Developing Complete Plan for Windfall

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SleeplessDIYer
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Developing Complete Plan for Windfall

Post by SleeplessDIYer » Tue Nov 20, 2018 7:11 pm

At this point, my situation still slightly hypothetical, but it's potentially realistic in the medium-term future. I'll lay out the general investment case first, but I'm ultimately trying to come up with a 360 degree plan to bypass the whole family office path. A MFO could be an option in the future just to go totally hands off in my later years, but I'm still young enough and my situation simple enough to manage a simple scenario on my own and not get overcharged with fees for playing musical chairs in the leveraged small-medium deal PE game. I've met with a few, and I was fairly disgusted. I'm aware of some of the various high-society relationships and stories enough to keep my guard up. It seems like good money though. That said, it's a sorry state of affairs that the would-be stewards would feel so untrustable for their rate but I digress. I have access to good accountants and lawyers and I don't have much use for concierge or access to the other clients. That might change! Anyway, below is the potential future setup for my current situation which is a barbell of 2-3 year's worth of cash (saving up for home) and a large, matured angel investment.

Emergency funds: Yes
Debt: None
Tax Filing Status: Married Filing Jointly
Tax Rate: 37% Federal, 5.75% State
State of Residence: VA
Age: 40
Desired Asset allocation: 60% stocks / 40% bonds, but open to allocating up to 75%+ if entering at the beginnings of the next long-term cycle.
Desired International allocation: Market-weight on stocks, but tilting US stocks for the next decade at least...after this cycle bottoms. :wink: International Bonds don't seem as interesting for the 37% tax bracket, but open to opinions.
I'm not all that knowledgeable about I and EE bonds, but I've been thinking about either going straight to treasury direct and managing a simple bond ladder with an excel sheet. I prefer to put the risk in the stocks and to keep the taxes low, but I'd be open to tax-managed limited-term to intermediate-term in one basket and a tax-exempt money market in the other. More diversification needed?

At these levels, the 3-fund feels like leaving money on the table. I'd be a religious 6mth-12mth rebalancer, perhaps open to drifting to higher or lower stock exposure in early or late long-term cycles, respectively, though probably not if I went with something more like a 50/50. It's just a question of completely passive vs. slight active to limit downside/maximize upside at the beginning and end of long-term cycles.
The core question is just how to allocate and into what. Moving on from there can go into the various ways to replicate a simplified VFO.

Total Stock Mkt vs. S&P500 + Small Cap Tax-Managed
I have mixed feelings on a Small Value tilt's higher turnover and its impact on taxes.
I have similar feeling about EM, but geopolitics in 2-3 years could make me a bit more open to it.
International is hard to say with the current snapshot of the world. Regions are a bit more nuanced in my head as I've been an expat for over a decade. Let's just say I'd tilt away from it, aka US tilt.

For the sake of the exercise, let's say I can sell the current investment for 8-digits or even low 9-digits, perhaps to consider qualifying for institutional rates in the largest allocations. It would be life-changing money, I know. That's why I'm here! That said, while I'm not a financial guru and how I got into my current high risk/reward scenario aside (blood, sweat, and tears), I'm fairly frugal. Other than a nice modest home, kids' educations, travel/consumables, etc., I don't see us needing more than the income/dividends on the portfolio, if that. There may be other income involved, but it's not really a consideration at the moment. I'm considering all income to be portfolio related.

Free reign for responses. I'm just open to hear what people would do in my situation: 8-9 digits, all taxable, 40, etc. I'm certainly a less is more type and a 3-funder would probably do the trick. That said, I can up the stewardship level with a bit more nuance. I would feel the responsibility to do it at least to have what could be substantially more marginal income which I would have the luxury to dictate how it got spent or donated. Mostly, the biggest challenges at these levels just seem like taxes. Asset Protection would be a follow-up.

Does Vanguard manage nuanced portfolios? I know they would do a 4-5 funder for 30 basis points as their semi-robo, but could they do something more nuanced for a super-low rate at this level of investment? For 30, I could pay a MFO. At the very least, I imagine that they could get me positioned into something interesting, yet simple, and just send me the re-balancing tool spreadsheet to manage it myself while they check in once a quarter or whatever.

EDIT: If anyone wants to suggest a 4-7+ fund allocation, that would be an interesting topic for me. Thanks.
Last edited by SleeplessDIYer on Thu Nov 22, 2018 7:51 pm, edited 1 time in total.

123
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Re: Developing Complete Plan for Windfall

Post by 123 » Tue Nov 20, 2018 10:13 pm

The basic 3 fund portfolio can work well even for an individul investor of substantial means. You can use Vanguard funds or funds from other firms. Many of the funds have share classes that have multiple levels of institutional pricing that might work very well for you. Generally the complete prospectus for each fund will identify all the share classes they offer and how large a position must be to qualify for any particular share class.

I don't think the Vanguard PAS service (.3% annually) accommodates anything outside their standard recommendations. You don't have to have your portfolio at one place. Some investors may use a financial adviser for a portion of their portfolio "nuances" since some investors are willing to pay someone to listen to them.
The closest helping hand is at the end of your own arm.

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Tue Nov 20, 2018 10:41 pm

123 wrote:
Tue Nov 20, 2018 10:13 pm
You can use Vanguard funds or funds from other firms.
Thanks for the response. I'm looking for something more detailed, particularly with the special considerations that go into the higher tax brackets.

On other funds, I'd be pretty happy with Vanguard actually. The only other things I've seen which peak my interest are the 0% Fidelity funds. I know they're making money through share lending, but I'm still wondering how else they get you, or if it's just that. It adds a level of risk I suppose...CS, for example, loves a big cash allocation which sits in their bank. Great companies for the business model they chose, I admit. It'll be interesting if we get more regulation around these types of things. A social purpose corp. (SPC) might be a future structure to compete in the investment space. I don't know any, but now I'm getting off topic.

