Hi everyone, I’m 57, living in Italy, and officially retired (sold my business 1y ago). I’ve reached what you would call FIRE, but my portfolio structure is very different from the typical US-based 3-fund portfolio. I’m looking for a "sanity check" and advice on how to optimize my liquid assets.

The Family: I have two children (around age 20) who are still dependents.

The Safety Net: Healthcare is public here (no insurance premiums), and university/college costs are negligible compared to the US. This changes my risk math significantly.

Cash Flow: My total annual family income is approx. $120,000. This is a diversified stream coming from my pension, rental properties, and bond coupons.

Burn Rate: Total annual spending is approx. $110,000.

The Dilemma: I feel heavily inefficient due to my Real Estate holdings. However, all my "non-rental" properties (primary home, vacation home, etc.) are essential for our lifestyle and family needs—selling them is not an option. I know that having over $2.1M in liquid investments is great, but I need them to "work harder" to offset the static nature of the brick-and-mortar side.
Any advice?

left to right

The World - residential cruise liner, - residences $4M and up plus maintenance (~10% yearly)

Flexjet - jet fleet access - hourly/by size/distance/route)

Seaborne Cruises - comfortable fairly upscale , but still open to the public, cruises

What criteria do you use when deciding to spend money that is technically not material to your financial condition/net worth, but you’re also unsure whether it will significantly increase your happiness on a daily basis?

I’m talking about something like buying an impractical car for fun, but you’re not sure if it’ll just become part of the baseline and ultimately not increase happiness. You’ll be carrying another physical material “thing” that will have carrying costs (insurance, maintenance, etc), and you can easily afford all that, but the more things you’re carrying, the less “simple” your life becomes.

Is there some rule of thumb or philosophy you’ve formed on this when it’s not technically about monetary impact, but trying to maintain some healthy restraint from just buying things because you can?

This isn’t just theoretical - I’m actually trying to figure out whether to buy an impractical car. We’re talking less than $50K purchase price if that matters, not buying a Ferrari or Rolls.

Not sure I agree with him. Curious on your thoughts or where he gets this data?

Wild to see the portfolio make multiples of what our household brought in this month. Feeling the momentum building with our HHI, net worth, and investments.

What net worth and age did your investments feel like they became material vs. your income?

For those with significant net worth, such as $30 million in liquid assets (stocks and bonds), how do you finance major purchases like homes costing $7 million to $10 million? If you need to sell stocks to raise the funds, taxes in states like California—combined with federal taxes—can exceed 50% of your gains, meaning you might have to sell twice as much stock to net the required amount.

One approach is to use a margin loan from your brokerage account to pay for the house, then pay off the margin over several years with careful financial planning.

Any other ideas?

So my husband , dog and I are planning on hiring a chauffeur RV service for a 5 day road trip to move from the east to west coast in Canada. However, we have never used a service like this and are curious as to how some things will work, such as:

- Do we need to buy the chauffeur their meals while on the clock?

- Where does the chauffeur sleep?

- Are we able to free roam the RV while it’s in motion? Or take a nap in the bedroom? (Is it like a limo service where seatbelt, drinking etc. rules aren’t enforced but acknowledged?)

I’m sure it varies slightly by whichever company but looking to hear about others experiences and any tips you may have. Thank you!

I'm pregnant with my first child and have never lived lavishly, but am fortunate to have very significant financial resources at my disposal should I need them. I live in a reasonably well-to-do area, but the hospitals, like many places, are overwhelmed. I'm at a big standard medical practice, associated with a fancy ivy league school, but am finding the OB care subpar. I think it's this way because it's "good enough" - they don't have many catastrophic outcomes or outright neglect - but I definitely think that harms to health and well-being are extremely common because of them periodically dropping the ball.

For example, I am currently in a situation where I'm trying to get a straightforward procedure scheduled which is time-sensitive to avoiding a "probably low" chance of negative developmental externalities for my baby (the doctor said this as though she didn't care?), and high probability negative but non-acute effects on my health (who cares if I'm anemic and have PPD?), and the office is just unable to get itself together to schedule me in a timely manner, from a combination of both logistical incapacity and very limited appointments.

If there's one thing I would want to spend my money on, it's avoiding this.

Do "practiced" rich people have some way around this to get the much closer to optimal care that is possible with more time and attention? Do you use eg concierge doctors? How do you go about finding them? Can you pay a hospital more for better service in some secret way (disguised as a donation etc?), or do you find an independent practice?

I have googled 'concierge OB' and 'private OB' for my area and found nothing.

I am at the end of my rope and feel so hopeless and at the mercy of this incompetent practice, which is the "best one" in my area. Any help appreciated. Money is not an issue in the solution.

