I am on the path to fat fire. My dream is to travel lavishly and stay at the world’s best hotels. I have a number in mind, but I am not sure if it’s enough to be able to afford to spend ~$1,000/night on all vacations.

If im in a city like Rome I want to stay in the nice hotel in the center with views of the sites. If im in Singapore I want to stay at the fancy historic hotel. If im in Hawaii I want to stay at the best hotel on the best beach.

If I take a few trips a year, how much do I need to not even think twice about spending thousands a night on a hotel?

Has anyone had experience with Lionards?

Or just generally mediterranean real estate?

Looking for a family home with land and less than 1 hour from an european connected airport

Im thinking about Portugal on D7 visa or Italy on the HNW €100k/year option in the future

Thanks

First post on this community, and doing it under a fresh karma-less Reddit profile because I've got the standard "employer might see this and recognize me" paranoia, so please don't ban me for it. Apologies if I miss any details that are standard for posts here, and apologies in advance for the lack of brevity.

35 years old, (very recently) married, no kids, ~$8M net worth, in MCOL city. Sold my company this year for $60M in cash to a large publicly-traded company. My cut was ~$14M, of which half was paid upfront. Whole team came with, business is intact, investors had a great outcome, etc. All in all a very big and unexpected financial success.

My handcuffs look like this:

• 50% revest over 3Y, paid in quarterly installments. Last installment is paid July 2027.
• There is effectively a 1Y "cliff" built into it because our indemnity of 15% was subsumed by the revest, and so I need to vest into the indemnity through July 2025 before I start getting quarterly checks (roughly $600k/quarter), and then the indemnity (~$2.1M) is released in Jan 2026.
• My joinder / employment agreement allows for full acceleration of the revest in the event of "Good Reason" resignation or no-Cause termination. Both Good Reason and Cause are very narrowly defined and should be quite easy to adhere to unless I do something truly unethical or illegal and get fired for Cause (highly unlikely) or tableflip (more likely) and decide to opt out.

As you can guess, I am highly incentivized to stay until at least Jan 2026, even more incentivized to stay through July 2026 when my NW will hit somewhere in the $12M mark, and if I were to stay through my full revest I'd land somewhere in the $15-16M NW mark if you include my comp package, not including investment returns or taxes (I did get QSBS on my shares so up to $10M in proceeds are 100% tax-free).

Financially, feeling great. I have a clear path to my ideal fatFIRE number, and compared to running a startup this new gig is pretty cushy, low-stress, and boring. And I feel dumb for even posting about this, because it is such a first-world problem.

But I am miserable here. New company is already doing stuff that totally undermines the promise of the acquisition, even just a couple months in. Nearly everyone I work with seems to be on autopilot or in zombie mode; endless corporate speak, jargons, acronyms, etc. I have been trying to spend more time in the parts of the business that give me energy and joy, but those things feel like they are eroding quickly and I'm having a hard time seeing how I do this for another 2.5+ years.

The good parts (besides the money): I still get to work with the same awesome team since they all came aboard and we are still intact, for now. My cofounder is still here, and we get to vent to one another often. It still feels like I have a "home" because the acquiring company is still keeping us as a semi-independent business. And if I ignore the hours of useless meetings and BigCo BS that I have to deal with, it's actually not that far off from doing startup stuff for much, much bigger money.

In talking to a couple of founders who exited, including one who was acquired by the same company I was acquired by, it sounds like there is some precedent for saying "Hey, it seems like this isn't really what we'd hoped to achieve here, I'm not happy, you're probably not getting the best out of me, how would you feel about paying out my revest early and saving yourself the $ on comp?" In one such founder's case, he was able to take off a year ahead of schedule and get the rest of his revest early.

So: I'd like to pick some people's brains in this community as to what they've seen work or not work in terms of wriggling out of a revest successfully and getting your $ early.

This post from another member of this community is the closest thing I've seen to my situation, and I've found myself re-reading it almost daily as I've been working through this, but it's more about how to soldier or not soldier through your revest instead of figure out a way to get out of it and convince the new company that it's not working out and that they would be better off making you whole and letting you go ahead of your revest.