Dottie57
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Re: Developing Complete Plan for Windfall

Post by Dottie57 » Tue Nov 20, 2018 10:48 pm

Most of your post is over my head. Many bogleheads play it simple. I don’t think the three/four fund portfolios are meant to peak anyone’s interest - just steady market returns.

nix4me
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Re: Developing Complete Plan for Windfall

Post by nix4me » Tue Nov 20, 2018 10:52 pm

If we are really talking about 9 digits in taxable then the real need is a Tax Accountant or a Tax Attorney.

You can manage the investments easily but the taxes are are going to be a real problem. A good problem to have, but still a problem!

A simple 2 fund would be enough: Total Stock / Money Market. Or S&P / Money Market. Bonds are no good in taxable. Real Estate might be a good idea.

Don't let some sweet talking agent sell you Insurance or Annuities!

Good Luck.

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Random Musings
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Re: Developing Complete Plan for Windfall

Post by Random Musings » Tue Nov 20, 2018 11:06 pm

SleeplessDIYer wrote:
Tue Nov 20, 2018 10:41 pm
123 wrote:
Tue Nov 20, 2018 10:13 pm
You can use Vanguard funds or funds from other firms.
Thanks for the response. I'm looking for something more detailed, particularly with the special considerations that go into the higher tax brackets.

On other funds, I'd be pretty happy with Vanguard actually. The only other things I've seen which peak my interest are the 0% Fidelity funds. I know they're making money through share lending, but I'm still wondering how else they get you, or if it's just that. It adds a level of risk I suppose...CS, for example, loves a big cash allocation which sits in their bank. Great companies for the business model they chose, I admit. It'll be interesting if we get more regulation around these types of things. A social purpose corp. (SPC) might be a future structure to compete in the investment space. I don't know any, but now I'm getting off topic.
When you get down to the zero funds vs Vanguard Institutional, it comes down to tracking error plus the fact that each TSM fund has a different benchmark (Schwab uses a different TSM benchmark as well). I believe the max spread in TSM benchmarks was 30 bps one year.

If you can get to institutional select, then you have really arrived.

RM
I figure the odds be fifty-fifty I just might have something to say. FZ

ThriftyPhD
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Re: Developing Complete Plan for Windfall

Post by ThriftyPhD » Wed Nov 21, 2018 12:36 am

SleeplessDIYer wrote:
Tue Nov 20, 2018 7:11 pm
Desired Asset allocation: 60% stocks / 40% bonds, but open to allocating up to 75%+ if entering at the beginnings of the next long-term cycle.
How will you know when you're in the beginning of the next long-term cycle? Will you know in the moment, or only a couple year after the 'cycle' has started?
SleeplessDIYer wrote:
Tue Nov 20, 2018 7:11 pm
Desired International allocation: Market-weight on stocks, but tilting US stocks for the next decade at least...after this cycle bottoms. :wink:
How much do you tilt? How will you know when the current 'cycle' 'bottoms'? Is that a numerical definition you would know in the moment, or only a couple years after it bottoms?

Personally, if I were to get such a windfall, I would carve off what I need to live the rest of my life, and put that into a 50:50 stock:bond portfolio. The rest (which, out of $100 million would be the vast majority), I would put 100% stocks. I wouldn't spend anymore of my time trying to time the market to eek out a couple bps of return. I would spend the time figuring out what to do with the money I don't need to spend on myself. Foundation? Donations? Fund research? As those plans solidified, I would move money from the 100% equity pot to make them happen.

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 1:08 am

Dottie57 wrote:
Tue Nov 20, 2018 10:48 pm
Most of your post is over my head. Many bogleheads play it simple. I don’t think the three/four fund portfolios are meant to peak anyone’s interest - just steady market returns.
Don't underestimate yourself. I totally support the simpler option, but splitting Total US into S&P500 and Small (tax-managed) OR splitting Total International into finer slices, perhaps kicking out EM for tax or currency reasons, etc. are still essentially the same portfolio archetype. It's just when it comes to the bigger numbers, the extra work to consider upping the number of funds might actually be worth something substantial, particularly on the tax side of things. Fees go up, but the tax-savings more than make up for it in the highest brackets. I've honestly had a lot of time to think through many different scenarios and products. I keep coming back to simpler is manageable...and manageable is better. That said, I only have more of a theoretical understanding of portfolio construction, so I'm curious about any other comparable experiences. Making a few tweeks to the 3/4 funder is the minimal necessary action just for tax purposes.
nix4me wrote:
Tue Nov 20, 2018 10:52 pm
If we are really talking about 9 digits in taxable then the real need is a Tax Accountant or a Tax Attorney.
You can manage the investments easily but the taxes are are going to be a real problem. A good problem to have, but still a problem!
A simple 2 fund would be enough: Total Stock / Money Market. Or S&P / Money Market. Bonds are no good in taxable. Real Estate might be a good idea.
Don't let some sweet talking agent sell you Insurance or Annuities!
Good Luck.
9-digits is still just a hypothetical. There's a pretty wide range of scenarios, but low 9s wouldn't be necessarily be an extreme outlier yet. Touché on the tax accountant. That's actually what I'm working on now. Executing the sale is the easy part if I'm well prepared in advance. Coming up with the cost basis isn't.
2 funds/US stocks only is tempting. I'm extremely positive about the US long-term economically. We'll see how things play out in the short-term financially. Certainly interesting times in the markets. Goodbye FAANGs, finally. (sigh)
I'll push back on the bonds in taxable opinion. Tax-exempt bonds would do the trick. It would definitely be better than the money market which is taxable still. I's and EE's are also interesting because they postpone the tax until maturity, if I understand them correctly. They're an area I am still learning about. The real issue is the state tax. Unless interest rate skyrocket, it's more of a question of putting cash to work without much risk and then having enough ultra liquid cash as a second or third allocation which I can use to re-balance without triggering a tax avalanche. TIPS don't work though because it'd all be taxed at ordinary rates, for example.
Small Cap has a healthy enough real estate allocation for me. REITs have a ton of churn which triggers hidden costs and isn't so great for taxable in high brackets. With those types of investments, I'd rather have control over the physical investments, i.e. home, rentals, etc. For example, there are homestead, estate tax, and asset protection benefits for sinking a large allocation into a personal home, not to mention the 1031 exchange benefits.
I appreciate the Annuity and PPLI warnings, as well as all kinds of other types of insurance as well. I've done a bit of homework on them. I'm very suspicious. I think there are some special case scenarios though, particularly if you have a bit green target on your back.
Random Musings wrote:
Tue Nov 20, 2018 11:06 pm
SleeplessDIYer wrote:
Tue Nov 20, 2018 10:41 pm
123 wrote:
Tue Nov 20, 2018 10:13 pm
When you get down to the zero funds vs Vanguard Institutional, it comes down to tracking error plus the fact that each TSM fund has a different benchmark (Schwab uses a different TSM benchmark as well). I believe the max spread in TSM benchmarks was 30 bps one year.
If you can get to institutional select, then you have really arrived.
RM


