Mentor Monday is your place to discuss relevant early-stage topics, including career advice questions, 'rate my plan' posts, and more numbers-based topics such as 'can I afford XYZ?'. The thread is posted on a once-a-week basis but comments may be left at any time.

In addition to answering questions, more experienced members are also welcome to offer their expertise via a top-level comment. (Eg. "I am a [such and such position] at FAANG / venture capital / biglaw. AMA.")

If a previous top-level comment did not receive a reply then you may try again on subsequent weeks, to a maximum of 3 attempts. However, you should strongly consider re-writing the comment to add additional context or clarity.

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I’m contemplating buying a new Range Rover ($125k). I’ve only ever bought used cars because of the depreciation. I have about $35m in NW that’s effectively liquid. I know as a % this is small and I can afford it, but it still feels irresponsible. Am I missing something?

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.

Hi, Fat Friends. I've decided to leave my financial advisor (underperformance, fees, etc) in order to self manage my accounts. Does anyone have any insight into who might be offering incentives to move a high 7 figure account? I know Robin Hood and some of the smaller brokerages offer 1-2 percent, but not willing to risk working with those types of companies. Any insight appreciated.

I’m 32, M, single, living in NYC, with a $6.5M NW. I’m struggling now with motivation. I’ve been a straight A student and achiever my whole life and did very well in my first 10 years in tech (where I received sudden and huge performance bonuses towards the end that led to this NW).

However, I joined a high growth tech startup earlier this year and left after 6 months - I just didn’t have the motivation for the upside compared to my peers to justify the grind and felt myself struggling day to day to keep up. This is a scary and foreign feeling to me, especially to be experiencing it at such a young age.

In parallel, I’m single and really want to prioritize finding the right partner to start a family with. I was in a serious relationship that ended this last year with a woman I loved who was very motivated in her finance career. I struggled to discuss money and my financial situation and wasn’t sure how exactly to split expenses (since I didn’t want to disclose too much too soon). Again, this was a foreign feeling - in past relationships, financial matters have felt natural but this was my first relationship since this NW increase that caused weird dynamics.

All of which to say - I feel strangely stuck. I’m struggling with motivation at work, I’m worried about the long term consequences of “getting off the treadmill” so early, and I’m not sure how to approach dating.

I’d love advice from this group about what the root causes of these issues might be and how to move forward, especially if anyone experienced something similar. Thank you!

[This post is for the week of November 25th.] Mentor Monday is your place to discuss relevant early-stage topics, including career advice questions, 'rate my plan' posts, and more numbers-based topics such as 'can I afford XYZ?'. The thread is posted on a once-a-week basis but comments may be left at any time.

In addition to answering questions, more experienced members are also welcome to offer their expertise via a top-level comment. (Eg. "I am a [such and such position] at FAANG / venture capital / biglaw. AMA.")

If a previous top-level comment did not receive a reply then you may try again on subsequent weeks, to a maximum of 3 attempts. However, you should strongly consider re-writing the comment to add additional context or clarity.

As with any information found online, members are always encouraged to view the material on  with healthy (and respectful) skepticism.

If you are unsure of whether your post belongs here or as a distinct post or if you have any other questions, you may ask as a comment or send us a message via modmail.

When I got my payout from founding a start-up, I determined that it was plenty for my life and I didn’t need outsized returns. That prof at Yale (Wasserstein) does some good content. Somewhere he says to ask yourself “would another million make you happier? How about double your NW?” And if the answer is no then live your life accordngly.

So I went PWM, 70/30. Don’t bloody lose it!

Yet all the time I am drawn to the fire of other investments. I nearly stuck a hundy in a pre-seed company. Liked the business, really liked the management etc. Luckily some good pals reminded me of my own words - angel investing is for morons unless you commit. Realise you are a beginner. Start with small cheques. Screen tons of deals etc. But if you don’t wanna do that - don’t do a one-off.

Then suddenly I’m getting in the weeds of crypto. And then pull out last minute.

Then I look at a stock I fancy… then remember the above!

