The $700,000 Pyramid

Presidential candidate Barack Obama is making headlines with his $32.5 million fundraising haul for the second quarter. For a ground-level look at where all that money's coming from, Sasha Issenberg talked to Boston's Democratic heavy hitters about the emerging power of small donors, published in the June issue of Boston magazine.

ROBERT CROWE, HEAD OF WOLF BLOCK PUBLIC Strategies, has so many photos of himself posing with prominent Democrats he’s raised money for that he doesn’t have room for them all on the walls of his office atop One Boston Place. So he redecorates according to which notable is on that day’s schedule. Lately, thanks to his party’s crowded presidential primary field, Crowe’s been redecorating a lot. “Not only are the candidates friends of mine, but I go back a long time with all these people,” he says. A framed snapshot of him with Delaware Senator Joe Biden sits on the windowsill across the room—“because he just came in,” Crowe explains. That was yesterday; next week he expects a visit from the senior senator from Connecticut. “Now I’ve got to get my Chris Dodd pictures out.”

Boston is the country’s fifth most lucrative market for federal Democratic campaign money, and despite all the attention given nationally to the growth of small-dollar contributions over the Internet, the fundraising scene here is still dominated by a cadre of major players, which Crowe refers to as the “family.” Heading into this year, with John Kerry contemplating another White House run, most of its members had appeared to be spoken for, but when Kerry announced in January that he would not run in 2008, they were suddenly free. New Mexico Governor Bill Richardson was the first to call Crowe for his support—an hour before Kerry made his decision public.

Among the other heavyweights calling Crowe was his fellow former Democratic National Committee finance chair Alan Solomont. After Solomont committed to Barack Obama, he tried to get Crowe to do the same. “I was surprised by Alan’s move. Barack was very lucky to get him,” Crowe says. In the following months, Solomont invited Crowe to events and arranged for him to meet Obama in Washington. “Alan’s a good cheerleader,” Crowe says. “He’s giving me a little sales job.”

But other local fundraisers wanted Crowe for their candidate, too, putting him on the receiving end of the aggressive courtship to which he had so frequently subjected others in the past. Essentially they were all after the same thing: a stapled stack of papers Crowe keeps on a filing cabinet near his desk. It includes “thousands” of names, by Crowe’s calculation, with a tally of their past giving and Crowe’s own notes on pitching them. While campaign contributions are public record, the filings require only a few hard facts, like the donor’s name, address, profession, and employer. The soft data that often gets a check written—the issues a donor cares about, which events were attended and committees sat on—resides in dossiers like this, and especially for campaigns with little money experience (like Obama’s), such private knowledge is essential to building a network.

All of Crowe’s suitors also had the same deadline: March 31, when campaigns would wrap up their fundraising for the year’s first quarter. When that date passed and Crowe remained a free agent, Solomont did not appear too worried. A little over a week later, he stood in front of Obama’s New England finance steering committee and delivered the good news: Obama had raised almost $25 million to spend during the primary season, just shy of Hillary Clinton’s total. “Probably the most important and exciting number to report is there were over 100,000 donors to Obama for America,” continued Solomont, who wore a brown blazer, open-collar checked shirt, and glasses that framed his bushy eyebrows. That was more individual contributors than Clinton and former North Carolina Senator John Edwards combined. Even more striking, Obama had started the quarter with a database of 20,000 names and ended with five times as many backers, whereas Clinton had started with 250,000 names and netted only 50,000 contributors. Obama’s network was expanding, while Clinton’s, if not contracting, had not been fully mobilized.

Fundraising has often been viewed by the press—and even by fundraisers themselves—as a tawdry means to a worthy end: rich people asking their rich friends for money to finance attack ads so the best man can win. The 58-year-old Solomont is certainly still a master of that (“I do this better than anyone in the country,” he says). But through his involvement with Obama he became energized by a grander mission: to build a web of small donors through personal contact and engage them continuously in the workings of the campaign. For him and his counterparts, Boston would be the test lab for this new ideal of fundraising, which would celebrate it as both the means and the end—as a form of political engagement unto itself, treated as nobly as carrying a petition or writing a letter to the editor. Solomont thought the approach could reawaken citizen involvement in politics, and in April he would test that theory. All he had to do to succeed was get a few thousand college students to part with their beer money on a Friday night.

DURING LAST YEAR'S GUBERNATORIAL race, Solomont raised money for Attorney General Tom Reilly. Some of his new enthusiasm for Obama—and yen for a campaign that will “personify and embody change”—seems like a form of penance. “Sometimes you can pick wrong,” he says, in an unusually pointed way. “There’s no question that my decision in this race was informed by that experience.” Solomont’s use of the word “wrong” carries a hint of moral self-approbation: that he did not just misread the political moment, but, by ending up on the wrong side of a generational and stylistic cleavage, also betrayed his true self.