Perhaps you're right. 6 of one, half dozen of the other. With these types of decisions, I tend to lean toward Vanguard just because even if I lose out on few basis points because of fate or chance, I'm supporting a better way for financial stewardship through Vanguard. Nothing against Fidelity, though they might need a logo update soon. Pyramids are so 1990s...B.C.
Imagine Institutional Select...maybe I'd get a VIP invite to an exclusive time-share presentation for Brazilianaires.
The higher it goes, the less most sane people want to arrive anywhere with others in similar situations. Anyone can just turn on the TV to see what money in the wrong hands does to people. I'm not so concerned about arriving. The ride never ends!

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 1:49 am

ThriftyPhD wrote:
Wed Nov 21, 2018 12:36 am
SleeplessDIYer wrote:
Tue Nov 20, 2018 7:11 pm
Desired Asset allocation: 60% stocks / 40% bonds, but open to allocating up to 75%+ if entering at the beginnings of the next long-term cycle.
How will you know when you're in the beginning of the next long-term cycle? Will you know in the moment, or only a couple year after the 'cycle' has started?
SleeplessDIYer wrote:
Tue Nov 20, 2018 7:11 pm
Desired International allocation: Market-weight on stocks, but tilting US stocks for the next decade at least...after this cycle bottoms. :wink:
How much do you tilt? How will you know when the current 'cycle' 'bottoms'? Is that a numerical definition you would know in the moment, or only a couple years after it bottoms?

Personally, if I were to get such a windfall, I would carve off what I need to live the rest of my life, and put that into a 50:50 stock:bond portfolio. The rest (which, out of $100 million would be the vast majority), I would put 100% stocks. I wouldn't spend anymore of my time trying to time the market to eek out a couple bps of return. I would spend the time figuring out what to do with the money I don't need to spend on myself. Foundation? Donations? Fund research? As those plans solidified, I would move money from the 100% equity pot to make them happen.
I could go lots of ways. Most generally, I follow some different TA and fundamental people online. It's more education than actionable information. I'm not a trader, but an indicator like the 50-day MA moving north or south of the 200-day MA is a well known macro metric that always gets mentioned. It depends on the situation. One might call for dollar-cost averaging into a position until perhaps an opportunity opens up or just do it one fell swoop after a solid enough correction for my tastes...with an appropriate finger to the air for psychological metrics and maybe a sentdex dowser. :wink:

I couldn't agree more with your opinion on set it and forget it. That's precisely why I'm thinking about it hard in advance. I'm perfectly happy to pay taxes and not to have to worry about taking high levels of risk or getting certain levels of return...IF I even make it to this hypothetical scenario. That said, I want to maximize the risk/reward while still keeping things relatively simple, not for the sake of it, but because as a steward, it maximizes the impact such a portfolio can have in the world. I want the portfolio to be a set it and forget type of thing, generally speaking. I look for Alpha in my work, in job creation, in philanthropy, in fatherhood. When the potential reality first dawned on me, I thought as you thought. I imagined all those I could help. Then I came to the conclusion that with a bit more attention to detail, the impact in those areas could be magnified...rather than in some HFT's pocket. That person is probably a great person too and deserves every fraction of a cent they skimmed off the top. We might have different visions of how best to give back, though, so I'd rather that decision be in my pocket. Just going 50/50 or a 2 funder, that would be easy, but is it selling myself short?

You mention one area that is a consideration for estate tax purpose. I totally see your point. At least as the law is currently, there are different limits with the estate tax. Also there is a substantial cost-basis upgrade for beneficiaries, whether the assets are in a trust or not. I'm totally with you on not fighting too much over a few bps, but getting in low or at least getting in somewhere at low risk by not going 100% stocks yet and then accelerating to 100% stocks while also decelerating back towards the end of life at highs, not even peaks, just highs, could potentially lock in a lot of capital gains for beneficiaries after death. The first part gets you in at a good spot, then you'll have to let it ride through a lot of volatility, but it shouldn't be a thing if you have all you need in another account. At 100% stocks in old age, you're hoping the market doesn't crash right before you die. Not like you'd care, but it could ruin or at least degrade the transfer of an estate substantially by dampening that bump up in cost-basis.

msk
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Re: Developing Complete Plan for Windfall

