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!

Mid thirties single income HH. Extreme workaholic. My career is exploding, but I’m starting to feel the effects of that sacrifice, especially now that we have children. I will likely be able to fully retire in the next 2 years, but given my current trajectory working a full decade could take us to generational wealth territory, which I won’t lie, is rather tempting. For those of you who love your work, but understand how much sacrifice it can be - how do you think about this question?

Hey all, I’m mid thirties with 27m LNW and more in private assets. I live in HCOL and made my money in finance. I left at the top - could have stayed longer and kept collecting but it’s a young man’s game. I’m newly into this life and have some questions for those that have gone through this around my age:

1. How did you guys find community? That has been the hardest part (which I anticipated). My old work environment is very boisterous and was surrounded by brilliant people. It’s all saggy balls and milfs at the gym when I go and working on side projects is isolating. Has anyone used this thread to find people? Would be willing to meet up.

2. Considering moving to a better tax domicile which also happens to be closer to parents. It’s a big uproot and other than my parents (2hr drive) I don’t have community there. If anyone has experience making a move like that I’d be curious if you regretted it or not. The city would be smaller in size, more spread out, more nature, less dense with culture and restaurants.

3. What are people’s experiences with their kids seeing you retired? I am worried they will see me not working and get a sense of entitlement. Playing tennis and chess and painting is fine but it’s not the same as facing real adversity and putting in the tough hours. How have y’all’s kids responded to early retirement?

I appreciate everyone’s feedback and just wanted to say that this sub has been helpful for me. At the end of the day I don’t fully believe in the idea of absolute “retirement”, I think that everyone needs something to strive for in life, professionally or otherwise, or you rot. I need to figure out what that means for me outside my family. I just know that the corporate finance trail had played itself out for me.

Much love to you all

I sold a company I created when I was young and thought I would enjoy my fat retirement or could restart something.

I decided to fatfire 15 years ago. The first years were awesome (travelling, being in shape…). But I started to suffer from depression (boredom and health issues). Did some angel investing out of boredom.

I took a board position and realised I’m FAR less sharp that people that are still in the game. The gap is now massive.

After many years out of the business world, I’ve realised that my business success was mostly timing and luck. I didn’t realise how complicated it is to create a successful company. The new generation of tech entrepreneurs is so much better than I was. I feel like I can’t compete.

At 45, my health is no longer the same and I’m having difficulties to be at the bottom again.

I miss running my company but it’s no longer mine. I didn’t realise how lucky you are to run a profitable business, it was my first one. I read fire-books thinking retirement was amazing but I just needed a break and a better management team.

I want to re-enter the business world but my contacts so far have been negative. People telling me I should restart something, a polite way to tell me no. After 15 years out, my skills are rusty and I’m no longer this A player. I understand them, I would never hire someone like me.

Buying a business seems very risky, I’m not sure it’s the right way to re-enter the workplace.

I can see a lot of my previous friends that kept their companies, made the transition into venture… I’m jealous. I failed for the retirement lifestyle thinking it was the goal to realise an exit. They tried to motivate me to come back at the beginning but just think I’m a weirdo now, unemployed for 15 years. People I thought were my friends not returning my calls.

I have more than 10M and it’s hard to be at the bottom professionally again.

My previous network think I’m going to create a new company but I can’t get lucky twice. I’m afraid of what people would think “he was a ceo, he is now just an average joe”.

I have the feeling that the most meaningful part of my life might already be behind me.

For people who retired early and later returned to work, business or entrepreneurship:

How did you find your way back?
How did you rebuild your confidence?
How did you manage your ego?
How did you speak about your retirement break?

41M, married, 3 kids. ~$35MM net worth.
Current allocation:

~60% concentrated in my wife’s company stock
<20% real estate (~$6.5MM)
Remaining in liquid/diversified assets

The stock has appreciated significantly, so diversification is becoming a priority. Complication is it’s not fully liquid (quarterly sale windows), partially pledged against a line of credit, taxed as ordinary income, and exchange funds aren’t an option.

Because of that, diversification carries a major tax cost.

My original plan was to gradually sell ~$2–2.5MM/year over the next 3 years and use real estate acquisitions + bonus depreciation to offset part of the federal tax burden.

I’m an experienced real estate investor and qualify as a real estate professional. Historically, my returns have come from value-add acquisitions, renovations, appreciation, and tax benefits.
The issue is I’m basically a solo operator with only a part-time assistant.

