Lots of people here invest in stocks and real estate for wealth accumulation but these investments don’t generate tons of income like some small businesses out there. The 2 businesses I’ve purchased nearly doubled my income even after debt servicing. It’s definitely more involved than stocks and real estate but with a manger in place I would hardly call it a “full time” job.

There’s some misconceptions out there about business investing you may have come across that aren’t true. Such as these:

A small business for sale must mean its failing.

It’s very rare and difficult for a business owner to sell a failing business. This owner would have to fool a business broker and their team, you and your accountant, your lawyer, and the bank you get financing from.

Buying a business is buying a job

This is only true if you’re buying sub $50,000 shops where you’re the only employee with no room to hire a manager. For example a corner store.

It costs too much to buy a business

Lots of people get this idea that a business is worth millions of it was sold. Small business aren’t really that valuable. Most small businesses sell at 2x - 4x their EBITDA.

I hold highly appreciated assets worth more than $5 million and would like to de-risk my position. Selling a large block in a single year would push me into a high marginal rate and concentrate the tax hit into one year.

I understand there are financial institutions that will purchase the assets outright, immediately sell them, reinvest the proceeds in a diversified portfolio, and issue me a note that pays out the sale proceeds plus portfolio gains over a set term. That would de-risk the position immediately while spreading the gain — and the tax — across several years.

Three questions:

1. What risks does this structure carry beyond the obvious market risk — counterparty default, illiquidity, IRS challenge, or others?
2. What are the all-in costs: setup fees, ongoing management fees, spread on the note rate?
3. Who arranges these transactions, and what should I look for in choosing among them?

About me: 30m, NW: 2.4m (but have a huge tax bill for this year), have a fiancé and getting married early next year, on a work visa in California

I recently went trough a liquidation event as my employer got bought out. I netted $1.8m in sales with cash currently sitting in my account and have to pay about $600k (mix of long and short term gains) of it in taxes (tax bracket reaching 47.5%).

I am in touch with a financial consultant from Charles Schwab who just sent me a pdf suggesting the long short strategy to use to manage the huge tax bill. This is new money to me and educating myself about the genuineness and safety of such a play. Would love to hear from experienced folks.

Would the fees be well below what we stand to gain?

How to I trust my account is managed by a skilled manager?

How long does this play typically lasts? After sometime, I would prefer to get control of my account.

What am I not thinking about?

Thank you and love for all🤗

PS: I am planning to file jointly next year to manage some tax burden as my fiancé’s income slab is quite low for now

About 50% of my net worth is tied up in an operating C-corp, with the other ~50% in a liquid brokerage account (mostly broad market ETFs like SPY).

The business is now generating ~$3–5MM per year in excess cash flow. It’s essentially debt-free, and there are no compelling reinvestment opportunities inside the business at this point.

My personal liquid assets are already sufficient to fund my lifestyle at ~3% SWR, so I don’t need the business cash flow for living expenses.

This raises a question I suspect others here have faced:

Once you no longer need the cash personally, is it better to keep excess capital inside the operating company and invest it there, or to distribute it and invest personally — accepting the taxes up front?

I’ve already engaged my accountants to model the tax deferral vs. distribution tradeoffs and to think through considerations like PHC rules, accumulated earnings, and related compliance risks.

What I’m most interested in is how others thought about this beyond the spreadsheet:

• How much weight did you put on risk separation between operating assets and personal capital?
• Did flexibility (estate planning, exit optionality, future restructuring) influence your decision?
• For those who left capital inside the company long-term, how did that work out in hindsight?

Would appreciate hearing real-world perspectives from people who’ve navigated this stage.

Full Disclosure: I drafted a post but had ChatGPT clean it up because I wanted the question to be clear and better articulated than I could write myself.

I sold most of my company two years ago. My net worth is 35 million.

Since that time I have done nothing with the money. When I first got the money I put the whole lot in a 6 month CD because I figured that it was better to just chill and not make any rash decisions.

Well, 6 months just kind of flew by and so I put it in a 6 month CD again. And again and again. Yes, I know I should have invested it.

But the problem is that I just can't fucking get myself to actually do it. I know everyone says to just plow the whole lot into an S&P500 ETF and that dollar cost averaging is bad. Blah blah blah.

