• How do they define “being the next Warren Buffet”? Isn’t that technically impossible, unless you believe in reincarnation?

    • Also, I never play the lottery, but if I did and won I would buy an island in Fiji, hire some folks to run it, and live the rest of my life importing good food and drinks and flying my friends out for vacations before the sea levels rise to the point that I have to buy a bunker in Idaho to hoard my franks and beans.

      • Anonymous

        Private Island sounds cool – Question who owns these Islands right now gov’t of Fiji?

        I bought one ticket and I am in the office pool for another dollar. When the jackpot is over 400 mil I play, it’s fun. I don’t watch reality TV but if a there is a single winner of the 1.5 bil jackpot I would watch a reality show that followed the winner for the first year.

      • PoPOVerWork

        Private Islands are over-rated. All fun and games until you have to find a barge to replace your refrigerator.

        • wdc

          Agreed. Having spent some time on private islands, I find it more hassle than it’s worth. It’s maybe ok for a week, max, but having to get the boat out (with all that entails– smelly gas, weather considerations, murder on the hair) every time you don’t feel like cooking is a pain.
          I’d rent the island, but buy a swank apartment in Paris.

        • With $1.B, or $800M or whatever it is post-taxes, I’m pretty sure I could afford the luxury of someone handling that hassle for me ;)

          • wdc

            But then you have the hassle of managing those people, most likely across a language and cultural barrier. And again, voice of experience says this is not a task to be taken lightly. (I’ll tell you someday about the time I had to negotiate territory between a resident butler and a visitor’s personal man. His gentleman’s gentleman, if you will. For extremely well-paid and highly-trained adults, they behaved a lot like teenaged girls.)

          • True. Multiple islands it is then!

  • jdc

    I’d buy my parent’s house, pay off some friends’ debts, quit my job and run for office against my horrible, no good, do-nothing, bible-thumping, batshit crazy representative in congress, Ms. Virginia Foxx.

    • anonymous

      Gotta be careful with handouts. Those people will be on the hook for the taxes.

      • CHGal

        Actually, the donor (you) is on the hook for gift taxes, not the recipient. And it’s not income, so it’s not income taxes.

      • The OP Anon

        Is there a tax burden if you buy their house and charge them $1/year in rent?
        From what I understand, the way to manage it is give the lottery ticket to a trust. Then you get payouts from the trust.

        • CHGal

          That’s technically a gift. But it’s got to be worth (the difference between $1 and the fair value of the rent) more than $14,000 a year to be taxable. Or $28,000 if you are married. You can give as many people as you want $14,000 a year before it’s taxable.

  • siz

    35 people in my office pooled to buy tix, so i’m in on that. our company will pretty much be wiped out when all of us retire tomorrow, but that’s not really my problem…

  • skj84

    Buying my ticket at lunch. If I win I’m paying off my student loans, my siblings student loans, my parents mortgage. Then set up special accounts for everyone. Also purchase a special beach house for the whole family to use. And live my most fabulous life. Incidentally my plan would not involve quitting my job. I like my job and would probably start taking classes to be even better at it.

    • LittleBluePenguin

      SAME EXACT here! I really should buy a ticket for the hell of it, that way when i don’t win I will know I at least tried! :)

    • Anon Spock

      800 million and you’re still working? Taking classes to work more? Wow!

    • anonymous

      There are few things more absurd than people who say, “I’m going to keep doing my job even if I win the lottery.” So you will have enough money to do anything you want for the rest of your life and you’re going to keep going to a regular day job at an office (or wherever) and reporting to a boss instead of, say, starting your own organization/art space/company/what-have-you which you are 100% in charge of and where you report to no one except yourself? That’s just silly and makes no sense.

      • anon

        There are few things more absurd than pronouncements about what other people ought to want.

      • LittleBluePenguin

        Who crapped in your cereal this morning? Sheesh! Believe it or not, some of us genuinely love what we do. Maybe we’d be able to hire other people to help us with the less desirable parts of the job, or maybe we’d just like to try to retain some sense of normalcy if we won the lottery. Your opinions aren’t the only “right”, non-absurd ones.

      • wdc

        Starting your own org is for egomaniacs. The smart money is investing in existing structures. Like how Warren Buffet donated his money to the Gates Foundation instead of creating a Buffet Foundation.
        Also, lots of people prefer to have a boss to take the heat and make the tough decisions, leaving staff free to get on with the work we enjoy.

      • skj84

        I really like what I do. My job is stress free, I enjoy my coworkers, and I help people. I mean, i’d probably take more vacations, but I see no reason to leave. Now if it was my old job in a hotel i’d be out like a light.

        • Anon Spock

          $800 million reasons quickly come to mind.

      • Anon Spock

        People who want to work in a regular office/restaurant/etc after winning a significant sum are those who likely have little going on besides work, so they’ll be bored. They’re not comfortable picking what to do without clear direction. They need structure and routine. Yes, I believe you love your jobs, but with $800, 400, 10 mil is there nothing else you’d rather do all week?
        It’s a bit sad to me.

