25m nw 37yo married with 3 and 1 yo. In London currently and love being in a city but want better weather. Thinking about moving now that we have pulled the trigger. Would love somewhere with good weather where I can be outside with my family in a great community with interesting people and things to do. Also very much value walkability and a neighborhood vibe. Not really a going out person or fancy food but good food is nice. Obviously good for kids with good schools and families as well. Family in the us which is becoming more and more important. Ideas?

Edit: to give some more ideas that might help understand my mindset.

La - seems like a good option with the right neighborhood. Don’t love that you have to drive everywhere but maybe with the right hood it’s fine and it’s not that bad.

California - feels like it might be the right option generally with the right city but trying to canvas.

Florida - maybe something outside of a big city or the right neighborhood but seems like it would get boring fast

Milan - seems like a very good option but I’m just not sure as Americans we will ever totally fine

London - honestly a perfect option if not for the weather but I just love being outside as do my kids and want to be outside most of the year

Tel Aviv - love this honestly but again just not sure culturally.

I’m trying to understand the merits and demerits of a VUL policy, particularly as it applies to a long term tax advantaged strategy.

My understanding (using example figures) is that one could contribute $50k a year for 10 years, where the annual fees are ~3k, and the premiums are invested in broad based equity funds which usually have an underlying fee load themselves. The contributions can be withdrawn starting in year 7 with no penalty. After year ten, the fees become di minimis.

Then the gains in the account can be used in the form of a zero interest loan, and the cash contributions can be withdrawn tax free. In essence, this recreates a Roth structure. The arbitrage comes from paying fees upfront vs. having no long term capital gains tax on the back end (say 25years from now). As such, this is really a product for high earners; I can find very little quality literature that applies to the HE/FAT scenario. Further, I understand these can be converted to PPLI products after $2m where one can then direct the investments into Private Equity or Hedge Funds, thus avoiding LTCG on those private investments.

For the avoidance of doubt, I am not talking about INDEXED Universal Life contracts which have caps and are tied to price indices instead of markets.

Could you please share experience or views on if this is actually a tax advantaged product or just snake oil? Any high quality resources would be appreciated as well.

Hi Everyone,

I was wondering if anyone knows any lenders that lend against the enterprise value of a business. I am currently in the process of acquiring a business that I gotten underwritten at a valuation of $18.4m and I will need about $5.5m in debt to finish the acquisition. Does anyone know any lenders that will not require any skin in the game from our side for this acquisition because we are tied up in a lot of other acquisitions. The business cash flows $150k+ MRR. If anyone knows any lenders, Please comment down below or dm me.

Thank you

I strongly believe that you once you have that first big cash out, doubling and tripling that number is theoretically easier than getting to the first cash out.

They say you need money to make money. And that first million is always the hardest.

I realize this question may be just as silly as someone who comes here with no money and asks how to get rich.

But let me phrase it this way:

If your initial cash out was $15 million, fully liquid, how would you go about getting yourself to the next level? Next level being 30 to 50?

Is it an impossible to answer question?

You’d need another lottery win?

Incredibly good luck?

Put another way: how do newly wealthy people really accelerate things to higher levels?

I have everything in management with Schwab split S&P 500, mutual funds, etc. I would consider that conservative yet safe.

But as a terrible example, 50 Cent made his initial money, and then hit a home run with Vitamin Water. Taking him into the hundreds of millions. I assume for every 50 Cent, there are 50 thousand others who lost all their money.

Regardless, what would you do if you considered the initial 15 million to be just step number one?

I'm in my 30s, UHNWI, single currently reside in Texas. I'm exploring the idea of settling down in either Los Angeles or Miami. However, I'm torn between the two and would love some insights from those who have experienced either or both cities.

In LA, I'm particularly interested in Westside areas like Beverly Hills, Bel Air, Hollywood Hills and maybe Malibu in the $10-$20m range. Also looking at Miami Beach which appears overall cheaper and I would prefer a condo there so can get away with spending half of that.

Considering my lifestyle preferences, which city do you think would be more suited for luxurious living? I don't commute, so factors like traffic are less of a concern for me.

Any advice or personal experiences would be greatly appreciated!