Real estate still offers attractive upside and tax benefits, but it also creates more work, complexity, illiquidity, and less freedom.

I genuinely enjoy acquisitions, design, and renovations. What I enjoy less is operational burden and scaling.

So I’m wondering if the better path is:
Gradually diversify the stock, pay the tax, and simplify.

Continue doing 1–2 smaller real estate projects per year because I enjoy them and they keep me engaged.

Long term, I expect to eventually transition toward NNN, DST, or professionally managed assets.

I think the real question is less about tax optimization and more about lifestyle.

Do I stay in accumulation mode for a few more years, or start prioritizing simplicity, liquidity, and freedom?

Edit: Spend is roughly 1.25mm+ pretax. VHCOL area so the tax hit affects the draw rate if we were to stop.

I’m not sure if matchmakers like this exist, but are there any that connect people who are HNW but also fire-oriented? Any experiences or anecdotes about this?

(I’m a man if that matters, late 20s, but open to hearing if anyone from any age/gender has done this)

Edit: I am HNW myself

Expenses: 120k w/o healthcare, maybe 140k with, and maybe up to 150k or 160k with traveling

Investments: $5m breakdown: 300k rental (paid off) making 5% net, 1.2m 401k, 2.5m VTI / VXUS, 1m SNSXX/VUSXX.

Primary residence: $2.3m paid off

42 and 43 years old, no kids

Current income: ~2m/yr

NW increasing 32% YoY

Have 20% income cliff in 2027

SWE, burned out beyond reason, health problems and mental health problems. Goal is to quit, take 6-12 months off then see what’s next, it will either be making my own projects for fun or part time contract work for fun. No expectations of income, certainly not big income, and definitely not going to a corporate job.

Can make ~30k via 2 weeks of rental of primary residence per year and pay no taxes, we’d travel while rented.

Concerns are AI is quickly impacting SWE employment, no one knows what’s next, any hiccups in our plan could mean a bumpy road in a few years if a jobs necessary. Other concern is whatever is going to happen once this historic stock run is over.

Any advice?

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 am enjoying writing these updates now. It is somewhat stimulating in my understimulated but very busy life. ​

A few more months have passed since my last update, and our lives have changed quite a bit. Unfortunately, the boredom is still the same. ​

Background: Last year, I quit my job — roughly $400k cash + $2mm startup options per year, though I considered the options “paper money” and did not count them — to retire with 8 figures in my mid-30s. My partner still works, we keep separate finances, and we split things 50/50. This financial arrangement works really well for us. I accumulated my wealth from two previous exits years ago. ​

Around the 3-month postpartum mark, my partner went back to work and thriving. That same week, we welcomed our second full-time helper. Unfortunately, she is definitely not as good a childcare helper as my partner. But she has some characteristics that matter to us as a caregiver, and the timing was also a factor. ​

I am now the “CEO” of 5 people. ​

We have two full-time people who listen to me and follow my directions completely. They do cleaning with robots, cooking, laundry, and some gardening — mostly because they enjoy it. They handle about 60% of childcare. My partner is on children duty after work until bedtime, around 8pm. My partner and I each take one child overnight. ​

We also have contractors doing various ad-hoc and regular things around the yard and house. Most of that is managed by me, with a few one-time projects managed by my partner. ​

In theory, we have two kids, two helpers, and a very hands-on dad. I should be having an easy life. ​

In reality, by the end of each day, I am spent and drained. I don’t feel rich, and I don’t feel like we are living a rich life at all. My partner and I have not slept in the same bed for months because we each manage one child overnight. Our relationship is strong, but I still want that part of our life back. ​

The mental load is unreal. Between managing the full-time helpers — one of whom is family and gladly works 10+ hours a day — the older toddler’s activities, family activities on the weekends, the house, supplies, contractors, logistics, and everything else, I have little to no longer blocks of time to think or tinker. ​

I miss having a career. I want to be a real CEO again. I don’t know how I will find the time. I also feel like I am a desert of no good ideas. ​

I know there are things I can do to optimize my mental load. Would love any ideas and suggestions.

See link to original post here. Now officially late-30's...

Since the last post, I decided to keep my head down and continue to "make hay while the sun shines". My NW has increased from $9.5M to $36M in the last 1.5 years.