Solomont made his fortune in elder care, but his first job out of Tufts was working as a community organizer in Lowell, where he lived out of a $23-a-week tenement and tried to get city residents to assert their tenant’s rights. It is a background similar to Obama’s as an organizer on the South Side of Chicago, and both men seem to have come away with an interest in the mechanics of mobilization. “I’m a product of the ’60s, an old lefty,” Solomont says. “I wound up in a business career, but I have more in common with people in the political arena than the business arena.”

Solomont first started giving politically in 1982, when Michael Dukakis reclaimed the governor’s mansion. “He was a young go-getter,” says Phil Johnston, who recently stepped down as chairman of the state Democratic committee. He takes credit for bringing Solomont into the race as part of a larger effort to build a fundraising apparatus in places campaigns didn’t typically dun for money. “We had grassroots activists, and we relied on them not only for organizational support, but for financial support, as well,” he says. The focus on smaller donors had actually begun in 1974, during Dukakis’s first statewide run. Johnston recalls the campaign’s organizing an event at a Sheraton during which 2,000 donors—many of them activists who had never before been asked for their money—paid $25 a head. “People would bitch and moan: ‘Twenty-five dollars we have to pay?’ They thought that was outrageous,” Johnston recalls. And that was before they discovered what that got them in hors d’oeuvres. “‘All we got were these little frankfurters!’” (“Dukakis, believe me, was a cheapskate,” Johnston says.)

If successful campaigns have been vehicles for social change, successful fundraising operations often rely on social aspiration. The model for a major presidential fundraiser hasn’t changed in years: hotel ballroom, catered dinner, cocktails with social register worthies. When invitations requesting a minimum contribution of $1,000 went out for a March 30 event for Hillary Clinton at the State Room, they were packed with familiar names from her husband’s fundraising network, including former DNC chair Steve Grossman, philanthropist Elaine Schuster, and former U.S. Ambassador Swanee Hunt, as well as a number of women, including Cambridge philanthropist Barbara Lee, particularly energized by the chance to back a serious female White House contender.

“I talk to my friends who are on the boards of the ICA, but I also talk to my dental hygienist,” says Lee, who is famous for maintaining the loyalty of her donor circle by surprising friends and contacts with small gifts and postcards from her vacations. “Women have to learn how to ask for their own campaigns. They are used to asking for other people.”

Solomont treated the State Room event as a foil. “We’ve all been to ballrooms with thousand-dollar-a-plate dinners,” he says wearily. He was busy imagining an event of his own: Obama’s big New England fundraising kickoff, to be held on April 20. For perhaps the first time in his fundraising career, Solomont wanted his success to be measured not in terms of numbers, but in terms of aesthetics. “We’re hoping to do a lot of things in addition to raising a lot of money. We want to personify and embody the change that this campaign is about.”

The festivities would, Solomont decided, feature both students donating $23 and major donors contributing 100 times that, all under the same roof. And they would be held at a facility whose amenities are rated by the NCAA rather than Gault Millau: Boston University’s Agganis Arena. Solomont relished the symbolic contrast between the déclassé college-hockey arena and the four-star meeting space. Anyone who wanted food during the fundraiser—even a little frankfurter!—would have to buy their meal at the concession stand.

PERHAPS NO ONE REFLECTS THE potential of Solomont’s new-style fundraising operation more than Mark Goodman, a 39-year-old venture capitalist who until this year had never written a political check or volunteered on a campaign. After reading about Obama for the first time in a 2004 New Republic article, he stood awestruck in his Cambridge living room as the Illinois state senator delivered his much hyped Democratic National Convention speech. When, this January, Goodman saw a website headline indicating that Obama was launching a presidential exploratory committee, he called his wife’s uncle, Jon Rotenberg, a former Democratic state representative. “I want to be involved with Obama,” Goodman told Rotenberg. “How does this work?”

A few weeks later, Goodman rode the elevator to the 13th floor of a South Boston office building to sign on to Obama’s New England steering committee, which was meeting there in a conference room at the law firm Foley Hoag. As he joined 50 or so people around a ring of folding tables, Goodman recognized only a few of them: One was Barry White, a Foley Hoag attorney he knew from White’s wife’s involvement with the board of the American Jewish Committee. The motley bunch belied the typical insularity of Boston fundraising. A mix of undergraduate students, career political operatives, big-name downtown lawyers, and first-timers like Goodman, most were strangers to one another.

By early April, Goodman had already collected more than $31,000 from 27 different donors. In addition to the weekly meetings in South Boston, he traveled to Washington twice as a member of Obama’s national finance committee. “I’m taking everything they ask me to do,” Goodman says. “There are two other things I’ve locked in on in this way. The first was when I decided it was time to finish my dissertation. The second was when it was time to marry my wife. This is the third.”