Hey all, longtime lurker and obvious throwaway acct

I'm 32 and live in a MCOL area NW 3.5M. No wife, no kids. The wife part may change but kids probably not

2.5M in a MM acct at 5.13%

1M in my business for operating expenses payroll etc

Also have 200k our of 500k left on my home loan at 6.5%

I've had a great run most of this has just come in the last 1.5 years, and I believe I'll be able to do this for another couple of years. Biz generates 8-10M+ each year and I'm keeping (gross) 1.5-2.5M. My goal is to get to the 10M mark, and put most of this in 3% treasury bonds, play it safe and take home 300k+ a year

My question is, am I being too conservative? I come from a VERY blue collar family and to be a multi M in my early thirties, nobody in my family has experience with that. I've been fortunate enough to read, research, study, and save almost every dime. I drive a car worth less than 60k and my house is not extravagant. I do have a money manager who supports my 10m + 3% treasury play but is also open to being more aggressive.

Right now I'm just putting every dime I can take in owner distributions in my 5.13% MM sock drawer. If interest rates drop on those, then I'll make some moves but for now it's paying me more in interest than I pay myself in W2 salary from my biz.

I don't know how many millionaires went broke and did it all again, I'm certainly too tired to even think about that, I've been gutting it out for 4+ years many hours a day to get here. Hence why I'm so conservative, but scared money don't' make money (so I've heard) and I'm not a total baby, I took a LOT of risks to scale to where I am in less than 2 years.

I have enough money to worry about how little money I have, it's not enough for me to FIRE but it will be in the next 3-5 years. Should I be more aggressive with what I have? Or keep saving?

Do you have an umbrella policy? I have 2m that’s $1400 yr. Is it worth it?

Seeking advice on how to take out cash from different accounts.
I am over 60. I have enough to use for regular expenses from pension payouts. But I am considering buying a house, in the neighborhood of 3 million. If I take that cash from 401K, I will pay tax for the entire amount at the highest bracket. If I take it from the investment account, I will pay tax on only part of it. But, investment accounts will not be taxed when they go to the kids after we die. They will still need to pay tax for the assets in 401k. Or should I take out a mortgage and pay it over time?
Am I thinking in the right direction? Any suggestions?
Thanks in advance.

Curious to hear from others in this scenario,.,

I’m 35 and sold a business a couple years - and am now sitting on generational wealth… I’m continuing to consult for the org for a few hours a week, but otherwise have a shit load of free time on my hands now.

I’m finding myself in a couple of new scenarios that I’m uncertain the best way to navigate

1. both old and potential new friends that have time, but don’t have $ to engage in fun activities…. With this group, I’d love to just pay for everything if it weren’t weird… like let’s go golf, go to a show, hell - even travel to a hockey game… like it is no sweat off my back to pay for it all, but naturally there’s a balance where A) some people would just start to leach hard off you and be otherwise in it for the free shit — and B) on other end of the spectrum are people who would be uncomfortable accepting that kind of thing and can feel down on themselves for not contributing…

2. friends that have the $ but not the time… not much to add about this group. Most of my friends fall here. They’re building careers and obv not available during work days (or many weekends for that matter).

… would love to hear from other early retirees on how to handle this kind of scenario. It’s funny how I didn’t even think about it until I was living it. Thanks!

I’ve been a happy first republic customer for years. The team I’ve worked with just moved over to Citizens and is making a hard pitch for moving.

Does anyone have recent experience or a strong perspective on Citizens?

ExpatFIRE is pretty much entirely people trying to LeanFIRE abroad, so I was curious to get the thoughts of people who have FatFIRED to southern Europe. My situation:

• 52 years old
• 6 million in equities
• 3.5 million in Bitcoin
• 2.5 million in home equity
• 4.8 million (after tax) of payments due over the next two years from company buyout
• 3 young children (10, 8, 2)

The wife demands a California climate. I lived and worked in SoCal for so long I don't think I could feel retired there. Also, 2.5m is all I'd care to spend on a new home (currently in PNW), and that doesn't really get you a dream home in Southern California.

I was curious if any of you have FatFIRED to Spain and would love to hear about your experience there.

Next week will be one year since at least the responsibilities of work stopped. There was some pay for the following six months, but work stopped May 1st.

Here are some observations from my side on the first year out:

I don't miss work, and my days are largely full.

When I was getting close to retiring, I though I would consult, or lecture, or something. I made it through some 10 months without even knowing what was going on back at my employer other than what is in the Linked in corporate feed. That includes two visits from the CEO where we talked about vacations and retirement rather than work. All the things that one thought were interesting an important, at least for me, I was able to set aside.

