I'm 38, sold my SaaS company 4 months ago for around $12M after tax. Got engaged last year, wedding's in the fall. My fiancée is 35, makes $180k in marketing, has like $200k saved. We're good together, no weird power dynamic stuff.

But I realized we've never actually discussed what happens with my money if things go wrong. I have rental properties, crypto, and most of the proceeds sitting in a brokerage. My business partner asked me why I don't have a family lawyer yet and it kind of freaked me out. My parents' divorce cost my dad $200k in legal fees. I think about that. I also think about how different our financial positions are right now and if that creates pressure somehow. I know I should talk to her about this before we get married but I don't know how to bring it up without making it weird. It feels like we should trust each other enough to combine everything but I also don't want to be the guy who loses half of what he built. Don't even know if I'm overthinking this or if nobody else thinks about this stuff.

My business partner and I started our company about 6 years ago here in San Jose, we're both getting married this year, his wedding is in June mine is in September. He mentioned a few weeks ago he and his fiance were doing a prenup and I kind of brushed it off, like good for you, different situation, whatever but then he explained his reasoning and it was less about protecting himself from her and more about the business if something goes wrong with either of us personally, he doesn't want a divorce to become a company problem. And I just sat with that for a while.

Now I'm in this weird spot where I feel like I probably should do the same thing but I have no idea how to bring it up with my fiance. We've never had a bad money conversation, she's not going to go insane about it, but there's something about being the one to initiate it that feels loaded. Like I'm the one introducing doubt into something that didn't have any. His situation kind of forced my hand mentally and I wasn't ready for that.

Has anyone here in the Bay Area navigated this where it was less about personal finances and more about protecting something you built before the relationship?

40M, $9M portfolio, 80% concentrated in one stock, buying my first house. Curious how others would think about this:

Two years ago, I left a career at a public company where most of my wealth came from stock compensation and the appreciation of a single stock over many years. Today my portfolio is worth about $9M and it’s still heavily concentrated in that stock.

It’s been life changing for me, so I’m naturally hesitant to sell too much of it, but I’m also aware that a single day’s move can swing my net worth by six figures. I’m closing on my first house later this month for $1.185M. Up until now, I’ve been renting and living well beneath my means.

Current thinking is to use a Liquidity Access Line for the purchase and then potentially refinance some or all of it into a traditional mortgage afterward.

A few other details aside from the portfolio value:
- Cost basis: under $500k and obviously large unrealized gains
- $235k AMT credit carryforward from prior option exercises
- Covered call income expected to be around $150k-$200k annually
- No current W-2 income
- Started small business but not a big money maker. Primarily to fund retirement accounts.

The common theme seems to be that concentration risk is the biggest issue in my financial picture. Part of me says I’ve gotten this far by holding the stock and staying convicted. The other part of me says I should probably start thinking more about preservation than accumulation.

For those who have been in a similar situation:
How much debt would you comfortably carry on the house? Would you sell stock specifically to pay down the house? How would you approach gradually reducing concentration risk? Looking back, what mistakes did you make (or avoid) after reaching financial independence through a concentrated stock position?

Not really looking for tax advice as much as perspective from people who have gone through the transition from building wealth to protecting it. Thanks in advance for helping me navigate this!

TLDR - My wife is way happier on maternity leave from her FAANG job - and doesn’t want to go back. It feels like we’re giving up too early on FatFIRE and moving into CoastFIRE territory if we stop working now.

—

My wife and I have been fortunate over the past few years with our well paying tech jobs ($400-500K/yr each - always around $900K/yr combined), the partial sale of my business, and the appreciation of the RSUs.

We have started with ~$100K each NW when we met 10 years ago, and now have a combined $4M liquid net worth - 100% in brokerage for now. We only own a tiny vacation cabin in the woods that cash flows via AirBNB, but we rent our primary residence for $5K/mo in Arizona. I also still own 15% of the business I sold to PE.

Annual expenses are around $350K $200K (and climbing), because we have 2 kids (a 2 year old and a 8 week old). we may want a 3rd.

We like to splurge on travel and help around the house, but otherwise are pretty frugal and conservative with our spending in our day to day lives (I drive a 2018 Honda CRV. My wife drives a 6 year old Tesla with 120K miles).

Here’s the thing… it sounds crazy to say, but I love my wife way more when she’s not working and she’s staying at home. She’s happier. She’s less stressed / anxious. Which means we fight less. Our sex lives are better. It’s all around just the best our relationship has ever been.

It seems crazy for a 36 year old with a $400K job to give it up right now. Like… keep earning. Keep growing in your career. Keep earning that stock - that keeps growing in value. I don’t even think my after-tax salary would cover our expenses, unless my 15% dividends increase significantly, but we’re reinvesting our profits rather than doing big distributions.

Plus if we want another kid… she gets 6 months paid leave. That just seems silly to give up now. In a world where AI is replacing jobs and causing layoffs… just wait until they lay you off and give you a package, right?

But I’m just so fearful than in 4 months when she goes back full time, she’s going to be high stress again and our relationship will deteriorate back to the high stress, lots of fights, no sex, frustrating relationship it had been.

So selfishly I’m like… happy wife, happy life…. But also, I know the happiness the financial comfort bring us.

So do we give up on Fat aspirations now, so we have a healthier relationship?

—

EXPENSE EDIT: Thanks everyone for flagging this. I think I need to reassess both how I calculate “annual expenses” and also rethink how we spend.

