magic internet money is going to elicit some ad hominem, but, aside from acknowledging the historical volatility, it’s kinda silly to deny that bitcoin is actually kind of an enormous and widely, though speculatively, accepted thing.

For my purposes, I’m considering it more like a high tech stock concentration, and basically think about call overwriting, tax loss harvest led rebalancing from other less performant investments, and assume a lower withdrawal rate until the situation becomes more comedic on account of potential, but not guaranteed, price increases


It's worth calculating what your annual spend would be without child related expenses. At least $40,000k/year of your spending is specifically child related and is only going to last 15-20 years rather than for the rest of your life. You don't need permanent cashflow or 25x expenses in investments to support expenses that are going to last less than two decades.

Related, your children won't be young forever. Three years more working is giving up a lot of hours and time with your kids in their pre-teenage years.

Is your real estate mortgaged? If so, how long until the mortgages are paid off, at which point your cashflow would presumably increase?

3. FI-ness: so lets say the 120k comes from real estate, and the other 120k comes from the 4.4mm taxable assets, that's about 120k right there, so technically, 4% rule applies, and the retirement accounts grow, but I estimated my taxes will be about 30-40k a year, so that needs to be grossed up to 240-280k a year of withdrawals / income needs.

4.4M in taxable assets would support $176k/year in spending using a 4% withdrawal rate.

Ron Scott

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You can’t use the assumptions underlying the 4% Rule with a portfolio that heavy in individual RE assets and bitcoin. Apples Oranges.