6 Crazy Things I’d Do with a Billion Dollars

Imagine you won the first billion dollar lottery jackpot in history. I searched Google for billion dollar lottery and the only thing I found was a charity that was claiming the first billion dollar raffle for philanthropy.

I’m guessing in about ten years we will see the first billion dollar lottery jackpot.

What would you do with the money? Of course you’d quickly do all the expected things: buy a cool new car, pay off your house and/or buy a new one, set aside for your kids’ school.

All those things are predictable and boring.

With a billion dollars, you actually have enough money to be an asshole. And you should.

Here are 6 things I’d do with a billion dollar lottery jackpot.


1. Never Wear a Pair of Socks or Underwear Twice

billion dollar lottery

Think about it. Your socks and underwear are a very important part of your life. If I had a billion dollars, I’d travel the world looking for the best underwear and socks. I’d then strike a deal with the manufacturer to send me 400 pairs each year, never packed in plastic or touched by a bare human hand. They would be immediately washed by my white-gloved laundry staff before wearing, and delivered to my chambers. After wearing them once, I’d donate them to Goodwill or Salvation Army.


2. Start a SuperPAC

billion dollar lottery

I work in politics, but I have been doing it so long that I am as disgusted with Congress as most people. I would start a superpac that would randomly target elected officials I don’t like and provide the money and resources to unseat them. One day it might be a US Congressman, the next day it could be some mayor of a small town who forwarded a racist email to his staff. If desired, I could target enough statehouse seats to advance any political idea of my choosing. If a politician did or said something totally stupid or harmful, I’d threaten them with an avalanche of money unless they apologized.


3. Build a Nuclear Bunker

billion dollar lottery

Yes, in addition to building myself a nice ranch out west, I’d dig down pretty far into the earth and build a bomb and blastproof bunker. I’d then stock it with 50 years of food and set it up so my family and I could live underground forever in the event of a nuclear winter or apocalypse scenario. I don’t spend my days worrying about these events, but if I had the resources to prepare for this, I’d want to continue living my awesome billionaire lifestyle, no matter what.


4. Start My Own Country

billion dollar lottery

I’ve always wanted to start my own country. I think this desire goes back to a high school project in government class where we had to create a new political philosophy and lay out its constitution and guiding principles. If I won a billion dollar lottery, I’d sink a large barge or megayacht in international waters and establish my own micronation. I doubt I would do this to live there, but I would allow other wealthy people to purchase citizenship and a passport. Plus I would use the title of King on my business cards and enjoy meeting with other wealthy dignitaries and royalty from other nations.


5. Never Invest in Anything

billion dollar lottery

That’s right. I wouldn’t use a single penny of my money to buy anything as an investment. I might buy a few houses around the world, but they would simply be places for me to sleep when I travel there. I’d buy no stocks, no mutual funds, no equities, and never loan any money to anyone. If a worthy endeavor wanted a low-interest loan and I liked their mission, I’d just give them the money. If I thought a startup had a unique and useful idea and a strong team, I’d just give them money. My time is not worth being spent keeping track of who owes me what. If I like you, you can just have the money.


6. Retire

billion dollar lottery

I can just hear the work-addicted now – “If I won a billion dollars I’d still work. I just have to work. I don’t know what I’d do with myself.” – gross! Not me. I’d tell my boss to go eff himself immediately. And I’d spend a hundred grand ruining his life, but that’s a separate matter. My life would become an endless pursuit of adventure, joy and happiness. I would answer to no bosses, and any project that started to feel like a job would immediately be ended, even if it were making money.



As a kid living in the country, I’d often thumb through the massive JC Penney catalog and imagine the nice things I’d put in my mansion if I were rich. Now that I’m 31, it’s pretty clear that I’ll never be rich, and I’m comfortable with that.

But it is fun to imagine what life would be like if you actually had a billion dollars. As you can see from my list of crazy things I’d do, I already know that an endless supply of money would turn me into a evil, paranoid and vengeful jerk, which is why I prefer to live my middle-class life of leisure. But I also know that I would be super generous to those I love and admire, giving away money to them with no expectation of ever being paid back.

READERS: What crazy things would you do with a billion dollars, or would you just be boring?

