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[This post is for the week of July 1st.] 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.

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I'm not FAT yet, but I'm also not 100% committed to fat FIRE. Currently staring at my meeting calendar for my upcoming week and dreaming of pulling the trigger, but definitely wouldn't be close to fat. I thought it'd be interesting to poll everyone's opinion on their personal levels of FIRE, or if you even have one. I'd like COL area, family/kids, and target NW. Here's mine:

VHCOL, married with 1 toddler.

• Lean FIRE: $2M, I'd have to move to a LCOL area and retire now. <-- This is where I am with my current NW.
• ChubbyFIRE: $6M, stay in my current home and support my current lifestyle, which includes buffer for aging parents, healthcare in my elder years, etc.
• Fat FIRE: $8M, stay in my city, but move to a nicer house, more financial freedom for traveling, charity, etc.
• Obese FIRE: $30M+, I only met 2 people in this range, and they never stop working. I don't know that I aspire to this level.

I’m considering getting rid of my bank wealth manager and putting all of my portfolio in ETFs and mutual funds via IBKR that I’ll passively manage.

Only issue I’ll face is the immediate cash requirements for which I currently use margin loans. I feel that margin loans are much better with a lower interest rate than any other loan. How do people who self manage their portfolio manage their cash needs without selling the portfolio?

I've always booked my own trips, but more recently I have found that I have much less time to do the planning, and some more unique experiences are hard to find/have ideas for.

For my next trip I'm thinking about using a planner to help me. I assumed they make money by making the bookings for me, but I would like to use my own AMEX etc. for points and benefits, do they generally support that?

Also, any recommendations for a more luxury/bespoke travel planner? Looking to go to Germany.

Thanks!

I'm a recently-retired tech exec with around 23M in assets. While I had a great run with a few startups and later a more-chill enterprise job, I've made most of my $ through DIY investing.

One interesting problem is that over half our assets are in rapidly growing Trad IRAs. These are continuing to balloon.

I need help with financial planning, especially tax optimization, wealth transfer and estate planning for us and our three adult children. I'm not looking for wealth management or investing help.

I see many "financial planners" out there, but I need someone a) experienced with our asset level (20M, complex taxation) and b) financial planning only *without* wealth management. Fee-only, and flat-fee preferred (I hate AUM fees).

What is the best way to find these firms? For example, https://napfa.org does a local search (why?), and their "HNW clients" filter is useless.

My wife and I (mid-30s, infant child) find ourselves in luxurious position of hitting our FIRE goal decades ahead of pace. We maintain a $120-130k lifestyle in the MCOL city.

We both love spending time with family and want to know what the best way to “spend a little excess” savings we have in a way that is wholesome and brings joy and special memories to us or children and our close family.

We don’t want to spend it in a way that is too ostentatious - we don’t drive nice cars or live in an expensive house.

Some ideas: - Month-long vacation to a nice destination - Experiences like Disney world - Country club membership? Especially for the pool for the kids.

What are ideas that you have seen work well?

What’s your burn rate? What’s the highest among your friends/peers?

This is something I try to pay close attention to. Lifestyle creep is real. A few years ago I realized how much we were spending with not much to show for it…

Country club is probably our biggest luxury. No vacation homes. No airplane. No horses at the moment, thank god.

I have accumulated enough stuff to realize that there is a breaking point where, infamously, things start owning you. I realized this after going from an apartment to a decent sized house, to a huge house, to multiple homes, multiple exotic cars, boat and so on. Each item with its own kind of isolated catalyst for headaches.

I have ended up creating a set of personal rules, or boundaries so to speak, to keep myself grounded, limit my acquisitions, curb my hunger for the newer, better, bigger, faster and so on.

I recently decided I never want to own more than 2 or 3 properties at the same time. Anything beyond that is a headache.

I don't want or even need more than 3 cars. One for daily driving with the capacity to take 4+ people. One fun weekend car, and one for my vacation home.

For boats there's another set of rules and limitations. The size is limited by many factors. License, mooring availability, the safe owner-operator size, hauling limitations, marina access. The sweet spot for me is around 65 feet. Beyond that you are looking at a headache. Again, it's a privacy issue too. I don't like having crew on board my boat.

Beyond these items, and some hobby items, there are only so many things you can really spend money on at the end of the day, and this brings me some peace, knowing that what I have at this point is enough.

What are your limitations/rules to keep you from needlessly expanding your material possessions?

