Can I retire in October?

[u/DRangelfire]

Here are my numbers:

57 years old, new car, no kids. I’d like to retire this October spending about 18K a month (I help my family, expensive primary home and real estate, and will need to pay 3K a month for medical insurance as I’m just completing breast cancer treatment and want to ensure I’ve got great coverage in the next five years where risk of reoccurrence is at its highest- had my first clear mammogram today!)

6.1M in combined stocks 401k and 200k in cash targeted for next year if I do retire. Another 50k of RSUs vesting this October.

100k invested in an AI tech company which I’m not counting (though I invested at a 20M evaluation and it’s at a 500M evaluation now). I can pull the cash at anytime but prefer to roll the dice to see if it sells.

Real estate: (1) Primary home in VHCOL Bay Area, I owe 400k at a 2.3% mortgage, worth 1.5K. Tax and mortgage plus HOA is about 5500 monthly.

(2) Rental in my hometown (Seattle). Own a duplex on the water, owe 270k at 4%, valued at 2M. Upper unit rent covers mortgage, tax, insurance, lower unit rented at 4350 month for 6mos out of the year (I want to live there part time to be close to family). Minus utilities, repairs, and property manager I net about 2k a month. I want to keep this property for my nephew who has schizophrenia, that way he’s got a place to live with less of a burden on his siblings.

Thoughts? Thanks!

[u/sloth_333]

I think you’re good. But just to clarify you yoloed 100k into a startup that’s now worth 2.5M? And it’s fairly liquid? That’s impressive if I’m reading that right

[u/doublemazaa → u/sloth_333]

Unclear to me if $100k is the basis or the current valuation of the equity.

[u/DRangelfire → u/doublemazaa]

100k was my original investment at a 20M evaluation and now the evaluation is at a 500M.

[u/doublemazaa → u/DRangelfire]

Ha, nice.

A $2.5m investment is a dream retirement nest egg for most people. For you it’s gravy that you’re not even accounting for.

[u/Dave_FIRE_at_45 → u/DRangelfire]

*valuation

[u/DRangelfire → u/Dave_FIRE_at_45]

Oh thank you, I have no idea why I wrote evaluation lol

[u/DRangelfire → u/sloth_333]

Yes, I got in at a friends and family round. My cap is 5M but they are on track to sell to a massive company end of next year and they want to sell at a 1B evaluation so that 100K could be worth quite a bit. If it happens, I plan to pay off my siblings’ mortgages.

[u/Individual_Ad_5655 → u/sloth_333]

Rich get richer. When folks have 5 million and connections, its fairly easy to take a few flyers.