The first million-dollar check I ever held was written by hand. It was donated to the organization I worked for at the time, and came in an envelope addressed to me. I told my staff to hold off on the champagne until the check cleared because, really, who handwrites million dollar checks?

But the check cleared, the corks were popped, and so began the first in what would be a series of successful personal fundraising efforts—$70 million and counting—and countless more for clients I have advised.

I recall sitting back in amazement, trying to put my finger on all the things we had done right to lead us to that transformative gift. Certainly, it was the product of months of hard work, but the seeds of that success—and the larger achievements of the campaigns that followed—were planted in an unconventional campaign many years ago, when I was just 12 years old.

It was 1978. My parents had uprooted our family from New York City to Salem, Massachusetts. From Central Park and Zabars to a puritan backwater of witches, townies, and docksider-wearing sea captain wannabes. I hated it. My saving grace appeared in the form of a powder blue minibus, swerving to a stop in front of our house. Howie Gordon, a ridiculously handsome former intern of my father’s, and Carly, his beautiful wife—real-deal hippies, both—stopped in for a two week stay at the tail end of their honeymoon, and ended up staying for twelve months. Howie looked like Jeff Bridges and talked like Lenny Bruce on acid. One night he showed us a slideshow of his wedding to Carly where neither one of them was wearing clothes. The revelations kept coming…

Over Thanksgiving dinner, we learned not only that he had been featured as a centerfold in Playgirl’s November issue—the first erect centerfold in its history, I might add—but that he had designs on winning its write-in contest to become Man of the Year, 1979. It would be, Howie said, his ticket to Hollywood: “If I win this, I can be the next Starsky…” he told me. “And you? You’re gonna be my Hutch!”

Today, Howie barely remembers our crusade. To him, it was mainly a way to keep me busy while my parents were at work. But to me? From the posters we plastered all over Salem to the voters we lobbied—the cute girls at Dunkin Donuts, the kids in my sixth grade class, the little old ladies in my grandmother’s living room—this was the most important election in modern American history. And it worked! In the summer of 1979 we got the news: Howie had won. He was Playgirl’s 1979 Man of the Year. He was on Donahue. He got a part in American Graffiti 2! (Although he ended up on the cutting room floor.)

To any stranger, we were just two total oddballs out on the street, shaking hands and trying to lobby the unsuspecting, apathetic, scandalized citizens of Salem. But our unconventional campaign, perhaps unwittingly, instilled in me a set of principles I still use today when advising clients on guerilla-style fundraising and capacity-building techniques.
 

Make Them Laugh, Then Make Them Believe

Our approach was funny, for one thing, and humor is disarming. Anyone who has ever asked another person for money knows how uncomfortable that conversation can be. Almost as uncomfortable as asking a total stranger to write in to Playgirl. Get them laughing, and suddenly the inconceivable becomes a little more likely. Howie was never afraid to laugh at himself. “I didn’t always look like this,” he would tell would-be voters when they looked at the washboard stomach revealed in his magazine spread. “I was a heavy kid. I had the biggest boobs in the seventh grade!”

Howie’s self-deprecation was key to our success, and brought a wildly foreign concept down to earth. But humor doesn’t sell if you can’t follow it up with substance. In our case, the “before and after” photos we brandished to drive the point home turned heads. Now the funny line that caught everyone’s attention had transformed into a visible show of discipline and hard work. The physical corroboration provided something every modern donor demands: quantified and/or qualified impact.
 

Secure Allies, Unlock Niche Networks

Another key to our campaign was aligning ourselves with powerful forces—like my grandmother, a woman who possessed a preternatural ability to make everyone around her feel loved and included. Winning her endorsement between an onslaught of leftovers at her kitchen table meant everything for our campaign. Her willingness to share that vote of confidence with the ladies at the Mahjong gathering she otherwise detested gave me a powerful sense of confidence—something every fundraiser needs. It also instilled confidence in the electorate. Just as humor disarms, aligning yourself with a respected figure results in your prospective audience dropping their guard a little more. It’s an entirely human reaction: “Oh, well, if she thinks this is a good idea, then it probably is. Maybe I’ll just give them the first degree, rather than the third.”

This approach is essential when it comes to convincing donors that they’re not jumping into the deep end of the pool all alone. Knowing that someone you respect has already made that leap increases the ease with which you can follow suit. It’s a phenomenon I’ve dubbed Gelt by Association.
 

Unplug! Show Up!

Woody Allen was right: Eighty percent of success is showing up. Although our campaign took place in the late 70s, before social media, the Internet or cell phones, I still make the case for shoe leather when it comes to winning the big ones. We roamed the streets, met unusual characters, and experienced rejection again and again. We got better at asking, refined our pitch, and we started winning. More than ever, I find clients asking me if it’s OK “to send that five-figure ask by email?”

No.

No! No! No, it’s not OK. People give to people, and that means looking them in the eye, asking with a sincerity, purpose, and urgency. It means sitting with that awkward silence while someone else considers your request. So put on your big kid pants and step away from the computer.
 

Engage Every Player On Your Team

Perhaps most importantly, though, was my understanding early on that Howie did not win in isolation. Anyone who thinks there is a role for a 12 year old, pre-bar mitzvah boy in a centerfold campaign is thinking outside the box—and recognizing that it takes a village. Howie recruited me, friends, family, anyone he met. I never played team sports, but I learned the lesson just the same. I am reminded of it every time I see an organization grow and expand. I am reminded of it every time I think of that handwritten million-dollar check. Yes, the check came addressed to me, but the donor who made that gift always talked about “that nice woman who answers the phone when I call. It says so much about your organization, that you would hire such friendly people, and that they feel as good as they do about working there.”

Who’s to say that it wasn’t that nice woman answering the phones who tipped the scales for our generous donor? Who’s to say it wasn’t the kid with the flyers showing his classmates Mr. November back behind the school that helped crown the Man of the Year?

Our campaign was funny. It was endorsed by the right people. It was an in-person, 100 percent analog, all-out team effort. We had no idea what we were doing back then, but we had passion and, man, we had instinct. Skills? You can learn them. But instinct and passion are more personal and far more important.

I found someone I was amazed by and I decided to do everything I could to help him realize his dreams. That was my instinct when I was 12, and it’s still my instinct today. In this instance we won and were rewarded for our efforts but even if we’d lost, I learned early how good it feels to put your whole self into a cause you truly believe in. If you can find something that makes you feel that way then the ultimate outcome becomes a footnote to the journey itself.

But million-dollar checks don’t hurt.

 
 

Copyright © 2017 by Lou Cove

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Lou Cove chronicles the campaign for Playgirl’s Man of the Year in his new memoir, MAN OF THE YEAR (on sale May 9th from Flatiron Books). Lou is also senior advisor to CEOs and Boards of Trustees at numerous non-profits, including the Harold Grinspoon Foundation and Girls Leadership. He is the former Executive Director of Reboot, a network of the country’s leading young Jewish creatives—among them writers, journalists, digital entrepreneurs, and creators of television and films. He hasn’t seen a new copy of Playgirl since 1980.