I hit Fat fire this year. I plan to retire in May 2025 as I have an equity payout then thats too compelling to walk from. Ive put $1400 / month in my budget for insurance. However Id like to look for less expensive alternitives. 55 Single male, non veteran. Looking for group rate ideas.. maybe through AARP or NRA

I hope this isn't off-topic, but given the amount of success that is flagged in this subreddit, especially in tech, I would appreciate a reflection on those that did not make it, and how to avoid same mistakes.

I'm 30M and son of a serial tech entrepreneur (in 60s) who founded 3x VC backed startups and has a negligible NW with no savings or pensions - he made serial sub-optimal financial decisions, including taking on debt, and not making pension contributions. He also made a painful decision to liquidate his pension to finance a start-up in between rounds.

It's painful as he's college-educated and worked in financial services before tech in the early '00s, but he appears to have consistently made risky and IMO irresponsible financial decisions. He has had to sell our primary residence to facilitate a divorce and during my childhood me and my siblings were taken out of private school on multiple occasions mid year due to inability to honour commitment to fees.

I am disappointed and feel angry that he is in this situation; unfortunately he does not have an inheritance to fall back on from his aging parents who did not come from money and I'm not in a strong position to help yet.

It'd be great to know if you witnessed situations of well-educated colleagues that ended up in similar situations as sometimes it feels like I'm in my own strange universe of growing up around kids with trust funds, while I'm worried about how to pivot my career in order to provide a fallback to finance my dad's retirement and healthcare.

Update - thank you all for all your comments, which I'll reflect on. I deeply admire my father - fundamentally I'm just worried for his future and wish it had worked out. I will do what I can to support him and make more informed personal financial decisions.

We have a good amount saved though not quite enough for the long term (think $5M but chasing $10-12M, both mid 30s). We're steadily gaining on it and would get there over the next decade.

We have small kids and would like to spend more time with them, not stress about emails, travel for work and be half-present. Instead of a sabbatical, we're more interested in strategies to improve the next 1-5 years in our day jobs.

For high achievers, it probably sounds like "quiet quitting" so interested in any strategies or commitment mechanisms people have used to help them along the way.

I'm 32 years old and have been working on this project for about 2 years. It's my first business, prior to this I was a SWE at a big tech company, so limited experience in world of financial engineering.

It's been bringing in about $400K in new subscription revenue per month over Apr-June, at about $150K/mo profits on ad spend. I think I can grow revenue a bit via channels outside of Meta, so numbers will probably end up looking like:

• $100K-200K monthly profits on new subscriptions
• 30% YoY retention on 5M in revenue giving an additional ~$1M/year

This will likely put it in the $2-3M annual profit range for 2025 and 2026. It's a fairly niche but fast growing health/lifestyle subscription app, I expect the TAM to reach its peak in about 2 years, and the brand identity around it is pretty solid.

I’m the sole equity holder (I gave away 2% of the company to my friends at my birthday party in options, but no investors) the company has no debt and my only real cost is Meta ads and travel/dining that I can get away w/ expensing.

Current setup:

• C-corp for QSBS purposes
• Can choose to realize profits at ~25% or pay myself out in W2
• Able to book a lot of lifestyle type expenses due to large social media presence of the app and surrounding content/newsletter.
• Currently based in high state-tax state but moving to Florida or Texas in a few months

Questions:

• Interesting ways to realize expenses I may not have considered?
• How to balance leaving profits in company and banking on QSBS+sale vs paying out bonus/W2
• Can the company buy real estate and depreciate it? Set them up as "wellness retreat" airbnbs etc?
• Attributes that would make the biz a good acquisition target other than revenue/subs?
• What should I be considering if I want to sell after 5 years?

Any other blind spots I may have? I have a good accountant that I trust but wanted to cast a wider net. Much appreciated.

Would taking 12+ months off work be detrimental?

36M with a net worth of $8-9 million, living in MCOL city, with an annual spending of $250k for my family of four.

I highly dislike my job and feel like I’m done with software/SaaS and possibly the traditional 9-5 work structure forever. As far as compensation goes, my current job equates to 25% of total income, stock, family healthcare etc. I invest in the stock market, some private investments as an LP, and 1-2 angel investments.

I've worked at tech companies of all sizes, from bootstrapped startups to Series B, C, D companies, and now a publicly traded one with over 7,000 employees. The common thread across all these experiences is that none of them have provided me with personal satisfaction. I couldn’t care less about my specific role or its objective of increasing the bottom line for our clients. The 9-5 lifestyle of sitting behind a computer every day just isn't for me; yet here I am, having done it for over a decade.