I'm under no illusions that I could have this conversation with the acquiring company today, but I'm mostly curious to hear if anyone else has advice or stories to share on this topic.

And if not, at least this was cathartic to write.

Hi everyone,

I’m looking for insights from anyone who has experience using Dechomia to handle private shares (or private asset donations) for a Donor Advised Fund (DAF). Typically, I’ve relied on Schwab Charitable or Fidelity Charitable for private share contributions, but in this case, Schwab recommended Dechomia due to their more conservative policies. This involves a $15 million donation to a DAF.

From my understanding, Dechomia specializes in accepting private assets (like the private shares i'm looking to donate) and then recommending the grant back to my DAF at Schwab, after the required holding period. I’ve reviewed their Form 990s, conducted background checks, and heard positive feedback from Schwab Charitable and Fidelity Charitable. However, my naturally cautious approach prompts me to seek additional feedback from this group, especially for a donation this large (to me).

Here are my main questions:

1. Was your experience with Dechomia smooth and seamless?
2. Did they recommend the grant back to Schwab after the 31-day holding period specified in their contract?
3. What fees, if any, did they charge?
4. Did the IRS ever scrutinize or question the transaction?

What am i missing or not thinking about?

I would greatly appreciate any insights or experiences you’re willing to share. Thank you so much in advance!

Married (36m and 34f) with a young child. We’ve both been working since our mid teens and have accumulated about US$ 15m, of which 90% is in real estate.

Asset value has been soaring over the past few years and we’re considering cashing out since it’s likely that there will be a market crash in the near future.

If we cash out, what should we invest in? Now having a small family, we have become quite risk averse…

PS: We’re weary of the stock market since it hasn’t worked for us in the past. Also, we don’t invest in anything interest related, nor take loans/mortgages.

Live in CA and in top tax brackets for both Federal (37%) and CA (12.3 + 1%), total tax bracket 50.3% (1% for CA mental health tax).

I was exploring DAF as option to reduce the tax burden for 2024 and did some calculations (picture attached) for both scenarios (No DAF vs DAF). I understand charity will gain the amount I will contribute, but I will be ultimately losing (or giving) dollar amount (50% of my DAF contribution) on top of tax I would have paid without DAF, even though on paper DAF contributions shows tax savings. 

So basically if someone is ALREADY donating to charity then it does help them to bunch the charity donations through DAF and save some tax through it but if someone is not doing charity donation already or not planning to do the charity donation at all to meet their life. Goals, then DAF is not a good option for them to save the tax. Am I understanding it correctly from tax or overall saving perspective or missing some points?

I am looking to hire a company (or companies) to help witH Tax Strategy planning/Asset Protection/ Estate Planning. Recently interviewed Anderson Business Advisors but they have a ton of negative reviews. Saw another firm called Creative Planning but they look huge and not sure if I'd get lost in the mix. Does anyone have any recommendations?

To be clear, I'm not interested in the technical aspects of wills, trusts, estates, etc but rather everything else about the process. What are the best practices for setting kids up for success? What pitfalls to avoid? What conversations should we be having and when?

I'm interested in it from the perspective of both the grantor and grantee but I don't know what I don't know. I did a quick google search and saw the names James E. Hughes, Jr come up - he's written about half a dozen books - but reviews are mixed. Would love some recommendations from people who've looked for the same!

[Someone at r/rich recommended I repost my question here. Thanks all!]

My money comes from inheritance, but my parents had me working minimum wage jobs starting when I was 15, and I've been meaningfully employed ever since.

So in a big way, I consider "working" a part of my identity, and it's how I relate to both friends and strangers. It feels good to work, it feels good to earn my own money, even if I don't need it. I also volunteer, which is great, but earning money just plain feels good.

However, ever since becoming a father, I just don't get the same satisfaction. Fatherhood has, for the first time, shown me what it means to sell your time for money. And I really don't like the implications of that trade off.

In the past, flying to NYC for a client meeting and being taken out for a fancy dinner...it felt like I was on top of the world.

But now? When I travel for work, I'm constantly checking in with my family, FaceTiming my kids, and generally wishing I were home. I'd rather be watching Frozen for the 1000th time than kissing the rings of people in my industry. And because I know I don't have to be working, the whole thing feels a bit perverse.