I did do a quick global tour earlier this month and chatted with a bunch of folks over coffee or a beer. It was fun to hear about what HAD happened without having to think about it as it was happening; kind of like history I guess.

Its easy not to worry about your withdrawal when the market is up

Last May 1 we were at $21m NW and $10m Liquid. We spend $1.1m over the past 12 months including $350k in taxes. We are at $23m and $11m Liquid today. Granted, the last 12 months have been great for equities, but it is comforting to have an up year in your first year (so far the sequence of returns risk has been in our favor).

Folks may wonder about the high withdrawals. We have a significant amount (some $250k a year) of an executive pension starting in 7 years, which changes our withdrawal math. We also have 95% of the max social security coming which we will delay until 70. Our SERP has no cola, so the Covid inflation hurt us, but we now appreciate how significant the COLA on SS is.

Roth conversion math is scary, and now we are doing quarterlies for the conversions.

We have about $5m in traditional IRAs which we have recently figured out we need to get converting or it will be taxed at the maximum rates when the RMDs start. The SERP and the Social security payments will push us into a middle bracket just there. We did the math and will be converting $540 a year (already done for 2024), but if the markets remain strong that $5m balance is likely going to be there when the RMDs start and we will still have some payments in the mid 30s% at the federal level.

US Medical Insurance is complicated, but the key seems to be the max out of pocket

We went with HSA compliant high deductible plans which are still not cheap ($1800 a month for the three of us still in the house). Max out of pocket ($8700 for an individual) comes quickly if your student athlete needs surgery.

You can't always get what you want

Real "first world problems" remain that the things we would like to spend more money on remain "difficult". Getting a contractor for a renovation still is challenging, and the particular replacement cars we would like (GT3 touring and Plug in Range Rover) are still seeing excess demand so not to be had. We will see how that shapes up in the coming quarters.

Just say yes

While we still have one kid in high school, we try as much as possible to immediately take anyone who makes a proposal of doing something with the "just say yes" attitude. At least one of us should be able to make it to NY for dinner in two weeks, or take a track driving course and so on. We did buy all of us those Ikon ski passes, and anytime a social contact said they were going to xyz for some skiing next week, at least one of us would join.

Anyhow, there are my random thoughts on our Fat early retirement one year in.

Don't miss work. Enjoying the ability to get out and see others.

Hope some part of this was useful for someone.

​

​

What is your favorite portfolio tracker software (aside from Excel) for tracking both traditional and alternative investments? I have a mix of RE syndications, private lending deals, equity/angel investments, oil and gas leases, traditional stock market investments, etc. Most of the software for portfolio tracking I’ve seen are geared toward public markets and/or more tailored (and priced) for family offices and wealth managers to use with their clients. Any great options for individual investors that you like? Ideally I’d love something that helps track a deal’s pro-forma compared to its actual IRR to help me decide which operators to double down with and which to avoid moving forward (or at least be able to ask more informed questions to those GPs)… but I’ll settle for a great tracker for now that handles all of these kinds of deals in a great visual dashboard. Thanks!

Hello, My first post here. I have been retired now for about two years. I am in my late 40’s and want to build our dream home for the family. I have $12M in private stock that is liquid, but let’s call it gooey in the same way honey is liquid. It takes time to organize a sale. I have other assets including about $4mil in real estate and $1.5M in publicly traded stock.

The challenge is that I don’t want to sell any more stock in these main holdings for a variety of reasons and my dream piece of property just came up for sale. I have been looking for a loan against my private equity stock of around $2.5 M so I can take on this project. Previously First Republic was my bank and would have written this for me, but now what they turned in to are not doing it any longer. Obviously SVB was the other popular choice before... I have not figured out who is filling this loan void and I am hoping someone here knows who I should call?

All I have found so far is stuff sort of equivalent to a hard money loan and I was hoping for something with a longer term. Something structured like a construction loan or long term line of credit against the private stock is my dream… thanks in advance for any help.

Looking for advice from those who have purchased, or swapped, a primary residence while FIREd.

Little about me, 45M, net worth around 6.5M. 4.7 in mix of stocks & bonds and tbills, rest in primary residence . FIREd about 1.5 years ago. Purchased a home in 2020 that was not really a long term thing. Thinking about swapping it for something long term.

