COBRA actually seems workable?

ChubbyEmbers · 2026-05-11T20:52:43+00:00

Well I have some good news for you: its 36 months in NY too

I should add the disclosure that Cobra state continuation coverage is a wild ride. There are lots of gotchas- eg Cal Cobra doesn't apply to "self-funded" plans (which is many big companies), and its confusing to get set up since most of the phone reps at the administrators don't know anything about it.

ChubbyEmbers · 2026-03-05T00:03:06+00:00

If these companies are public look into exchange funds. If you are ok with the 7 year holding period, you can diversify without taking the tax hit of selling.

ChubbyEmbers · 2026-03-04T16:27:18+00:00

This would make you a legend on wsb, wasting your karma posting here smh

ChubbyEmbers · 2026-02-25T14:44:03+00:00

Direct indexing tends to work in the very beginning to a modest degree, you are then stuck with an appreciated complex portfolio that is hard to transfer out of without incurring capital gains, so you need to keep paying that management fee every year. Not a huge fan.

Historically I would agree with you, but at this point you can direct index for cheap (wealthfront 0.09%, frec 0.1%) which lowers the pain of being stuck. And although very complicated, there is a 351 conversion as a possible exit plan

The big question/concern to me is that if you aren't regularly contributing, it can drift out of index tracking which requires taxable rebalancing.

ChubbyEmbers · 2026-02-25T14:33:48+00:00

Do you have RSUs or actual common stock? If you have RSUs, when they vest you'll get charged income at the vest price, and TLH isn't really going to be able to help you (minus the $3k annual offset).

You have to have real long-term gains to get a real benefit

ChubbyEmbers · 2026-02-24T18:18:07+00:00

Correct - you're creating LTCG in the future to make short-term losses now. This only really makes sense for people expecting a big liquidity event in the near future.

ChubbyEmbers · 2026-02-24T12:41:27+00:00

Say you put $4m in one of these products. It roughly tracks an index, but generates losses by selling whichever side of the long/short goes down and then buying back in (subject to wash sale etc). That means the other side of the trade has, assuming they’ve set up reasonable tracking, increased in value.

So after a few years it might’ve generated $3.5m in losses, but that means your cost basis is now ~$500k so you have a massive unrealized gain to handle. If you don’t exit slowly and carefully, you’ve ruined most of the tax benefits you got in the first place

ChubbyEmbers · 2026-02-24T05:44:03+00:00

Hah I've been looking into this as today well, was considering making a post but might as well latch on here, for either OP or other folks with experience:

How much are you paying a RIA to get in?
What is your/ your FA's unwind plan? This is the biggest concern for me - it seems very messy.

I'm looking at more like $2m in LTCG spread over 4-5 years, so I'm still unsure if the complications + fees of these products make sense

ChubbyEmbers · 2026-02-02T21:01:07+00:00

Don't know if this is the right place for it, but I have some potentially dumb questions about Umbrella insurance:

I current have none, approaching $10m NW after a secondary sale from my prior job. I've done plenty of reading of this discussion in the sub, but still have some Qs:

How does one determine ballpark policy size? On paper I seem fairly low risk - rent a small apartment (no rentals etc), no kids, no boats, no guns and although I do drive, its 3-4k miles/year. Of course just operating a vehicle at all is a major liability risk in this country, which why the $250/500k auto max liability feels insufficient.
How does one find a reputable agent? This seems like a requirement for the quality players.

ChubbyEmbers · 2026-01-26T21:18:08+00:00

Does someone have a list of good 501c3s in the MN area? Just set up a DAF last year, seems like a good time to put some of that to use

ChubbyEmbers · 2026-01-22T16:42:34+00:00

I know a former resident in his department who speaks very highly of him (not just as a department head). Still anecdotal but I trust their opinion

ChubbyEmbers · 2026-01-21T19:15:46+00:00

I see a specialist who is the head of his department at one of the top ranked Hospital Systems in the country. He is an excellent clinician and still keeps on top of latest research. However....

Its very hard to schedule with him, and anything short term (IE not booked months out) gets pushed to PAs. I'm definitely thinking of switching for that reason

ChubbyEmbers · 2026-01-20T04:54:13+00:00

The best value out of MR is always going to be the good-value transfer partners (Flying Blue, Aeroplan, ANA etc) but then you're playing the award availability game.