After easily collecting the first 15 or so checks from family and close friends—whose donations were as much as a favor to him as a show of support for Obama—Goodman next sent out an e-mail to the 150 people in his address book, describing the lure of Obama’s “judgment and the quality of his thinking” and directing readers to Goodman’s personal fundraising portal on the Web. Then Goodman began to block out an hour a day to make phone calls, following up on his e-mails. “I’m not a natural ask, but I’m getting more comfortable,” he said after six weeks of soliciting contributions. “There is no trick, no secret. If you’re passionate about it, you’ve got to be articulate: communicate why you’re behind that person.” When trying to sell the Agganis Arena event, Goodman took prospective donors through the perks that came with each price level: an opportunity to meet Obama at a private reception for $2,300, just a seat in the stands for $460. “I get a little sales-y,” he concedes, a bit guiltily. “I want to engage in a conversation. People don’t respond well to speeches. A couple of times it wasn’t going anywhere before I got them to ask me a question. Then it opened up.”

Many of those whom Goodman contacted were, like him, new to this side of politics. Andy Mims, another venture capitalist, wrote a $250 check. Goodman worked on his business partner at Brookline Venture Partners, Ken Levine; the longtime Republican eventually donated to Obama’s campaign and is now considering voting for him. When Goodman mentioned a fundraiser being held at the Cambridge home of Harvard law professor David B. Wilkins to his sister-in-law Alison Ross, a 28-year-old BU law student who also had no campaign experience, she wrote a check for $2,300. “I don’t remember if he said, ‘Can you go?’ or if I said, ‘Can I come?’” she recalls. After learning that Obama was scheduled to come to campus for the kickoff event, Ross got a bundle of the $23 student tickets from one of the undergraduate organizers and started hawking them to her classmates. She sent an e-mail to friends, and included a link to the event listing on the social networking website Facebook. “If one of your friends signs up, all their friends see that they signed up and think, ‘Maybe I want to go, too.’”

Goodman had already prepared his next step. “Your network will dry up—or they’ll be tired of hearing from you. But it’s not just about talking to your network, it’s about getting those people talking to their networks,” Goodman says. “That’s what I’m going to start focusing on after that event. I’m going to go from being a player to being a player-coach.”

IN MARCH, AT A RALLY IN CLEVELAND, Obama exhorted everyone in the crowd “to pony up $5, $10 for this campaign. I don’t care how poor you are, you’ve got $5.” Some in the national media took the line for a gaffe. Instead, the candidate may have been unintentionally revealing his finance strategy. Like Amway, it’s about getting people to buy in—with the idea that once their dollars are committed, they will be, too. Ross is intimately familiar with the psychology at play. “When you get someone to write a check and then they actually go and hear and see the candidate,” she says, “it’s very difficult for them to back off from that.”

As the April 20 event at Agganis Arena began, Obama bounced along a catwalk flanked by two big video screens and an American flag worthy of a Sun Belt car dealership. “How we doing, Boston?” he asked. “This is how we hold a fundraiser, right?” From a luxury box high above the floor, surrounded by friends and campaign staff, Solomont looked on, juggling his digital camera and a bottle of Dasani water. That morning, he had put on a dark blue suit, a tie dotted with American flags, and a white French-cuff shirt just so he could wear stars-and-stripes cuff links. “Out in Nebraska everyone wears red on game day, and for some of us this is game day,” he said.

Solomont counted the preliminary take from the event: A total of 5,700 tickets had been sold, bringing in over $700,000, including more than $100,000 from students alone. It was a sellout, albeit one short of the $1 million goal floated in the weeks prior. (Clinton’s State Room event had exceeded $1 million, and from only a fraction of as many guests.) As he scanned the arena, Solomont never seemed to be more than a few degrees of separation away from any dollar raised there. The host committee included Paul Egerman, eScription CEO and a longtime Kerry fundraiser in tech circles, and his wife, Joanne—they used to carpool their kids to Sunday school with the Solomonts. Mike Bergan, a 27-year-old public affairs consultant and Johnston’s nephew, was selling $230 “Generation O” event tickets to young professionals. There was Mitch Robinson, a Tufts senior and former teaching assistant in Solomont’s course on the Clinton presidency; after Solomont enlisted him to peddle $23 tickets, Robinson roped in Dan Grant, an Illinoisan who had worked on Democratic campaigns but never before raised money. The two sold 250 tickets at Tufts, distributing them outside the library and in the dining hall, and began attending the steering committee meetings (except when they were held on Fridays, when Robinson had to be in math class).

Two suites down from Solomont, Mark Goodman perched on the ledge of the box. He had gathered about 50 donations and brought some 40 attendees, and had seen many of them in the arena. Goodman’s sister-in-law Ross was there, having successfully sold 118 tickets to her BU peers, as was his partner, Ken Levine—whose 16-year-old daughter had decided on the spur of the moment to donate, too. “A couple of last-minute cancellations prevented me from hitting my goal by a few hundred dollars,” he said. “I learned that you probably have to get commitments for about 120 percent of your goal to actually hit it.”

Goodman noted that he had never been to a political rally. He leaned out and surveyed the crowd, filled with students who had lined up around the block to stake out a spot close to the stage, many of them wearing the main act’s T-shirts—a green St. Patrick’s Day “O’bama” edition was popular—and carrying signs bearing slogans such as “We Love You, Barack.”

“It’s amazing. It’s like a U2 concert,” he said. “Now all we have to do is get them all to vote.”