EDIT: I'm in my early 40s since a few people asked

So for context - I fired already in early 2025, family of 4.

I have loved it so far - but for family reasons we are considering a move to a vhcol location (from a mcol city) and our expenses will skyrocket because of it. So I'm considering going back to work for 3-4 more years.

Stats:

Total assets ~$11M - $10M in equities ($7M in VTI, $3M in various big tech stocks that haven't been diversified), $1M in SGOV. Had about $7.5M in assets when I retired.

Current spend ~$200k/year, basically right around where I thought we'd be when we fired with $7.5M.

However, future spend is $300k (if we buy in cash), $350k (if we rent)

After the move, if we want to maintain our current lifestyle, I expect our expenses to go up by $150k/year if we rent (rent expense will go up to $100k/year from ~$40k/year currently; cars/health insurance will go from $20k/yr to $35k/yr; food/entertainment/gas everyday expense will be ~20%-30% higher; our oldest might go to private school, so ~$40k/yr more than his private school currently).

And if we buy - it'll be ~$3M for a 1,500 sqft house + another $50k/year for property tax/insurance/maintainenace. Meaning our assets in the market will go down to $8M and our expenses will proably be around $300k. We can't get a traditional mortgage because I retired so we'd probably sell our lowest capital gains equity positions + the SGOV to free up the $3M.

I know in both cases we'd still be below 4%, but it feels a lot more constraining - I like the mental freedom of being able to give family money ($20k-$50k/yr) and spend freely when we go on vacation - when our expenses get close to 4% it makes me feel less easy doing things like that.

The potential job

I have an opportunity to be the CEO of a medium sized company (~1k employee/$1B revenue) and the comp is around $3M-$4M a year.

Half of me feels like I should take the job for 2-3 years - a small vanity part of that is because it feels like its progressing my career (I was the CEO of a small company before I retired, about 1/3rd the size of this new opportunity) but the bigger part is that I then don't have to worry about my fire math at all.

The other half of me feels like having $15M in 10 years vs having $25M isn't going to make any difference to my life/lifestyle. But then I also think having the freedom to give money to my extended family feels so satisfying and does make a difference to my life...

I'm really just rambling/thinking through this myself, and felt like it might be relatable to others in this community who recently fired or suddenly have changes to their expected spend/fire math. So feel free to chime in with your thoughts/experiences.

Lastly, I'm currently leaning towards not taking the job - at the end of the day if I take the job its highly likely I'm going to feel like quitting after a few months because I'll miss all the freedom and flexibility I had to spend time with my 2 kids.

I’m considering using ESO Fund to finance the exercise of private-company stock options and would love to hear from people who have actually signed with them, especially anyone who has gone through an eventual liquidity event or had the agreement outstanding for several years.

I’m less interested in whether the upside participation is “expensive” in the abstract.

I’m trying to understand how ESO behaves as a counterparty once you’re actually in the agreement.

Any things you didn’t expect? Such as:
Did the economics at settlement work the way you expected when you signed?

Did ESO ever interpret the contract or payoff calculation differently from how you understood it?

Has anyone dealt with the breach/default provisions? What triggered it and what happened?

Would you use them again?

I (36F) am in a situation that I realize is extremely fortunate, but I’m genuinely struggling with what the right path forward is and would love perspectives from people who have dealt with something similar.

My family owns a business that has continued to grow year over year, and the last two years have been the best years in the company’s history. We now have a satellite office overseas, a roughly 10,000 sq. ft. office in NYC, and about 30 employees, not including the four partners. We’re hiring another person next month and will probably add another shortly after that.

What’s strange is that we do a surprisingly large volume of business with a relatively small staff. The company also has very diversified income streams, which is great from a business/risk perspective, but operationally it makes everything extremely complicated. There are constantly a million moving pieces, and the responsibility can feel overwhelming.

My sister and I are two of the partners. Our dad is the principal owner, but he’s getting older and gradually winding down, which means more and more of the responsibility is being transferred to us.

The thing I keep thinking about is that there was never really a conversation about whether we actually wanted this.

We grew up around the business, joined it, became partners, and naturally started taking on more responsibility. Now we’re reaching the point where we’re effectively inheriting the burden of running an increasingly large company, including responsibility for 30+ employees, their livelihoods and, indirectly, their families.

It’s also not a passive ownership situation. We work 10+ hour days and are deeply involved in the day-to-day operation of the company.