I've looked into margin loans and the interest is pretty high. So my plan is to liquidate around 1.6M of tbills , then repay that after the sale of my primary residence. The downside of this is I'm losing the interest on 1.6M while I sell the old home plus some cost while floating both homes.

Anything I'm missing? Anyone else do something like this?

Using alt account because.

I'm an attorney at an east coast firm. I am at approximately at 80% of my FIRE number, which means that if I were to cash out now, I could cover my monthly expenses, but I want that extra 20% as a safety net. If the market keeps moving the way it does, I expect to be at 100% by EOY or in 12 months. But I could pack up and go now.

Ever since realizing that I could go now, my motivation has nosedived. I keep thinking about the books I want to read, instruments I want to play, games I want to explore, countries I want to visit, time I could spend with my parents while they are still around... Instead I am working on bullshit discovery disputes. Who the hell cares.

Why am I not leaving: golden handcuffs. The firm has a LARGE class action that is going well. I am entitled to a percentage of the payout and have a sizable lodestar. The court recently denied defendants' MSJ, and class cert should be an easy win. Trial is next, assuming class cert is approved. If defendants have any sense, they will settle rather than go to trial. If I am right about that, then wrapping up motions and settlement negotiations could conclude by or before EOY. Court approval of the settlement will take a few more months and then the paycheck should be on its way, so 12-18 months from now (though anything might happen of course). I expect the payout to be roughly equivalent to my FIRE number, which would double my FIRE comfort. So staying on until the case pays out makes sense, it's a massive payout if it works out.

Meanwhile, other cases continue... none of which excite me but which I work on. They don't seem to matter to me - I keep having to remind myself that the clients rely on me here and that I have a duty to them. As said, I have zero motivation left to work. Even just making token efforts is grueling. I have asked the firm for a six month sabbatical, and the answer was "no, not if you want to keep your lodestar."

Has anyone dealt with this? How do you motivate yourself when you have the FU money to walk but there's just this big juicy carrot a year or so away that would make walking away the unsmart option?

Tldr without any prompting a business acquaintance managed to save me over 200k usd on some particular investments. There was no contract and he has no expectations for a reward for his service but I feel it justifies some recognition. Is there a rule of thumb people use, is 1% of the gain spend on a dinner or tickets for some concert or something. Or am I overtaking this and just leave it.

I'm currently fatfired and I have minimal unrealized capital gains, and I also expect to have tens of millions in capital gains that has not happened yet, but I do expect to happen later this year or next year. Therefore I'm in a very unique situation where it's very beneficial to go to a tax haven, even if it is just for a year, but I have to do it fast.

I'm seriously considering going to a tax haven as a Canadian and I'm wondering if anyone has advice or contacts to accountants/lawyers that can help advise this. Seems like Nomad Capitalist is not recommended. How about Expat Money?

Also, I would LOVE to have a minimal minimum stay requirement for tax residency. But it seems like most popular places have a 6 month minimum stay requirement. Is there any place that doesn't have a 6 month requirement? I'm even willing to have a minimal amount of capital gains tax, say <5% to have a 2 month or less minimum stay.

Thanks everyone

What necessary (not luxary ones like full time cook or nanny) work and service do you delegate that added value and time to your life? How did you decide the ROI for those?

To start with -

• we do have Home cleaner and Gardner coming every 2nd week.
• we do use Tax Filing services and annual financial review with a flat fee-based advisor.
• Both kids are in high school or college so does not need nanny's help.

Some other things for which we are still looking for a good solution -

1. I do think I can use a travel and booking service but it is hard to find good travel agencies these days in age of internet and google flights. I would surely love to pay someone to find hotel, fights etc for our family travel/vacations based on my requirements and budgets.
2. Cooking - Tried cooks coming to our house but end up stopping that as that become a work by itself and somehow we prefer food cooked by us or go our for dining with friends.
3. Some other not so frequents errands - like shopping for insurance etc.
4. With so much onlne shopping happening these days, hope there is a Uber/Doordash for returning items.
5. We have tried grocery delivey service but does not like the quality of fruits and vegetables delivered as delivery person many time will bring almost spiled products. It does take time but we do go to Costco for grocery but its also kind of serve as adult's visit to toys r us.

​

I've got a 37 ft powered boat I keep in NYC.

I'm curious what the cost / logistics would be to ship it to Europe for the summer (and back). Has anyone done this?

