If I win the lottery…

Or more likely, though still unlikely, a big jackpot

As much as I complain about nonprofits, I do realize they often play a useful role in this world. Remember, I’m not against nonprofits. I’m against bad nonprofits. I’m also against tax policy that plays favorites.

As the subtitle implies, I am VERY unlikely to win a lottery because I very rarely play a lottery, and even if I played, the odds of winning (as you very much should know) are vanishingly low. When in Las Vegas, I will put a little money into a progressive slot machine with a huge payout. Where in a given year I might put $6 into the state lottery (Powerball or Mega Millions), I will put $100 into a progressive slot machine in that same year. There are two reasons for this:

First, the odds of winning the Las Vegas Megabucks jackpot is about 6 times greater than the Powerball or Mega Millions. So the odds are better—why this is relates to the second reason below. That cannot completely explain it as it is still a stupid longshot. But when in Vegas . . . it is more fun and accessible to play.

Second, I have a philosophical problem with state lotteries. In short:

• The state shouldn’t have a monopoly on lotteries since this

  • is not a legitimate function of government

  • and allows them to have very bad payouts than would otherwise exist (this is why the odds are so bad compared to private alternatives).

• The state shouldn’t be involved in lotteries since they

  • play on the innumeracy of the ignorant,

  • are regressive in nature,

  • give undue legitimacy to gambling making it seem like not gambling (compounding the first two items),

  • and help fund broken systems.

Okay, end of philosophical diversion. Back to what I would do despite the unlikelihood. As they say, a girl can dream . . .

Suppose that after Uncle Sam takes his enormous cut of my winnings, I am left with $100 million. What would I do? What would you do?

Let’s not kid ourselves. Before any charitable giving, I would make sure that I and my family were taken care of. “F-U” money isn’t a shortened version of “for you”. Still, I would have a lot to spread around. And part of that would indeed be a strategic play that returned benefit to me. Don’t let me mislead you. We’re almost all Randians more or less when it comes to charity, and I’m no exception.

My philanthropic endeavors would be a combination of out-right giving and leveraging nonprofit structures to create a legacy of giving opportunities. The latter part is where personal benefit would mostly come into play. Setting myself and select family and friends as employees and board members would enable status and income (personal gain) along with (hopefully not just potentially) good stewardship. This would be good for the soul (if done right) and good for the cause (again, if done right). Yes, this is dangerously close to a lot of what I criticize nonprofits for. Ironclad, well-written bylaws and large distribution requirements might help mitigate the inherent risks. I don’t think I want a large foundation out living me and my direct heirs.

In terms of out-right giving, this is where Ayn Rand and I part ways (on this issue specifically). I do think we have a moral duty to others. I would fund my Catholic parish as well as my local diocese and local Catholic foundation, I would also consider gifts to other organizations both in my diocese as well as Catholic organizations elsewhere. But that consideration gets to the difficulty of giving to organizations afar where I cannot have as much confidence in how well they are doing at the mission I want to fund.

Other direct gifts would come from entities I would create to continue funding of organizations or people who match up with my values. This would include giving to Catholic entities. Beyond that would be Reason Foundation, Cato Institute, The Institute for Justice, FEE, CEI, American Institute for Economic Research, Pacific Research Institute, Independent Institute, Emergent Ventures, and Arnold Ventures to name a few standouts. The latter two are a recognition that the best funding (dare I say most effective altruism?) comes from direct funding. Along those lines I think the foundation I would create to run my self would be structured along these lines. Yes, we would look like we are just throwing money at good ideas because good ideas need funding.

Other ways of giving would include starting a nonprofit(s) for indigent defense and public defenders. I might simply find good ones already in existence to directly fund, but this seems to be an area of need left currently unfulfilled.

The idea of currently unfulfilled would drive a lot of my giving. I have my doubts, to say the least, about a lot of large nonprofits already in existence. I would rather skate to where the puck should be.

What would you do with $100 million beyond thinking of yourself?