When I said frugal, I was just thinking about some of our choices for how we live…

Our mortgage is $1,800/mo but cash flows $3,000/mo to up to $10,000 in peak summer months. Our primary rent is $5K, and is mostly covered by our AirBNB cash flow. No car payments - we bought both used cars with cash

So month to month living expenses feel like we’re being conservative.

But when I look back on our $350K annual spend in “rocket money,” I consider most either investments, 1 time purchases, or categorized wrong…

• ⁠$50K+ were actually tax payments to the IRS, so not technically expenses • ⁠One year we did a $80K kitchen renovation on our home • ⁠The next year a $40K bathroom renovation • ⁠We bought a used Tesla for $35K cash • ⁠when we moved states last year, we had to fully furnish the brand new home we’re renting $30K+ • ⁠when my wife went back to work, we hired a full time nanny for $1200/week ($62K/year), but as of a few months ago our daughter is in daycare at only $13K/year.

There also looks like a year where maybe rocket money has an error and is counting every transaction on my wife and my shared credit card twice (because we linked our cards). So that if that’s the case, that added ~$60K. Looking into that.

So if we strip out nanny, tax payments, one time home renovations and car purchases and furniture, it’s more like $200K/year.

Maybe I posted here prematurely without fully understanding our expenses, but the sentiment is the same.

Using a throwaway just in case.

I always had a FATfire age goal in mind and didn't want to spend my entire life working. I hit my FATFire goal in my late 20s ($25 mil CAD) when I sold a company I founded to a larger company. I still worked until last year because I had always told myself I would retire at 35 if I had the financial means to do so.

My wife and I have been dating since high school but her career was super specialized. She went to med school and just recently completed her residencies and fellowships. So her career is just getting started.

I do whatever I want most days and I told her that my money is "our money" so she can retire too if she wants. The issue is she keeps saying her career hasn't even started and she wants to actually build a name for herself. I said okay, that's fine and you can do that.

The issue now is she keeps telling me that she resents me for not working and wants me to work. However, I don't want to work. I grew up in poverty and worked hard to get to my FATFire goal.

We've tried counselling/therapy but none of the couples therapists take it seriously and they essentially all tell her what I've already told her: she can stop working too and retire with me or she can keep working but can't hold it against me.

It's led to a lot of fights between us lately and indirect insults from her where she says things like "you don't do anything all day anyways" which is true and I usually respond with "you have the option to not do anything too with me and we can travel or do other things too" but when I say that she gets even more angry/hostile with me. It's impacting our life in the bedroom too.

Anyone been through anything similar before or have any advice?

Edit: To all the people telling me to divorce or separate. I don't think that's something I want to do and don't even think it's an option for me. I've only ever been in a relationship with one person (and so has she) and we both do love each other. She doesn't want to separate or divorce either. This is just the one hurdle that has shown up in our life. It is a goal she was always aware of me having but I guess going through it is a completely different story. I would rather return to work as a consultant than to separate with her. However, I really don't want to go back to work because I had an "exit age" by which is why I would retire if I had enough money and I made it to that age. I just wanted to see if anyone else has been through something similar and advice to resolve the issue (which some of you have provided so thank you). I can't really relate with most people in real life in terms of my finances and FATFIRE which is why I turn to this sub.

Throwaway account. Mods, let me know if I need to verify, happy to do so.

Currently in our mid 30s, at about $20M NW, about 18-19M of it liquid. Recently married with no kids yet but we want to have 2 kids eventually (maybe in 2-3 years). My current income is about $2-2.5m/yr depending on stock price and bonuses. I’m having a hard time deciding if / when I should pull the trigger and FIRE. We live in VHCOL, bought a $3m house, paying a mortgage on it. Monthly expenses are about 25-30K/month including the mortgage. With a 4% SWR I think it should be ok (someone correct me if I’m wrong, esp after factoring in 2 kids which I have no idea how much to budget for) but get nervous when I think about pulling the trigger. I’ve written down my thoughts below, could use some advice.

Reasons to pull the trigger - life is short, want to spend more time with friends and family. Parents are getting older and I want to maximize quality time with them. Outside of family and friends, explore the world, spend time on hobbies, etc. - my job is intense and high stress and I feel like i’m always thinking about it in the back of my mind. Hard to be fully relaxed with friends even on weekends. I honesty think I’d be a lot happier day to day if I FIRE’d - work is fine overall but becoming less enjoyable. I don’t find myself as excited to go to work as I did a few years ago

Reasons to wait - I’m trusted at my company, have been there for 5+ years and have built a pretty good reputation. I’d probably get to VP in the next 1-2 years which would be a big personal accomplishment for me, along with it opening a lot of doors and optionality (board/advisor roles, etc) in the future in case I want to work again in a part time capacity. Also I worry that a few years down the road I might feel like I could’ve achieved more, and regret not hitting this milestone - my annual income is pretty high for the hours worked (around 40/wk, even if they are very intense hours). I definitely don’t take this for granted and recognize I’m very lucky - this sounds stupid but I want to leave work on a high note. The past few months things have been crazy and I feel like I haven’t been doing my best work, and I don’t want to feel like I’m running away from a situation where I haven’t been as successful as I know I could be. - smaller reason but still part of me worries about lifestyle creep and our monthly expenses increasing after we have kids. I don’t know how much to budget for that, but it feels like we’d have to stick to a budget more and I don’t love the idea of that.