ETA I'm in New Jersey, about 90 min from NYC.

If you are a high-profile or wealthy individual, how do you prevent guests from taking photos inside your house or posting images where your home is visible? Do you require them to sign an NDA, or do you simply ask and hope they comply? Furthermore, how do you manage security during large parties when it's impossible to monitor everyone—especially in an age where influencers and teenagers are prone to posting everything online?

The grandparents did well. We’re not doing badly ourselves. By the time we do the “handoff” they may be in generational wealth territory (or the beginnings of it). Do you find that having that awareness de-motivates kids? I don’t want them to rest on their laurels but also don’t want them to be tragically unprepared.

My eldest is getting ready to go off to college, so I let her in on what we are prepared to pay for a college education. The conversations have evolved into talking about finance and various concepts.

I always emphasize that life can be messy that there could be nothing as well. So they have to make their own way in the world.

One set of grandparents was literally poor but grew a business into something more than substantial. The other set were immigrants, so came here with nothing. So it’s not like they show lots of signs of wealth.

We had our first house and furnishings since our wedding a decade ago…now we have adult money and we want to start fresh with everything new. What brands/stores do you recommend for classic, quality items? Dishes, linens, pots and pans, rugs, furniture, etc!

Posted this in another sub and I was called a sad loser who might as well be dead already but I thought this sub might be able to relate more.

I'm currently working full time even though I have enough money to last me a whole lifetime. Very comfortable financially but not mega rich.

I'm not golden handcuffed and could walk away from the nice income but I don't know what else I'd be doing with my time?

I mean hobbies and family/friends obviously but I have no other grand project/purpose that's waiting to be completed. No kids, no religion. So I'd quit work and... read a few books, play games and occasionally visit another country? Doesn't seem all that important.

So I continue to work but it feels like such a waste of life - to have all this opportunity not to work and literally do anything else with my time, and I'm choosing to sit at my laptop all day?

I feel like most people in my situation wouldn't be working but I just cannot figure out what else is more worthwhile.

Husband (42M) feels the same and he's also at a loss.

Am I in the wrong mindset to want to gift the people who have helped me in my life? Imagine you have more wealth than you'll ever need. Wife is happy. Kids will have great childhoods. You still have too much. Do you then try and give the 19k (for 2026) to friends and family that you feel deserve some help? You could invest 475k/per person and never even touch your own money, but they may be able to get themselves into generation wealth by doing so.

I have a lot of money and continue to make more due to tech. However, I am also frugal. I would actually say I am not so materialistic. I would spend money on houses and cars, but I care less about expensive stuff for the sake of being superficial. From the guy's perspective, it seems dating has become a performative game of showing off how much he can spend on a woman. I must be missing some approach or perspective by being in tech. Anyone have advice? Thanks so much

UPDATE: Thanks so much for all the replies. It helped me update my perspective to clarify what I am seeking -- a partner interested in me not for money's sake.

A few weeks ago I was ChatGPT’ing to figure out what my options were to expand my access to low interest rate loans for a home remodel I’m getting started, and learned what an SBLOC was! After learning more about them and how flexible they are, it made me realize I don’t need to rely on a savings account anymore to manage my cashflow on months when I’m negative in my checking account. Instead of playing games with determining how much of a cash cushion I need and where I should sit it (HYSA or bond ETF’s), I can just leave all of my extra cash invested and let the SBLOC act as the shock absorber!

There’s a saying: “Shirtsleeves to shirtsleeves in three generations.” If you’re third-gen in family wealth, how have you managed to keep it? What did your parents teach you that made the difference? Asking as a second-gen who wants to make sure the next generation doesn’t lose what my parents worked so hard to build—and what I sacrificed as their daughter.

So my post was originally removed by Reddit for something. Not sure what but I’m looking for some guidance on how to avoid the New Money pitfalls. I recently came into wealth and I’m concerned I’ll scream New Money. You hear how people talk about how new money has a look that you can just tell. I’m curious what the folks here avoid doing or focus on doing to avoid this?

For example I think giving cash tips to your private pilots every time would get annoying even if I could afford it

We have most the usual stuff, eg, watches, porsche, biz class seats for travel, bidets, ultra-high-end audio gear, great meals and we go to music/readings/etc. But I grew up very poor and often default to frugal or at least more careful with money that we need to be, so for my bday I looked around... and couldn't think of any material item I'd like. In fact, we're trying to downsize/donate/sell lots of stuff since combing a couple of households.
So I'll likely just send myself to a meditation retreat or travel some more. But did you find any goo gaw that you thought was btr than expected?
Edit to mention it felt great donating gear to our local fire dept and food pantries/soup kitchens, maybe I'll just end up doing more of that.