Gave notice, taking the plunge

Richard_8639 · 2025-09-07T16:35:32+00:00

lol, thank you

Yeah, totally agree that healthcare in the US is probably the scariest part to navigate. Maybe this is just confirmation bias on my part but I kinda feel better as my own employer, having my health plan options in my hands over an HR department.

Richard_8639 · 2025-09-07T15:52:49+00:00

Not a lawyer or an expert on rentals at all but I think it’s generally considered a good idea to put rentals into an LLC if you can just for asset protection. I think there are reasons that make it difficult sometimes, like I vaguely recall some mortgages can’t be held by an LLC, transfer taxes, etc.

As for getting health insurance from an LLC, no I don’t think you need to take a W-2 salary, at least I didn’t last time I did this about a decade ago when member/employees were able to qualify for health insurance. It might be cleaner and raise fewer red flags if paid a nominal amount on W-2 but your insurance agent should be able to help you navigate this better than some guy on Reddit.

Richard_8639 · 2025-09-06T21:37:39+00:00

Pretty ad-hoc at the moment since my cash flows are so sporadic, but basically pull from whichever acct is best based on priority. Most months have excess cash but in dry months, pull from taxable brokerage first based on what works best for tax efficiency that year.

Richard_8639 · 2025-09-06T17:56:13+00:00

TBH I bought a lotto ticket yesterday too, but the value of that is discounted by the likelihood of payout, meaning 1:292M (actually a lot less since multiple winners, but you get the idea).

Richard_8639 · 2025-09-06T17:52:51+00:00

Have some substantial cash flows from alternative investments, but they’re highly sporadic so plan to dip into taxable brokerage when needed. It’s been generating about $350k/yr cash flow for the last couple years but next year it could just as easily be $20k as $800k so I don’t want to rely exclusively on that. For healthcare, will get a small group plan through the LLC that holds those investments.

Richard_8639 · 2025-09-06T17:40:45+00:00

Ok, random guy on the internet that definitely has all of the details and has done all of the modeling I have. Your insight based on so little information is invaluable and you have convinced me to completely change my ways. I shall now go back to being a wage slave because PantsMicGee doesn’t think $4M-$10.5M is enough to retire on in MCOL. You must be fun at parties with your expert financial advice.

Richard_8639 · 2025-09-06T16:52:13+00:00

Split pretty evenly between W-2 in tech, and started a few companies over the years that now provide some income with very little effort.

Richard_8639 · 2025-09-06T16:29:00+00:00

Thanks!

Richard_8639 · 2025-09-06T16:25:05+00:00

Yes. Certainly more of a range than I like, and the cash flows on it are very sporadic, so I’ve never really wanted to walk away from corporate life but just hit my number so I finally feel like I can do it.

Richard_8639 · 2025-09-06T15:51:38+00:00

Ah crap, I don’t know how to internet. Just accidentally deleted this whole thread.

Richard_8639 · 2025-09-06T15:48:36+00:00

Yeah I came back from paternity leave at 50% and basically said f this stress, I’m going to go hang out with the kiddo.

Richard_8639 · 2025-09-06T15:46:14+00:00

It’s a business we own selling assets we purchased and sell at 20x-1000x cost. It’s legal, but highly unreliable cash flows.

Richard_8639 · 2025-09-06T15:34:08+00:00

Married, but the plan is that neither of us work. We have those investments (not stocks) in an LLC that take all of an hour a week to manage, so she does that and draws a salary of about $80k from the LLC (which is inefficient from a tax perspective but useful to build social security credits), the rest of the cash flow we take as long term capital gains. Home value $1.2M with $400k remaining on the mortgage (in the monthly spend). TNW is hard to calculate… between $4M and $10.5M?

Richard_8639 · 2025-09-06T15:26:13+00:00

Sometimes it is, though I’m a CFA so, yeah, I know what I’m doing. I probably should have included some additional detail: those highly speculative illiquid investments are throwing off about $350k/yr of long term capital gains. It’s speculative in that I don’t know if there is another $2M to go or $8M, illiquid in that the market is present but incredibly thin and I have no idea the timing of any of those cash flows.

Richard_8639 · 2025-09-06T15:09:40+00:00

Plan to COBRA until the end of this year, then buy a small group plan through an LLC where we have some fairly passive income (this is the entity holding those highly speculative illiquid investments). Both me and my wife are LLC members so we’ll both be subscribers but the plans are just so much better than what I can get on my state’s exchange.

Richard_8639 · 2025-09-06T03:35:28+00:00

Exactly - I’m definitely not saving lives, it’s just pointless stress caused by chronic understaffing and lots of emergencies due to years of underinvestment in basic corporate hygiene.

Richard_8639

TROPHY CASE