First and foremost, please don’t ever use the term “triple Ivy” again. On behalf of everyone you will ever meet, thank you.
I’m torn on this one. On one hand, there are some tried-and-true things that will likely help you down the line. Join your local Democratic or Republican club. Attend fundraisers for local candidates—or even better, host them. Knock on doors and phone-bank for your party’s nominees. Those things aren’t foolproof, but if you do them cheerfully for a few cycles, you’re much more likely to earn the support of party insiders.
Though that can work, it wasn’t what I did, and I only advise it to certain types of people. Ultimately it can be just as effective to find a cause you care a lot about and immerse yourself in it. For me it was cofounding a charter school. For you it could be anything, as long as it’s something you’re passionate about. Learn all you can, meet the big guns in that policy space, and better your community in some tangible way. And then, should you decide to run, you’ll have a solid bloc of supporters around your signature issue. It won’t get you the party’s support, but it will brand you as a genuine citizen as committed to the community as to your own political advancement.
Ideally you can focus on the second approach, with just enough of the first to not be ostracized by your local party. But you’ll have to choose your mix. Given your three (!) degrees, my guess is that the first approach is more your style.
Q: I saw the documentary about you, and now I want to run for office. But I don’t like asking for money. What’s your advice? —Name withheld, via Twitter
Do one of the following: 1) Start a business and get rich so you can self-fund; 2) Marry a rich girl/guy (more options if you’re here in New York than in most states); 3) Befriend a billionaire who will instinctively know to fund an independent expenditure on your behalf without your asking; 4) Run for town council or another office with an electorate under 10,000 people; or 5) Ditch your political dreams.
Q: Do yard signs matter? —S.S., San Diego
In the movie Singles (1992), Bridget Fonda’s character asks her boyfriend (played by Matt Dillon), whose taste tends toward voluptuous women, if her breasts are too small. “Sometimes,” he replies.
And so it is with yard signs. In a presidential election they don’t matter. About 95 percent of the country has already made up its mind, and those who haven’t have ready access to nearly unlimited information about the two candidates.
In low-information down-ballot elections, especially primaries, signs matter, especially for little-known underdog candidates who are desperately trying to raise their visibility and to show the support of people who are well respected in their neighborhoods. Signs can also help candidates keep their supporters psychologically invested in the campaign.
Q: I have a friend in politics who’s headed to prison, and he wants to hire a prison consultant. The one he contacted wanted $7,500 up front. Is it worth it? —C.M., New York City
I’d do it for half that. Oh, and tell him not to eat the Snickers. That one’s free.
Q: I’m a Democrat running for the state House. There’s a well-known libertarian billionaire who gives mostly to Republicans who wants to contribute to my campaign. I disagree with him on most issues, but he likes me. If I accept his money, it could cause me problems in my primary. Plus I don’t want to look compromised, like his pawn. What should I do? —Name withheld
First, the only way you should feel compromised is if you think the money would sway you on issues. The way I see it, taking donations from ideological opponents shows your strength of character, not your weakness. Now after you vote against him, he may not give to your re-election campaign. But as Jesse Unruh, former speaker of the California Assembly, once advised a candidate worried about the influence of lobbyists: “If you can’t drink their whiskey, smoke their cigars, eat their steaks, screw their women and vote against ’em in the morning, then you got no business running.” Words to live by.
As far as it causing problems in your primary, do the math: The more of a problem it could cause, the more money he’d better give you to make it worthwhile. If you live in a state without donation limits and he’s going to give you five grand but cost you 10 grand in bad PR, don’t take it. But if he’s going to give you 25 grand, take it. Talk to some folks to see how badly it would hurt your campaign, and then gauge the potential financial cost of image repair.
Q: I love prison movies, and my favorite is The Longest Yard with Burt Reynolds. Was there a football game like that when you were in prison—and, if so, what position did you play? If a movie were made about the game, who would star as you? —J.B., Louisville, Ky.
I haven’t seen The Longest Yard, but yes, I sort of played in a prison football game. We used a basketball and played on an indoor court with a basket, but since calling a foul could result in bodily harm, it actually felt more like football.
If there were a movie made about it, I think Matt Damon would play me. However, my wife thinks it would be Michael Cera.