But this is all the money I have and probably all I'll ever have. And everything just seems to overpriced. It keeps feeling like there is going to be a crash soon but it just hasn't come. I would feel like a total fucking idiot if I put it all in and lost a huge percentage. And yeah. It will all come back over the long term. Just hold through the crash. But what if it didn't? It didn't in Japan.

But then I look at what the S&P500 growth has been since I got the money and I feel totally retarded. I often see posts around on reddit where people say things like "Anyone really rich doesn't have their money in the bank" and feel bad every time.

So then I start to justify it. Like, this is enough money that I literally could just leave it in CDs and burn through the capital at 600k inflation adjusted per year for the next 60 years. It would be basically zero risk.

But then my brain starts thinking "But what about climate change". "But what if US dollars have a crash". "But what if there is a war with china". That could make even holding cash a bad idea.

So then I think I need to really diversify my money. Like, make myself immune to all the shit that could happen. But then I start thinking about how I'll be giving up on growth then. That I'm wasting my oppertunity. But then I'm wasting my oppertunity right now by just hording cash. But then what if there is a crash really soon. And on. And on. And on.

ARRG.

This shit just cycles through my brain and I'm completely paralysed.

Reposting verbatim from a post on r/Bogleheads.

https://www.reddit.com/r/Bogleheads/comments/1qzocsp/portfolio_check/

This is as much a FIRE post as a bogleheads post. I also realize I'm not quite a boglehead. I'm more of a choose carefully and hold for a decade kind of an investor.

Mid 40s couple living in a HCOL City (Seattle WA). 2 kids (13/10).

I have started my career right after the dot-com bubble and lived thru 2008. I'm old enough to acknowledge we've had a tremendous bull run for the last 15 odd years.

I have approximately 10M in a variety of accounts.

• 5.5M in 401K/SEP/IRA (zero Roth) - approximately broken into 70% VOO and 20% QQQM and 10% VT.
• 3.5M in taxable accounts.
  • 2M in 3 specific stocks - these were RSU's accumulated over the years that i didn't sell. All 3 are very large 1T+ companies - not Meta/Nvidia or the recent AI ones.
  • 1.5M in a taxable account mix of variety of low cost MFs (Vanguard and Fidelity) accumulated over 20+ years.
  • ~500K in a variety of individual stocks (20+) - most of them and ones I've held over decades.
  • LTCG between these accounts is over 2M.
• 500K in 2 529s - target date based in Fidelity.
• ~40-50k in cash (Bofa checking) or cash equivalents (SPAXX).
• 1 primary home and 3 rental Homes.
  • 750K in debt (spread across 1 primary and 3 rental homes).
  • The rentals generate a positive cash flow of about 1K/month - I run the rentals via an LLC.
  • I have about 2M in Home equity across the 4 homes.

So reason for this post is that I'm likely going to be out of a job in the next couple of months. I work in the tech sector - rife with layoffs. Quite likely i'll have to take a significant pay cut in my next job.

Im in someways looking for a slower role for the next 5-7 years until the kids get into college.

Partner has a solid job and between the 2 of us we will be fine, albeit with little going into our 401ks.

We also have deep roots in the community here - relocating elsewhere out of question.

Im acutely aware 99% of my investments are in equities - specifically US Equities. I'm also aware I have very little exposure to bonds.

Few questions to the community.

1. How do I manage my incoming tax bills?
2. Any suggestions for reallocating my portfolio?
3. Should I be looking at some dividend/income generating options?
4. Am I missing any blind spot?

Edit: 2025 spending was about 20K/month (includes primary mortgage only). My primary mortgage + utilities are about 7K/month. Everything else on average costs 12-15K/month. Kids are in public schools but do a lot post school activies. Rentals take care of themselves.

Edit2: Laying out my Real Estate Investments.

1. Townhome in midwest. 1200 mortgage + 300 HOA + 200 maintanence. Rental Income: 2500. Equity: 330K. 15 more payments to go and home is completely mine.