I prefer not to charter since my timelines / dates vary greatly depending on what my wife and I decide to do.

Mentor Monday is your place to discuss relevant early-stage topics, including career advice questions, 'rate my plan' posts, and more numbers-based topics such as 'can I afford XYZ?'. The thread is posted on a once-a-week basis but comments may be left at any time.

In addition to answering questions, more experienced members are also welcome to offer their expertise via a top-level comment. (Eg. "I am a [such and such position] at FAANG / venture capital / biglaw. AMA.")

If a previous top-level comment did not receive a reply then you may try again on subsequent weeks, to a maximum of 3 attempts. However, you should strongly consider re-writing the comment to add additional context or clarity.

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Hey there,

I'm 40, married with 3 kids, and living pretty comfortably with $50MM in index funds. 3 months ago, i sold my 30-person company to a public company with over 100k employees. Since the deal closed, we've hit some serious integration bumps. My enthusiasm has waned, especially since I received 90% of the cash from the sale up front (hahaha). The team trying to integrate us doesn't really understand what we do, even after six months of thorough due diligence.

A big part of why we got a good deal was because we made the company better than it was, and frankly, I was the guy who kept our sales engine running. Now that the money is in the bank, the old 24/7 hustle and bustle just doesn't appeal to me anymore. Frankly, I want to tell the acquirer that it is not my problem anymore and that I will now work 40 hours a week, but I know that they will not be able to manage the company and that sales will drop by 60%.

There are about $3 million in holdbacks over the next two years that I'm tied to, and I'm seriously considering resigning. However, I'm concerned about how that decision might affect the release of those funds In addition, there's a minority shareholder I care about who is not yet financially independent. If I leave, he'll be on his own, which worries me because he's been a big part of my success.

I'm thinking about moving to FATFire, but I want to handle this situation responsibly. If anyone has faced similar circumstances or has any insight on how to handle these post-sale challenges, your advice would be invaluable.

Thanks so much!

edit: to clarify, the minority shareholder got a good payout as part of the deal, mid 7 figures. Not enough to retire, but definitely nothing to be ashamed of!

Thinking about hiring a PA and EA in one but am unsure that I will have enough work for them.

I run a company but have been cutting down and handing over tasks to others. I am CEO and probably will be until I sell in a couple years. I currently work about 15 hours per week and feel happy where I am. I make good coin so money is not the issue ($5-8 million EBITDA and reasonable growth trajectory).

I have kids and a stay at home wife. We have cleaners once a fortnight for several hours but no other staff. I do a lot of stuff myself as a form of exercise, such as mowing lawns, and we don't want people in our home every day. We are very private.

I feel that I don't need a PA more than a 8 hours per week spread out, but if I had one, they would do cleaning, shoping, putting together furniture, errands etc. we don't want someone to raise our children, or to follow us everywhere like a butler. Taking over the little annoying things home owners have, like fixing a sprinkler, or cleaning a car etc. would possibly free me up for more family activities, hobbies, fitness activities, and may lead to new things once there is more space in my head and time.

Work wise, the same applies. I often have nothing that needs doing, but on other occassions may put together a spreadsheet or make some calls for quotes on whatever. It would free me up a bit (maybe cut 2 or 3 hours out of my 15 making that time better utilised either work wise or home).

So they would work partially at my home and my office.

Has anyone that has actually done this, go any advice ?

Is it asking too much to have someone do these things that are different skill sets, even though the tasks are generally basic and I can teach them nonetheless? I certainly don't need two separate individuals as that would be a job in itself.

43M, 2 kids in high school, living in VHCOL area.

• $2M in primary residence, fully paid off.
• $500k in HYSA
• $7M in stocks.

The FatFIRE number I set years ago was $10M, and felt like I am close to hit that goal. While I am not in tech, I've been diligently investing into tech stocks over the years, so the $7M is comprised of concentrated positions across 4 big tech, with LT unrealized gain around 50% of the full amount.

My problem is I am struggling with the approaches I would take now that I am closer to my goal on how to balance minimizing volatility or minimizing tax implication. Here are my options I think:

1. Cash out everything. Pay the one time >$1M tax. Move the remaining to VOO. Low volatility, high tax implication.
2. Leave everything as is. Withdraw as needed. High volatility, low tax implication. Additional benefit is the potential to get the step-up on the cost basis when I pass them to my kids later.
3. Move to exchange fund. Doesn't reduce tax liability, but would reduce the volatility quite a bit.