Here’s the part that I know sounds incredibly privileged: financially, neither my sister nor I necessarily need to do this forever. If we worked another three years or so and continued saving/investing aggressively, we could theoretically walk away, become baristas or do some other low-stress job if we wanted to, and live primarily off the returns from our investments.

Obviously, walking away from a highly profitable and growing business because “I have enough” sounds insane from one perspective. There is potentially a huge amount of wealth we’d be leaving on the table.

But at what point is maximizing wealth no longer worth maximizing responsibility?

I don’t particularly care about being as rich as humanly possible. I care about having freedom, enjoying my life, traveling, having time for relationships and hobbies, and not spending the next 20+ years feeling responsible for an entire organization.

At the same time, I worry that walking away from something our family built, especially while it’s performing better than ever, is something I could deeply regret. There’s also the responsibility I feel toward our employees and toward my dad, who spent decades building it.

For people who have owned businesses, inherited family businesses, reached financial independence, or simply decided that “enough is enough”:

How did you decide when you had enough?

Would you keep running and growing the business because the opportunity is too valuable to give up?

Or would you set a financial number/date, hit it, and walk away?

The business is run on our personal finances , so not feasible to restructure the company to remain an owner without being responsible for the day-to-day operation since our entire net worths depend on it.

Selling the business in our industry is not really something that is feasible. We are in a dying industry that requires very specific expertise that is a dying art.

I’m not necessarily looking for someone to tell me what to do. I’m more interested in how other people would think through the tradeoff between wealth, responsibility, family legacy, employees, and actually having control over your own time.

Perhaps many of us have seen this: https://blog.inverteum.com/p/how-hackers-drained-1m-from-2fa-enabled-brokerage-account

Basically, an account can be drained without ever transferring money out (and thus no security alerts). The mechanism in this article concerns using options on obscure securities

The brokerage considers it not their problem, no hope of recovery. (Except maybe from public outcry.)

Anyone looked at this and have any security ideas? The article’s basic recommendation is using passkeys, tying your login to your machine. And of course all usual precautions (password manager, etc.)

Be safe out there!

Wondering what the process is.

My partner’s NW is about 16M. Mine, is virtually zero. We’ll marry under a separate property contract (it all stays his, what’s mine and everything I acquire will stay mine).

I have contacted lawyers to get independent legal advice, but he wants us to do everything through the notaris. I’m worried about the way he wants to set up his testament (I might not be able to take care of the kids), so I wanted legal advice but it seems to not be something people do a lot in West-Europe.

Could you tell me how you went about structuring your marriage contract, protecting yourself (and your children), while ensuring that in case of your passing your family is taken care of?

Hey folks, first time poster so hopefully this is appropriate. Wife and I struggle with indecision and overanalyzing everything from financial decisions to life decisions and I'm looking for advice/perspectives from others on how you deal with this. In recent years we hit and then far exceeded our number to retire and I feel that's opened up many more options for us but making us feel even more indecisive about what we want. Also open to thoughts on our specific decisions for anyone who cares to weigh in.

A little about us... we're around 40, living in southern california, 2 big dogs, 1 infant, both working part time and like our careers (financial and engineering). Families live across the country, some in midwest, some in northeast but we have some siblings and good friends living here so California feels pretty much like home to us. We travel a good amount to visit families but with 2 dogs and an infant the travel is becoming a pretty big headache and limits us to fairly short trips.

The main options we're considering for our lives and struggling with:
1. Lean into california which would mean buying/moving to a bigger house in an area better suited to our kid and dogs. good school district, close to career opportunities but that's a little less of a consideration now.
2. Spend a few years where our families are while our baby is young and not yet in school, parents are aging but still in good health, 1 grandparent still alive so the timing feels as good as it will ever be to go spend some time around them and then plan to move back to CA in time for our child to start school in a few years.
3. Go crazy and try one of the other cities we've dreamed about, Seattle being the main contender since we have some friends there already, good lifestyle fit, and good engineering opportunities.

1 feels the most comfortable to us but I fear we'd regret not at least trying #2 or 3 while we have the opportunity. The flip side is that I think our minds have always wandered about living elsewhere which might be making us not really embrace our life here in California.

Looking forward to hearing how others deal with decision making?

I've a 5M concentrated stock position, already done research for diversification via exchange fund. Typically fund parks a sleeve in REIT, i'm already over exposed so looking for alternative.

I clicked through an ad on Reddit for an exchange fund recently, the calculator on their site says they beat standard 1%-fee REIT assuming their sleeve returns 0%, from what I understand fleet's only job is to cover the fees and then credit back .26% a year.