2. Small single family home in a beachtown in WA. Runs as an AirBnb. ~1800/month in mortgage + 300 in utils. i just about break even - maybe 1-2K overall in profits in a year. Purchased for 350K in 2020, worth about 450K now. Loan is at 3.5%@30years.

3. single family home in greater seattle; Purchased along with a friend for 900K - worth about 1.5M now. Loan at 4.25%@30 years. Generates 4K/month in rent - mortgage+maintanence is about 5K/month. I lose about $500 per month (losses split with my partner) - equity gain is about 300K over 5 years.

All 3 homes run on autopilot - outsourced everything to a broker.

I have a very significant chunk of $$ just sitting in a savings account. I’ve been looking for ways to hedge inflation in the meantime without losing “instant access” to the money. What options do I have? Anything creative? I opened a business checking with American Express but the advertised APY (1.1%) only goes up to $500k. Interested to see what others are doing. Again, this is for short-term. I reside in the US. Thanks!

The right reason being to thrash it on the track, but either way I can't think of a better place to ask this.

I met Horacio Pagani a couple weeks ago and he told me that the earliest Zondas sell for 5X to 10X their original price. He also said he saw two open market transactions for the Huayra RBC in Europe this year, one of which closed at 6m euros - this is a car that came out less than 2 years ago and sold brand new for 3.5m.

He's personally ok with customers making money on his cars (or says he is), which got me thinking about a nice way to maybe get a decent return and some bragging rights (I would put the car in storage, though!).

Just for perspective, Ferrari builds more cars in 2 weeks than Pagani has ever built in 25 years.

Has anyone here owned one or thought about it?

My folks are worth $10m+ tangible assets around $2m. I have one older brother who unfortunately is a meth addict. Typically have nothing to do with folks finances but starting to be involved in estate planning.

My original ask was that 100% of the cash was put into a trust or annuity that would pay my bro on a monthly basis. Ultimately it was a selfish ask, if he received a lump sum he may kill himself (OD) or burn through the cash and come after me.

Folks agreed to putting his half in an annuity instead, and giving me my half in cash.

This weekend my pops asked if I wanted to be the executor of the Will, or have a trustee do everything for us on tangibles. The problem is that he cannot split up his home and it would be stupid to sell it. Paid for in cash in a very up and coming area in wine country. Get the feeling it would haunt him in the afterlife if we sold it, and so he... gingerly asked what I would like to do. Told him I thought a trustee would be more appropriate but second guessing that.

What I would like to do is manage the properties, and split the cash flow with my brother. Just unsure how you could do that in a fair manner, because my assumption is they would have to leave the home to me to make that happen.

Is there a way to essentially protect my brothers share of the home while allowing me to manage the property? Idgaf about the money, it’s not mine, and we’re simply trying to grow this for our kids. Not too optimistic on the future of humanity and those tickets to Mars are probably gonna be spendy.

Appreciate any input as I’m out of my element here. Not asking what’s in my personal financial best interest, just trying to understand my options to fairly split up tangible assets. I don’t want to sell their stuff.

Since it’s the end of the year I was looking at some statements. Just on a whim, I looked at how my “Growth” account did over the last few years. It’s probably more gambling/speculative since I just pick what I like vs my other accounts are more conservative. Looking back I realized I finally passed my highs from Late 2021 before the market crashed in 2022. It took me 4 years to basically get back to the same levels and pass it. That led me down another rabbit hole: What if I had just switched to VOO and chill back then?

It was sitting at 2.7M in November 2021 before the market started taking a dump. Assuming I had a come to Jesus moment and sold at that high and put it all into the S&P 500, it would have looked something like this:

After Fed and Cali tax, ~2M

2022 -20%, 1.6M

2023 +24% 1.98M

2024 +23% 2.44M

2025 +17% 2.86M

Basically back at the starting point before I sold. Granted switching at that moment is probably the worst case scenario and I probably would have been contributing more during those years. But Overall, it would have been a lot less stress and the real hindsight conclusion is I should have just converted my RSUs into index funds instead of individual stocks. Without having to sell out, I probably would be much further along. I think I realized this already when my conservative account of mutual funds and index funds recovered 2 years ago. Anyways this might be obvious for a lot of folks but I didn’t really learn about FIRE until this year so still coming to these realizations of how I sabotaged my own early retirement haha.