To make matters more complicated, I'm very good at what I do, I'm sought after, and I've worked hard to get here. It also feels very good to do something you're skilled at. Stepping away from my career would mean losing contacts, losing touch with advancements in the field, and generally it feels like it would be impossible to "come back" after a hiatus. But I kind of just...don't care anymore.

So in a weird way, I don't need the money, but I feel like I need the work. I'm afraid that quitting my career would lead to a life of boredom, and that I'd lose my ability to relate to my friends, and the world at large.

Anyone care to share some perspective?

I guess this is a pretty simple question, but I'd like to take $150k in cash out of the bank. Will this be a problem with the bank, will it be a problem with the government? Do I need to call ahead or can I just show up, etc?

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36M; married with 4 kids not yet teens NW: $14m excluding business value Income: $3m+ from small business that takes 15-20 hrs work/week Spend: little under $300k this year as we spent heavily on vacations, health stuff, therapy, etc. but this is exorbitant for us.

I've grinded pretty hard the past 15 years. Last 3 years I knocked it out of the park with a small business idea. 95% of wealth came in the past 2.5 years.

All my life I've obsessed about money and finances and have recently exceeded my goals for feeling financiallg safe and I still can't stop thinking about how much money we have -- not worrying about running out but literally just thinking about the number. Like the number $14m swims in my head for no reason. When it's $15m then that number will consume my thoughts. Theres no decision I'm trying to make with my thinking -- it's just a seamingly mindless consuming thought.

I'm sad about the time that has gone by and the relationships I've hurt as I've pursued financial security. But even where I'm at the number is like this big mental suck rather enabling me to pursue other things that are meaningful to me like my kids, wife, relationships, and intellectual interests.

Has anyone been stuck in a mental rut like this?

Personally I'd like to stop working and just pursue relationships and intellectual interests but I feel like I owe it (to whom I have no idea) to continue to work since it feels like a lot of money for little effort. Selling the business is not possible.

Long-time lurker, first-time poster.

Seen some articles on SBLOCs on this sub and others (r/personalfinance, r/investing), but primarily for use cases like - using cash to buy property or alternative investment (crypto, privates), or for one-off cash needs like home renovations, without needing to liquidate stocks and thereby pay capital gains.

Our (39M, 29F) use case is a bit different.

We're at a combined income level (~$450k) where income tax rates are getting to be pretty brutal; so, we're looking into ways to reduce taxable income, while leveraging the assets we already have. Roughly ~$400k (non-retirement) in the markets currently. The idea would be to take out an SBLOC on a portion of our portfolio to use for day-to-day spend, and put more of our paychecks into tax-deferred retirement accounts. Even if the interest rate we get at our level isn't amazing, it would still be far below the 30+% income tax rate.

Risks I've seen from research so far:

1. ability for lender to call loan principal at any time (usually if/when the securities backing the loan drop below a certain percentage of LOC)

2. variable interest rate - looks like most but not all banks offer only variable interest rates for SBLOC; risks if rates increase and you can't pay off interest on monthly basis, etc.

3. needing to be careful to not max out LOC (risks related to #1)

Any advice, things to look out for, and pros and cons from folks who've tried this or researched this before?

I am M55 (married W52) and $7.5m liquid. I still carry $3M term life insurance but don’t really have a need for it. MCOL area, home is paid for. 2 children in college with 529s projected to cover costs (not included in liquid above) Premiums are modest ($2,900 per year) for coverage for 9 more years. Keep or cancel?

I currently use Morgan Stanley Wealth Management, and while I’ve liked certain services (the loans against my portfolio used to be useful in a low interest rate environment), I can’t help but see my investments are lagging the market quite a lot. For example: I’m up 15% YTD, when the Nasdaq is up 29% (potentially not a fair comparable, as large cap has done well and that’s a concentrated index).

I am looking for something mostly hands off, mid 7-figures. I don’t need the ability to borrow, but that was nice. Mentally I like the concept of low fees and mirroring the markets.