        • skj84

          Ok, you do raise a good point about doing other things. I would probably go back to school, subscribe to all the performing arts memberships I want, take dance classes and travel more. But I do like the structure of work. Plus I feel working could help me stay grounded. You always hear stories of people who hit it big and then go off the rails. Spend all thier money of frivolous stuff. Working would help me stay grounded.

          • CHGal

            I agree but 40 hours a week would cut into those other things. I’d get something part time or freelance.

          • Anon Spock

            People go broke because they overestimate the value of what they’ve won (under 10 million is peanuts) & they don’t know how to manage money. Working a job doesn’t help either problem, but it does cure idle hands syndrome. A need for structure isn’t per se bad, but that’s a lot of time you’re not enjoying yourself and helping someone else make money.
            I want to help people too, but I’d just volunteer.

        • wdc

          So rude. Perhaps you’re not very good at your job, or it’s an unimportant job? Like, you’re just a cog in a machine and you don’t feel like you’re making a difference? (See what I did there?)
          My job gives me opportunities that are not otherwise available at any price, and I enjoy them.

          • Anon Spock

            You say cog in the machine like it’s a bad thing. Zero stress job, can come and go as I please, good pay…I love it! I’ve never picked a job for the feels nor would the feels play into a scenario with overwhelming wealth, but hey, that’s just me.

          • wdc

            Sucks to spend half your waking hours doing something that doesn’t excite you, though. People who are saying they would keep working even if they didn’t need the money are saying that they love what they do. And you belittle them for it.

          • Anonoly

            Because it’s BS. If your job were that captivating you’d be doing it instead of spending time here.

        • Anonoly

          That’s why my wife’s mom is still working (and commuting 1.5 hours each way) even though she’s 80 years old and has multiple properties and more money than she could ever spend in her lifetime. She just doesn’t have anything better to do.

          • Anon Spock

            Hold premature babies, walk shelter dogs, volunteer elsewhere. At least it’ll help her stay sharp.

  • KH

    One of my best friends has a Mustang which he constantly customizes. He is incredibly proud of its uniqueness and posts pictures of it on Facebook constantly. I would use my winnings to buy everyone in his neighborhood the exact same car, thus leaving him with an utterly commonplace car. After a few weeks, I would, of course, buy him a much nicer car than the original. I’m not a monster.

    • GGG

      If I win, I’m giving you a cut so you can fulfill this amazing plan.

    • elbeech

      Agreed. That’s great. Except maybe buy him a scooter instead.

  • textdoc

    I bought a ticket a week ago — my first lottery ticket ever.
    I’m thinking about maaaaybe buying another one today, even though I know I have a better chance of being struck by lightning than winning.

    • anonymous

      I would buy a home in Miami, LA, NYC and then Yatch to sail the Caribbean as needed. I’ll buy into a private plane share. I’d pay my family members to divorce me. I’ll be broke in 10 years. By then I’d have done everything I wanted to so don’t care.

    • textdoc

      If I won, I would hire a personal assistant and/or professional organizer. And a personal chef. I’d keep a catsitter on retainer so that I could do lots of travel without having to worry about my cat.
      I might plow some money into a campaign to get D.C. to adopt a deposit system for glass bottles, aluminum cans, and (if possible) plastic bottles.

      • skj84

        I’d definitely hire a Personal Assistant. And a hair stylist to do my hair every morning. I would also hire a chauffer to drive me and a personal security team. Unless I can claim anonymously, I’d rather not want to risk people trying to take advantage.

  • hippy

    I’m keeping my job after my win, but I’m going part time. I’ll donate the money needed to hire someone to cover the rest of my job, or whatever.
    Then I’m going to build a big architectural showpiece of a group house, with private living quarters but with shared kitchen and other common space, for me and a half-dozen of my closest friends. We’re going to live the communal life, and probably go on talk shows and stuff about how the village is the hot new household configuration. We’ll look out for each others’ kids and snuggle each others’ pets and cook big healthy meals, and when we’re old and the kids are all gone, look out for each other.

    • The OP Anon

      So basically a kibbutz?

    • womp

      you’re my kind of person!

  • Anon Spock

    Live a relatively simple life: pay off debts, buy a nicer car but nothing too crazy, travel.
    Work…Hell no!
    Do some volunteer work.
    Make sure my future brood is set up.

  • jcm

    I generally dislike the lottery, and never play it, but a billion dollars is a billion dollars. I saw a smart take from Matt Levine yesterday:
    “for me, being two bucks poorer (with probability .999[lotta 9s]) would not impact my quality of life at all, while being $1.4 billion richer (with probability .000[lotta 0s]1, and yes I know there are taxes and a lump-sum haircut) would impact my quality of life really quite a whole lot.”
    So now I’m two bucks poorer.

    • just me

      I always see it as having $3-4 worth of fun dreaming about what I’d do with the money, so no harm done!
      And for the record:
      Pay off all my debt
      Do something REALLY nice for my parents
      College funds for the nieces and nephews
      Buy one of those corner lot Victorians on the Hill
      Rent a ridiculously posh private island in the Caribbean and fly all my friends out for a week for an awesome vacation
      And shoes. Oh, the shoes I could buy….

