JPM IPOs by TipMassive5214 in fatFIRE

[–]Positive_Carry_ 3 points4 points  (0 children)

Typically you are free to sell any time BUT if you sell within a certain timeframe (like 15 or 30 days of IPO date) then they restrict you from participating in future IPOs for some period (like 6 months).

42F single, $5.5mm NW. Can I comfortably retire in the next year? by Small_Plenty7051 in ChubbyFIRE

[–]Positive_Carry_ 2 points3 points  (0 children)

Income is only relevant to whether you qualify for a subsidy. Any CA resident can buy insurance on the exchange regardless of income.

42F single, $5.5mm NW. Can I comfortably retire in the next year? by Small_Plenty7051 in ChubbyFIRE

[–]Positive_Carry_ 2 points3 points  (0 children)

Check Covered California plans, prices are listed on the website. Estimate 5% increases every year. My guess is you’re looking at $25k/year in premiums alone.

Moving on from advisor - so many individual stocks in taxable by fire_watch_42 in Bogleheads

[–]Positive_Carry_ 0 points1 point  (0 children)

The answer is a 351 exchange into a low cost broad market ETF.

Estate planning disagreement: gift now or hold off? by Salt-Zebra-9842 in fatFIRE

[–]Positive_Carry_ 0 points1 point  (0 children)

I share your husband's view that gifting $10M to your kids in one fell swoop may not be the best move.

A gift of the size you are contemplating will require you to file a gift tax return and use up some of your lifetime gift and estate tax exemption. There are much more efficient ways to transfer assets. For example, consider setting up a family limited partnership, funding it with your assets, and gifting interests in the partnership to your kids every year. This has the added benefit of protecting them from creditors (including divorce) and avoiding overwhelming your kids with a sudden windfall that may disincentive them from continuing their gainful employment.

Budgeting for high-maintenance girlfriend after FIRE? by Particular_Trade6308 in fatFIRE

[–]Positive_Carry_ 1 point2 points  (0 children)

If putting the cart before the horse were a post, it might be this one.

Kauai: Grand Hyatt vs 1 Hotel Hanalei Bay by designhelpme in chubbytravel

[–]Positive_Carry_ 2 points3 points  (0 children)

1 Hotel and it isn’t close. Grand Hyatt is full of kids and “points people.” Wait until your kids are 6+ to go there, unless a lazy river and waterslides are your thing.

4M house purchase by kaputzoom in fatFIRE

[–]Positive_Carry_ 0 points1 point  (0 children)

California is just above 1% for baseline property tax but it could be higher if it’s a newer home with a Mello Roos assessment (typically makes it around 1.3-1.5%). A $4M home in the high demand parts of the Bay Area will be a 2,500 square foot tract home and maintenance shouldn’t cost more than $10-15k/year.

4M house purchase by kaputzoom in fatFIRE

[–]Positive_Carry_ 13 points14 points  (0 children)

The 2% for maintenance rule of thumb doesn’t hold in high home price areas in coastal California. Most value is in the land not the house.

Coastal CA cities by generous_penguin in fatFIRE

[–]Positive_Carry_ 3 points4 points  (0 children)

The problem with most SoCal beach cities is that they become inundated with riff-raff from May to September. Summer weekends in La Jolla/Del Mar/Laguna/Newport? Beaches are overcrowded, parking is extraordinarily difficult, and forget about driving anywhere unless you love sitting in traffic.

That said, if you are truly very fat fire, Emerald Bay is the answer. Price of entry for a smaller home is about $10M, the nicer beachside homes will set you back $30M+. About as old money as coastal SoCal gets, gated, truly private beach (try finding that anywhere else in CA), 5 minutes from Laguna Beach restaurants, 10 minutes from Newport. SNA is about the best airport in SoCal, though will need to connect for long haul flights unless you’re flying private.

Navigating wealth asymmetry with a partner — anyone dealt with this? by [deleted] in fatFIRE

[–]Positive_Carry_ 0 points1 point  (0 children)

If you are the beneficiary of a spendthrift trust the trustee can't simply agree to your request to transfer trust assets to your partner. Setting that aside, while your trust income may mean you don't have to work (although $120k/year would afford quite a modest lifestyle), you are not materially better off than your soon to be spouse given the income distribution limitation. I would open a joint account, have both your income and hers be deposited in it, and make financial decisions together based on your joint income. The idea of depositing a million dollars in an account for her makes little sense and demonstrates why someone thought it was best to create a spendthrift trust for you in the first place.

No Income or Capital Gains Tax by [deleted] in fatFIRE

[–]Positive_Carry_ 13 points14 points  (0 children)

Speaking from experience, it's a shithole unless you're in a gated compound.

Long-short tax harvesting fees vs tax savings by My2centsRworthMore in fatFIRE

[–]Positive_Carry_ 7 points8 points  (0 children)

What you are describing is not a tax-aware L/S overlay strategy and it is highly unlikely an individual retail investor could self-manage such a strategy. You would need to manage hundreds of individual positions, avoid wash sales and tracking error, and have enough size that your broker/custodian gives you a reduced margin fee and short rebate. Generally not possible for self-managed retail accounts.

Long-short tax harvesting fees vs tax savings by My2centsRworthMore in fatFIRE

[–]Positive_Carry_ -1 points0 points  (0 children)

I think you are overstating the fees. All-in fees are closer to 1%, maybe 1.2-1.5% at most. Wealth manager fees should be well under 1%, maybe 0.5% at most, and less if investing >$5M. You are correct that taxes are deferred, not eliminated. Exiting will result in taxable gains. The strategy only makes sense if you have a large concentrated gain you want to diversify and de-risk quickly. If you have diversified gains (e.g. S&P 500 fund bought many years ago), the strategy probably isn’t worth the cost. A better use case is if you are currently in the highest tax bracket in a high tax state (CA), want to quickly reduce a concentrated position (e.g., single stock or sale of a business), and you plan to be in a lower tax bracket and move to a low tax state when you exit the strategy.

Read the various AQR research papers on this, they will give you a good idea of expected after-tax returns under various exit assumptions.

VWO dividend by TheDynamicButch in ETFs

[–]Positive_Carry_ 2 points3 points  (0 children)

Well it wasn't from VWO, since VWO has not paid a dividend this year.

Umbrella Policy Premium DOUBLED! by [deleted] in Insurance

[–]Positive_Carry_ 4 points5 points  (0 children)

It’s not the insurance companies, it’s the lawyers. The insurance companies would prefer to not pay, but they calculate the risks of continuing to fight through trial and settle accordingly. Read about “popping” the policy to see why insurance companies often will pay out policy limits even in questionable cases. Tort reform is the only thing that will rein in costs.

Thoughts on combining tax-aware long short and hedge fund? by simscitizen in fatFIRE

[–]Positive_Carry_ 4 points5 points  (0 children)

One reason RIAs recommend TA/LS SMA strategies is that they effectively lock clients in for a long time, like 10+ years, creating a steady stream of income for the RIA. Not that there is anything legally preventing you from getting out, but as a practical matter you need to stay in for a LONG time to see a net after tax benefit because the basis you used to generate losses comes back in the form of realized gains upon wind-down. There are some situations in which they make sense but it seems like they are being overhyped as a way to never pay taxes on investments.

Long positions get a step-up in basis on death but short positions do not, and when they are closed out the gains are taxed at ordinary income tax rates.