I’ve seen people here recommend Fidelity Wealth. Anyone else who fits that mold? Thanks

Realizing that I am living primarily like a middle class person with more money, and that that's probably not an optimal strategy. What advisors have you added that are actually useful? Is one type of advisor the QB that can set you up with accountants, lawyers etc? I used a financial advisor at one point but switched back to self managed, and have used accountants for more challenging tax years to good effect. Who doe you all actually have on retainer, bonus points for specific Bay Area recs/specific banks etc. also are there books that help you understand this stuff better?

I am imagining that if I put x million into the right private wealth advisor then I will suddenly have access to the right estate and trust planning, accountants, maybe even people to set up household staff etc. but I have no idea if that's true or if I should always need to find each person independently. I guess I'm really asking, how do I learn to be an effective rich person faster?

I’m a currently chubby woman (~$5m NW) and on the verge of getting fatter through a major event. I will go from $5m to about $40m. I am totally self made but from a poorer background. I’m American.

The man I’m dating is great. We have the solid relationship we’ve both desired for a long time. We’re both in our 40s and have all the elements of a long lasting relationship. I’m thinking he’ll pop the question in a few months.

Here’s the issue: he knew me before I had money but we didn’t start dating until years after I got to where I am now. He knows I’m obviously doing pretty well but he doesn’t know that it’s in the millions and he has no idea of how wealthy I’m about to become. I’m trying to keep it that way until we get to the prenup stage and I have to disclose.

He’s a traditional, hardworking salt of the earth type of man who is going through a career change so he doesn’t have a lot of money right now (he does have savings and some assets). He’s said several times that he wants to take care of me financially, not knowing my true financial situation.

I’m fine with being with someone who is not at my same financial position and have always been very independent. But now I feel like I can’t do some of the things I want to do with my money like lavish vacations or buying jewelry because it will make him feel bad. I’ve worked hard. I’m still young, I look great and I’m ready to have fun with my money!

He’s been ok with it so far but is beginning to seem uncomfortable and sad when I talk about taking trips. Not in a resentful way but more like it makes him more worried about his current career change. Overall he’s amazingly supportive and he says I’m perfect to him (beautiful, great sex, smart, funny). I think he’s amazing too. He’s asked few times jokingly if I’ll leave him for a richer man. I really don’t care how much money either of us have but the last thing I want is for him to feel like he’s not being a man.

I’m starting to worry that my wealth is going to ruin a great relationship because of the emphasis on traditional gender roles. It’s making me sad and I don’t know what to do. I want to go on an expensive trip in January and I want him to go with me but now I’m getting uncomfortable about asking him because I don’t want him to feel bad. I want to share with him but I’m thinking I need to pull back.

Anyone experience this or have advice?

tl;dr: I’m a fat woman dating a man who is not and concerned the difference in our finances is going to cause problems

EDIT: he knows I’m well off already because he knows what I do for a living and my success has been publicized a bit. He just doesn’t know how rich I’m about to become.

I have a real estate sale windfall of about $750k in 2023.   I'm moving out of the real estate business and am not interested in a 1031 or other similar investments  I want to start formulating a charitable donation plan, but am not ready to start donating in earnest just yet.  What tax deferred options, which are not DAF,  allow me to continue growing principal ?  I'd really like to be able to keep investing in individual stocks, especially if I can write covered calls against them. 

I'm 53, never married, no kids, no legacy, and networth of about $15m and don't really buy stuff anymore.I have about $4m in unrealized stock gains, which I'll also eventually donate through this same vehicle.   At some point, I'll also want to write some checks to impact minded start-ups that aren't charities, but will operate for social good and not profit.  I understand there are some AGI restrictions related to DAFS, but I haven't looked into that issue yet.

Perhaps a lot of people on this sub own Rolexes, pateks & perhaps RMs.

I have friends who have perhaps 15M NW but 2M of that is in watches.

Now we all know unless you’re a watch dealer, watches are a terrible investment overall.if you’re lucky it keeps its value and just about keeps up with inflation.

Is it worth having maybe 5-10% of your networth tied up in watches, that percentage could be invested in stocks allowing you to fire much quicker then sitting on some watches.

I understand this is purely opinion based/it’s a hobby for some. I also own some high value watches and are toying with the idea of buying more.

What’s everyone’s opinion on this sub?

