Using box spreads to finance life?

So I've been planning to move back to the US in the next 12 months - and was looking at buying a house, and also tax planning/withdraw strategies (I fired 18 months ago). I happen to come across box spreads (european SPY box spreads) as a way to effectively borrow money at near SOFR, while also offering short/long term capital loss for the 'interest' paid.

That got me thinking - with my now almost $12M in assets (80% VTI/SPY/QQQ and 10% old legacy vested RSUs that I'm planning to sell after I move back to the US for tax reasons, 10% SGOV), if I fund my full expenses with dividends and box spreads (I'd have about $100k in dividends + take out $150k/yr with box spreads) and roll it over every year - I'd still be able to keep my debt-to-asset ratio at less than 20% basically until I die. And thereby pay minimal taxes forever.

Is that right/sound? What am I missing?

I know there is risk if markets drop 80% or what not, or if VTI growth slows dramatically over the next 40 years, or if interest rates spike dramatically to the 1970s levels, etc - but all of those seem like tail risks that either means I'm screwed either way (if the trigger/shock event happens suddenly and is sustained - like WW3), or I'll be able to modify behavior to de-risk (reduce spend, stop rolling over the box spreads, etc)

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u/jcc2244 — 10 days ago
▲ 16 r/Salary

[CEO] [London] - $2.5M

​

NYC/Bay area for the first few years

\* 1st year, FAANG (not SWE): $37k contractor => $50K FTE

\* 2nd year, FAANG: $60K

\* 3rd year, FAANG: $75K

\* 4th year, FAANG: $85K

\**5th year, bschool: -$60K*

\**6th year, bschool: -$60K (+$35K from internship)*

\* 7th year, MBB consulting post MBA: $190K

\* 8th year, PM at startup: $180K

\* 9th year, PM at startup/promotion: $230K

\* 10th year, switch company, PM at other company: $375K

\* 11th year, promotion: $450K

Moved to London

\* 12th year, role change to GM/same company: $550K

\* 13th year, more stock grants vesting: $650K

\* 14th year, back to FAANG: $450K

\* 15th year, left for non-FAANG: $950K

\* 16th year: $1.5M

\* 17th year: $1.2M

\* 18th year: $2.5M (LTI payout related)

\* 19th year: $1.4M

\* 20th year: $300k (retired in March of that year)

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u/jcc2244 — 5 months ago
▲ 45 r/fatFIRE

FIREd last year, tempted by some opportunities - want some advice

FIREd last March (see post here) - since then our NW has gone up to about $10M-$11M.

My wife is still working and making about $200k/yr.

I've loved the past 14 months of retirement - spent time with the kids, flown across the world to see family/friends multiple times, explored a ton of my 'to-do/to-explore' list, etc etc

I'm still really enjoying it (currently vibecoding various passion projects).

Throughout the last 14 months, I'm still consistently getting executive recruiters reaching out to me about potential opportunities, and I've generally not been interested in them. However, recently there has been 2 that have made me wavier a little.

Both of these opportunities are aligned with my passion area (and skills), and I'm tempted. But also I don't want to take on more responsibilities again...

One of the opportunities is with a very big private company, doing something in the space I'm interested in, with a lot of freedom/autonomy, very little short term financial pressure - this company has the resources ($, brand equity, distribution, etc) to really have an impact in the area I'm passionate about (and the same area where my current personal passion projects are) - but I'd have to be an organizational leader/building a team to a good size (hundreds of people+) over the next few years, and I'm not sure if I'm motivated enough to take on that kind of responsibility again.

The other opportunity is with an established and well funded/profitable startup that has been around for a long while, and has gained significant traction recently. This one is also operating in the same space I'm passionate about - I'd basically be the right hand of the founder and be groomed to take over from the founder.

Both opportunities are tempting me... comp is kind of irrelevant here since I'm not taking these for the comp (the big private company's total comp would be around $800k/yr, the startup would be around $250k/yr + ~$500k/yr in equity based on the valuation from the latest round).

I think I should just stay retired, but part of me is itching to take one of the opportunities because they align so much with my passion space anyways...

Any advice from those of you who've retired and gone through similar experiences/thoughts?

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u/jcc2244 — 5 months ago

Hi parents,

I'm a parent myself (4 year old and a 10 year old). When my kids go to bed I usually read them a bedtime story, but then the 4 year old will ask for more and more again and again (the 10 year old also use to do this when he was younger haha).

Most nights I'm just too tired after 1-2 stories and don't have the energy to read anymore, so I'll turn on a meditation music (from youtube) or some kind of ambient music (from youtube) to help put them to bed. It works and isn't too bad of a solution.

However, since I'm unemployed currently, as a side project I decided to try to create a better solution for myself. So I made a story narration app that will read classic stories (I have 20 so far, like 3 little pigs, hansel & gretal, the little mermaid, snow white, etc etc) and also has the option of creating persionalized stories (where my kid is the protagonist).

Its worked great so far, now I usually read 1-2 stories then finish with another story on the app.

The stories also have ambient noise (you can select forest/ocean/rain/etc ambient noise) that plays in the background and continues when the story narration is finished, so its great for me to turn off the lights, play the story (the usually last like 5-10 minutes) and then we both doze off.

I wanted to try to publish the app just to see if others would find it useful (the free version has unlimited use for the classic stories since those are basically free to serve; however, there is also a paid version but only if you want to generate a lot of personalized stories, since that has a real cost associated to operate).

Currently I need some parents to use the app and see if they find it useful/and improve it before I launch it - so if you're interested and have an android device - DM me and I can share (its through Google Play's internal test program, so its safe/verified by Google play).

Thanks!

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u/jcc2244 — 5 months ago