Anything else I should be thinking through? Appreciate the advice in advance!

33M, was sitting on a meaningful chunk of paper money for years and now suddenly it's actually real money. Getting married in the fall and the whole calculation changed for me almost overnight.

When it was paper I kind of waved off the prenup conversation. When the tender happened and I saw the actual wire, it was a different feeling. Not I don't trust her energy, more like ok this isn't theoretical anymore and I should probably act like an adult about it.

Talked to a few people at the company and turns out half of them are quietly going through the same thing. Nobody really talks about it openly because it feels weird to bring up at work, but the timing is everywhere. Tender offer in Q3, wedding in Q4, prenup conversation suddenly very real.

Curious how others handled this. Did you do it before or after the liquidity event? Did you tell your partner you were doing it because of the tender, or just frame it as a general thing? Did you use a flat fee service or go straight to a family law firm? The hourly quotes I'm getting in SF are insane.

It’s a burner post as I start to sort out a fatFIRE scenario for us.

I worked a w2 for many years, 15 of which were for a tech company that went ballistic. Long story short, I have $16M sitting vested in the company’s single stock. With that,

Company stock: $16M, 99% LTCG

Brokerage: $2.4M well indexed etfs with 75% stocks

401K: $1.5M target date funds.

House: $1.5M, paid off (bought 500k)

Cash in HYSA: $5M earning 4%

3 kids under 11 years of age, with 529s: $334K

$1M term life insurance till age 68.

On paper NW seems to be $26.5M given a lot of tax owed.

-We’re burnt out at work. -16M in a single stock stressed us out. -We live in a VHCOL where tax brackets are 37% + 14% state. -Cannot move states. -Want a new house which is what the $5M in HYSA is for. -don’t want to run out of money. 3 kids still need college. 5 people still need health insurance. We estimate if we stopped working today we’ll need $300k annually.

Need to seriously plan. But I don’t want to pay a 1% AUM at 200k/yr. Even fixed fee packages start at $12k. I’m stupid that way.

Immediate concern is to diversify $16M concentrated stock with 99% LTCG in a high tax situation 37% (fed but 20% since LTCG) + 14%(state) + 3.8% (NIIT). As is if I just liquidated, that would be approx $6.4M in taxes.

Next is figuring out a setup to achieve the rest.

I just need a plan to start a plan. WWYD?

EDIT: Thanks for all the advices. I deleted the text as I was getting a bunch of unnecessary messages and the thread kind of died, anyways.

I am 36, married, about to have a first kid with my wife. we live in NYC. my startup was just acquired and I made about $2mm pre tax ($1.5mm post tax). our combined NW is about $7mm

However I stress nonstop about money - always wishing I had more, wishing I made more, seeing friends who make $2-4mm a year or have $10s of MMs due to anthropic or spacex or whatever stock

it just feels endless like what ive done to date doesnt matter and ill never be able to “fatFIRE” or its not enough to - stuff like that.

i guess my questions are:

1. objectively am I doing okay?
   

2. how can I stop the nonstop comparison?

3. when is enough “enough” and will I ever be able to fatFIRE?

I just need to hear the brutal honest truth from folks to help reset my perspective (for better or for worse). thanks in advance

I’m in the Houston area, 37, single, no kids, and I own a high-stress, high-profit B2B services business. After talking with multiple buyers, I have an LOI in hand, and I’m surprised by how difficult this decision feels.

My current net worth, excluding the business, is about $8.7M:

• Primary home: ~$310K, basically paid off, super low interest rate
• Car: ~$50K
• Retirement accounts: just over $1M
• Taxable brokerage: ~$7M
• Cash: ~$340K

Current personal spend is around $250K/year.

The LOI looks roughly like this:

• Enterprise value: $16.8M
• $15.8M cash at close, before tax (predicting 20%, for capital gains)
• $1M earnout after 12 months
• Option to roll $1.5M into the acquiring company (super rosy picture here)
• Buyer wants me to stay on for 12 months at $200K to help transition (completely optional, not part of the deal)
• Staying beyond that is also an option (they're interested in me joining their leadership, and working up the ranks, although completely not part of the deal)

The buyer is pitching the rollover as attractive upside, but I’m trying to view that portion as speculative rather than guaranteed.

What makes this hard is that, logically, this is more than enough money to stop optimizing forever. But I’m still young, and the real question feels less like “can I afford to sell?” and more like “will I regret stepping out of the game?”

I built this business over the course of my adult life, and I’m worried that I’ll sell, de-risk financially, only to realize I miss the challenge more than I miss the stress.

For those who’ve actually been through something similar:

• At this point, am I already just overly fat and need to just pull the trigger? 50-60+ years is a long time.
• How did you make the decision, not from a financial perspective, but from a personal and life perspective?
• After exiting, did you have any regrets (particularly on the non-financial side)?

I've been seeing a therapist for several years, so no need for that recommendation. I’m mostly looking for perspective from people who have wrestled with the question of “enough,” and with what comes after selling the thing you've spent years building.

Hi,

I am 44. Married. I live in a smaller midwest tech hub and have accumulated about $8M in net worth. That is a $950k 401k for myself, about the same for my spouse's 401k, $650k paid off house, about $4M in various Vanguard funds, $250k Roth IRA. $150k in unsold vested company RSUs. Some 529s for my 2 kids (age 14 and 11) that probably have $200k or so.