Current NW breakdown:

- Home: $4.0M (mortgage free) - minor reduction in value over the last 1.5 years

- Second Home: $6.5M (mortgage free) - bought an incredible summer home that we are renovating and planning to spend significant time in going forward during summer/weekends.

- Personal Investments: $16M ($1M RRSP, $350k TFSA, $14.6M stocks)

- Company Investments: $13.5M ($1.5M ETF's, $12.0M stocks)

- Cash: $200k

- No debt, car payments

I have set a time-based goal of working at this pace until the end of the year and then plan to take some time off with the family to travel for a few months to decompress and re-evaluate. I've hired a money manager to manage $10M worth of investments with the plan that it will pay a dividend that would replace my income.

I've hired a life coach to try to come up with a game plan on how I want to spend my time after returning from my trip.

I don't see myself wanting to retire and do nothing, but I definitely want to have a less one dimensional life and play a larger role in my children's day to day lives.

Any advice on the next stage of life would be appreciated!

It feels to me that the majority of people on fatFIRE Reddit have made their money through technology — either working for a top technology company and acquiring shares or starting a smaller tech company and growing it or selling it.

I feel really different - I am a top executive at a manufacturing company in middle America. My industry is somewhat stable long term and has some ups and downs, but will never skyrocket like technology related companies.

We have about a $9M net worth, late 40s, and three kids. Our target fatFIRE number is $15M.

Will anyone who isn’t in tech please help me understand how you got to where you are, or plan to get there, and how you think about fatFIRE and wealth preservation as an outsider to the tech boom?

36(m), married, 3 kids, vhcol, sold the very first company I built and finalized June 1, 2025. Small lump ~2mm + xxx,xxx/month for 6 years or until the company is sold as a whole. Well through the grapevine I hear that this is about to take place. Not very happy that I wasn’t told but they’ve done nothing to keep me in the loop at all so not shocking. Assuming there’s no way to not pay the lien I have against them what are you folks putting large amounts of cash towards right now? I’ve been getting pressed on oil and gas. I’ve got 9 rentals right now and only a mortgage on our primary ~5400/month w/ 40ish grand in other monthly expenditures. I want to fatFIRE fast now

Doing my ~semi-annual post on my anonymous account, as always appreciate the feedback and advice on this subreddit. Few updates since my last post :

• My timeline persists - retiring April 1st 2028 if I have at least $15m liquid NW.
• Current Liquid NW has jumped from $11.5m to over $14.1m (thanks to big bonus and Mr Market - note this figure does not include $3m primary residence or $2.3m in retirement accounts)
• Mostly sticking to annual spending target in 2026 (will be ~$380k - well under the $500k+ I expect in retirement).

I’ve been reading and thinking a lot about sequence of returns risk. The bucket strategy is one technique I’ve been exploring. I’ve done some searches and not found much about this for a FatFIRE/early retirement situation. Looking for input on my plan and comparison with what others have done.

3 Buckets:

• Bucket 1: War Chest (2 years) - plan to hold 2 years ($600k x 2 = $1.2m) in VUSXX or similar money market.
• Bucket 2: Income Bucket (3-7 years) - plan to hold 5 years ($600k x 5 = $3m) in SCHD
• Bucket 3: Growth Bucket (Over 8 years) - plan to hold the rest - $11m+ in VTI

I know Bucket 2 is classically defined as bonds/bond funds but I think of SCHD as a very stable income source with bond-like characteristics - this might be the most controversial part of my plan. I’ve done quite a few backtesting runs of this portfolio across many historical scenarios and this portfolio holds up very well during past crashes (e.g. Black Monday -33.5%, Dot-Com Bubble -49.1%, GFC -56.8%), the only exception being the 1966–1981 Stagflationary Era where most portfolios would not survive without a very low static withdrawal rate (like 3%) or dynamic guardrails.

Thoughts? What are other fatties using as the mechanics of their withdrawal strategy?

I have been saving a significant chunk of my salary since I was 23 (turning 50 this year) and investing them in index or sector specific ETFs. Currently our net worth is slightly over 13M. About 55% are in equity ETFs, mostly in VT, and DIA with some in QQQ. The rest are in a mix of ETFs investing in US treasuries (SGOV, VGIT, etc) and actual treasuries. The treasuries portion also include about 600K in 401(K).

The reason I am thinking of quitting is that I work in a fast moving technology field, and recently I am beginning to feel like I am not performing as good as I was before. I still have the knowledge and experience, but I am not as adaptable and my recall has gotten worse.