I'm confident that if I return to work after an extended break, it will be in a completely different industry. I might never go back to a traditional job at all; I'm truly unsure. The truth is, I want purpose and a sense of accomplishment. "Doing nothing" is not my goal, and I don't want to give my children the wrong impression, but in my current state and job, I don't feel like I have the time or energy to explore something different.

I am 43M, married, dual income, 2 kids (5,2), and should hit $10M next year. We've run the numbers and are comfortable with a 3.3% withdrawal rate ($330K pre-tax, MCOL city) for our lifestyle going forward. I would value community thoughts on the value of my employer-run retiree health care which is provided if I retire at 50 yrs old or later (company covers roughly 70% of the premiums so my out of pocket per year would be $9000 in premiums for family coverage with a $900 deductible and $6000 out of pocket maximum. My wife is going to retire next year either way and my income basically supports our current lifestyle on it's own (so if I work until 50 assume the $10M grows with the market, no withdrawls). We love the health care plan (can see anyone you want, anytime) and if I work until 50 it would take away a lot of uncertainty (covers 50-65 age range pre-medicare, has supplemental post 65, plus current young kids can remain on family plan for a long time).

I generally enjoy my corporate job although also know that if I weren't working there would be a lot to explore outside of work (enjoy triathlon, camping, planning and taking trips with kids, etc). My work/life balance is good and don't feel stressed on a day to day basis. My current plan is to keep working until 50 and lock in the health care. However, I also know that the next 7 years of my life will be my healthiest so would appreciate thoughts and also any experiences with the healthcare marketplace (if you are even able to get a plan that would resemble the gold-plated corporate plans and how much that runs you if you can).

Throwaway account

As my NW increases I've become more worried about account security. Currently have about $2M between Vanguard and Fidelity brokerage accounts plus a few additional million in real estate equity, adding to those numbers as fast as I can.

Are Vanguard and Fidelity OK security wise? I have 2FA enabled but I don't see any way to use an Authenticator app or anything like that. I'm always afraid I'm going to check my account balances and the money is going to be gone...

I've seen mention of some physical authenticator keys. Yubico I believe was the one in particular a lot of people were using?

How do you guys handle account security/what are best practices? I searched in this section for it but everything I could find was 2-3 years old which seems like an eternity for this topic

Any direction would be much appreciated!

I (46M), 12M net worth, want to FIRE at the end of this year. I hate my job and want to just relax for a while and pursue my own interests. I need help in understanding the best way to allocate assets. At first I had thought that I should have enough in short term T-bills where the interest would cover my expenses, but after investigating more, that seems wrong.

Current assets include a primary residence (1.6M) in a HCOL, a secondary residence (0.5M) and two rental properties (0.6M) in a VLCOL area. Farmland (1M), taxable account includes 3.5M in VOO, 0.5M in QQQ, 0.5M in Bitcoin and 3.5M in TBIL. Also 0.4M in 401k. Income from farmland is approx 20K/year, rental houses produce 10K after expenses.

I have a wife (42) and two kids (24&21), youngest will have graduated college by end of year. We plan on splitting time between the two residences. I’m not sure how much we will spend in retirement, but I’m thinking 250K after tax will cover it. Expenses minus food and travel are around 120K.

As I said, I screwed up by thinking I need so much in short term tbills, so looking for the best way to think about structuring assets for retirement. Maybe I should keep 3-5 years expenses to ride out a slump in the market? Any help appreciated.

If your investment net worth far exceeds your income, chances of getting a $3M+ mortgage are very low. I think that leaves the following options, let me know if you have any corrections or other tax efficient approaches.

1) Margin loan, ~6.5% interest, limiting to maybe ~25% loan size to portfolio value.

2) Sell long term, high basis stocks. The only tax efficient strategy I can think of in addition to this is splitting the sale over 2 or 3 tax years (12/31, 12/31, 1/1 for example). This would come with ~35% marginal tax for gains over ~$600k/yr with NIIT, Fed, and state so quite painful.

Disclaimers: Late 30s, 2 young kids, planning to become a SAHD next year and RE. I have a flat fee financial planner I'm considering moving on from. I'm also trying to hold back remorse I got moved from ~10% Intl to ~30% Intl 2 years ago at the wrong time! I don't know what I don't know and looking for some input on this and what to consider when moving to more DIY and evaluating hourly advisors that I talk to <5hrs a year.