Any other approaches I am missing? Appreciate the advice.

I’ve done the math, played with the calculators, read the advice, and even though I know I’m financially ready to FI I’m afraid—I’m not mentally ready. I hate my toxic job and my paycheck is 45% of a safe withdrawal rate (3%) of my NW. I’m 45 years old. I know I should prioritize my health and happiness at this point. Can someone please tell me their story or some info that might shake me out of my fear of giving up “more money”? I’m overvaluing the paycheck and treating it as though it’s “free money”, not appreciating the cost. What do you think can help me pull the trigger and finally say FU? Thanks in advance.

Update: Thank you all for the advice and perspective. To be clear I don’t want a different job (even a low stress job)—I want the courage to fire (because I can fatfire now and I want to enjoy retirement). Some of these comments have given me a lot of courage. The job is terrible and those of you who said something along the lines of it’s like I’m waiting for it to get so bad that I’m forced to leave are spot on. So I’m setting a deadline—not for my job to get better (it won’t) but for me to pull the trigger. I’ll be firing this summer whether I feel ready or not. Thank you for slapping some sense into me!

I'm looking for a traveling teacher to educate three young kids full time. The job would consist of a whole lot of travel, and would pay fairly well ($70k-$120k per year), but we want to find somebody with proven credentials and background, who speaks a English and one other language, and probably backed by a trusted agency.

I have heard that this subreddit has a lot of people in the same situation looking for a traveling teacher for their kids, so I thought I'd ask those that have done this!

Thanks a million!

I have had a relationship with JPM private bank now for about a year. This is my first private banking experience as my company has just reached the point of spinning off significant cash over the last five years. I see lots of discussion in this sub about private banking so I thought there might be some interest here.

My experience has been GREAT. I started to look for a private bank after realizing the estate tax exemption is slated to automatically go down next year and would impact me and my estate in a big way. JPM suggested an "Intentionally Defective Grantor Trust" and working with my attorney and a firm in Delaware we got that done and I am so relieved to have a plan. JPM is the trustee and that is not nearly as scary as I had worked it up to be in my mind as I am the investor officer of the trust.

My banking team has helped me invest in some things that would not have been available to me through my old relationship at Schwab like some sovereign debt of other countries and some alternative asset investments.

It is new to me to have to call in stock trade orders and things like that--it is like the old full service brokerages in the seventies and eighties in that regard--but I don't trade much. I get free wires in my checking so I wire even some relatively small amounts of payments sometimes just to keep from generating a check (I had two checks washed last year in my regular checking account at another bank by some thieves and that was a mess to clean up.) I get access to JPM's stock research site and I like digging into that research--it is sort of a hobby for me.

I like my entire family has access to the bankers. My adult kids can get answers to questions and advice on investing and access to things they would not have access to otherwise.

I am glad I found this sub and I hope this post is interesting to some of the group. I do not consider myself retired nor do I plan to as I like running my company and grooming the younger folks to run it after I am gone. I do come and go as I please and travel as I wish so its as close as retirement will be for me I suspect.

I see a few people getting SOFR+80bps on old fatfire posts. Has anyone negotiated a SOFR+110bps or better rate with Schwab in the past 12 months that I can use as reference?

Major first world problem here, but interested in this groups thoughts. Feel free to remove but thought other fatties might have some insights.

A few years ago, my wife and I bought what was intended to be our forever home ~15 miles north of Seattle. We are in the second row of homes off the puget sound in our neighborhood, with an incredible west facing view (so, houses directly on the water, a road, then us) The summer sunsets make every 80 hour work week up til this point worth it, no question about it.

When we purchased the home, there was a utility pole on the road that was blocked by a tree in the yard. Unfortunately, that tree has since died and had to be removed, and so now we look at a utility pole backlit by sunset and the Olympic mountains. We’re debating planting a new tree, but it would take quite a long time for it to block the pole. My question is- has anyone ever pursued moving a utility pole? Or even having a utility company bury the line? Is that even something that can be done? I don’t even know where to begin, but if anyone else has ever had a similar experience, please let me know.