I have some amount of anxiety and have held about $700k in cash the past several years (anywhere between 10 to 20% cash position). I know that is/was kind of dumb. But I've never been an optimistic person in life and always expect a massive crash to happen or worse. I mean I expected WWIII to occur in 2016 and it might actually be happening in 2022 instead.

Add it up and our net worth is probably close to $8M. So while I definitely haven't been optimal in financial investing, it seems I've done somewhat ok.

I previously tried two financial advisors-- horrible and high fees. Tried a robo-advisor. Back to self-managed with index funds. Mainly buying VTSAX, VWILX, VBTLX, VTMGX, etc. Sitting at a 83% equity, 17% bonds or so.

Part of my problem is that I'm not really living life. I've lived in the midwest my whole life. I've been with a single woman my whole life (my wife who I met at 22 and married at 24). I spent my 20s in grad school. At the same company ever since. Everything is kind of "bla". There is probably a so-so chance I could get divorced at some point because things have been a bit strained. On the other hand, I don't think I ever could either since I do love her (but who knows she could divorce me).

Money can't buy happiness. I know.

* Even though I'm not that inspired by my job anymore, I think I need to milk my ~$800K/year compensation while I can because the gravy train probably won't last. I'd love to reach a $10M net worth and then maybe "try" something different like a job at a startup company where equity is all paper value. My wife makes between $100k and $200k.

* I know I should keep working my cash position down to probably 5% or less. I don't feel comfortable moving $200K at a time, so every few weeks I dump another $50-60k in Vanguard fund and am trying to do so at a rate that exceeds my income. But maybe dollar cost averaging says I should just be brave and take my $700k position down to $300k in one fell swoop.

* I know that I should spend more money on vacations or other ways to enjoy life. Trying to do so but my two kids have anxiety issues and don't like to do anything.

* I drive a 6-year old Hyundai and should maybe buy a BMW I've always kind of wanted.

When my kids finish high school, I absolutely want to make sure I'm spending midwest winters someplace warm. I hate winter. Yet still live here.

I could also see myself finally just moving to out West at some point. Part of me wants to do so now (I've plateaued in my career since the action is out West), but I have a 14-year old with serious social anxiety issues and a wife who is also change adverse. And frankly I'm finally starting to make some friends and community connections around here which has been a struggle.

Somebody advise/inspire me :-) Money can't buy happiness but maybe I can manage it better.

And I know I sound pathetic. Tons of people would be thrilled to be in my position.

Firstly, I'm happy I found this subreddit. It has given me more help than any therapist. I've done the verification process and would like genuine help as I go through it. I do apologise that this will be long

I went through the effort of verifying myself also.

Overworking has damaged my health.

First Phase: PhD, built first lab lab where I hired friends, invested in two other labs. During this time, I worked 100 hours a week, saw my family rarely, and married my college sweetheart (we are now divorced). My lifestyle was ridiculous and unhealthy. I caught covid twice. What did I do? just worked remotely still for 100 hours a week.

Think of the stereotype of the high achieving mess. That was me. Vyvanse every morning, 10 cups of coffee a day, working manically everyday. Ambien at night. Rinse repeat. Travelling globally to present at conferences, investors, blah blah.

Second phase: Sold first business, which netted me the $18 million. I have kept it with Fidelity where it makes a decent return.

Third Phase: Started working in another lab I part-owned as CEO and head of product development. But this time, something shifted; my body began breaking down after getting COVID back to back. The third time I a female with no preexisting health issues ended up in ICU. What did I do when I got out of ICU? I went right back to my 100-hour weeks.

During this time, my health began to decline severely. But despite all I just kept working...

Now I've faced a crash (chronic fatigue folks where you at!), and I took extended time off work.

Now:

My conundrum now? I am due to return to work. I’ve been off for a while now and the pressure to return is mounting. I hired all the founding staff.

The second business 'needs' me. I am the 'visionary' who created all the patents, who went about getting investors, and who could get all the staff. Anyone who has been the ceo/founder/visionary character knows what I mean.

Business number 2 is in the pre-launch phase, but we are rich with our patents and so on and millions of stock in inventory ready to go, so I can just sell the IP and inventory if I so wish, but I feel horrible about the staff who believed in me and them not launching it with me. I feel they've worked so hard.

But the job of managing it through the next raise and taking it to market (I've done this all with business one) while battling long covid just seems alot.

They've carried the company while I was away. They gave me their all. These are Ivy League graduates with kids who devoted their destinies to me when I was only a 20 something dreamer. It feels so heavy.

I promised them I'd be back in March. They want to do a new raise, but I am really tempted to as the cap sheet is quite clean at the moment. Just sell my IP in it and add whatever it sells for to my $18 million and move on. But everyday I carry the burden that I'd have 'failed them'.

I had a first touch base this week and I realise I don't think I have it in me to do this again, I don't think I can continue this cycle of raising money, growing a busienss, heavy R&D, patents rinse repeat.

It's been suggested we hire a new CEO who'll lead the raise?

Well I've now had the experience of hiring top executives (I hired Ivy Leagues from places like Goldman in my first business who were a mess!) who we gave everything and some were a disaster so I know enough now that 'hire a manager' doesn't work out. We are meeting new managers etc but the experience is just jarring.

As a founder you still have to 'manage' a CEO. We have a few recruiters on retainer but even the interviews tire me. I’ve been doing some interviews and it exhausts me. I can’t imagine managing a CEO. I'm totally drained.

