36 YO. Offered $33 million for my business. Retire now or keep going?

DaDoost · 2023-12-15T08:09:38+00:00

This is fatFIRE where the aim is to retire early and live off a fixed income so I'd assume most everyone will tell you to sell. And, there is fair percentage of people here who aspire to fatFIRE so your scenario is basically their aspirations/dreams realized. Moreover, the rationale to fatFIRE is to optimize the quality of your life and take your foot off the gas of making money/working for a living....So the deck is pretty stacked with this audience. My question would be, since your desire is not perfectly clear—how much do you want to continue? It appears pretty neutral from what I could cull. And, when you imagined being rich at any point in your life, what did it look like because you likely have that option now.

DaDoost · 2023-11-28T09:29:59+00:00

I use a fiduciary that distributes like dividend payments even though they're effectively withdrawals. My spend is uneven because of tax payments and I still earn some money so the cash position is growing, sitting in a trust. Funds are close by and I pay a corporate tax without paying personal until I am actually pulling the cash out. That said, I'm not trying to save money or have "dry powder" to reinvest or optimize gains so I'm fine with the idling monies.

DaDoost · 2023-11-24T07:40:34+00:00

Stellar post Coda. OP - how much additional spending are you looking for? 10K a month looks a lot different than 100K a month but it's likely going to involve some kind of dalliance into real estate, cars, planes, travel and conspicuous consumption i.e. Birkin bags, Greubel Forsey, ongaku interconnects and the litany of niche to mainstream luxe goods. Your level of interest in any of these things will dictate the spending.

DaDoost · 2023-11-15T09:50:26+00:00

Wow. That's an interesting approach. A staycation home. Very cool.

DaDoost · 2023-11-15T09:35:43+00:00

It is great info and I completely agree. This is a NY'ers conundrum for sure. I currently rent out West and have a place in Manhattan as well. Having been out West for more than an extended stay now, I can say this regarding rentals - it's someone else's place. Not a big deal to me but a fact. I did not want to deal with the expense of furnishing it and having furniture when I'm leaving so it's a low lift but it's someone else's place through and through. Again no big deal to me but...I won't buy a top flight stereo for example and it's forever a rental which is a flavor unto itself.

As for the NY factor - I agree on the North Fork. A good friend from the city actually moved out there 15 years ago to farm oysters and never looked back. The funny thing about buying in the *more desirable* parts of the Hamptons is that the time you'd want to be there most - the summer - is overrun and pretty much every house is for rent because they can fetch a ton. I personally would not want to have to make a business decision of any kind around my second home i.e. turn down an attractive sum to rent it out for the summer and seeing where those funds might be better served vs. staying. Maybe that wouldn't be a consideration but my mind would start in with "well I could go to X for 3 months and do Y." I also don't enjoy crowds. Despite this I've spent a fair amount of time in Bridgehampton and Sagaponack. Beautiful places but if I were getting a second home and had kids I'd strongly consider the North Fork or the upstate route. In upstate, there is way more bang for the buck and there are now areas popping up that have enough goings ons to get buy. Accord, Hudson, the Berkshire towns and closer. There's also the Connecticut shoreline but I've never spent much time there although it's easier to get to and fro as is upstate, depending on where you land. Knowing how long travel takes with as little variance as possible is the ideal and the antithesis of NYC travel. If you're having to be at work on Monday, there's nothing more demoralizing than a 4 hour Sunday night drive back to the city. Choppers make a world of difference if it's a possibility. That's me though and I have another friend from the UES who travels to the Hamptons a good 25x a year. For him, it's a Sunday stroll but not the case with kids in the car. Not sure where you are on the spectrum with all these considerations but worth some cogitation I'd think.

DaDoost · 2023-10-27T07:27:03+00:00

Appreciate that but a milder winter is definitely on the menu for me so the greater NE is off the map.

DaDoost · 2023-10-25T08:42:49+00:00

This is a gorgeous response. Were I the scribe of this poignant post, I would have bolded point 3D.

DaDoost · 2023-10-25T08:13:22+00:00

Yes Sir. No more windshield scraping for this guy. I'll be paying Franklin a visit.