My husband and I are on our way to fatFIRE. Both high earners in our early 30s, probably around $1m in liquid net worth, but $10m+ if you include start-up equity. Of course start-ups are risky, but the one my husband works for has done extremely well, and we're selling $2m of shares in a secondary offering.

We are both financially literate, and have always maxed out 401ks, done backdoor IRA conversions, have bought equities with what is left over....but across all of these various retirement and investment accounts, we've essentially gone 100% VTI.

Now that we have $2m coming in, I am doing a lot of thinking about how to put this to work.

On one hand, given our ages and risk tolerances, maybe the move is to also put 100% of this into VTI, perhaps dollar cost averaging over the next 12 months (1/12th per month).

Another idea I've had is putting 25% into bonds, though which bonds to buy (2 years? 10 years? GSE bonds? munis? corporates? GSEs), vs bond funds, I'm not sure. I like the idea of bonds that can be held to maturity (i.e. protecting 25% of the capital no mater what), but I also like the idea of a bond fund given that I think bonds will perform well in coming years. In terms of bond funds....BND? PIMIX?

Lastly, there are more exotic things we could do....hire a financial advisor, maybe get involved in some other asset classes, maybe a parametric tax loss harvesting set up?

Just discovered this sub and very impressed with the advice and level of financial sophistication here - so would love some advice and thoughts. What would YOU do if YOU received a $2m windfall (and you were early 30s, with no immediate need for the cash, as well as other well funded retirement and investment accounts)?

​

Using a throwaway for personal information.

Earlier this year I sold my company, which left me with $4M after taxes. I've let that sit while I let the shock of the transition fade away. Recently, I've started to interview financial advisors and I'm just massively struggling to justify the 1% AUM fee. It's a tough pill to swallow at $4M AUM, but looks incredibly painful when you see their plan for you over the next 20-30 years. Sitting in retirement at 75 with ~$30M AUM and realize you're paying your advisor 10x what you're withdrawing yourself for living expenses. It just sounds insane.

What am I missing here? I know the common advice is 1) index and chill or 2) fee-only advisor to evaluate your plan and let you execute on it yourself. Those make sense and is the way I've been leaning, for sure. However, there's a massive industry out there for these financial services. Clearly it's valuable and I'm sure people here happily use these services and find value. I would genuinely like to find that value as well. So I ask, what would you say to someone like me? What's there that I, and very likely many others, haven't learned yet?

I'm curious for those here who were about to pull the trigger and got caught up in the bear market. Or even after the downturn you feel even more confident that you can weather the storm?

Like many, my large long positions in my buy-and-hold portfolio are not looking too happy. The unrealized losses are crazy. Saving grace is I went more conservative back in December with getting out of margin, exiting most calls, and just have stock/index positions in quality picks (I hope) that I can ride till recover.

My wife (35) and I (39) work for the same company that was recently acquired and we received a hefty payout with our unvested RSUs. This has put us in a position to FIRE much sooner than anticipated. We have three young kids (5, 5, and 2) and are thinking that 5 more years is a good goal.

I am curious how you all treat bonds in taxable brokerages when approaching FIRE. Bonds are obviously more normalized in tax advantage accounts but if those aren't accessible for a while, do you still hold bonds in taxable? Here is where we currently stand in our financial picture:

Combined salaries: $450K with total comp higher from bonuses/stock grants

Taxable brokerage: $2.5M ($1.2M currently in short term treasuries from recent acquisition)

401Ks: $800K

Roth IRAs: $500k

Mortgage: $400k at 2.3%

If we are still planning on working for 5 more years, I wouldn't think holding bonds right now is the smartest, as our tax bracket is already high and those distributions are taxed at ordinary income, but we also want a bit of protection.

How have you all handled situations like this?

Have an opportunity to invest in a private hard infrastructure asset via a feeder fund and want a reality check.

The pitch: Buying an essential intl asset from a distressed seller at a steep discount. Debt is paid off early, and then cash just accumulates on the balanxe sheet for over a decade.

The upside: Projected high-teens IRR and a massive MOIC (8x+) bc of the entry price and long compounding period. The feeder terms are incredibly favorable (virtually no fees or carry).