    • Anonoly

      I’ve thought the same thing, however, going to 7-11 or wherever and buying the ticket is such a nuisance to me that it does significantly impact my quality of life for that day. So that’s why I don’t do it!

  • Anonymous Coward

    get a new house (of course). a car, personal trainer. some photography equipment and classes. new house for the parents, car for each parent.

  • CoHi

    I’d buy my mom a house (she’s never owned one), pay off my and my brother’s mortages, buy a sweet row house in the heart of Logan or the Hill, and buy a place on either Lake Austin or Lake Travis in Texas. I would get a big block of season tickets to the Caps and Longhorns for all my friends who are fans. I’d quit my job and play and travel for a while, then maybe run for office or start a nonprofit (or donate heavily to one that already exists). I would also put 90% or so of the money in trust for future generations (and to keep my mitts off of it when I get delusions of grandeur). I admire families that have (reasonable) trust safety nets for their family members. It makes affording a home and a life so much easier for your progeny. I don’t have any kids (yet), but that prospect is pretty exciting.

  • shmoo

    I’ll tell you what I’d do, man: two chicks at the same time, man

    • skj84

      yo, you don’t really need a billion for that.

    • anonymous

      Nice “Office Space” reference…

  • above7-11

    I’d spend most of it on booze, women and fast cars. The rest I’d just waste.

  • Anon

    I’d buy PoPville.

  • Philippe Lecheval

    Those odds give me hope that some of the people I know of will someday be struck by lightning.

  • AnonV2

    First thing meet with a lawyer to draw up a trust to receive the funds; DC is one of the places where somebody has to be named to accept the winnings, but I think that can be a lawyer acting as the executor of the trust. Privacy and whatever anonymity can be had through legal means would be paramount (a determined person would be able to find out who you are, but that legwork cuts out 99% of the scammers, “entrepreneurs” and people otherwise too lazy to actually try to impact your life negatively). CFP and tax advisor drawn from close associates wherever possible. With that much money a professional wealth management firm may actually be the best route.

    Educational trusts for the kids and all of our friends’ kids, enough to pay for private through grad school with modest annual disbursements after age 30 for any remaining money. I don’t want them growing up as trust fund babies at 18. If they are still dependent on mommy and daddy’s money at 30 we have failed them in other ways. Various other family trusts, LLCs, etc for other structured needs and to help out friends.

    Other than that, nothing flashy. Good but unremarkable cars (OK, maybe something fun for sunny day drives, but a classic, not a modern hypercar). Nice house with all the room (in and out) that we need in an established neighborhood in the city (I would dearly miss our current ‘hood in many ways, but c’mon). Beach house for the extended family close by. Maybe pied a terre somewhere in Europe. Would do high end rentals for anything else (islands, mountain vacations). If I can’t drive to it in 3-4 hours I wouldn’t want to own more property that would see limited use.

    A large bulk of the rest in trusts for charitable purposes (education primarily). Job would be an extension of current hobbies; nothing that needs to make money, but is fulfilling personally. When the kids are grown enough give them the gift of seeing the world and the people who inhabit it, not through organized tours aimed at the wealthy. Require them to work (see the educational trusts) while providing the financial structure to make it happen. I wouldn’t care what it was as long as they find something worthwhile to do with their lives and work hard doing it.

    • This is exactly what I would do. Nothing flashy. Except I would only fly first class because I really, really hate flying coach these days.

    • Oh, and I only buy tickets in Maryland since you can accept the winnings anonymously there. I guess then you have to pay the Maryland fee and DC taxes, but whatever. Privacy is worth it.

    • Nathan

      Yeah I think my first actions would be to start with a trust lawyer and then head over to Goldman Sachs PWM or JP Morgan Private Bank.

    • Speaking of Office Space references, you sound just like Samir “You know what I would do if I had a million dollars? I would invest half of it in low risk mutual funds and then take the other half over to my friend Asadulah who works in securities… “

  • Rich

    probably one of the few liquor stores that doesn’t sell tix.

  • Tall E

    I was sucked into buying tix too, even though i’m fundamentally opposed to what is a regressive tax. If I won, I’d take that annuity, quit my job, and spend some time figuring out how I can contribute more to the organizations I volunteer at. I’d set up my nieces and nephews with college funds. Beyond that i’d probably take some time off to travel for a while before starting a new venture.

  • The OP Anon

    Interesting argument in the NYT’s about why the annuity is better. In short, due to the fact that you end up getting the full $1.5bn eventually and that is ultra-safe tax-free growth.

  • wpk_dc

    I resisted and resisted, even dissed a couple friends on FB who bought tix and posted their hopes to win last week. But today, I told myself Why not? and bought $20 worth. We’ll see tonight/tomorrow. I hadn’t bought a lottery ticket in a couple years (today was probably the third or fourth time in my life). But I know I’m gonna win this ;)


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