Post by msk » Wed Nov 21, 2018 2:34 am

Once you are into 8+ figures you have to face the reality that unless you spend wastefully (buy a yacht or a private jet) your portfolio is for heirs and charity. I was on the board of a pension fund and no matter how much you think you save on fees (or even collect on loaning stocks) the only thing that mattered was whether all the fancy managers ever beat the SP500 (or some other world index,
; pick whatever). They really, really struggled and often they did not beat the chosen index. I think I did learn a lot both from my own dabbling over >3 decades and sitting on the board of that pension fund and my simple advice to anyone with assets north of 8 figures is just to put the whole lot or the bulk of it into an ETF like SPY at the narrow end or VT (worldwide at the broad end) and relax. The annual withdrawals are small enough, < 5%, that you do not even have to watch the ups and downs of the market. 95+% of your portfolio will continue to thrive and survive as long and as well as capitalism does. When the market goes high, just donate a million $ or two. Market low? No splurging on a yacht that year. That's what I have settled on myself and advised my heirs to do (in my will). And pay for good tax advice. You can carve off a small slice, couple of million? to follow your market timing whims, play options, etc. and you will have years of beating the market, and years of under-performance, but as you age you will come to the conclusion that the excitement is not worth it. The depression you get when your guess goes wrong is annoying and unnecessary. But people occasionally do build vast portfolios using individual stock picks, so have fun!

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 9:30 am

msk wrote:
Wed Nov 21, 2018 2:34 am
95+% of your portfolio will continue to thrive and survive as long and as well as capitalism does.
Yea, if capitalism fails, we have a larger set of problems. :oops:

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Watty
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Re: Developing Complete Plan for Windfall

Post by Watty » Wed Nov 21, 2018 10:05 am

SleeplessDIYer wrote:
Tue Nov 20, 2018 7:11 pm
Free reign for responses. I'm just open to hear what people would do in my situation: 8-9 digits, all taxable, 40, etc.
1) Estate tax planning. If you get hit by the proverbial Mack truck tomorrow the estate taxes would be huge. If you live to be 95 then you need to set up your investments now so they they will grow in a way that will work well for estate taxes. If you park the money somewhere and then try to do the estate tax planning in ten years then it may be very expensive to move the money around later.

2) Hire a good fee only financial planner. This is different than a tax advisor and the fees structure will be tiered so that with such a large amount the percentage will be low. I would also hire a second one that charges by the hour to review what the first one is doing to keep them honest and to give a second opinion. One thing to watch out for is that "fee based" is different than fee only since they can also take a commission in addition to the fee. I have not used one but in other posts people have talked about the Garrett financial planning network for when you need a financial advisor. You can search for old threads about them.

3) Consider moving to a state with no income tax and no state estate or inheritance tax. You may be able to live part of the year in different places and keep your tax residency in a low tax state. The rules for this are not always clear so get professional tax advice on this. If you receive the money in January then there may still be time to establish tax residency for 2019 in a low tax state to avoid the Virginia taxes on that, but I know little about how that works.

mgensler
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Re: Developing Complete Plan for Windfall

Post by mgensler » Wed Nov 21, 2018 10:17 am

You mentioned estate planning. If you have kids, talk to a lawyer about setting up a GRAT. This needs to be done before you sign the LOI.

It sounds like you need to do something with your time after the sale. I suggest putting some thought into what you want to do. You're an expert at your business. Don't assume you will be an expert at picking other people's businesses to invest in.

Gretchen
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Re: Developing Complete Plan for Windfall

Post by Gretchen » Wed Nov 21, 2018 10:42 am

If you expect to want to make any charitable donations ever, check with your tax adviser on putting some of the new cash into a Charitable Gift Fund at Fidelity or Vanguard right up front. We chose Fidelity because of the lower startup cost, but you are in the league where Vanguard is an attractive possibility. You take the deduction right up front, and then distribute at your leisure.

msk
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Re: Developing Complete Plan for Windfall

Post by msk » Wed Nov 21, 2018 11:51 am

There are about 10 countries that do not levy personal income tax, some quite pleasant to live in. Switzerland is rumoured to have some scheme that limits even billionaires' annual tax to around 200k Euros. Being a US citizen has its own headaches when living abroad, but with a 9 figure portfolio it may well be worthwhile investigating. Berkshire Hathaway stock never pays dividends so you only pay capital gains tax on the shares you sell to consume. But Buffett is not going to live forever... I would thoroughly investigate tax residency outside the USA. Monaco?

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 12:05 pm

Watty wrote:
Wed Nov 21, 2018 10:05 am
SleeplessDIYer wrote:
Tue Nov 20, 2018 7:11 pm
Free reign for responses. I'm just open to hear what people would do in my situation: 8-9 digits, all taxable, 40, etc.
1) Estate tax planning.
2) Hire a good fee only financial planner.
3) Consider moving to a state with no income tax and no state estate or inheritance tax.
1) On it. Getting my cost-basis worked out first.
2) I'm skeptical about this one. What is it that you think they could offer..and for how much? If I went this route, I'd likely go full Multi-family office.
3) I'll be talking to my accountant and the estate planners about this one. There are other qualitative factors to consider here though like access to extended family, etc.
mgensler wrote:
Wed Nov 21, 2018 10:17 am
You mentioned estate planning. If you have kids, talk to a lawyer about setting up a GRAT. This needs to be done before you sign the LOI.
It sounds like you need to do something with your time after the sale. I suggest putting some thought into what you want to do. You're an expert at your business. Don't assume you will be an expert at picking other people's businesses to invest in.
Can you say more about the GRAT and LOI process? Do you have experience in this?
What I will do with my time is pretty easy. I have tons of avocational interests on the backburner as well as a lot of causes I'd like to help out. Family first though. Maybe I'll have to dust off those teenage dreams of being a rock star or a fighter pilot! Who knows? Maybe the Space Force will have a high eligibility age limit!
Your wise to note that once a success, not always a success. My skills are more about identifying the right people above all.
Gretchen wrote:
Wed Nov 21, 2018 10:42 am
If you expect to want to make any charitable donations ever, check with your tax adviser on putting some of the new cash into a Charitable Gift Fund at Fidelity or Vanguard right up front. We chose Fidelity because of the lower startup cost, but you are in the league where Vanguard is an attractive possibility. You take the deduction right up front, and then distribute at your leisure.
Personally, I'd like to be involved at a close level. Otherwise, I'd rather just pay the taxes. Not to knock charities, but there are quite some foul shenanigans that go on in the 501 world. Unless I can guarantee some level of transparency and oversight, it's not for me. Outsourcing charitable giving is a ripe opportunity for shady business and seems more like a problem with the system rather than a solution. The creme gets skimmed. Moreover, with what's about to take place with a few of the largest most trusted charities, I'm expecting a pretty large overall of the whole non-profit world. It'ß important to be thinking now, but I'm also interested to see what happens when the dust settles.