52Y and 50Y old couple with 2 kids, VHCOL, I make $500K and Spouse make $1M annually, both in tech, we are at 44% effective tax rate

* I want to retire now (tired for corporate life) and Spouse want to work for another 2-3 years so kind of thinking of us going in half retirement situation.
* All our savings from W2 income and index/stocks investments. No real estate or business investments till now.
* I want to work on some other investment opportunities for next 2-3 years (like Real Estate investments which potentially help us save some tax as well) till Spouse retire and then we will both retire fully and travel (kids will be at or done with College by that time).
* Spouse working for another 2-3 Years will add another $1.2M in invested assets.

Assets Currently at Half Retirement: $8.25M
Taxable accounts: $6.65M
Tax Deferred and Tax Free Account: $1.6M

Liabilities Currently at Half Retirement:
Mortgage: $450K left at 2% Fixed rate for next 11-12 Years
$2.5M equity in house, not planning to move during retirement

Net Assets Currently (if we pay down Mortgage): $7.8M

Assets Estimated at Full Retirement: $9.4M (assuming market does not fall 20-30% in next 2-3 Years and Assets growth just meet inflation):
Taxable accounts: $7.6M (assuming $1M new assets additions from 2-3 years of more workings and savings)
Tax Deferred and Tax Free Account: $1.8M (assuming $200K new assets additions from 2-3 years 401K and ROTH IRA contributions)

Liabilities at Full Retirement:
Mortgage: $350K left at 2% Fixed rate for next 9-10 Years
Net Assets at Full Retirement (if we pay down Mortgage): $9M

Recurring Expenses after Retirement:
Annual Expenses Estimate: $200K as floor OR $250K (including some extra discretionary items).
These estimated annual expenses include $45000 of Annual Mortgage payments and $35000 as Medical Insurance costs.
Assuming $9.4M total assets, this will be roughly 3% annual withdrawal ($282K) and assuming 15% as total long term capital gain, that should leave roughly $240K for our annual expenses.
If the market turns very bad, one option is to pay down the remaining mortgage of $350K to reduce the future annual expenses by $45000 and then bring annual withdrawal to around 2.5 to 2.75%%.

One Time Expenses after Retirement:
Lump Sum Expenses for the first 10 Years of Retirement: Roughly $1M
This includes some Education expenses for kids, car changes, house remodeling, kids marriage etc. Have some one in 529 for kids education but will need some from my investments as well if they decide to go to a private college or do masters, hence this lump sum amount.

Asset Allocation: 50% US Stocks, 25% International, 15% Short to Intermediate Bonds, 10% Money Market Funds

Question 1. Can I half retire now and we both can fully retire in 2-3 years? Looking at my cashflow for first 10 years of retirement (showing roughly $3M expenses including $2M of 10 years annual expenses as floor and $1M in one time expenses), we are feeling little uncomfortable and feel I should work for another 2-3 years to add another $600-700K in savings even though I am very tired for corporate BS.

Question 2. Based on a CAPE ratio of 34, market valuation seems very high and it may go down in the next 2-3 years or 2-3 years after our full retirement. Do we need to worry about bad sequence of returns at 3% withdrawal rate (EDIT: 3.25 - 3.5% withdrawal rate)? If Yes, What steps/plan should we take now to avoid a possible bad sequence of returns at our full retirement time? Seems like we have following options, which one you suggested is best for our situation -
(a) Stay flexible in withdrawal after retirement based on market returns and inflation at that time, based on our assets size and assets allocation we should be able to ride a bad market sequence of return by withdrawing little less during bad market times and not making any change in our investment plan from point “b” or “c” below.
(b) Create a Bond tent around retirement years by increasing the $ allocation to Bonds, like 3 years before retirement and 3 years after retirement. What kind of Bonds investments will be more suitable for us with our situation/assets size and current market conditions for Bonds/interest rates?
(c) Keeping a fixed amount for 5 years expenses in very safe investments (like bucket approach)

Question 3. We are planning to take $1M cash out from current investment for some real estate investment with an expected CAP rate of 5%, how will that impact my plan?

EDIT: I am thinking of this Real Estate not as hobby even though it will help me stay busy. I am planning for this for some diversification, income and possible tax benefits purpose. Hopefully I will be able to save some tax from spouse's W2 income using these real estate investment (hopefully by qualifying as a Real Estate Professional).

Question 4. Should we pay down mortgage before we retire in 2-3 years to reduce the withdrawal rates at retirement as higher withdrawal may kick in 3.8% Net Investment Income Tax as well?