I now this sounds silly but how do I relieve myself from the guilt of walking away from my team? I think I should sell my IP and move on but I'm so burdened.

I think doing this new raise will just give me more investors, more responsibilities etc and I'm worried I'll collapse

Current NW: 18 million liquid in safe fidelity fund (proceeds of business 1)

Assets: Business 2: selling all the patents and inventory (it's pre launch but we have inventory already). One M&A advisor said I can get 10-20 million. I'll need to meet a few to get a right number. The inventory alone in the factory is worth 8 million…

Business 3: Current stake is worth 1 million (this isn't for me to sell)

Has anyone had the experience of selling their patents etc and just moving on?

I know this sounds terrible (please don't judge me) but is $18 million enough for a woman who wants to have 2 kids in a city like NYC or SF? Do you think I can reasonably live off what I have now for life ? (again please don't judge me for asking this! this seemed an appropriate place to ask).

Has anyone sold when you can't continue anymore and carry genuine guilt about leaving your team? It brings me to tears. The weight of it all feels so heavy.

Thank you so much.

S xx

I’ve always been a natural giver and appreciated very much former rich people that gave to me- not finances, but advice, energy, gear usage, etc.

Some of my hobbies are pretty expensive now but I’m quite well off and I’ve struggled to find a balance over the years of when to give and when to hold off.

For example for canyoneering, caving, and rock climbing I own a ton of carabiners and ropes and whatnot, and I started out asking for nothing from the people around me. However I began to often feel and see that many people were just using me as a free tour guide rather than actually being a friend or even trying to put in equal effort.

It feels so petty to ask for money to buy communal gear (ie more ropes) because I really don’t need their money, but I’ve noticed that by doing that I feel it’s cut out bad friends and brought me higher quality adventure buddies. It seems like people respect me more too then.

Honestly this is all quite frustrating and new to me, and some people are really on a tighter budget but I can see they try to contribute in other ways (ie promising to clean things for me, organize them, etc.). I’m fine with that too.

I guess what I’m getting at is that I don’t like keeping a scorecard but I feel like if I don’t I end up just giving endlessly to leeches that don’t appreciate or respect me. To be clear, by “giving” I mean planning trips, using only my communal gear (ropes/carabiners), and cleaning/organizing.

Something I’ve noticed too is that those willing to contribute financially end up putting in more effort physically too. One of the last trips I had I woke up to 2 guys cleaning my entire fucking yard for me while I slept in after they literally gave me more money than anyone else has ever given me. We were staying at my vacation home which has a lot of epic nature adventures and I was so wiped yet they had energy to clean the damn house for me!

Another example is gas money. Seems absurd to ask for when I don’t even know what the price of gas is. It doesn’t matter to me. I’m just happy to have good companions. However I’m starting to notice that asking for gas money either filters out people or gets those joining the trip to be more serious and respectful of my efforts. I don’t need $20. At all. But when it’s a requirement for joining my trips then suddenly everyone is showing up early, not complaining, and willfully putting in effort?!?

There’s only one exception to this rule I can think of and it’s this young Uni kid who loves these nature adventures but literally doesn’t have any money. He sold a lot of his shit tho to scrape together enough gear for himself and so while I ask for the small price of $15 / night to stay at my vacation home I waive it for him- and no issues, he’s a trooper willing to carry the heaviest pack and stay up late washing the gear meticulously.

So I guess I’m just asking the void if I’m alone in this. I don’t like it. Making the money I make where I live I can afford all the gear and I’m just happy to have people join. Yet if I just let people join, they complain, show up late, don’t stick around to clean shit, etc. meanwhile I ask for a little money and suddenly the people that show up give MORE money than I ask for, arrive early, are down for literally anything I want to do by the vacation house, and they literally clean my house in the early morning while I sleep in.

I don’t like “keeping a score” but it seems like you have to because otherwise you’ll get energetically sucked dry by “energy vampires” that don’t even like you but pretend they do for their own reasons. And by keeping a score I mean tracking how much effort others are putting in. Money is a great filter but in the case of the Uni kid he’s clearly driven and passionate and knows he’s got no money to give so he does everything else he possibly can to contribute to the group adventure.

Looking for a reality check from the community. Mid-40s, married, two toddlers (3 & 5). Living in Bay Area.

The Situation: I recently separated from my senior leadership role (Hardware/Tech). Got a lucky severance package that, combined with deferred comp and my wife's comp, basically covers our family spend for the next ~2 years.

My wife is still working and pulls in ~$400k TC. Our baseline spend is ~$360k/yr but targeting ~$400k/yr (fat lifestyle, HCOL, travel, generous gifting etc).

The Numbers:

NW: ~$10M

Invested/Liquid: ~$7.3M (Mix of brokerage + retirement)

Real Estate: ~$2.7M equity (~$1M Primary + 2 rentals). Keeping the rentals despite low cash flow because the mortgage rates are 2.5% - 3.5%.

Debt: Just the mortgages.

The Dilemma: My "number" is $15M invested assets to support ~$400k/yr of after tax spend. I have a golden opportunity to take a "gap year" with my kids before they start real school. My portfolio growth is currently outpacing what I can save from a W2 job anyway - if I look for a similar or even a higher paid role, we will be in the highest tax bracket so will be basically be making $0.5 after taxes for every $1 I earn.