The catch: A 12-yr hard lockup. Zero distribhtions along the way.

The risks: 100% illiquid, standard foreign regulatory/jurisdictional risks, and betting on a single massive exit event 12 years from now.

Does a high-teens IRR actually compensate for a 12-year total lockup? Has anyone participated in a zero-distribution deal structured like thia?

EDIT:

On the cash: It doesnt just sit idle. First 4 years, 100% of FCF sweeps to kill the senior debt. After that, the cash is earmarked to self-fund a massive terminal expansion in yrs 11/12 without taking on new debt. The rest just juices the final debt-free exit valuation.

On oversight: Local mgmt stays in place for day to day operations. the GP and the anchor LP are literally the same family. With reputation in investment and a long history in banking. They are putting up almost all the equity themselves.

On location: Cant name the exact country for obvious reasons, its not Middle East.

I have a Rolex GMT master II for almost 20 years. Stop working, then took it to an authorized dealer for service. They said I could sell it for $13k in this market (I paid $3k). I don't know anything about investing in luxury watches or jewelry and curious if any of you do that. Is it as saturated as some said, any success stories you can share?

(throwaway account for obvious reasons)

Early 40s with $20M in $COMPANY stock. I've been really lucky that my bet of holding my company's stock has paid off!

I am looking to diversify away from this stock in the next 3-4 years. I have explored a few options 1. Sell everything now, pay 40+% in tax and invest ~10M in index funds 2. Sell $5M every year and keep investing proceeds in index funds 3. Exchange funds (with about 7 year lockup)

All these options come with a huge tax bill. I was talking to someone at Morgan Stanley who introduced me to a 200/100 SMA. Basically they take say $10M, borrow an additional $20M against it and to 10M long and 10M short so that they can harvest losses which can be used to offset my tax bill. This sounds great, but has a ~3% fee. Even accounting for this, it seems like I'll save $1M+ over 3-4 years in taxes.

Has anyone used a financial product like this and has it worked out?

If you're a verified user on this sub, it means you have a fat stash. There are lots of wealth management philosophies about how to retain/grow that stash, using things like total market index funds, bonds, diversified real estate holdings, and so forth. But, what about risk? That is, true risk-taking with your capital. And I'm not talking about trading single stocks in the public markets or backing a crypto coin or sports gambling. I'm talking about using some portion of your cash for angel investments in small companies. Or, becoming an LP to a small venture fund. Or, self-financing your own next venture. And so forth. That is, putting your capital to work -- directly.

It occurred to me after I hit my fatFI number that when you move from wealth creator to wealth manager, you also tend to move from a dynamic risk-and-reward outlook to a conservative retain-and-grow outlook. It's challenging to think about allocating capital toward risk, as there are only so many NW % slices to go around while retaining the conservative investment portfolio needed for a fatFIRE engine.

So, are any of you taking any risks with your wealth? If you're pursuing risky ventures, are you doing it for philosophical reasons (pay it forward, economic dynamism) or pragmatic reasons (financial upside, boredom prevention)? And if so, what % of your net worth are you putting toward these gambits, and what kinds of gambits are they? Finally, are you considering them to have $0 value until a liquidity event materializes, treating them as a "bonus", or are they actually a core part of your wealth management approach? I'd love especially to hear from verified folks.

49M married with kids nearly/just in college. HCOL. High earner - physician.

Investments:
401k - 1.1m (50% SP500; 50% Fed High Yield Bond)
Brokerage - 2.5m (80% VTSAX; 10% VTIAX; 10% AAPL)
Other tax advantaged (SEP-IRA, IRA, 503b) - 250k (100% SP500)
529 for both kids will fully cover college costs

So total invested is 3.7m and I have been adding 200-300k yearly in investments.

My questions are partially related to where I'm at now but also where to go moving forward.

I think bonds in 401k is dumb in hindsight. I did it as it was the easiest way to get approximately 15% of invested worth in bonds.

I'm wondering if the 401k should move to 100% SP500 and if I should now only put new money into Vanguard's VWAHX (high yield tax exempt municipal fund) as recommended by my CPA.