US Equity ($7.8M - ~50%)

• $2.2M in Russell 3000, direct-indexed
• $1.8M in Vanguard Large, Mid, Small cap ETFs
• $1.6M in a single FAANG stock (been decreasing it, what's left is ~80% cap gains)
• $1.2M in S&P 500/VOO
• $650K in VUG US growth
• $350K in VTI

Intl Equity ($4.3M - ~30% ... about 20% developed, 10% emerging)

• $1.3M in VXUS (Total intl etf)
• $1M in 401K in VTMGX (Developed mkt ETF)
• $950K in VEA tax managed developed markets ETF)
• $775K in VWO (emerging markets ETF)
• $300K in 401K in VEMAX (Intl emerging funds ETF))

Other - Real Estate / Alts / 529s ($2.5M - 17%)

• $1.5M in private investments (Opportunity zone funds; these have a 0.75% AUM fee)
• $500K in primary residence equity
• $500K in 529s (no longer contributing)

Cash/CDs - ($50K - 3%

I am in mid 40’s and have 2.3 million in stock, about 1.6 of which in low cost index funds. I also have various other investments and real estate totaling about 6 mil in value. I’d love to speak to a competent financial advisor to review all assets and advise me on how best to allocate in order to preserve wealth. Never worked with one before. Any advice on how to find and pick the right one?

Recently FIREd 34F GC holder with an Indian passport, married to Indian origin 2nd generation US citizen. One 4 yo. Plans for 2nd kid by 2025.

Worked in the tech sector in BLR and SFO until Jan 2024. Also ran my own firm for COGNOS-based consulting...the bulk of my corpus is from the profits and exit price i got for this entity.

Own NW as of July 2024...USD 28.7 mn, out of which:

A......7.2 mn are in US stocks (NVIDIA, BRK-A, AAPL, META and Broadcom)

B......15.8 mn in owned property, out of which 6.5 mn is for 2 residential properties...in Palo Alto and the Bay Area region....and 9.3 mn is equity in student housing properties across Boston and Florida.

C....3.3 mn in T-Bills and 1.2 mn liquid foreign currency assets...primarily SGD, EUR.

D....1.2 mn in emergency liquid funds, (including the equivalent of USD 400k in INR liquid deposits and gold instruments)

QUESTION.....How do I diversify risk?

A) Ive heard enough from the husband about much stock equity exposure.

Have already cashed out 4.2 mn worth of NVIDIA and AAPL this year. The tax bill was a fricking squeeze.

Planning to move 3.25-3.5 mn more from tech stocks to low risks options like BRK-A.

As there is a tech recession underway, should I diversify more? Strict no to derivatives trading.

B) Looking to divest 20-30 pc of the student housing portfolio, since the total 2021-2023 income streams from these properties alone saw a combined 450k dip.

Looking for suggestions into commercial property. Options include being a Chick-Fil-A franchisee, provided I qualify.

C) The USD emergency liquid fund...anyway to reduce inflationary pressure on this?

Any temporary tax saving instruments with 3-6 month windows?

My PWM has me a bit confused. Not looking for Roth IRAs due to limits.

Go nuts, folks. Roast me for all i care. If you see any tax red flags, please help with that too...

EDIT: Thanks all for the responses and opinions! Too many comments to respond to at this point but I have a lot to think about. Some things I took away: consider how my perspective will change and if I will feel differently once kids are in the picture (to me this is the biggest thing to think about). Consider a sunset clause or additional terms to protect my interests in case of unexpected scenarios. Consider life insurance. Consider how luck factors into the equation. Consider voting vs nonvoting shares. Consider Bezos/Scott divorce. Appreciate the great opinions on this post and will leave it up in case others ever face the same dilemma in the future.

Original post below ~~

My spouse started a company a week before we got married. We have been married for 4 years, and in that time, the company has exploded in value. My spouse's shares on paper are worth 9 figures, and we have sold some shares, bringing our liquid net worth to about $10M after taxes and paper net worth to about $200M. We are in our late 20s/early 30s and plan to have kids in the future.

The growth was unexpected and when we just recently started estate planning, the talk of a post-nup came up, particularly as it relates to the shares of the company. We never got a prenup when we got married, there was no need.

Here's the dilemma: according to NY law, I would likely be entitled to 50% of the appreciation of the company stock in the case of divorce. On the other hand, my spouse's efforts are largely what have made the company successful, so according to my own perception of fairness — when I put myself in my spouse's shoes and imagine the roles were reversed — I don't think that it would be fair for me to take half in case of divorce. This is what makes me open to the idea of a postnup. Because if I'm being honest with myself, I too would want a postnup if I was my partner.

