I used to play a lot of poker. Every Friday night for nearly three years, I was at the Mayfair, a poker club in a Manhattan basement. There were big games in the other room — with Joey Bagels (he became Joey Knish in the semi-fictional film Rounders) and dotcom kids. I played in a small 5-10 stud game with Big Phil, Arnie the Garmento (he always wore the same sweater with holes in it), Gracie (she brought class to the place), Trichter, Scott (our fish), and a bald Aussie math major.
I made shoe money. One day, I spotted some gorgeous $550 cream-colored, patent leather, knee-high Nancy Geist boots. I had to have them, but that wasn't going to happen on my Dress for Success salary. It took me nearly 20 hours of play over two weeks, and those people bought me the boots.
Ultimately, those boys from Staten Island and South Philly gave me more than sexy boots. They taught me nearly everything I know about running a not-for-profit. With apologies to Kenny Rogers, here are four lessons.
You've got to know when to hold 'em ... Every poker hand is like a fund-raising pitch. Your first bet needs to be high enough to garner respect from the other players, but not so high that you scare them all away. It also can't be so low that you make them think you're desperate. And that first bet has less to do with your cards than with who's at the table, where you're seated (are you the first to bet? the last?), your reputation, and chutzpah. I've heard foundations say they ignore requests for under $100,000, but a first-time ask for $5 million won't get a second look either. Every entrepreneur knows that chasing early funding is similar: What can you request with a straight face and still get a "yes"?
Know when to fold 'em ... You should fold about 80% of the hands you're dealt. That's hard to do — you get itchy to play or you're tempted to see if you can string something together. Dress for Success was once asked to provide suits for women seeking restraining orders in court. We wanted to help. We had the inventory. But our purpose was to support women looking for work. Our board debated it passionately and decided that we shouldn't muddy our mission by getting involved in something complex that we didn't fully understand. That slope would have been too slippery — we wanted to say yes, but we had to say no.
Know when to walk away. And know when to run. Sometimes you suffer a bad beat and you have to move on. In the office context, this is especially relevant to personnel. Firing an employee is never fun, especially if you hired the person. It's like starting out with a nice pair in the hole. You're starting strong, but it never gets better. The best thing is to just cut your losses quickly. If that new employee turns out to be a loser, better to fail fast.
This has been the hardest lesson for me: I fall in love with cards, and I fall in love with potential in employees. Do Something, my current not-for-profit, once hired a successful tech entrepreneur to be our CTO. He took a huge pay cut, which made us feel lucky to have him. He wanted to redesign our site. This was a bad use of our time and resources, but he kept arguing for it. I'd be crazy to ditch the genius, right? Wrong. He didn't understand our priorities or our agenda. Delaying a decision to cut bait is expensive and affects your head. We finally let the guy go.
You never count your money when you're sitting at the table. There'll be time enough for counting when the deal is done. Don't gloat. Even when you win a gigantic pot, you don't want your benefactor to feel cheated — or stupid — because you want to play with her again. And counting your chips is distracting. Every second spent examining your own stack is a second you're not using to suss out others' cards and nerves. In the not-for-profit context, droning on about how much money you've brought in doesn't help bring in more. Plus, it's off-topic. Your goal is to build a more effective organization and reach your group's goals, right? So communicate your strategy for change, not how much change you've got.
About seven years ago, I had my first-ever straight flush — and two dumb, beefy guys stayed in with me until the river. It doesn't get sweeter than that, so I no longer play. But I still have my boots and my lessons. Every day at the office, I remember that it's not about the hand you're dealt, but how you play it.
Nancy Lublin is CEO of Do Something.
A version of this article appeared in the September 2009 issue of Fast Company magazine.