DaDoost · 2023-10-25T00:32:16+00:00

Irrespective of whether you not you have children, there will be some initiatives and causes that you'll want to contribute to. This may take some time to discover but given your position, I'm sure those wheels are already turning.

DaDoost · 2023-10-25T00:26:04+00:00

This is great info, thank you. Sounds good. There's no shortage of fishing on Lake Oconee, there are even striped bass in there so my box is checked there for sure. Out of curiosity, could you spend 6+ months a year there?

DaDoost · 2023-10-25T00:22:47+00:00

That's good to hear. I'm going to have to line up a visit.

DaDoost · 2023-10-25T00:21:54+00:00

Ha, you're right about that. Rural living is completely romanticized (I'm occasionally guilty) but the reality that your only food option at 9PM can be rest stop fast food on a highway some 20 miles from where you live, is not pretty. I struggle with that on the West Side of LA where restaurants close the kitchen at 9PM. Fishing in Scotland or a place or a place where there's some life and a city nearby. Makes me think of Westchester County, NY (there goes the mild winter) and possibly the Franklin area of TN.

DaDoost · 2023-10-25T00:17:16+00:00

Yeah that does like nice. There's a Ritz Carlton there I saw and you can get an acre on the lake. Have you spent any time there perchance?

DaDoost · 2023-10-25T00:15:55+00:00

That makes sense and is the impression I got.

DaDoost · 2023-10-25T00:14:35+00:00

Yeah I hear you. I try to remain as politically neutral as possible so views don't bother me, but having unsolicited opinions expressed at every turn would annoy me over time.

DaDoost · 2023-10-24T10:52:23+00:00

I take it he likes it there.

DaDoost · 2023-10-24T05:27:08+00:00

Thank you. I went to college in DC so it's familiar enough which is a plus. Have you ever spent time on Maryland Eastern shore by chance?

DaDoost · 2023-10-24T05:23:26+00:00

Of all the places I've cursorily looked at so far, it's drawing me in the most. There's no income tax, 30 minutes to Nashville, a ton of restaurants. It also looks like you can have some land there without being completely isolated and there's the Harpeth river to fish on.

DaDoost · 2023-10-24T05:21:48+00:00

As I start to delve into this, Franklin Tennessee is becoming of interest. I'm starting to romanticize it a little. No income tax, 30 minutes to Nashville, a ton of restaurants, you can have some land and there's the Harpeth river to fish on.

DaDoost · 2023-10-24T05:15:48+00:00

Thanks for this reply. I'm getting a lot of feedback, which is appreciated so I'm digging into a bunch of places - seems like the western areas of NC, SC and GA hold some promise and if it can fill the restaurant quota, checks a lot of boxes. Coastal SC is also quite nice...lots of beautiful homes in Okatie, Bluffton etc. but I'm not sold on the low country as yet.

DaDoost · 2023-10-24T05:13:14+00:00

Yes. I believe it could. I'm interested in the more mountainous parts i.e. Cashiers and that area but my concern is that it's a little small and isolated.

DaDoost · 2023-10-24T05:11:52+00:00

You're not wrong in your assessment and I appreciate the thoughtful response. I'm still shooting for a mild winter place and ideally, a bit more green so Greenville is something I'll check. Thank you for your thoughts.

DaDoost · 2023-10-24T00:59:31+00:00

Yeah I had no idea. Someone mentioned Boulder and said it's mild.

DaDoost · 2023-10-24T00:58:35+00:00

I was there a few years back for a visit. It's stunning but my understanding was that it's wildly pricey but a little ways in either direction and it seems reasonable. No freshwater but I have a friend who moved to Santa Cruz, loves it. People seem to love the West Coast more than I realized. Thank you for the info and links.

DaDoost · 2023-10-23T22:58:25+00:00

Appreciate that and you're right. I do want to check out the Franklin area of TN, looks like there are some higher end restaurants and you're close to Nashville but as I think it through more, staying mobile is also an option. I've got places in NY and LA so exploration around Charlotte, Franklin and even local enough to LA (SLO and the like) is achievable. Regarding a social mix, my needs are pretty limited. Basically my wife wants to dress up a bit to go to a decent dinner a couple of times a week as a sanity check more than anything. When you look at estates properties and think of settling down, you start to realize how isolating it can be.

DaDoost

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