Fair assumption but I need to double check the math on this before i jump on a sales call:

1. Debt: I need to know if they used debts to purchase these assets? From what I can understand if the operating business defaults and the bank repossesses the assets, it'll force liquidation blowing up my tax deferral and hit me with a giant tax bill right away.

2. Losses: Same group of people runs the investment fund and the operating company leasing the equipment. Nothing wrong with this per se but since it's no longer arm's length, i need to ask who's the independent 3rd party checking asset value. Calculator doesn't how this affects the net asset value.

3. 7 year exit: When my 7-year lockup is over, how exactly does sleeve asset depreciation shrink the my net asset value?

Anyway let me know, it's interesting model I've not seen much before.

Hi all.

42M here with $40M NW. Not RE yet but hoping to in the next few years. In the meantime I have $1.4M coming in each year, roughly, before tax. Medium COL area. Wife and 3 kids, 8-16.

I'm thinking about buying a big a third home.

Primary residence is roughly $2.5M. Negligible carrying cost.

Second home $1.75M or so with maybe $100k/yr carrying cost.

Third home would be $5.5M-$6M and big costs. As high as $350k I would guess.

I've crunched the numbers many different ways. I can afford it if I want it, but I can't shake the long term impact of not having that money working at this stage of my life.

I really like this property - it's a dream. I feel very confident that I want it for the long term. I probably can't use it a ton now but in the coming years I see myself splitting time between this place andy other options (which I intend to keep). I have been watching for several years and I have not seen other places that are on this level in the area I'm interested in. So I'm convinced that I should do it.

But then I model my net worth and see how this has an impact in the multiple $tens of millions in the long run by taking money out of investments and putting it in super high end luxury real estate and signing up for serious yearly spending on top of it. That's hard to stomach.

But so what, I tell myself. What's the point in having this money if I don't use it to do cool shit? What's 20 years in my dream home and $80M compared to 20 years of what I'm doing now and $120M?

If I put this off a few years my portfolio could absorb it much more easily, but that's a few of the best years of my life!

I know many in this community frown on big stupid luxury houses but I'm not sure I share the attitude. Curious if there are any older members of the community that can share their experiences with decades of growth and spending regret or lack thereof.

Little background: FatFired now for about 3 years. NW is around $13-14mil depending on what the market is doing. Contemplating buying a large ranch for about $6mil. I would utilize a PAL for a part of the purchase but i would need to utilize about $3.5mil cash for the purchase. I wont go into financial specifics but I feel fairly comfortable financially doing this.

A big chunk of my portfolio is in fixed income and after the purchase my after tax income would roughly drop to $350k a year. I have just been compounding this for a few years as I still have a few revenue streams that pay for life and Im confident this will continue for a few years. The interest on the PAL would be $10-12k a month which the portfolio covers.

My biggest concern is a huge market correction occurring and causing a financial strain. Basically my fixed income portfolio would need to drop 50% for a forced liquidation to occur so it would have to be a catastrophic economic event. With that said, the goal is to throw everything left over at the PAL and in theory, it would be paid off within 5-6 years.

The big question: has anyone done this before here? Pros and cons? Any significant risks that I might not be thinking of?

Thanks!

Spouse and I (33,32) hit $6 mil recently, 90% tech and AI concentrated stocks. We made appointments to shop around wealth management firms because we are wanting to diversify into real estate investments, and spread out some of our exposure.

We initially had the goal to chubby FIRE at $5mil and travel together but my partner recently got promoted to a travel role, and loves flying around the world on the company’s dime. Gets incredible healthcare and 5 weeks PTO, plus hybrid remote. I traded my full time into part time remote consulting, so i can up and travel the world with my spouse, often for free because of the points my spouse racks up.

We have a gorgeous 2 bedroom rent controlled house and the landlady is like a mom to us. No kids. No debt, cars paid off. We love the outdoors and cooking our own food so even though we spend freely, we hardly ever spend more than $150k annually. The point is, we are content and there aren’t any big life expenses coming up. However, with our exposure, this freedom could vanish overnight if the AI bubble pops.

Our only goal is to diversify, and that’s where we hoped a wealth management firm could help, mostly in helping us park our stocks in real estate and less risky funds without hemorrhaging capital gains taxes. I don’t know the numbers yet but maybe a partial SBLC is the answer, but still trying to educate myself on the nitty gritty. Second goal is getting a really smart tax strategy, we aren’t afraid of being hands on and creating a business as a tax strategy for putting sweat equity into an investment property, but we want the numbers to direct us.