Burner account. FIRE nightmare. 37M; Wife 31F kids 6 and 4, 3. Sold a business 1 year ago and resulted in a NW of +-$22M CAD. (No prenup… I know…)

The day before I fatfired, 1 year after selling the business, wife told me she wanted to leave me (how’s that for timing). 8 months later after plenty family travelling and regular couples therapy, all was going well - She told our therapist our relationship was great 1 week prior. Then out of the blue this week she says she wants to initiate separation, and that I’m her best friend but she’s not in love with me. We have been together 11 years. The therapist has identified that she’s a severe dismissive avoidant who’s sitting on a lot of childhood trauma; and past relationship hurt that hasn’t been dealt with or communicated to me. The therapist thinks we can make it work in the long run if there is gradual work on healing the past but I need to be patient as this unfolds over a period of time. I have to try be secure as she is flighty day to day, and therapist confirms this is outside of my control.

Question: I feel betrayed and hurt - and each occurrence of her changing her mind on our future is mentally tough. I’m really torn in the event of a divorce, losing half my time with kids, half net worth, and starting over at 37.

My life goals outside of financial/work have always been being with a supportive, loving partner and having a family whom I can love and support back. It’s tough when you’re not 100% in control of the outcome as I am here.

For those of you who’ve seen or been through anything similar to this - what’s your advice? Is 37 too old to start over? Is it worth continuing to work at it and be patient as I lose more time? I’m very cognizant of time and if this had happened later in life or happens again as time goes on, it would give me less chance to start over.

$11M vs $22M also changes lifestyle plans a fair amount. If I did return to salaried work, positions in my city would likely only pay $150 000 a year.

Any wisdom appreciated.

Hi, im a high net worth British citizen but living and tax resident in a EU country not the UK. I want to put into savings a 7 figure sum. It seems prudent to spread it over a few savings account to benefit from the govt backed insurance. Looks like Hargreave Lansdown do exactly this https://www.hl.co.uk/savings/savings-account/how-active-savings-works- however they say you have to be a UK resident. Anyone have experience of whether that's negotiable and if not is there a similar thing in Europe where i can open and manage multiple savings accounts from one app or website?

Basically, if my one single account were to be compromised and siphoned off, my retirement is done.

I'm extremely security focused (from the software/security world) and have put all of the necessary controls on my Vanguard account. But I really don't trust them - there are easy ways around U2F. Plus, once you're on the phone with them you're just a few security questions away from wiring the funds somewhere else.

I keep all of my investments in a just three funds (us, intl, cash) - so theoretically "sharding" them across Vanguard, Fidelity, Schwab doesn't change anything about my portfolio. It's not like Vanguard gives you any "real" benefit to UHNW status.

The question is whether I'm just creating more hassle than it's worth to split across brokerages/accounts, or whether it's worth it for that extra layer of retirement insurance.

Hello! I'm curious if anyone here is involved in philanthropic work and how deeply. Family foundations? Charities? How do you give back?

I'm starting with Forward Global and looking at the benefits of developing a family foundation so appreciate the insights. Many thanks!

Without a full understanding of the deferred compensation plan, I went with lump sum option. One person I talked to at Fidelity mistakenly mentioned that the election is only applicable for each year and I can change the election for next year without affecting the previous years’s election. I should have double checked with our plan but I didn’t. What she said was not the way our plan is set up.

I clearly don’t want the lump sum option as it would just increase the tax liability when I retire. I do want to move to either 5 or 10 year distribution, but that means there is 5 year delay in the distribution according to IRS rules.

What are my options now? I probably will move to the five-year distribution after a five-year delay. I am trying to find the positives in this one in spite of my mess up. One thing I can think of is I can start converting some of my 401(k) to Roth as soon as I retire, in the 5 year period, before def comp distributions kick in. I’ll be in a lower tax bracket.

Is there something I can do given my current situation? Am I totally screwed or am not in as bad a situation as I’m thinking?

The other option is to just stop contributing to def comp. The funds I have there aren’t much and won’t cause a huge tax liability when I retire.

I have confidence that my employer will be in business many years after I retire.