I love the subject, however my I stand by my original logic for PWM 70/30 ETFs (mostly) being an infallible strategy for me. Indeed my man at the PWM serves as an excellent barrier to remind me of my philosophy. I did end up buying one stock, but he challenged me to come back to him with my thesis the following day which I agreed made sense. (RDDT ftw!).

Anyone else suffer from the lure of the chase?

Married, 2 young kids (36/35yo) HCOL. Total NW 2.6M including primary. (450 equity- Rate is 2.7) 700k retirement 700k brokerage, 600k MM cash, 300k rentals. Combined income 5-750k ~past 6yrs (took us a while to get here -fluctuates on quota). Both in Tech sales… Annual burn about 110-130 depending on vacations etc. Max the retirements + tax adv accts and DCA out of cash position to the brokerage $2750 a week; bogleheads style. Looking hard at deploying some of the cash for a modest family “beach” house (really just near the beach ~600k purchase price) We will use it nearly 35%-40% of the yr. Strong network in the area. Should we plunk about 50% down to keep payment lower? Refi later when rates come back to earth…and feel no stress when quotas go up. Or do we sink less and offset some costs via ABNB? Maybe some tax efficiencies there. Or do we stay course and go HAM in market? Are we too young for this and delay gratification? Enlighten me with second home experiences and potential other opportunities… Target fatfiRE age 45.

We’re getting ready to remodel our master bath. Other than the obvious like heated floors, heated towels, anyone care to share suggestions/experiences on how they made fat their master bathroom?

I love my job and I want to work till my mind is sharp. I'm in my early 50s and my plan was to work till late 60s. My lifestyle is very modest and money has never been my goal. I am thankful that I have a reasonable amount to live a comfortable life. That said, I have been dealing with serious health issues off late, which has led me think of early retirement as a possibility.

My family is totally unprepared if anything unexpected happens to me. I wanted to start planning for it and trying to make a list of things to do.

1. I do have a basic living trust and Will, but I do want to sit with an estate planning attorney to see if I need to do something more to help ease the transition.

2. Making sure all my accounts have the beneficiaries set up correctly.

3. My wife nor kids dont have any idea of the liquid assets - They dont know where the funds are parked nor how to log into any of the accounts. I'm making a list of these accounts and placing the list in the safe deposit box at the bank.

4. I own several individual stocks and this is something I dont think my wife nor kids would want to manage. I have to come up with a plan to move them to low maintained ETFs like VOO or QQQ or a combination of both over time.

5. I never liked paying 1% to anyone to manage my money, but I may have to think of that option for my wife and kids.

6. Came up with a simple Financial plan document that outlines the list of things to do and the exact order to do these things in my absence.

I know most people here are planning for a happy retirement in here and dont want to spoil the party, but I wanted to put forward my situation and see anyone has any suggestions / advice for me.

I'm kind of new to Reddit, but amazed at the wealth of knowledge here and how helpful people are.

Thanks!

Recently moved an 8+ figure portfolio from Vanguard to Schwab to take advantages of Schwab's more complete product (better margin/PAL lending rates, free Amex at that level, integrated checking, etc.).

They assigned me to a "financial consultant" (or whatever their term is) to help bring me in and get everything set up. He's been great at helping the transition, getting my negotiated margin/PAL/money market setting coded in, etc.

But now that things are pretty much settled, I wonder what people use their relationship manager for. I've always been pretty much a set-it-and-forget-it/Boglehead type, and I work with my CPA for taxes. I know the account execs generally are not CFPs and do not offer investment advice. I realize they come "for free" with the account and are not people I should turn to for complete financial advice.

So -- I'm curious. For those of you with fat portfolios who have a "my guy" at a brokerage who isn't an investment manager: what do they do for you? Are there any services or value adds I should be looking for?

Or, are they the person who sets up your account and then just shows up as a contact when I log in to my account, never to be heard from again?

Any recos on a good brand for a second floor home safe. Enough space for some guns, gold, cash, watches, important docs, ect….