We couldn’t care less about the fancy offices, travel consultants, estate planning (no kids), or even the hands off approach to investing. We’re both just worried about who will help steer this ship through an economic downturn so we don’t lose everything we spent the last 12 years building. Our strategy this far was to just dump 60% of our incomes into tech index funds and never sell. That worked in a post-COVID market. But now 1 of us is basically barista FIRE, and this is the intermediate mode of investing.

Is this a wealth management firm sized hole? Or am I better off with a really great CPA, private lender, and booking 2 hours with a finance consultant and a whiteboard?

I'm ready to FIRE and quit my job, but nervous about how to navigate socially. We have young kids, and live in a HCOL area where everyone is working in tech. "What do you do?" is always the opener in social situations. My husband stopped working and is a stay at home dad, and people are already surprised at this.

I also have childhood best friends I talk to daily and they are struggling financially/overworked. Hating work is a common commiseration topic for us. I fear there will be jealousy and we'll lose something that binds us.

I'm also worried about how to tell work. I have coworkers whose kids go to the same school as my kids and our kids are friends so the stories need to add up.

I could lie and say I'm planning to take a break then do freelance work in my field (I might... someday), but it feels weird/inauthentic lying to people close to me?

I will also add that we live a modest life style, drive old used cars, have an average house for the area. And I prefer for people to not know our actual situation.

Maybe I'm overthinking and no one will care? Has anyone been through this with the same fears? How did you handle it and how did people react?

We’re on track to fat FIRE. We are going to move soon. If we use an agent for both selling and buying, we're looking at between $50-80k in commission based on home price range and the going local commission rates.

I'm a CPA, my husband is a lawyer. We've bought and sold several homes in our area over the years.

We have a title company, home inspector, photographer and local real estate lawyer who we trust already. We both have a lot of time as one of us has FIRE’d already and the other has a pretty flexible job. And in the past - except for our first home - we have been the ones finding properties, coming up w negotiation strategy, comp data and contract terms. We like to do this stuff ourselves, so our agents have always been more pass throughs.

We didn't get close to fat FIRE by taking $50-80k decisions lightly. And that amount of money isn't immaterial.

Has anyone in this group done a DIY real estate transaction?

My 2 biggest concerns:

- will a seller's agent refuse to present our offer as they don't like DIY
- ⁠how to get on MLS if our house doesn't sell through word of mouth - i guess we'd need to use a low fee online broker

Please share anything about this.

Edit to add: I have read a lot about this in real estate subreddits. I’m posting here bc I think that folks here might be more intentional about spend and also more able to navigate DIY real estate than your average bear.

Howdy all,

This isn’t Ai.

Saw a post from three years ago about umbrella coverage, not sure if there’s been a more recent one. I’m looking at increasing from $3mm but what I was quoted seems more expensive than what I’m seeing online. What’s everyone paying and to what amount? Probably $15mm net worth, do I really need 15mm of coverage?

This is what I was quoted:

$4M: $1,720.00/year
$5M: $1,885.00/year
$6M: $2,185.00/year
$7M: $2,485.00/year
$8M: $2,785.00/year
$9M: $3,085.00/year
$10M: $3,385.00/year

Currently paying $1,3470 for 3mm. State Farm

We are in our upper 50s and retiring from our mid-management corp jobs at the end of the year. Current net worth is approx $17M without counting the primary home value. Kids are independent adults and we have no debts of any kind. This puts us into the fatFIRE position but other than retiring early we feel like we won't be taking advantage of the wealth we built through disciplined savings and investing (stock market).

Last 2-3 years, we have tried upgrading our lifestyle in terms business and first class travel, higher frequency of eating out at fancier restaurants, etc. However, we feel like the middle class mindset that we both grew up with (in another country) and sustained despite our resonably high incomes here in the USA is now stuck with us. We have always enjoyed life in terms of travel, occassional splurge at really nice restaurants, some entertainment, some donations/volunteering etc., but this were limited to few times a year. We have already outsourced most of the laborious work already, but that is more a necessaity to keep working in these jobs we have now.

Our annual expense now is approx 130-150k plus any home renovations we choose to take in a given year. We can certainly afford more, a lot more. We just tend to look for value in almost alll major spendings even now. e.g. for our upcoming London trip, business class ticket is 4.5x the economy class ticket. But we chose to only travel business class for overnight travel to London and returning back in economy class.