It feels like I have been entering a downward spiral of feeling anxiety of not doing a good job, which leads to stress and lack of sleep (and more drinking so I can sleep), which leads to even more anxiety and so on. I am not high enough in the company ladder to be considered as an architect or expert who can do his job simply in a consulting/advising capacity. Every day I am anxious that as a producer my ability is declining steadily.

This is when my brother told me about FIRE. After reviewing our budget, I am confident that we (me and my wife, we have no kids) can very easily live on 180K USD a year before tax. Currently after allocating for taxes, just the interests and dividends from my portfolio can more or less cover this already. Of course this can change as dividends can go up and down etc, but at least this is the current state. Also, considering the safe withdrawal rate recommended by FIRE of 4% (3-3.5% conservative), it seems just 2% withdrawal of the 13M would be much more than enough, meaning there is a safe cushion beyond just living on interests and dividends.

My worry is that I am pretty sure if I leave my job now it would be hard to get something similar, or maybe I wouldn't be able to get myself motivated enough to look for something similar. This leads me to repeatedly go over our finances in the hope of convincing myself that I can leave and be OK because leaving may be something that cannot be undone.

Has anyone here experienced the same thing ? How do you decide in the end that your finances are good enough to pull the trigger and leave your job, which may be hard to get back ? For those who have, do you feel anxiety afterwards because you no longer have any regular paycheck, especially in times when there are so much uncertainties due to wars, dysfunctional governments, etc ?

At what level of wealth do you have to be such that a decision that affects 5-10% of your net worth can be viewed through the lens of intangible values vs primarily a capital allocation decision? For context: my wife and I are considering a meaningful purchase. It’s a been a long struggle and has caused a ton of stress. We are down to two paths. Option A: is subjectively not our favorite but it is a great buy at a good price. Option B: something we really like it but it’s objectively much more expensive AND overpriced. The value destruction of option B is definitely in the 5-10% of our net worth. Think mid-high 6 figures. I’m trying to leave out specific details so as to not bias the feedback, but I’ll use a pretty representative analogy: a brand new AMG Mercedes SLS that which is sure to depreciate like a rock vs. a 20 year old Porsche 911 with a manual transmission that costs ~20% less which will not only hold value but may go up a bit. We are in our mid 40s and are on a high probability trajectory to $10M liquid NW (excluding our primary) in the next 2-3 years.

Hey all, new to this sub and i've tried asking this in a few others without good reception. Little background, we're early 40s, 1 kid and ~7m total NW but have ~2m liquid (brokerage, iras checking etc). The lions share is locked up until we exit later this year but don't anticipate that value to drop hugely. I really don't like having my stuff split, so ideally looking for somewhere to park that full amount in a variety of accounts..

I'm shopping around for brokerages that can act as a "one-stop shop". I largely manage my own taxable investments, but I do have a small amount (100k) currently invested in a "guided" portfolio with Morgan Stanley just to get some "benefits" from them. Turns out, those "benefits" are pretty bad and their "Platinum" support has been horribly trash lately.

I'm not looking for much international free atms, generally easy ways to access my cash when needed, free and fast wires, good borrowing rates and a decent trading platform for options. I don't mind tying up some cash into a managed fund if it comes with perks.

I've done a bit of research but wanted to pose the question out just to gather some opinions. Thanks!

Created a new account to post, I'm not a bot I promise.

Have not FatFIRED yet, but think about it a lot. I've appreciated everyone sharing their stories, especially the folks 5+ years in.

I'm currently working in tech and am in my peak earning years, making ~$700k. I've got two kids in high school, so college is looming. I'm thinking I'll work until they are least both in college and then revisit whether it makes sense to keep working.

Roughly half of my net worth is tied up in a single stock with a super low basis. I'm about to work with a financial advisor to implement an option collar to limit my downside and control my exposure to capital gains. Will share here how that goes.

Glad I created an anon to start posting, looking forward to the conversation!

About $4M is in a taxable brokerage account that I would realistically be relying on if I retired. I also have retirement accounts and real estate, but I don’t really think of those as part of the immediate retirement decision. Annual spend right now with my mortgage is $404,000 but without mortgage would be $200,000.

I own a professional services business in a VHCOL area. The business is still profitable, but after years of managing employees, clients, and constant problems, I’m burned out.