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David Jay
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Re: Developing Complete Plan for Windfall

Post by David Jay » Wed Nov 21, 2018 12:17 pm

SleeplessDIYer wrote:
Wed Nov 21, 2018 12:05 pm
3) I'll be talking to my accountant and the estate planners about this one. There are other qualitative factors to consider here though like access to extended family, etc.
I think you are under-appreciating the flexibility that 100M would give you. A relatively humble condo in a zero-tax state, declared as your primary home. A magnificent "vacation" home in your preferred location, close to family, etc.
Prediction is very difficult, especially about the future - Niels Bohr | To get the "risk premium", you really do have to take the risk - nisiprius

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 12:24 pm

msk wrote:
Wed Nov 21, 2018 11:51 am
There are about 10 countries that do not levy personal income tax, some quite pleasant to live in. Switzerland is rumoured to have some scheme that limits even billionaires' annual tax to around 200k Euros. Being a US citizen has its own headaches when living abroad, but with a 9 figure portfolio it may well be worthwhile investigating. Berkshire Hathaway stock never pays dividends so you only pay capital gains tax on the shares you sell to consume. But Buffett is not going to live forever... I would thoroughly investigate tax residency outside the USA. Monaco?
I've looked into that whole world pretty well as well as a lot of the off-shore shilling of financial products, etc. The only option that truly makes sense for US citizens from a purely tax savings perspective is to set up residency in Puerto Rico. I'm not sure how long that will last though or if those deals will be honored if Puerto Rico becomes the 51st state. They're pretty bankrupt as it is...
If there are reasons to make up the losses in fees, scams, headaches, etc. by going abroad, then by all means. I've done it on a very low budget for over a decade with little use of intermediaries to resolve paperwork problems. I'm certain that from a fee, service, and tax standpoint, it's going to cost more, not to mention potentially being far from family, friends, etc. There has to be either an income/career advantage or some other location specific draw that isn't merely financial for it to make opportunistic sense in my book.
IMHO, the political environment in the US is at one of the most tense moments ever, but the reality behind the scenes is different. Actual reforms made, turnover in government, turnover in C-suites, etc. etc. There are MASSIVE changes taking place that people are unaware of with the distractions of the media. Economically, the US is setting itself up to survive the coming storm and thrive like never before afterwards. It's where everyone is going to want to be. While I think it might be one of the most competitive places for taxes soon, the excitement of being in the place where THE things are happening will be worth paying a premium, regardless.

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Re: Developing Complete Plan for Windfall

Post by Grt2bOutdoors » Wed Nov 21, 2018 12:25 pm

If you truly hold 8 to 9 digits, I and EE bonds are truly a rounding error for you. Between you, spouse and trust you can purchase collectively $50k a year. It will take you 40 years to get to $2mm. You can look at zero municipalities that are highly rated and state tax exempt, but why bother with zeros if you could instead collect the coupons as they roll in? You would qualify for institutional level pricing. If you need a strategy, a meeting with a fiduciary only advisory service may be helpful. Even paying $10-20k one time is likely cheaper than 30bps for PAS which may recommend the cookie-cutter 4 funder (which the jury is still out on). Don’t get fancy, fancy is what brings on high expenses and an “education”.
"One should invest based on their need, ability and willingness to take risk - Larry Swedroe" Asking Portfolio Questions

123
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Re: Developing Complete Plan for Windfall

Post by 123 » Wed Nov 21, 2018 12:32 pm

If you can qualify for mutual fund institutional shares and have a personal account for your own "nuances" (play money) I don't see that you gain much with any variation of family office (FO). Once you give others the authority to spend your money it's a whole other level of keeping track of what they are doing, whether it's just bills or investment selection. Unless someone has a lot of specialized knowledge and interest in a particular field it's doubtful that they will reasonably achieve above-market returns on a very large portfolio over time. The risk is that an early "win" or two builds up confidence and bets increase and it all washes out.

Hired help to tend to the landscaping or pilot the yacht or aircraft is fine. Hired help to manage and spend your money takes a lot of oversight. It is extraordinary easy to hide embezzlement, happens every day. Only a fraction of embezlement is every detected let alone prosecuted. Few people with significant wealth want to show up in court and testify as to what a fool they were to trust someone.
Last edited by 123 on Wed Nov 21, 2018 12:36 pm, edited 1 time in total.
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SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 12:35 pm

David Jay wrote:
Wed Nov 21, 2018 12:17 pm
SleeplessDIYer wrote:
Wed Nov 21, 2018 12:05 pm
3) I'll be talking to my accountant and the estate planners about this one. There are other qualitative factors to consider here though like access to extended family, etc.
I think you are under-appreciating the flexibility that 100M would give you. A relatively humble condo in a zero-tax state, declared as your primary home. A magnificent "vacation" home in your preferred location, close to family, etc.
I probably am under-appreciating it. I don't yet have the mentality of magnanimity that comes with wealth or, as Bobby Axelrod in Billions would say, "FU Money" https://www.youtube.com/watch?v=ky6wBYQl0yc. The legal nuance is beyond me, so I'll leave it to the professionals. It certainly hasn't gone unnoticed that Teton County, WY has an average annual income a few multiples above the second on the list, NYC. I guess it makes it easy for the KC FED to fly fish with their buddies every year. VA and likely some other states are pretty strict about connections to the states. You really have to prove that you have no interests/business in the state. They may still see it as residency to have any number of established connections to the state like a second home. Again though, I leave the rich man's problems for the lawyers.
Last edited by SleeplessDIYer on Wed Nov 21, 2018 12:42 pm, edited 1 time in total.