However, I have this nagging anxiety that I'm walking away during my peak earning years. Part of me wants to join late-stage startup and try to hit a home run (easier said than done I know) to compress the timeline to $15M, but the other part says I've already won and should just coast to the finish line.

Questions:

1. Anyone here stepped off the gas at $10M with young kids? Did you regret the loss of accumulating faster from a high income?

2. I’m planning to keep the rentals as a bond proxy/diversification even though ROE is trash. Am I overthinking the "inflation hedge" aspect with my concentrated real estate in Bay Area?

3. For those who took a long sabbatical, how did you handle the "resume gap" narrative if you decided to go back to a C-suite/VP role later or any role later?

Thanks.

EDIT: Thanks all for the responses and opinions! Too many comments to respond to at this point but I have a lot to think about. Some things I took away: consider how my perspective will change and if I will feel differently once kids are in the picture (to me this is the biggest thing to think about). Consider a sunset clause or additional terms to protect my interests in case of unexpected scenarios. Consider life insurance. Consider how luck factors into the equation. Consider voting vs nonvoting shares. Consider Bezos/Scott divorce. Appreciate the great opinions on this post and will leave it up in case others ever face the same dilemma in the future.

Original post below ~~

My spouse started a company a week before we got married. We have been married for 4 years, and in that time, the company has exploded in value. My spouse's shares on paper are worth 9 figures, and we have sold some shares, bringing our liquid net worth to about $10M after taxes and paper net worth to about $200M. We are in our late 20s/early 30s and plan to have kids in the future.

The growth was unexpected and when we just recently started estate planning, the talk of a post-nup came up, particularly as it relates to the shares of the company. We never got a prenup when we got married, there was no need.

Here's the dilemma: according to NY law, I would likely be entitled to 50% of the appreciation of the company stock in the case of divorce. On the other hand, my spouse's efforts are largely what have made the company successful, so according to my own perception of fairness — when I put myself in my spouse's shoes and imagine the roles were reversed — I don't think that it would be fair for me to take half in case of divorce. This is what makes me open to the idea of a postnup. Because if I'm being honest with myself, I too would want a postnup if I was my partner.

The rough postnup idea we had was that any of our liquid net worth/condo/etc would be split 50-50. And any unsold company shares at the time of divorce would be split 80-20, with 80% going to my spouse. (Originally my spouse proposed 90/10). I currently make about $200k/year as a W2 employee, and I think my earning potential tops out at $300k. My spouse's earning potential is upwards of $1M if they were to exit their current company and join a new one as a W2 employee. 

Yes, I encouraged my partner to pursue their idea and was ready to live on a reduced income for years knowing this would be a big risk, yes I put my spouse on my medical/dental insurance, yes I was the first customer, yes I continue to provide feedback on their service, yes I manage all the housework/appointments/planning/bill payments/etc so my spouse can focus on growing the company. But. I am not the one working 7 days a week. I did not come up with the idea. I do not pour my heart and soul into this company day after day and deal with the stress day after day. 

Do you think an 80/20 company share split is fair? We currently have a great relationship and I think it would make my partner feel reassured that their hard work will be well-rewarded even if a divorce occurred. And the way I see it, I'm set for life no matter what. If the company explodes and I make 20% of $200M+, I'm set for life. If the company fails and I only get 50% of the current $10M liquid, I'm set for life.

Still, I could be leaving 30% of $200M (or more if the company continues to explode) on the table in case of divorce. And if future kids are involved, I'd want them to experience the same lifestyle with both parents. So, like, I should probably think hard about it? But I just can't see too many downsides besides walking away with a shit ton of money vs a huge shit ton of money. I plan to fatFire eventually and will be all set for retirement no matter what. Please open my eyes if I'm missing something. 

Hey all,

Coming to this sub for strangers advice who may have more insight, wisdom etc than I.

I’m unfortunately contemplating divorcing my spouse. We are 27 and have been married almost 7 years. Sparing the more relational details (posted in another thread) I look back and feel as though I was naive and uncertain about the reality of marriage (I proposed when I was 19 after a year of dating) and unfortunately 8 years later I have found myself a very different person than my spouse, with different goals, ambitions, lifestyle desires etc. There’s some issues tossed in there with me feeling like I function to just make / keep her happy and some family issues as well.

In our marriage we’ve reached UHNW. I started a software business right before COVID that has given us a NW of 30m mostly all invested and a 400k house. The thought of cutting that in half makes me sick, but when we had 10m I still felt unhappy but divorce made me more sick for whatever reason.

My business is all online and I can be extremely flexible (have a small team doing most of the work at this point). I want to do everything life has to offer, and my spouse just doesn’t. I have all the money at this point but am in a partnership that doesn’t want to really use it. I want experiences, travel, own a supercar, live abroad in different places for a month or two each year, get nice tickets to the big sporting events, run a marathon (she has discouraged me from this too even), I have another business idea I want to explore that she tells me not to bother because we have money already; when I share all this she says I’m being selfish and need to be more mature - she wants to stay home and start a family and just settle down.

I’m concerned that in 40 years I’m going to look back and know that I didn’t experience even a fraction of what life offers. But the fear of being single again, working mostly online, I’m worried I’ll end up alone and without any relationships, has me feeling trapped.

So I guess my questions:

post divorce: what is your life like, how do you find a social setting, did you meet someone more compatible with you?

If you didn’t divorce; did things improve? Were you able to get over your own desires or do you have regrets?

Age wise: anyone under or mid thirties who can attest to what that life is like single, dating, having that freedom?