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  1. I would travel the world indefinitely, buying houses in places I liked. I would buy a plane and have it decked out ready to go whenever I was ready, and have a pilot on standby. I would enjoy time with my family and spend time with friends, and throw some silent blessings in there for those who I think deserve it.
    Bec at Dreamline Diary recently posted..Holding my GroundMy Profile

  2. I would buy a huge island! And never wear the same thing twice.
    Michelle recently posted..Spending, Life, Income and Food updates…My Profile

  3. What a fun post! I’d give a gob of money away to people I know (and don’t) without worrying about whether or not I got a tax break on it!
    Marie at FamilyMoneyValues recently posted..Vote for us in the Personal Finance Olympics!My Profile

  4. I think the national lottery in Spain is the closest thing to this out there. It’s hard to even imagine that much money. It really is an amount that makes money not an issue. It’s interesting that you wouldn’t invest anything. I think I would still invest to get even richer and because with the amount I could invest it would be the ultimate gambling addiction. I’d probably go to extremes like you with wearing stuff once and just retiring right away. When you have that much money, it is quite unlikely that you’d get bored during early retirement. There would just be too much to see and do.
    Modest Money recently posted..How Airline Credit Cards Cost You MoreMy Profile

  5. LOL @ this post. It’s fun. I hope you’d give the one-wear socks to charity after you wear them! I’d give the majority of my money away. To not-for-profits, charities, good causes, etc.

    Oh, and then start a dog rescue.
    Daisy recently posted..Getting Another Dog & Rehoming Fees for PetsMy Profile

  6. I would get one of the NetJet packages.

    So John, we’re friends right? If I just needed the money you’d be more than happy to give it to me? :)

    You’d get asked by people everywhere for money and you’d NEED to start your own country to avoid all of the requests.
    Jason @ WSL recently posted..5 Reasons to Buy a Home in This MarketMy Profile

  7. This is a fun exercise! I’m with you on starting my own country and declaring myself King. My first edict would be to outlaw leaf blowers. Next would be deportation for anyone who drives around with their car windows down and loud music blaring. :-)

    I’m not a car person, so I think I’d rid myself of cars and rely on taxis and transit. (What kind of great message would it send to my countrymen if the billionaire King rides the bus!) I might buy a big sailboat and hire a crew.

    I wouldn’t move; we live in a great area. But we’re a long way from family and old friends, and it’s a bit costly to get here. So the main benefit would be to buy everyone airfare a couple times a year.
    Kurt @ Money Counselor recently posted..Investing Terms BasicsMy Profile

  8. Good luck one day being able to enjoy telling your boss to go eff himself. You don’t have to be a billionaire to make that happen. The socks and underwear thing? Too funny. I have no clue what I’d do with that much money. I know I’d give a LOT of it away and that I would never want my children to know we’re rich. I might even pay people to make them think we’re not rich…yeah, that’s it! I think I’d turn into a nightmare myself. With that much money, is there anything you can’t do? Can’t you pretty much pay someone to make anything happen for you? Kind of crazy how much power comes with money. Like you calling yourself a king….you totally could! And everyone would kiss your ass like you were one. Your brand-new-underwear ass….lol
    Michelle recently posted..Dance Like No One’s LookingMy Profile

  9. hehe. “I’d tell my boss to go eff himself immediately, then I’d spend a hundred grand ruining his life.” I love how your blog is never run-of-the-mill.
    L Bee and the Money Tree recently posted..Week 3 of the No-Spend ChallengeMy Profile

  10. This was so much fun to read,and got me really thinking about what I would do if I had a billion dollars. The first thing I would do is purchase an air strip with my own plane and helicopter, and never drive another day in my life. Second, I would purchase a mansion for every continent. Last, invest nothing for retirement.
    Anthony Thompson recently posted..Self Manager – How to Masterfully Practice the Law of ReciprocityMy Profile

  11. Ha ha. Great ideas! I love the feeling of a fresh pair of socks or underwear, so I totally know what you are going for there.

    I think I would still work, but on my own terms for my own company. I have an entrepreneurial itch, so I would invest in starting new companies. I would not, however, ever have a boss again.
    Eric recently posted..Mint Alternative: Mint.com vs. ManillaMy Profile

  12. This is hilarious! Nice work on these. I’ve always want to have a money-bin like Scrooge McDuck from Ducktails (back when we were kids). Although I don’t think physics will allow you to actually swim in your money quite the same way.
    My Money Design recently posted..Lessons in Retirement from the Movie “About Schmidt”My Profile

  13. If I had a billion dollars I’d take my sweet new ride on a road trip around north America then take my private jet to the next continent and start over. I’d bring friends and family too if they wanted and buy a few vacation homes along the way.
    Lance@MoneyLife&More recently posted..Passive Income: Not As Passive As You ThinkMy Profile

  14. I would become Tony Stark. Sounds geeky but I want an Iron Man suit.
    Adam Hathaway recently posted..The Baby Steps I Took To Living My Dreams and How You Too Can Begin TodayMy Profile

  15. Honestly, I’d be boring and start my own nonprofit. It’s not too exciting but I’d LOVE to have a billion dollars to help others. I think I could do a lot for refugees with a $1 billion.