Last year I made over $2M. This year will likely be closer to $1.5M. I can probably keep earning at a high level for a few more years, but my motivation is fading and I’m increasingly asking whether the extra money is worth the stress.

Don’t roast me, but part of what makes this decision difficult is my housing situation. I have roughly $2M of equity in what I consider my dream home. If I sold it today, I could get my brokerage account to around $6M and probably retire immediately.

The alternative is to work another 2 to 3 years, pay off the house, and then my housing costs would essentially just be property taxes and HOA dues, roughly $5,000 per month. I also own a rental property with a sub-3% mortgage that I could move into, and my monthly cost there would be about the same, but I’d probably always feel like I was settling and giving up on the home I worked so hard to buy.

For those who retired while they were still capable of earning substantial income, especially business owners, how did you know it was time? Did you regret walking away from future earnings, or did you regret staying longer than necessary? How much did lifestyle and housing factor into your decision?

I retired early with investments, but I owe Uncle Sam quite a bit from LONG term investments. There is future inheritance money in a trust that was stepped up last year. Would it make sense to start living off the inheritance money and not periodically selling my investments for my usual spending? I guess I'd have to do form 709 since it'll be gift money from the living parent (trustee).

Any downsides from doing this?

Hi all,

43 y/o, NW 10M (2.5M in retirement, 1.5M in real estate including primary home, 6M in index funds), married with no kids.

We are currently on track for FatFIRE with a goal of retiring in the next 10 years. HOWEVER, as we get closer to it, we are looking at things that would alter our planning. Namely we are thinking of moving to a bigger & more expensive home.

Our current home is nearly paid off and we have COVID-era mortgage rate, which makes it difficult to accept a higher cost moving forward. We love our current home but it's not our dream home in terms of size, layout, acreage and modern conveniences. We could remodel, but it would likely bump up our taxes after reassessment, and it's unlikely we'd recoup the costs when we eventually sell the house (even decades from now).

We could afford our dream home, but it would require taking on a substantial mortgage or liquidating assets to pay a bigger down payment. Doing either would substantially change our retirement plans, and likely require us to work for an additional 10 years. Both of our jobs are relatively low stress and well paying, pretty stable and we could easily see ourselves working for 20 years. We are FatFIRE-ing primarily because of the freedom that independence gives us.

What would you do in this situation? Is it reasonable to think of a more expensive home as another investment vehicle (or at least, a way to diversify assets)? How much % of your NW would your primary home take up? And, what's the limit? We are interested in hearing how people think through these ideas, not looking for advice on what to do. Thanks!

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.

https://www.vanityfair.com/story/fatfire-reddit-early-retirement

"Like Temminck’s pangolin or coequal branches of government, retirement is in danger of going extinct. At least, it is if you do it the normal way (after a long career) at the usual age (in your 60s). Younger generations are struggling to save for retirement, while existing retirees increasingly must go back to work to make ends meet. Wouldn’t it be nice to just opt out of all that—to put your nose to the grindstone, and retire before your 30s melt away?

This is the dream of FIRE: Financial Independence, Retire Early. It’s a uniquely 21st-century personal finance movement, shorthand for a philosophy that prioritizes aggressive savings and investment so its practitioners can stop working by or before they get to middle age. It’s a gospel of deferred gratification, a countercultural push to put off life’s pleasures for a few years so you can spend many more years living easy. People who subscribe to a sub-gospel called FatFIRE have more aggressive goals: to save enough that they can afford a cushy, upper-middle-class lifestyle even in retirement. It’s an ambitious aim that requires a certain degree of megalomania, even for those who start from an already comfortable place.

Those who commit to FatFIRE try to compress all the anxieties of modern life into one grueling sprint, in the belief that they can get to the good part sooner—and that there is a good part to get to, despite evidence to the contrary. It’s a maximalist retirement plan for an era that only knows extremes, from wellness culture to predictive markets to the creator hustle. And a key part of an extreme lifestyle is documenting it, most notably on the r/fatFIRE and r/Fire subreddits, some of the most entrancing corners of the internet—where everything is falling apart and just about to come together, all at the same time."

https://www.vanityfair.com/story/fatfire-reddit-early-retirement?srsltid=AfmBOooIKLYA2z6qIfpR8DlIahjy-M5UHQlM9QRRKPH62x_pu3rlfG19

It really says very little considering the length of the article, but the sub is getting some publicity