The post says he won't make "yacht-and-helicopter money"... I think helicopters are cheaper than he thinks. On a billion-dollar acquisition, I can't imagine the near-cofounder having less than 1% (hopefully quite a bit more). This means at least $10M, which should be plenty for a helicopter. Maybe I'm reading his comment too literally.
For a helicopter, you need a hangar, a pilot, regular maintenance, insurance, fuel/oil as well as membership/pad fees if you actually want to fly anywhere besides airports. You could do a small helicopter for $200,000-$400,000 and then about $30,000-$40,000 a year in recurring costs before pilot, fuel and oil. You can expect $300-$400 per hour of flight time. If the 10 million is invested and has a return of 4% annually, the helicopter will cost 10% of the max you can pull out without depleting principle. That also doesn't include loan payments if you didn't buy the helicopter outright.
So, helicopter money is a lot higher than it looks.
You can become your own pilot and mechanic, buy a big plot of land and build your own hangar and helicopter museum, get a helicopter that runs on diesel, open a McDonald's franchise and use the oil to run your helicopter. I ran some numbers and this turns a profit. You can also sell helicopter tours of your helicopter museum for more $$$ and possibly be the first McDonalds to offer delivery by helicopter. With the profits you can buy a 2nd helicopter which, by my number, doubles everything!
Full disclosure: I'm a bad mather, but I'd be a great rich person
My sense is Marco is looking at the money in terms of: "how much yearly income can my money generate, and what kind of lifestyle would that be?" (kind of like thinking about a retirement account). In that sense $10M in savings is not enough to start buying yachts and helicopters assuming he doesn't want to blow all the money at once like a stereotypical lottery winner.
More importantly, he makes it clear he'll never have any money worries if he's careful. That implies a decent amount of money, and I think that's what most people on Hacker News really wish they had.
Charles Simonyi would commute to the MS campus via helicopter and we all know about Paul Allen's yachts. I think it's more about it being similar to buying a second home or a nice car to normal people. I.e., you may or may not notice the expense, but it makes your life easier or more pleasant.
Are you implying that he is predisposed to blow it like a lottery winner given the fact that hasn't worked there for years and was really just the beneficiary of luck and inflated valuations?
I took the implication to be exactly the opposite of your line of thought. Given that his article is about all the work he put into Tumblr, I'd say he is not likely to have a "lottery winner" relationship with money.
If he wasn't a real founder, it would be very rare for him to start with more than 1% and that wouldn't be anywhere near that after ~5 years. I doubt he has more than .25% after all the VC funding rounds and the associated dilution.
Then there are the likely VC liquidation preference multipliers where they'll get a larger piece of the pie.
He's been gone since 2010 so I'm guessing any options he had were exercised so it should be long term capital gains. Figure in taxes and take away any previous exercise costs and I bet it's around 1-1.5 million that he's cleared. A nice sum, but definitely not "yacht-and-helicopter money".
I think he was referring to a yacht so large that you can land your helicopter on it (ie. http://www.youtube.com/watch?v=jynvdeg6uWw) in which case it's not the helicopter that's expensive...
Dock fees, fuel repair costs, insurance, and the salary for a licensed captain if your Yacht is over a certain size add up. Boats are not cheap. Even "small" (anyone with a automobile license can drive it) 40ft ones. My buddy's family owns a 45 ft Yacht and the joke at the harbor is BOAT = Break Out Another Thousand. Where they dock it they pay $10 per foot per month in dock fees which is cheap for the area. 5 miles down the coast it's $30/foot/month.