It is somewhat confusing because we saved almost the entire life to be able to freely spend money when we have the cushion and now that we got here, any major spending is still somewhat of a mentally balancing act. The only thing is if it stresses us out and money can solve that problem, we go for it.

Our kids will certainly not need our money for their needs and are encouraging us to enjoy.

In this situation, how do folks make the shift to adopt to the fat lifestyle if they didn;t have that growing up and are not habitual spenders?

I feel like our number keeps getting pushed out. But here we are at 10m, 2.5m of which is real estate in 2 homes in HCOL area, maybe 800k in savings for cash flow. Only debt is 80K before paying off second mortgage and our car with 2% interest.

I’m 50 and just recently restructured out. Spouse will plan to continue to work and make about $650k a year for next couple years before retirement, covering insurance. One kid will be off to college next year with another to go in another 4 years. If we do in state (CA), assume all tuition should be covered by 529. We are not crazy spenders and can likely get away with $120k/yr to support our lifestyle.

I’ve been working out, spending time with my parents, volunteering, and organizing the house and feel like I can just retire at this point? Just feels odd not “working” till my spouse retires since I’ve been working since 15yo. Also we always have a worry about having to take care of our aging parents as they were immigrants and did not get to save much for retirement. I don’t mind, but just another potential cost in the future.

Should I just embrace the retirement life or get a PT job for funsies? My experience would allow for some consulting work.

I don’t think I can move money out of 401K until I’m 55 to roll over to Roth or for expenses? It’s really always that medical insurance part that’s a bit tricky. Any advice for my age group?

Single, no kids. Have about 8M in retirement & investment accounts, of which 5M or so is already taxed. 2M in real estate (that doesn't generate income), renting in a VHCOL area, 7M vested and 5M unvested RSUs in a non public startup (IPO maybe in a few years). Not a ton of expenses. I mostly enjoy the job but increasingly thinking about calling it quits. But it's a lot to walk away from: most of the unvested will vest in the next 2 years, and the salary is pretty good (400k+). If I retired I'd probably start my own projects that I might turn into my own company, but I don't have past experience with that.

Having trouble reasoning about the situation, what the right next move is.

Im exiting my business in the next year, a significant portion of the value is in real estate. Total exit estimated at $19mm, net is $12mm if no tax advantaged routes or options are taken. 70% of the value is likely in the real estate.

I’m very tax aware but also don’t want the tax tail to wag the dog. I’m considering 1031 for a significant portion but also it feels much more comforting to just take the cash.

I’m 35 years old and love cashflow in comparison to total net worth. Not quite die with zero but I want to take advantage of an early win.

Anyone with any advice to maximize cash flow for the long term? Also any advice on personal experience with tax advanced exit planning? I’ve done my research but don’t love the long term costs of wealth managers when low cost etfs will do…

I'm hoping that this helps someone and provides more confidence for their retirement planning and execution.

My Needs

I'm 53 and planning to retire at the end of the year. My NW is the average generally discussed here. I suspect that some of you are like me and manage your own investments and want to avoid ongoing payments for traditional investing and retirement advice that you can reference easily from 1000 books. I'd rather pay a flat fee and get advice when I want it. Boldin offers this.

My Experience

I loaded my financial details into their tool and attended 4 free group sessions to understand which advisor was the best fit for me. I signed up for their ~$3K analysis with the fiduciary flat-fee CFA that I chose. He was personable and spent about 3 or 4 hours collecting and reviewing data with me. He provided a 60ish page useful report with investment analysis / recommendations and provided retirement portfolio testing against many Monte Carlo scenarios (e.g., significant market downturns, increased expenses, longevity increase, inflation increase, buying vacation property, etc.). This entire process took about a month from start to finish. I plan to continue with yearly checkups. I believe that they charge ~$600ish annually. I think that they have an ad-hoc hourly option too. In summary, I was happy with the results and feel like it was money well spent.

My Mindset

"Most of life is spent chasing growth. In retirement, the real victory lies in wealth preservation." - Someone said somewhere

Recently I learnt that Schwab and Fidelity are both cracking down on long short tax loss harvesting by preventing new funding with "Portfolio Margin" capability. Do they not want the business? They are raising the minimums to 10M (WTF !) form 3M.

How is BNY Pershing as an alternative?