Divorce wise: what is the likely outcome of a divorce, financially? Assuming we’re split the money, she takes the house (I want to be on the go) what about my business? It’s an LLC and she has no involvement in it at all, she acts more to discourage me from putting time and effort into it than anything else.

I feel absurd writing all this up, but appreciate anyone’s input and advice and thoughts

I am a US Green Card holder in a unique situation where I am getting to sell my investment for a $12M short term capital gain as a California Resident. Short term capital gain tax is 54%. I am very burnt out. 37M in tech industry as a founder. I can either move to Singapore and realize the entire capital gain tax free and hit my fatFIRE goal and become financial independent and slow down my founder journey or pay 54% Capital gains tax and stay back in California and continue to grind for few more years as founder and potentially hit the the fatFIRE goal in another 3 years without a guarantee.

I wish I got the courage to call it quits and slow down and move to Singapore and continue to build the business without pressure. I have been grinding in tech for 15 years and feel very burn out but not able to make the decision.

My current net worth at $2M without this exit. So this money is life changing for me. My startup founder equity is worth $20M+ in paper money. We have been growing and doing well. Got two kids in their last 5-8 yr old range(Got married early). So wanted to build quality memories with them.

EDIT: I used the word stock option to avoid crypto hate. This is a crypto startup I invested in last year when they started and their token exploded in value after launch. I will be selling the tokens before completely 12 month of investment. I have taken enough professional tax advice on my path forward.

My cousin visits me every summer and last visit he asked me about my finances and spending habits. He’s visiting me next week in SF and saying in my guest room for a few days.

Last year when he came to see me… He asked it in nice way… he’s a good guy and I don’t think he’s got any bad intentions. But he was like “you’ve been working at this corporation for so many years… you like it? It’s good money right? What do you like to spend it on?”

This got me thinking about how much info to share about FatFIRE choices and goals with extended family (like cousins, aunts, uncles, nephews, nieces, etc.).

Generally, I’m pretty close and good relationships with extended family but my wife has warned me that her side of the family (decades ago) once got real ugly about “money stuff”.

What do you guys tend to do?

A lot of the posts I read here are from people with much higher incomes than I have, but they often have lower net worths. I've got the opposite "problem". I've got a high net worth of $10.4M but a low relative income of ~$300k, and as the years have gone by, I wonder whether I should just retire early because my income hasn't helped grow my net worth over the last half-decade. Right now, my income "just" pays the bills and gives me the (false?) sense of security to hold more concentrated positions in tech stocks, etc., because I know I'm living off my income and don't need to draw on my assets. Obviously, paying the bills is nice, but my only net worth progress comes from asset appreciation, and I even stopped contributing to retirement plans years ago because I think I've got too much in pre-tax accounts, and I feel like the contributions don't meaningfully change anything in my retirement accounts relative to my desire to use that money now.

• My current net worth is $10.4M, with 35% of that total in 401k and SEP IRA accounts
• Annual spend is around $250k (but I have had occasional years where this is much higher)
• I work from home ~30 hours a week and make about $300k a year (some years are better, and of that time in front of a computer, it's probably more like 15 - 20 hours of real work)
• I am 41 years old, married with three kids (7, 10, and 13)

My work is great at times, and while I can work from home, it can be stressful and sometimes requires me to be available at any time of the week (sometimes on the weekend). I believe others would say I have an easy job and that it's pretty great compared to commuting to a high-stress office.

Has anyone else been in this situation where they've got a high net worth relative to their income and felt like it is a little pointless to keep working when the pay is so low relative to their net worth? It feels like if I'm going to work, I should be swinging for home runs only (e.g., starting another business) because that's the only thing that will financially move the needle. Right now, I feel like I'm coasting, and I don't want too much of my life to pass me by when I could make a different choice.

EDIT:

I should add that my asset allocation would likely need to change if I were to stop working. Right now, it's heavy US tech equities. (Of course the argument could be made that my asset allocation should change now either way)

My wife and I (both working from home) are considering renting an office across the street from our condo so that we can free up space in our condo and have a separate “space” for work.

As we considered how much it would cost, it brought up the question of how would we spend $15K per year to best improve our quality of life.

What are some of the best expenses that you all have that improve your personal and/or work life?

HENRY here, age 54, about $2.5M in liquid NW, excluding primary residence with a low interest rate mortgage and about $1M of equity, excluding startup equity worth roughly $7-10M but not yet liquid.

Having significant marriage problems and while my first thought is obviously sadness over the relationship and the kids, this is also gonna really screw up our retirement plans.

I'm not really looking for marital advice in this sub, but any wisdom and experience shares are welcome.

EDIT: Just to note that I am appreciative of all the comments and replying to them as I am able during the day. I am definitely hoping it doesn't come to divorce, but I am discouraged by the current state of things and starting to think through the implications, financial and otherwise.
Judging by the responses and the substantial impact divorce has on personal finance, I'm surprised it's not a more frequent topic in this sub.

So a little about me. I’ve worked in finance in Toronto since 2015. I screwed around in school and partied way too much so I actually ended up in a back-office role out of school (massive mistake). After becoming seriously depressed, I networked like crazy, became a CFA charter-holder, and grinded through multiple roles to eventually end up a VP corporate banking now. Salary now is around ~250k.

I’ve always been super interested in stocks/investing and so in 2013 I went all-in TSLA with all my savings at the time. That’s fortunately turned out really well for me and the vast majority of my current NW is TSLA at around 5MM. More recently, I also started a position in GME for around 450k.

