Colby Underwood and me: 11 months with the most important person in Seattle politics

If you follow politics just casually, the name means nothing. He rarely appears in news articles. He's aggressive behind the scenes about promoting his business, but he also understands that publicity can backfire on clients. So he keeps a low profile, and those who need to know, do. But ask anyone who has taken a serious look at running for the Seattle City Council and they will likely say the conversation eventually gets to Colby Underwood.

I call him Colby in this piece because he and I practically lived together for nearly 11 months in 2005, when I ran for council. He spent more than 15 hours a week at my house, coached me through 4,577 phone calls, overheard family arguments, managed my moods, and ate our Doritos. My dog Wilbur got to like him more than me.

By 2005, Colby was already well established as the city's leading fundraising consultant. Today, he is a unique power in Seattle politics. It might be nice to get the endorsement of Peter Steinbrueck, Norm Rice, the Sierra Club, or the dailies. And it's a big help if the mayor backs you with his organization. But Colby is a special force, because his participation gives you instant credibility. With Colby, the big boys and girls in politics know you have a shot at raising the $150,000, $250,000, or perhaps even $300,000 needed to mount a serious run. That possibility terrifies incumbents and intimidates potential rivals.

Of course, at this point you get caveats: Some will run regardless of money. Some will win regardless of money. Some can do fine with other fundraising consultants. And some, like me, raise big money but still lose. There are no guarantees. But with Colby Underwood, you're in the hunt.

By his estimate, Colby Underwood Consulting has helped candidates and causes raise more than $42 million in five years, including $7.1 million in 2006 alone. He employs eight people. He invests in property. He takes his parents to Hawaii.

He's 29 years old.

After helping Greg Nickels beat Mark Sidran for mayor in 2001, Colby went on to raise money for congressional candidates Darcy Burner and Dave Ross and others around the region. In a race against City Council incumbent Jan Drago, Colby helped me raise more than $220,000. Burner recently signed him for a second try against U.S. Rep. Dave Reichert in 2008. The campaigns of Barak Obama and Hillary Clinton are wooing him.

To run in Seattle, you might pick as your political consultant Cathy Allen of the Connections Group, John Wyble of Moxie Media, or others, but as your fundraiser, the first consideration is often Colby Underwood. This year, in the five races for Seattle City Council, four candidates hired him: incumbents Tom Rasmussen and Jean Godden; Tim Burgess, who's running against incumbent David Della; and Venus Velazquez, who's running for an open seat. Colby has no one in the fifth race, where no serious challenger has emerged against incumbent Sally Clark; she didn't hire Colby but does understand the importance of raising big money to scare off opponents. She has raised more than $100,000 working with Linda Mitchell of the Connections Group. Follow the money here.

When I decided to run in late 2004, Wyble told me I needed to raise $150,000. I nodded, went home, and told my wife that he was crazy. I liked Wyble enormously and respected his wisdom, but that much was an impossible sum.

But Colby made it possible. Here's how.

You start with a simple Excel list of everybody you've ever known. Your siblings. Your parents' friends. People you know from church, from your kids' school, from work, from the neighborhood. That friend from high school 30 years ago who moved to California? Didn't you have a crush on his sister in first grade? Put both of them down. Then put a number next to each of their names. That should get you to $20,000 or more as your first tier of fundraising, about a month or more of daily phone calling. It may seem like the hardest thing you've ever done, especially with people who have never donated to a campaign. But it's the "easy money."

Colby sits you down and maps out who you call, in what order, and what you say to them. He plans the entire fundraising campaign — the goal, the amount expected per month, the dollars to be raised for each hour of call time, each solicitation letter, each fundraising event. His office prints the three different letters to those you called — sorry, I missed you, thanks for the conversation, thanks for the pledge. Unless people give you a flat no, you call them at least three times. If they give less than the maximum, you call them again later in the campaign. He also tracks whether people made good on a pledge; if not, another letter.

Throughout the campaign, Colby stayed in constant touch with Wyble and my campaign managers, Kenneth Hanks and Ellen Smith, a rising star in Democratic Party circles. Each week, he'd revisit the plan, chart the effectiveness of calls, and make adjustments as needed. If you're having a marvelous run with lawyers known by your brother, you'd stay on that list.