KyleAAA
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Re: Developing Complete Plan for Windfall

Post by KyleAAA » Wed Nov 21, 2018 12:41 pm

Small value has historically been more tax efficient than total market, so I wouldn’t let that dissuade you from tilting in a high tax bracket. A three fund portfolio is perfectly fine for a 9 figure portfolio. There is nothing about having more money that magically makes market timing more effective. In reality, pretty much any reasonable asset allocation will be fine. You could even go 100% stocks if you want to maximize expected value for your legacy. I’m assuming you’ll be withdrawing 1% or less anyway, so it doesn’t matter. Sure, at that portfolio size you can shave off $200k per year in taxes and cost savings by getting fancy. Whether that is actually worth your time is another matter. If I had $100mm, it wouldn’t be.
Last edited by KyleAAA on Wed Nov 21, 2018 12:46 pm, edited 2 times in total.

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Re: Developing Complete Plan for Windfall

Post by KyleAAA » Wed Nov 21, 2018 12:43 pm

David Jay wrote:
Wed Nov 21, 2018 12:17 pm
SleeplessDIYer wrote:
Wed Nov 21, 2018 12:05 pm
3) I'll be talking to my accountant and the estate planners about this one. There are other qualitative factors to consider here though like access to extended family, etc.
I think you are under-appreciating the flexibility that 100M would give you. A relatively humble condo in a zero-tax state, declared as your primary home. A magnificent "vacation" home in your preferred location, close to family, etc.
You’d have to actually live in the condo half the year, though. Otherwise it’s tax fraud.

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 12:45 pm

KyleAAA wrote:
Wed Nov 21, 2018 12:41 pm
Small value has historically been more tax efficient than total market, so I wouldn’t let that dissuade you from tilting in a high tax bracket. A three fund portfolio is perfectly fine for a 9 figure portfolio. There is nothing about having more money that magically makes market ting more effective. In reality, pretty much any reasonable asset allocation will be fine. You could even go 100% stocks if you want to maximize expected value for your legacy. I’m assuming you’ll be withdrawing 1% or less anyway, so it doesn’t matter.
Good advice. "Market ting" This needs to be included in Investopedia. :wink:

lhl12
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Re: Developing Complete Plan for Windfall

Post by lhl12 » Wed Nov 21, 2018 12:53 pm

I would consider Fidelity's offering for very high net worth clients - their Fidelity Family Office Services group:

You might decide to stick with Vanguard but Fidelity is generally viewed as comparable while having better service and better technology. At your asset size that tradeoff might be more valuable to you.

Gretchen
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Re: Developing Complete Plan for Windfall

Post by Gretchen » Wed Nov 21, 2018 1:01 pm

[/quote]
Personally, I'd like to be involved at a close level. Otherwise, I'd rather just pay the taxes. Not to knock charities, but there are quite some foul shenanigans that go on in the 501 world. Unless I can guarantee some level of transparency and oversight, it's not for me. Outsourcing charitable giving is a ripe opportunity for shady business and seems more like a problem with the system rather than a solution. The creme gets skimmed. Moreover, with what's about to take place with a few of the largest most trusted charities, I'm expecting a pretty large overall of the whole non-profit world. It'ß important to be thinking now, but I'm also interested to see what happens when the dust settles.
[/quote]

I'm with you on this. The bulk of our charitable giving is to a nonprofit where I sit on the Board and the Finance Committee, my church and a few of its related endeavors, and the educational institutions that made it possible for us to earn a good living and retire in comfort. I agree that just donating in the blind can lead to real regrets.

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 1:07 pm

Grt2bOutdoors wrote:
Wed Nov 21, 2018 12:25 pm
If you truly hold 8 to 9 digits, I and EE bonds are truly a rounding error for you. Between you, spouse and trust you can purchase collectively $50k a year. It will take you 40 years to get to $2mm. You can look at zero municipalities that are highly rated and state tax exempt, but why bother with zeros if you could instead collect the coupons as they roll in? You would qualify for institutional level pricing. If you need a strategy, a meeting with a fiduciary only advisory service may be helpful. Even paying $10-20k one time is likely cheaper than 30bps for PAS which may recommend the cookie-cutter 4 funder (which the jury is still out on). Don’t get fancy, fancy is what brings on high expenses and an “education”.
I wasn't aware of the limits. Good to know.
USAA has a VA Muni but the fees are absurd. I'd rather try to be happy with Federal tax-exempt than try to chase munis in states or cities that give good rates because of poor management. That's hidden risk for me. There's also a spectrum of interest rate risk vs default risk that I learned recently that can be hidden in certain munis. I'd have to find that discussion again, but again, it just made me feel like I could be lending to the Detroit or Chicago mayor's office...nothing against Detroit or Chicago! :wink: I can pay taxes in my state and up my level of civics participation to make sure that money gets a good return in my state and community. Same thing as paying less tax in a poorly managed place with high sales taxes, right?
123 wrote:
Wed Nov 21, 2018 12:32 pm
I don't see that you gain much with any variation of family office (FO).
Hired help to tend to the landscaping or pilot the yacht or aircraft is fine. Hired help to manage and spend your money takes a lot of oversight. It is extraordinary easy to hide embezzlement, happens every day. Only a fraction of embezzlement is every detected let alone prosecuted. Few people with significant wealth want to show up in court and testify as to what a fool they were to trust someone.
I would only allow the MFO advisory control, not discretionary. I'd negotiate a small fee for them to maybe put a small bell or whistle on the portfolio and re-balance a passive portfolio, but it wouldn't be for the investments or club deals. The main reason would be to have more focus on personal projects, less distraction, and, in particular, some of the concierge stuff: heir education, access to a mind trust, billpay, travel, staffing, etc. It's probably better just to contract a concierge service in that case or set up a SFO and get the incentives aligned correctly with healthy oversight. Only the paranoid survive, right?