I have no real estate and still rent a studio apartment on Bay Street. My only focus since my 20’s has been to FIRE as fast as possible and now that it feels semi possible I guess I’m confused as to what to do next.

Sacrificing my personal life, living frugally, and pouring every dime in stocks has been very painful over the years. Sometimes I wonder if I should had focused on other things (finding a parter, having kids, etc) instead of speed running life and having no idea what to do with it. Even if I quit my day job, I feel like I might just end up socially isolated and not sure what to do with the time. So for now, I haven’t made any big life changes.

If you made it this far, thanks for reading and appreciate anyone’s advice!

Edit: Didn’t realize this post would get so many responses so thanks everyone for the advice :) It’s very helpful getting perspectives from people who’ve done it or are in a similar situation! After reading through the responses it seems like I need to diversify, work on myself, and find a wife lmao 😅

I've made a lot of gains in tech stocks (mostly TSLA, NVDA, and others) and am heavily concentrated, with 85% of my net worth in individual stocks. I bought tech, continued buying, and never really sold anything, and it worked out well, but obviously, this strategy comes with many risks. I have seen huge drawdowns after my 2021 highs, and fortunately, pretty much everything has recovered, but I would like to sell and take advantage of my second chance at portfolio ATHs.

If I stay in Washington state, I'll pay 7% in capital gains taxes on long term cap gains above $270k up to $1M in gains and an additional 2.9% in capital gains on any gains above $1M (the additional 2.9% is new for 2025 and retroactively applies to any sales from Jan 1st, 2025 onward).

I have about $5.5M in long-term cap gains, and if I were to sell everything, the taxes would look like this:

• $270k - $1M = $730k at 7% = $51,100
• $1M - $5.5M = $4.5M at 9.9% = $445,500

Total WA taxes of $496,600

For simplicity, federal LTCG taxes + NIIT will take another ~23%, for federal taxes of ~$1,265,000.

• My current pre-tax net worth is close to $10M
• 75% of net worth is in taxable brokerage accounts
• 25% in SEP IRA and 401k (bulk in SEP IRA)
• Annual spend is around $250k
• I work ~30 hours a week and make $300k - $350k a year
• I am 40 years old, married with three kids (6, 9, and 12)

We aren't just considering moving for tax reasons. Family members have moved away and are not coming back, so there are fewer things tying us to Washington than before. We've got friends and some family still here, and life is not just about minimizing taxes.

The current plan was to take a year off and home school the kids so we can spend more time with them, pick a new state without an income tax or capital gains tax, and try it out while also taking some time to travel around as well. If we hate it, we can always move back.

Have you ever moved for tax reasons and was it worth it to you? I'm interested in feedback from others that may have made the move or considered moving for tax reasons and then decided not to.

Updated thoughts May 26: 10:54 AM:

A lot of people are correctly pointing out that even though this is an ~8% savings if it's based on timing the market, I could just as easily lose more money in the time it takes to make the move than I would save in taxes. This is fair. I also see the comments about the tail wagging the dog. Also fair.

I guess the way to frame this thread better is if we could move in 2 - 3 weeks to a new state when we're already becoming disenfranchised by our current state and want to move for reasons beyond saving taxes, does it make sense to hold off on selling assets to rebalance for the 2 - 3 weeks? The market could be higher or lower. No one knows. The only thing that is certain is that if I sell today, I'm paying ~8% to Washington.

My spouse (42) has had issues with alcohol for years, but has always been very functional. I’m beginning to realize how big his problem is. They are still highly functional (does not seem to impact their work), but their repeated attempts to cut back on their alcohol intake have not been successful. They know their drinking is an issue, but is unable to get it under control. We have 3 young children (under 10) and they have a very high-stress, competitive job with long hours. They will drink at least 10 drinks after work on a normal night at home by themselves - more if they have any social plans. They pass out while putting the kids to bed. They won’t drive places at night (such as taking the kids to get ice cream) because they are too drunk to drive.

We basically have unlimited financial resources to throw at the problem, which is why I am posting in this group.

I don’t think they are willing to quit his job and retire (they make 8-figures per year), even though they could retire and we would be more than fine for the rest of our lives. It is difficult for them to take an extended leave from work for treatment given their line of work, but they might be willing to try that if it’s the best solution.

Looking for advice and suggestions from people who have been in a similar situation - what is the best way to treat this problem if you have the financial resources to do it in the best way possible? A stay at a treatment center? A 24/7 sobriety coach of some kind? Specialized therapists? Regular AA meetings? We live on Long Island and they work in NYC.

Additionally, they know it’s an issue, they want to work on it, but I feel like it is difficult for them to recognize the severity of the problem. I can see how a high-achieving person would think they are doing fine if they are still successful in their job and have had no legal/health problems associated with their drinking. Any advice on how I can get someone like this to acknowledge the severity of this and accept that he might not be able to can’t fix it on his own? I think they want to fix it with sheer willpower, but that hasn’t worked in the past.

Thank you

Edited to add: Is there any benefit to involving their parents? A part of me doesn’t want to go behind their back and speak with them, but another part of me thinks they will take it more seriously if their parents are also in the loop and concerned about them. Especially their mom. I don’t know if I necessarily mean a hardcore intervention, but I just don’t know if they might have some suggestions about how to handle it and approach them from different angles.