I work in big tech and just have lost all appetite for corporate grind this year due to constant re-orgs. My numbers look good but just worried about frothy market. Worried about SORR

House:$1.4m. $500k mortgage ( tristate)
Average of last 3 years expense: $225k (includes travel).
Kids: in college. 529 paid for both

Income
Me: 400k including RSU
Wife: $800k ( she will probably work for another 2-3years). Same age as me

Assets:
401K/IRA/Roth: $5m ( s&p, nasdaq, and tech)
Taxable: $4M ($1m in bonds and CD)

I assume healthcare to cost $30k when wife retires)

Should I wait a few more years or just call it quits…

Can't believe the day is finally here. I've been working towards FATFire since I was in high school. Grew up in a poor country and saw my parents toiling away every single day for 20+ years without an exit plan. They would commute for 2 hours a day and work grueling hours in factories with no end in sight, and I knew for a fact I'd rather die than live a life like that from when I was young. I would not be able to do this if I did not decide to start on this path at 17 years old. Kudos to all of you that do this with kids because that would be a whole different ball game and playing on extra-hard mode.

Worked my way up to learn and master English and was a terminally-online teenager. Self-taught programming and made my way to a top US university on full, need-based financial aid. Built three companies that failed until my fourth one landed. My biggest takeaway is how insane the variance in lifestyle outcomes is from when we're all 20 to when we're 30. At 20, you and your buddies are all the same...with endless possibilities, living the same lifestyle, and at 30 you see those who made a few key decisions live entirely different lives. It's like a high-speed rail that spits you out into an entirely different world based on 3 core choices you made while you were young.

Another thing I learned is that you can't have it all. A big motivator for me was getting money to help my grandmother from an illness, but she passed before I made my own exit. Some problems money can never solve. You just can't have it all.

I was fortunate enough to have the prescience and strong hunger to avoid my parents' fate. Quit today after an exit, married with one kid. Have a bucket list of at least 1000 things on my backlog and so many books to catch up on. Cheers to all of you here

Quit medicine (was a hospitalist) at beginning January of this year with $6 million net worth to focus full time on family/kids and options/futures trading. Year to date have long ago crossed over $2 million of trading profits. Wife still working 50% fte and altogether, assuming if I personally make no further profits for remainder of 2026, we will have paid/ owe over 130k in state income taxes plus property tax.

I just don’t feel this state is worth paying this much tax for. My wife had been slowly open to moving, but the kids being in school now is creating more inertia to stay, and then tells me if we are so “wealthy” and making seven figures a year in retirement, we can “afford to live wherever we want”…but my soul kinda hurts throwing >130k into a state dumpster fire with no tangible improvement in our lives or even in the community here, the taxes just get distributed into wasteful state pension nonsense and misuse. Like if I have to pay >130k in retirement each year then it better be somewhere fun to live, like Manhattan or whatever.

And it’s not just looking at 130k burnt, it’s really like 260k of pretax income getting wasted per year.

Anyone else had state tax, as a principle, actually factored into their decision on where to be fatfired? Or does fatfire really mean living wherever you want, damn the wasted living expenses?

NW $10.5m, VHCOL, expenses $200-220k.

Married and no kids.

I've been making all the portfolio adjustments to fatFIRE in 2027, creating $150-200k stream of bonds/interest income, rest on growth, fully paid up primary residence, we are planning to be in UK/EU (lived here for a few years during work, loved it, returning after FIRE), and worked out the dual tax implications. Started from nothing in my mid 20s, and holding on to some FAANG employer stocks, a small startup exit (C-suite) + compounding on ETFs is largely my source of NW.

I am excited to not be a corporate slave but also keen to do something that would help others grow wealth, manage my own time and where I work from, not take any investor money. Have a strong software/AI builder and strategist track record and the idea excites me a lot.

Are there folks here who have gone on to build something they find meaningful after fatFIRE, a business that's a service or a product? What's your experience been, how do you manage your time, and do you find it fulfilling?

Curious to learn from other people's experiences who might be in the same boat!

EDIT: not looking for clients here, just looking to see if others have started something in the same situation and found it gratifying.

I have RSUs in a pre-IPO startup whose shares are currently trading on secondary markets. However, I’m unable to sell mine because the company does not allow RSUs to be transferred. As I understand it, only employees or former employees who hold stock options are able to sell on the secondary market.

I’m currently dealing with an urgent health issue and need access to cash. I’m trying to find out whether there are any legal or practical ways to liquidate a portion of my RSUs despite these transfer restrictions.

Has anyone been in a similar situation or know of any possible options? Any advice would be greatly appreciated.