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Watty
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Re: Developing Complete Plan for Windfall

Post by Watty » Wed Nov 21, 2018 1:09 pm

SleeplessDIYer wrote:
Wed Nov 21, 2018 12:05 pm
2) I'm skeptical about this one. What is it that you think they could offer..and for how much? If I went this route, I'd likely go full Multi-family office.
For the first couple of year not making any dumb mistakes, sleeping well at night, and getting through any market dips will be a high priority that they could help with.

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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 1:34 pm

Watty wrote:
Wed Nov 21, 2018 1:09 pm
SleeplessDIYer wrote:
Wed Nov 21, 2018 12:05 pm
2) I'm skeptical about this one. What is it that you think they could offer..and for how much? If I went this route, I'd likely go full Multi-family office.
For the first couple of year not making any dumb mistakes, sleeping well at night, and getting through any market dips will be a high priority that they could help with.
Haha, true! I was hoping for something more specific like setting up some of the satellite funds for kids' college or other financial matters, etc. They'd have to be more of the complete type as I can handle most on my own with an accountant and an estate lawyer. I expect that a lot of what a financial planner could do for me, I could probably get advice on from my accountant. I don't expect to need much consoling. I have earned my reinforced steel breast plate against volatility! 90% losses. Twice. Just held and held. It was too difficult to time or organize a sale, but I knew the investment well and had hurricane day funds to make it through. It's an excruciatingly painful but necessary lesson. I can handle a 50% drop in the stock market across a diversified portfolio. Plus, I have a hawk's eye on macro and politics enough to understand narrative and direction not to capitulate because of media FUD.
lhl12 wrote:
Wed Nov 21, 2018 12:53 pm
I would consider Fidelity's offering for very high net worth clients - their Fidelity Family Office Services group:
You might decide to stick with Vanguard but Fidelity is generally viewed as comparable while having better service and better technology. At your asset size that tradeoff might be more valuable to you.
I'll look into this, particularly if an SFO becomes the right path to head down. I'm supportive of Vanguard's business structure and ethos. It would take a lot to overcome it. While not everyone can manage their financial lives, I'm very much concerned with the lack of basic financial education in the US and with the malfeasance in financial services uncovered and continuing since 2008, particularly driven by misaligned incentives and a lack of integrity in the stewardship of the nation's wealth. Granted, Fidelity seems to be on the better side of things, but wealthy citizens need to be willing to put their foot down for those that cannot wherever they see rot. Pocketbook-protesting. It's not an anti-capitalist protest. It's simply that capitalism doesn't work without the middle-class that has been eroded away. And that shoots everyone in the foot. Enough with the diatribe...nothing personal.
Does CS have family office services? I think their much smaller though. I don't use them, but I like their banking services offerings.

mgensler
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Re: Developing Complete Plan for Windfall

Post by mgensler » Wed Nov 21, 2018 2:51 pm

Re: GRAT and LOI

You can place a percentage of your shares of the business in a GRAT. Once the biz is sold, the shares are exchanged for a percentage of the sales price. The funds can be invested in stock market. You must live for ten years, but after that you can pass the funds to your kids and avoid the gift tax limits. You will need to do this before you sell the biz and to be safe before the LOI is signed.

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Re: Developing Complete Plan for Windfall

Post by Grt2bOutdoors » Wed Nov 21, 2018 5:02 pm

Baird institutional intermediate tax exempt supposedly has a more stringent view of acceptable credit risk. The yield may be less, but that is because the fund restricts what type of offerings they will purchase.
"One should invest based on their need, ability and willingness to take risk - Larry Swedroe" Asking Portfolio Questions

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Re: Developing Complete Plan for Windfall

Post by pennywise » Wed Nov 21, 2018 5:24 pm

Grt2bOutdoors wrote:
Wed Nov 21, 2018 12:25 pm
If you truly hold 8 to 9 digits,
OP does not.

It seems to have escaped folks' notice or the respondents are enjoying a theoretical walk down high-net-worth-ville, but there is no huge sum of money to be managed. The first post established that these are the musings of someone with a HYPOTHETICAL FUTURE 8-9 digit net worth.

OP is certainly fortunate that his imaginary scenarios have elicited some thought provoking and well considered responses from people who have experience managing actual high net worths :wink: .

wrongfunds
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Re: Developing Complete Plan for Windfall

Post by wrongfunds » Wed Nov 21, 2018 5:38 pm

I sympathies with you completely. I have the same anguish every time the megabucks/mega-millions goes above the half billion dollar mark. It is very agonizing trying to figure out how to make the perfect plan for my windfall. To be frank with you, I do have sigh of relief when my ticket misses the winning numbers.

Did that help?

Dottie57
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Re: Developing Complete Plan for Windfall

Post by Dottie57 » Wed Nov 21, 2018 6:24 pm

pennywise wrote:
Wed Nov 21, 2018 5:24 pm
Grt2bOutdoors wrote:
Wed Nov 21, 2018 12:25 pm
If you truly hold 8 to 9 digits,
OP does not.

It seems to have escaped folks' notice or the respondents are enjoying a theoretical walk down high-net-worth-ville, but there is no huge sum of money to be managed. The first post established that these are the musings of someone with a HYPOTHETICAL FUTURE 8-9 digit net worth.