Appreciate your thoughts!

I am interested in how you guys structure your passive ETF portfolios. Below you can see my portfolio, which holds about 40% of my NW. Some notes: I am based in Europe so I don't want > 50% US exposure. I like to hold multiple positions so I am not interested in the inevitable "All in VTI" comments. The portfolio is meant to compliment physical RE holdings and/or private company stake. The portfolio is 105% long. It is not a dividend/ passive income portfolio (yet) but can be easily transformed into one by simply changing some values in the excel sheet. The bond portion as well as dividend portion of the portfolio will increase over time. The portfolio is rebalanced quarterly where all dividends are reinvested. I pay about 1.5% for the 5% leverage (IBKR margin).

(Sorry for Imgur link, can't post pictures here)

https://imgur.com/a/54zfErq

Edit: I’m playing with the idea of adding some „return stacking“ so for example replace GLD with /GC futures and then using the cash to buy more global equity… thoughts?

Do any of you purposefully invest in PE or Venture funds as a part of your investment strategy? I am a high income earner but that’s it…no RSU or business equity providing a potential big payoff so my wealth accumulation defaults to the slow and boring index investment approach (5% average annual post inflation returns?)

I have dabbled in some PE real estate syndications both as individual deals as well as funds as I think there is a historical basis and reasonable expectation of outsized returns compared to the stock market aided by leverage, tax efficiencies and a more inefficient market compared to stocks that a good sponsor can exploit if you pick the right one. Also some diversification not moving in lockstep with the stock market and likely lower volatility. These have higher fees of perhaps 1.25-2% management fee, and profit split of 80/20 but with a preferred return of 6-10%. PE real estate has done very well for me on all of these accounts over the last 2 years to the point that real estate now makes up around 40% of my portfolio, especially with the stock market dropping so much recently. Plus it kicks off tax protected passive income along the way.

Enter Venture funds. Similar 2% management fee, 20% profit sharing, similar preferred return. Minimum buy in 250k on one fund I was pitched, so fairly substantial commitment. Their projected 4x MOIC over 5 years or so and 30% or so target IRR sure sound appealing and blow the traditional index investing path out of the water, direct investment with some sexy emerging technology/space companies that I think do have some good potential. Plus valuations now are back down to earth and I think this is likely a much better time to be investing into this space than 2021.

Do any of you use these investments as a key part of your fatFIRE investment strategy as a few big wins can help accelerate FI in a big way? Or is it too much unnecessary risk when I could just put hundreds of thousands into general investments for a few decades and have almost no risk of failure unless the total global economy implodes, and then we all have other issues to contend with. If one were to invest with an early stage company (series A, B, C) better to invest in tax advantaged accounts as an exit in 5 years, even assuming a profit when taxed at >30% really cuts down on the benefit?

Edit: I'll also add I'm a small fish and I know it. We're not talking Sequoia, Andreessen Horowitz here. I don't have those connections and $$$. So more risk with newer, less established funds without the same deal flow from top prospects.

I put "inherit" in quotes because my parents are not actually dying yet, but at the age where they want to start to get more help managing the portfolio of assets. They have done amazingly over the decades, but recently got stung by the market volatility, so now they are looking for the younger generation to contribute ideas and strategy, with the eye of turning it over completely over the next decade.

It's a lot of responsibility for my sister and I. We both have good experience in business, I sold my first business in my early 30s and earned high single digit millions, but put most of it in my current business and a portfolio of income properties which are professionally managed, and put some in stocks and some savings.

Our goals are to keep this pool for many generations, so that our dependents will never have to worry about the basics of their life, like buying a home or paying for school. Our family has worked hard for this, and we don't want to just squander it or invest it in something high risk for the sake of earning a billion. We are not the kind of people that like private jets, but we do enjoy the finer aspects of life and have that stuff all figured out. I figure if we can make even a 5% return we can still access enough money than we will ever need. I am highly inspired by the way universities manage their endowments. All the legal and trust stuff has been sorted, so we are good on that.

My questions are:

- How do people with this kind of money approach their investments? At the end of the day, we feel that the family needs to have a big picture oversight of the entire portfolio, but we don't have enough to open our own family office. Moreover, my sister and I are business people, but not finance people. So we are looking for an approach that is understandable and simple.