As people started to notice our monthly donor reports, I gave an interview where I joked that fundraising was easy — just make thousands of calls and money rolls in. That irritated Colby because it completely undervalued his system. Of course, the essential ingredient is the candidate's willingness to work and his or her effectiveness when making the pitch. But Colby brought an invaluable dimension to the effort. He saw the entire universe of donors and how to approach them. For example, if you want to raise money from environmentalists, you start by meeting with Jill; if you impress her, she'll tell everybody to give you money. Or Joe is annoyed with your opponent, so call him. Ruth is highly respected in the Asian-American community. Call Anne, but after you're raised $30,000 or she won't take you seriously. Call Bob because he just gives to anybody who calls.

Colby operates from a belief that giving money to candidates is as natural as breathing — so yes, call that eye doctor you saw for an hour two years ago. He should give. And what about his wife? She needs to know her husband's on board! Call her, too. He scoffed at my insistence that it was rude to call people during the dinner hour or call people who would never dream of donating to any politician. That guy's unemployed? Ask for something. No excuses! I did and got $5.

As a journalist observing politics, I always regarded fundraising as the colorful but slightly sleazy side of politics. Wrong. It's more like sanding the side of a battle ship with a toothbrush — tedious hard work. Most people just want your general views on issues. Only once did a potential donor ask for something I considered improper, a pledge on how I would vote on a re-zone. Colby had no problem with my refusal to make that pledge.

As Colby tutored me, we went back and forth on the relevant movie metaphor. Was he Yoda and I Luke Skywalker? Colby preferred to think of himself as Morpheus mentoring Neo in The Matrix, a better metaphor since he knew secret codes to donors' wallets, detected threats, and mapped my path through invisible terrain. He drew on relationships that went throughout Seattle politics. It drove me crazy that Colby regularly saw Drago's political consultant from a different race. He swore he didn't share confidential information about clients, but I pestered him for back channel reports. Let's make some calls, he'd reply.

If running for office is a crazy decision, the actual running makes you crazier. You lose sleep, strain personal relationships, agree to give 60 seconds to complex issues ("how can the city solve the housing crisis?"), subject yourself to judgments by people who are not always pleasant ("you smell of Greg Nickels," said one Democratic party activist) and, worse, sometimes act like a jackass. Colby was my rock. When he walked into my house, ducking his head under the doorway, bellowing "Show me the money!" he knew how to get me to work. Two days after my dad died in February 2005, the calls resumed. I was glad for the distraction from grief, but I had no script for questions from old friends: I haven't seen your dad for a while. How's he doing?

During those many months, Colby and I did everything we could to keep up our spirits, telling jokes and speculating that the other side would go nuts over our success. Borrowing an idea from Dave Ross, I kept a brass school bell on the table. If I got a $100 pledge, I tapped the bell lightly. For $650, I shook it hard. For a couple's maximum donation of $1,300 I danced around the kitchen, banging the bell, which was almost as loud as Colby's laughter. But that ended quickly. "Back to work. Where's my money?" he'd yell, annoucing the next number for me to call. What will be the result — $50, $250? His eyes locked on me. His fingers hovered over the keyboard, ready for the number.

During call time, there was no rest, not even for a bathroom break. He sneered at the only meal I had time for — a fold-over peanut butter sandwich — then wanted his own. Get back on the phones, he ordered. He got annoyed if I misheard the numbers he announced in rapid order, but who wouldn't after three hours of calling?

Once to tease me, he carefully called out my own number and I dialed it, like a doofus. He jumped up, laughing, his enormous frame straining the chair till it made cracking sounds and nearly broke. After the campaign was over, I reinforced the chair with glue and screws and invited him back for dinner.

• O. Casey Corr writes the Mudville blog for Crosscut. He is a Seattle-based writer and consultant who previously worked for The Seattle Times and Seattle Post-Intelligencer. He also worked as a senior advisor to Seattle Mayor Greg Nickels and ran for Seattle City Council in 2005. You can e-mail him at casey.corr@crosscut.com.