I've got ~3M ISOs vested (~$60K to exercise all of it) at a pre-IPO tech startup. I have high confidence the company plans to IPO in 2025. The world of startup equity is new to me. Can someone who's been in a similar boat confirm my thinking on the tradeoffs to exercising theses shares? I see three paths:

1. Exercise now before IPO and if the stock price at IPO is $1/share then my total value is $3M minus $60K? Assuming I sell after the lockup period then my tax burden is ~$2.9M capital gains?
2. Exercise now before IPO and if the stock price is $0/share or less than the FMV then I've lost $60K. No tax burden.
3. Exercise after IPO? What happens in this scenario? Is my exercise cost just going to be equal to the share price?

Thanks for your help!

I'm in the process of re-evaluating my current banking relationship and looking to the community for any advice on things to look out for.

I have a 7 figure pledged asset line and hold nearly 8 figures of assets with my current bank. I've been with them for about 10 years. Obviously preferred interest rate is a major perk, but any other things like preferred underwriting, travel perks, upgrades, etc? I'm currently looking at Schwab, Wells Fargo and US Bank, but any other suggestions to reach out to?

Let's assume 20% capital gain tax rate and quarterly contributions. Would you select a portfolio like Parametric Core that specializes in tax lost harvesting while attempting to almost match a benchmark like the s&p 500 (1% lower but after tax 3% higher). 0.5% management fees, not planning to retire for 20 years. Or just buy s&p 500 and international index directly no fees.

Edit: removing this option: "Or a portfolio strategy that is intended to outperform the s&p 500 by 6%." No one can tell the future.

I have umbrella insurance as an additional policy at USAA. They notified me that one policy is being cancelled and another is disallowing umbrella for auto accidents. I assume it’s for the litigious state I live in - GA.

Curious who you go through for $10-15mm of coverage?

I used to do taxes myself. Then I was like “this is a pain and I’ll pay someone to do them for me”. After that, instead of having to dig around for documents so I could do my taxes, my tax preparer instead emailed me to submit a bunch of them to their online portal, and throughout the process we had to go back and forth several more times (my taxes are somewhat complicated and span several states). It felt like much of the effort was collecting the documents and I was still doing it.

Now I’ve decided I would like to take myself as far as possible out of the equation. What’s the best way to go about doing that? Can I ask my financial institutions to send copies of tax documents to an accountant or other proxy? I get that some aspects of my daily life are hard for tax folks to find out without me but most things seem like they shouldn’t need me.

I recently left my job at a 6-year-old startup which is now raising a new round of funding. I was an early employee with substantial stock - there is a buyback opportunity with this round of funding which would value my stake at $18M and allow me to sell up to $10M.

I’m 30YO in a VHOCL area with a net worth of $6M - mostly index funds, some t-bills — and a low (but growing) burn rate of about $100k/year. I’m close with the company’s exec team + board, and I think that they + the team are truly exceptional. Between the top notch team, relatively conservative field (B2B SaaS in a well-established, large market), 100x upside potential, and my already large liquid NW, I’m inclined to hold most of my stock until post-IPO (most likely 5+ years down the line). I can afford the risk at this age, especially given my >$500k earning potential should I choose to go back to work, which I’ll likely choose to do eventually anyway. I'll have enough to chubby/fatFIRE no matter what -- this excess won't meaningfully impact my quality of life, yet could be super impactful in future philanthropy.

I’ll likely sell at least 15% of my stake ($3M), but even then my remaining [relatively illiquid] stake  in the startup would be 70%+ of my total NW. That’s high. A lot of the wealthiest folks I see did so with a similarly concentrated portfolio on one great startup, although I recognize the survivorship bias there. Traditional advice would cap such a risky investment at ~20% of one’s portfolio, and even the most aggressive traditional investors wouldn’t go above 40% or so.

What would you do? What have you done in similar situations? What stories can you share that might help me make a better decision here?

As much as I trust you all on Reddit, I’ve also talked to trusted financial advisors, my CPA, and a corporate lawyer about all of this. I understand the tax consequences and associated risks of my different paths forward reasonably well. But I’ve come into all this money (including my liquid assets) relatively recently, and it’s taking some time for my financial plan and overall worldview to catch up. I’d like to know what you all think.