OP is certainly fortunate that his imaginary scenarios have elicited some thought provoking and well considered responses from people who have experience managing actual high net worths :wink: .
I thought I was misunderstanding all. Thanks for clarification. Lots of terms I have never heard (MFO, braintust with regards to finances). Op’s Posts seem a bit manic.

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Wed Nov 21, 2018 11:23 pm

Grt2bOutdoors wrote:
Wed Nov 21, 2018 5:02 pm
Baird institutional intermediate tax exempt supposedly has a more stringent view of acceptable credit risk. The yield may be less, but that is because the fund restricts what type of offerings they will purchase.
Are you talking about Munis or Federal? I saw the munis offerings and they want 30 bps. Don't you think that's kind of excessive?
pennywise wrote:
Wed Nov 21, 2018 5:24 pm
Grt2bOutdoors wrote:
Wed Nov 21, 2018 12:25 pm
If you truly hold 8 to 9 digits
OP is certainly fortunate that his imaginary scenarios have elicited some thought provoking and well considered responses from people who have experience managing actual high net worths :wink: .
Let me know if you have any questions.
wrongfunds wrote:
Wed Nov 21, 2018 5:38 pm
I sympathies with you completely. I have the same anguish every time the megabucks/mega-millions goes above the half billion dollar mark. It is very agonizing trying to figure out how to make the perfect plan for my windfall. To be frank with you, I do have sigh of relief when my ticket misses the winning numbers.
Did that help?
You have to pick the right numbers! :oops:
Dottie57 wrote:
Wed Nov 21, 2018 6:24 pm
pennywise wrote:
Wed Nov 21, 2018 5:24 pm
Grt2bOutdoors wrote:
Wed Nov 21, 2018 12:25 pm
If you truly hold 8 to 9 digits
OP does not.
It seems to have escaped folks' notice or the respondents are enjoying a theoretical walk down high-net-worth-ville, but there is no huge sum of money to be managed. The first post established that these are the musings of someone with a HYPOTHETICAL FUTURE 8-9 digit net worth.
OP is certainly fortunate that his imaginary scenarios have elicited some thought provoking and well considered responses from people who have experience managing actual high net worths :wink: .
I thought I was misunderstanding all. Thanks for clarification. Lots of terms I have never heard (MFO, braintust with regards to finances). Op’s Posts seem a bit manic.
For clarity...
While it depends on the appraiser, I'll give a conservative number of high 7-digits at the moment. It's tough to precisely value at this stage. It's been a long slog of about 12 years of cutting edge tech, but we're finally looking at an exponential-growth phase beginning S2 2019 or S1 2020 which will likely last through the decade. Whether it's next year or 2020 or 2021, I'll likely just sell a nice lower 8-figure portion to secure the future. Maybe more if I just want out or don't feel as positive about the future prospects. I said hypothetical because it's more a question of when, not if. That said, nothing is certain.

As for the terms, MFO=Multi-Family Office, braintrust is just a group of experts, etc. And I agree. My posts are a bit manic. It takes a bit of that to be successful in the business I'm in, so I'll consider that a compliment. :D - "SleeplessDIYer"

msk
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Re: Developing Complete Plan for Windfall

Post by msk » Thu Nov 22, 2018 2:01 am

My own NW is only 8 digits, not 9, but I do have a very small handful of relatives/friends who are into 9 digits and one even into 10 (according to Forbes anyway). Of course all made their wealth through being entrepreneurs taking huge risks. So they are not risk averse. All reside in countries with nil personal taxes, but nevertheless I am always amazed at WHY do they continue taking huge risks? A chap lost $125 million on gold futures despite a warning from his financial advisor (a distant relative of mine, otherwise I would never have heard of the fiasco), another lost a few million $ on trying to play arbitration in bonds issued by different countries, USD/Euro or something like that, etc. I just stood there bemused as he explained how his bet had gone awry. Me with my little pot? I am opportunistically liquidating individual stocks and steadily placing all into VWRD (Vanguard World run from Ireland, equivalent to VT) and iShares accumulative equivalents. My remaining concerns: Can I trust Vanguard and Black Rock/iShares? I think Yes! Can I trust IB not to pull a Madoff or some other fancy thing??? You can never have 100% security. The nice thing with concentrating everything into one account at IB is it's easy to instantly check your NW on a smartphone :greedy Residing in a tax haven also narrows down the available list of large brokerages that you can access, hence for now mine is IB only; scratched off a few for various restrictive banking/market access reasons, etc. I have come to the firm conclusion that complex investing can only pay off if you PERSONALLY have the talent for it, regardless of advisors. Obviously the guys with 9 or 10 figures do have talent for something, but that may not be in arbitration in USD/Euro bonds or guessing the trajectory of the price of gold. Tax advice and financial engineering cannot make a $125 million loss entirely palatable. Keep the bulk simple. Play only with play money.

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Thu Nov 22, 2018 12:22 pm

msk wrote:
Thu Nov 22, 2018 2:01 am
I have come to the firm conclusion that complex investing can only pay off if you PERSONALLY have the talent for it, regardless of advisors.
This may be the wisest comment on Bogleheads.org.

Pure genius is exceedingly rare. A lucky genius who works hard...even rarer. Sometimes it's just dumb luck and a bit of sweat to open the doors of opportunity. The wealth that gets spent poorly is the wealth that is inherited, ill-gotten, or charged with someone who's uncontrollably viced in some way. That's not really a secret, but it's not all that clear when the public only hears of the minority wonder kids of Silicon Valley or whomever. Financial education needs to start early in school. It's at least a question of national interest, if not national security.

Prediction: With lots of chatter about reworking the global financial system, the days of offshore banking and tax havens which facilitate massive tax evasion are going to end before 2024, if not much sooner!

SleeplessDIYer
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Re: Developing Complete Plan for Windfall

Post by SleeplessDIYer » Thu Nov 22, 2018 7:52 pm

Thank you all for your replies so far. Interesting stuff!

Happy Thanksgiving!

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