  16. Awesome! Buy my parents a house, give them a fund.
    Set up a fund for my brother’s college education, as long as he made A’s and B’s and worked part time during college summers.
    Buy companies that I could run (eh…my own empire? Yes!).
    Travel the world.
    Fund or set up charities that aimed at helping kids get a higher education.
    SavvyFinancialLatina recently posted..Saving, Debt, and Personal Goals for July-December 2012My Profile

  17. I wouldn’t tell my wife that’s for sure! It’d be gone in a week!

    I’d have to buy a huge Boat, the sort you can put a helipad on, sail it to Monaco and watch the grand prix from it!
    Money Bulldog recently posted..Want to pay off your debt? Why A Little Means A Lot!My Profile

  18. I like number 1 – not wearing the same socks twice. I would also arrange my transportation situation so I never sit in traffic ever again. Not just in rush hour…I mean never. Something along the lines of what the President gets to do!

  19. Probably I’ll try to buy an island, you don’t have to sink anything to buy that. Offer select citizenship, costlier than private space travel. Good idea!
    SB @ FPR recently posted..Lowermybills.com review, does it really lower your Bills?My Profile

  20. I’ve always wanted an island. AND to own a big company. I don’t want to work there…except doing the cool parts. I’d own Microsoft just to test new technology. I’d own Barnes & Noble to take home whatever books I want. And I’d own Dairy Queen to BAHHAHAHAHA!!!! weigh 750,000 lbs.
    AverageJoe recently posted..Renovating the Rental HouseMy Profile

  21. Good post… I already have flashes of how I will go to work in the morning and have a little chat with all my “friends” there. Talk about being an asshole…. Of course I would by the company I work for and inform everyone that … “Tonight everyone dines in Hell”.
    Except the above dream, I would buy an island and open the best resort on Earth.
    Gekko recently posted..Choose your words wisely!My Profile

  22. I’d switch my job to full-time philanthropy. Also, screw socks, I’d live somewhere where I never need to wear socks again :)
    Jacob @ iheartbudgets recently posted..Why We Have a Credit Card (and Why Maybe We Shouldn’t Use It)My Profile

  23. I definitely would have a personal jet. I’d also look to own a house in every country, as opposed to a private island (which does sound tempting).
    JP @ My Family Finances recently posted..Average Family Spending On Back-to-School Shopping in 2012My Profile

  24. I love this post John .. great! You know I read somewhere that Madonna requests a fresh pair of new underwear everyday so it’s certainly not uncommon. I would do the same, fresh socks and underwear and fresh bed linens.. ah..
    Cheers Mr.CBB
    Canadianbudgetbinder recently posted..Mr.or Mrs. Money Bags… Is that you?My Profile

  25. Oh my, I love the socks idea! I looooooove the feel of a new pair of hands fluffy socks, I would do this too.

    I think I would sit on the money for a while, I would pay off my mortgage, penalties and all rightaway and then sit on it… just to let it sink in. :) Oh, I would also pay my siblings and my parent’s mortgage and any debt they might have and set up some sort of trustfund for my niece and my younger siblings. :D and a week to cuba… oh and I would quit my job the same day… gahh so many things I would do!
    Andrea recently posted..We have liftoff!My Profile

  26. That’s a lot of socks! Some day’s you’ll go through multiple pairs-exercise socks, dress socks, wool socks at night. I’ll be your sock handler for $100K a year, deal?

    I bet you could become a T.V. spokes persons for some luxury sock company with that lifestyle too.

    I’d keep ‘working’, but only doing work I choose to do. Hire out the yucky parts or parts I want to learn myself.
    Brent Pittman recently posted..86% of Millionaires Are Self Made, You Can Do It Too!My Profile

  27. I am SO glad I stumbled on your blog because this is a bad ass post! I LOVE your idea of ordering 400 packs of underwear haha. Hilarious. As far as what I’d do, wow, I don’t even know where to begin!! I think that after paying off my outrageous student debt, I’d get myself a really awesome house with a really awesome reading room full of books and comfy seating with no phones for people to bother me. Oh! And I’d want one of those computerized closets like Cher had in the movie Clueless bc that was pretty sweet.
    Budget Blonde

  28. Why not invest in real estate?:) Now it’s cheap enough and may make money in future. However, tech startups are great field to invest too.
    Alexander Collins recently posted..5 Signs You Are Ready to Switch from a Demo to a Live Forex AccountMy Profile

  29. Bahaha! I’d love to have an island of my own, named after me (or a name of my choosing).

    I’d like to have the choice to never cook again – I’d get a personal chef.
    eemusings recently posted..Link love (Powered by haloumi and Skype dates)My Profile

  30. I would do the underground nuclear bunker too. I’ve been thinking about it for quite some time now, since the Mayan prediction. Alas, I still don’t have the cash to spend, and Dec. 21 is fast approaching…:-)
    Amy Turner recently posted..Credit Card Debt 2012 FactsMy Profile

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