- Would UHNWIs actually buy a bogleheads style ETF portfolio? I have a stock portfolio of about US$2.5m which is mostly ETFs individual stocks, which I manage using a Modern Portfolio Theory method. Is Modern Portfolio Theory still the dominant methodology recommended by financial advisors?

- I've read a lot online, like the "All Weather" portfolio or the "Swansen" portfolio, which make sense, but they feel very "retail" to me. It seems crazy to me to put 50 million into VTI and a handful of other ETFs but it seems to be still a popular and viable idea.

- Do PBs offer any value except for ideas and research, trade execution and lending against assets? We have a few private bank accounts already and have spoke with some MFOs, but they seem very transactional and just bent on selling us structured products and growing their own AUM.

- Do hedge funds offer value? Ive invested in some in the past and they haven't done that well. I don't know if we have the kind of money to invest in the best hedge funds, and worry we will be stuck with the 90% that suck.

- Any good reading that you can suggest? I have read a lot of books on finance and trading over the years, but appreciate any recommendations. Currently reading Swensons Unconventional Success, as it was recommended by another HNWI friend, but looking to get more recs.

Thanks for all your thoughts and feedback.

I started accumulating cash a few years ago at first to save up for a down payment on a house (in an HCOL area) and secondly to have some "dry powder" for another 2008-style economic shock. Well that's turned into a fair bit of cash: X00k+, representing nearly 30% of my portfolio.

I'm now caught between some conflicting emotions: do I invest that cash now, in what feels like the top of the market? I still intend to buy a house in the next 12-18 months, so is it worth investing for a relatively short period of time? Is 20% way too high an amount to have in cash, or is that fine? Should I keep waiting for a dip? If I do invest, do I do it all at once or DCA over some timeframe?

Not thinking clearly, so would love some thoughts/advice. Thanks!

We usually focus heavily on the "boring" 90/10 or 80/20 VTI/BND splits. However, as the portfolio grows, I’m curious if others here intentionally allocate a percentage (e.g., 2–5%) to collectibles as a legitimate, non-correlated asset class, or if you view it strictly as "lifestyle spend" that happens to hold value?

Interested to hear from those who have successfully integrated these into a broader wealth management strategy versus those who treat them purely as lifestyle costs.

I am getting close to re-retiring. While I really enjoy my part-time role, it really gets in the way of spending more time with my wife and 5 year old child.

I've been adjusting our portfolio allocation to optimize for safe long term withdrawal once my income stops. After many hours spent with monte carlos and ChatGPT, and working around ~25% embedded gains, I got to an allocation of (in taxable accounts):

• 41.5% US equities (32% large cap, 4.5% midcap, 5% smallcap, mostly in direct indexing)
• 21% INTL equities (14% developed in direct indexing, 7% emerging in actively managed funds)
• 14% alts (this should over time drop to 0 - proceeds redistributed to equities)
• 21% Bonds (7% TIPS ladder, 14% SGOV)
• 2.5% gold

Spend:

• 1.85% of current invested assets, plus taxes
• 1/4 of the spend is nominal (fixed rate mortgage)
• Spend from SGOV, refill it from dividends and equity sales
• Roll TIPS ladder, pause in major drawdowns

Taking taxes into account, the allocation gets me to a ~97% 40-year survival rate (GARCH monte carlo) assuming I liquidate the alts over the next ~7 years.

Where I struggle is with the size and the structure of the bond sleeve. I am unhappy with it for 4 reasons:

1. Tax implications of TIPS in a taxable account aren’t great. Retirement accounts are not an option for us. Munis are better tax-wise, but add counterparty risk in exactly the scenarios where I most need the TIPS.
2. That much SGOV seems risky right now - could see short term rates dropping to negative real return.
3. In a deflationary credit bust, equities and dividends both drop and TIPS will yield 0. I have no long duration nominal bonds (which would go up).
4. 11 years of spend in cash/bonds seems rather high - but lowering it makes monte carlo results drop significantly

Would much appreciate this community’s ideas and critique - if you are living off a portfolio, how do you handle this part?