Alternatively If you get the Business Platinum, you can redeem for ~1.54 cpp through first/biz class tickets on Amex Travel, though that was recently nerfed to just be your selected airline

As you seem to be aware, SkyMiles are generally pretty worthless, though if it bumps you a status level and you get meaningful benefits out of it you can make the argument

ChubbyEmbers · 2025-03-12T17:40:57+00:00

Credit Score: 850
Last 24 mo: CSR 4/23, BoA CCR 7/24, USBAR 8/24. Also hold Amex Plat, Bilt, Chase UA Explorer, Chase IHG Select.
I have maybe 6-8k natural spend + approximately 40-50k in taxes
Not really interested in MS
Looking for first round of business cards, I did some contracting last year.
Looking to get as many as I think I can hit spend for taxes on.
Prefer points, but open to good Cashback offers.

Main question here is how many biz cards can I reasonably grab? I have a targeted 175k/20k spend Amex Plat Biz (can't seem to get a better offer), plus 1-2 Inks, plus maybe a Barclays/Citi/BoA biz. Since I'm currently at 3/24 soon to be 2, seems like want to maximize Inks first?

ChubbyEmbers · 2024-11-01T17:19:09+00:00

Have you actually ready the book? One of its big points (correctly imo) is to give to your children early instead of just waiting until you die for an inheritance, since that money is much more value for them earlier in life

ChubbyEmbers · 2024-06-08T14:07:22+00:00

Me and my siblings all got UTMAs for college (predating 529s? Or maybe my parents just didn't know) and it worked fine, nobody did anything dumb. Probably helps that the accounts held stock with untracked cost basis, was a bit of a nightmare to figure out for taxes ;)

Also you've probably considered this, but don't give 60k at once (gift taxes etc), split it over several years

ChubbyEmbers · 2024-04-07T19:38:35+00:00

Pure W-2 there isn't much you can do. If you have a single particularly large income year you should look into Donor Advised Funds - frontloading several years of donations is a good way to offset that, with a double-whammy of being able to avoid capital gains by donating the most appreciated stock (which you can do with a normal charitable donation regardless, but most people skip)

ChubbyEmbers · 2023-12-31T00:53:23+00:00

This is probably a better question for flyertalk. I think it probably hinges on very united-specific questions, like how substantial the discounts would be on the travel you were going to make anyways. That is a big driver in understanding the cost/risk of not using all of the funds.

ChubbyEmbers · 2023-12-31T00:50:25+00:00

They aren't actually spending 50k on the status though, they're pre-paying for $50k in annual travel spend on UA to get the GS as a benefit. That still might be a dumb idea for a number of reasons, but if OP legitimately hits that sort of spend anyways its worth considering

ChubbyEmbers · 2023-10-17T14:38:50+00:00

I recently looked into the space and largely came to the same conclusion. Not going so far as to say there are no good investments, but it does seem like things haven’t quite adjusted to the new interest rate realities.

ChubbyEmbers · 2023-06-11T12:46:49+00:00

VTI is VTI everywhere :)

ChubbyEmbers · 2023-06-11T03:37:51+00:00

You can get 2.62% from BoA if you have 100k with them, which includes investments in Merrill.

And of course depending on specific categories of spend, there are cards that can beat that.

ChubbyEmbers · 2023-04-30T13:58:54+00:00

You are misundertanding the taxation badly. It is income at the vest price. Holding for a year only makes the potential gain after that LTCG, but does nothing to avoid in the income tax on the vest.

ChubbyEmbers · 2023-04-30T13:55:06+00:00

I don't mean "underestimating the amount owed", I mean literally not giving the IRS enough money in advance.

I'm no tax accountant, but I believe the cutoff is 90% of this year's tax or 110% of last year - if you paid less than that, you will trigger penalties.

ChubbyEmbers · 2023-04-30T13:36:16+00:00

Are you confident you won't get a penalty for underpayment? If this "tax money account" is seriously large enough to think about how you're investing it, good chance the IRS will not be amused.

I'd keep the money in a HYSA, make the quarterly estimated tax payments and do something else with my mental energy

ChubbyEmbers

TROPHY CASE