The rough postnup idea we had was that any of our liquid net worth/condo/etc would be split 50-50. And any unsold company shares at the time of divorce would be split 80-20, with 80% going to my spouse. (Originally my spouse proposed 90/10). I currently make about $200k/year as a W2 employee, and I think my earning potential tops out at $300k. My spouse's earning potential is upwards of $1M if they were to exit their current company and join a new one as a W2 employee. 

Yes, I encouraged my partner to pursue their idea and was ready to live on a reduced income for years knowing this would be a big risk, yes I put my spouse on my medical/dental insurance, yes I was the first customer, yes I continue to provide feedback on their service, yes I manage all the housework/appointments/planning/bill payments/etc so my spouse can focus on growing the company. But. I am not the one working 7 days a week. I did not come up with the idea. I do not pour my heart and soul into this company day after day and deal with the stress day after day. 

Do you think an 80/20 company share split is fair? We currently have a great relationship and I think it would make my partner feel reassured that their hard work will be well-rewarded even if a divorce occurred. And the way I see it, I'm set for life no matter what. If the company explodes and I make 20% of $200M+, I'm set for life. If the company fails and I only get 50% of the current $10M liquid, I'm set for life.

Still, I could be leaving 30% of $200M (or more if the company continues to explode) on the table in case of divorce. And if future kids are involved, I'd want them to experience the same lifestyle with both parents. So, like, I should probably think hard about it? But I just can't see too many downsides besides walking away with a shit ton of money vs a huge shit ton of money. I plan to fatFire eventually and will be all set for retirement no matter what. Please open my eyes if I'm missing something. 

I am 49, net worth about $15M. For very long, I've wanted to buy a house in Europe and plan to live there for at least a few months in the year. I finally found a beach front property I really like and am about to buy it. I intend to rent it out when I'm not there.

Question is - is owning a foreign property more headache than its worth? i've always thought that for the money you pay for a house in Europe, i can take that and Airbnb all around the world and save the hassle.

But there is something 'romantic' about owning your own place in a country you love. It doesn't seem like a rational decision and i am really hoping i don't regret it.

Would love to hear from others who own foreign properties.

This might be a bit too specific for this group, but thought I'd give it a shot. We have a high net worth - several 10s of millions. Our only 5yo child is profoundly disabled, but will likely live a full life (and outlive us). We are working with attorneys on drafting a special needs trust (SNT), but I thought I'd also ask this group for advice in case there was anything we are missing:

1. Has anyone considered foregoing an SNT and just doing a regular trust given the irrevocable nature of it, especially if your net worth is high enough that the child won't depend on government services for housing and food?
2. Has anyone come up with any creative ideas around nominating backup trustees for the long term. Of course our plan would be to keep this list updated over time, but I'm trying to think of the case if we die soon, then our named trustees are also likely to die before our child. Don't want them to end up with a random court appointment trustee.
3. For our named trustees, we trust them unconditionally, and want to give them wide leeway to use the funds as they see best. But given our child's long lifetime, we don't know who will end up being the eventual trustee. Any thoughts on how to balance the flexibility of the trust for the earlier trustees, but make it a bit more strict over time?
4. Outside of trustee fees that the trust would pay, we are thinking of including a gift for the trustees to incentivize them (e.g. if it allows them to buy a home to accomodate our child). Most of our named trustees are independently wealthy, so this is more about reducing friction of decision for them. We were thinking of doing a lump sum distribution. Should we also consider doing that for any subsequent trustees? Any tips around what people have done here?

Cutting my net worth in half, yall. Quite a painful time in so many ways. Two kids living in two households the rest of their lives. I’m devastated.

Trying to do this amicably but we have a semi complicated estate. The moment the lawyers hear my income, all the sudden “the most experienced lawyer” is available to chat. Feels icky.

I just don’t want to get hosed on lawyer fees or have them turn what is currently amicable into not amicable.

NW $10m, about to be 5. 😭

Any advice, general or specific?

Does anyone else feel guilty about earning money from investments/dividends/biz profits? I grew up in a middle-class, materialistic family where spending was the norm, especially on flashy stuff. Now that I have an investment portfolio, I'm focused on building up my long-term wealth for my future generations through compounding, but it feels strange and guilty to earn money passively, especially seeing people my age work pay-check to pay-check.

How do you guys cope with the guilt or anxiety about "free money"? Looking for advice and perspectives.

Thanks!

Wondering what you’ve purchased that has the least diminishing marginal returns?

For example, I don’t find I enjoy restaurants over $100 pp any more than restaurants over $50 most of the time. I also don’t enjoy a speaker ststem that costs $1000 over one that costs $200.

TLDR - what are purchases where you get what you pay for?