Steve Grubbs, an Iowa businessman and political strategist, has been a player in his state's Republican caucuses for two decades—mostly, as a losing player. In 2012, he worked for Herman Cain. In 2008, it was Tommy Thompson. In 2000, he worked for Steve Forbes. In fact, his last Iowa caucuses winner was Bob Dole, in 1996—the most conventional candidate of the bunch.
It’s a quixotic record, creative and idiosyncratic, and one that puts principle above conventionally determined considerations of viability—which is why it makes perfect sense that prospective 2016 presidential candidate Rand Paul has hired him as a top Iowa strategist and technology consultant. Paul and Grubbs didn’t decide to work together to burnish their records. They’re both visionaries, political imagineers. For both, winning is not the only thing—it’s what you win. “A lot of strategists will look at the polls and go with the frontrunner,” Grubbs said. “I’ve always been a risk-taker.” And as many members of Rand Paul's national network are meeting Wednesday for a closed-door summit at a Washington hotel, Grubb has an important place in the circle.
“He could win the Iowa caucuses, if he chooses to run,” Grubbs says, sitting in what he calls his home's “Great Leaders of Western Civilization” library, surrounded by images of George Washington, Abraham Lincoln, Teddy Roosevelt, and Ronald Reagan, among others. Grubbs' statement is not in keeping with the etiquette of most Iowa strategists, who typically seek to lower expectations ahead of the often unpredictable caucuses, the first contest in nomination balloting.
For Grubbs, the appeal of Paul revolves heavily around his interest in protecting personal privacy and his desire to leverage technology in a possible presidential campaign. "Rand Paul is the most outspoken voice in Washington for protecting electronic communications from the government," he said. "Technology is taking us to a place where we have this crossroads, whether we continue with a centralized government or choose the path of a decentralized, crowd-regulated approach."
For all of Grubbs' iconoclasm and his shared vision with Paul about the role of government, it may be Grubbs's deep knowledge of Iowa politics that closed the deal. "He's been on the inside, as far as being in the legislature," Paul said during a recent interview in Chicago. "He's been on the outside, as a successful entrepreneur. He's known as a businessman as well as a political consultant. I've been really impressed with his ability to find, seek out, and get us access to meet people. If we get involved in something in Iowa, it needs to be a coalition."
Paul also hired A.J. Striker, a former chairman of the Iowa Republican Party with ties to his father, former presidential candidate Ron Paul.
In Grubbs, Paul is hiring someone who is full of compelling contradictions: a technological visionary and iconoclast who’s also an Iowa insider, an old hand who knows how to reach the young. “He’s an innovator and knows how to close the deal,” said Steve Forbes, who spent hundreds of hours with Grubbs ahead of the billionaire’s second-place finish in the 2000 Iowa caucuses, behind then Governor George W. Bush of Texas.
Back in 1999 and 2000, those who attended Forbes events in Iowa were often provided a chance to get a digital photo with the candidate printed for them before they left, an idea Grubbs helped implement. "Today, we don’t think anything of that,” Forbes said. “But back then, that was a huge, big deal.”
And Grubbs has kept up with the times. He's designed a mobile app and web tool called Voter Neighbor that allows people to tag friends for a get-out-the-vote postcard with a targeted message mailed by a campaign they support. He's also built an app called Mobile Voter that allows candidates and volunteers access to voter data stored back at a campaign headquarters while working door to door, as well as play campaign videos for people during doorway conversation.
"Mobile tied to cloud will be ubiquitous in the next campaign," Grubbs said during an interview in Chicago. "The technology will also allow for much more personalized campaigns."
A father of four who never left the town where he was born, the 50-year-old is more casual and relaxed than many in his profession. That isn't to say he's not highly organized, creative, constantly connected, and competitive. He's also a little geeky.
His techy tendencies and competitiveness can be seen on his iPhone 5, where he tracks the number of steps taken each day by friends and family members who also carry Bluetooth-connected Fitbit tracking devices in their pockets. The sensor measures every step he takes toward his exercise goal of 10,000 a day, roughly 4 to 5 miles.
Grubb’s political interest cross-pollinate with his even more idiosyncratic businesses, which blend both old and new. Victory Enterprises, a political consultancy, and VictoryStore.com, a printing business, do polling and campaign strategy, website and app design, and print about 1 million campaign signs in election years. VictoryStore.com lists 16,000 items on Amazon.
All of it is headquartered in an old elementary school he once attended—a building he bought from the local school district for $106,000—and his one-time Sunday school teacher now works for him as his personal assistant. "I haven't gotten very far in life," Grubbs deadpans while giving a visitor a tour.
At his home a few miles from his office, Grubbs has rehabilitated what he believes to be Iowa’s oldest wine cellar, a stone structure in his backyard that dates to 1868.
One of his latest projects is a $55, Bluetooth-enabled talking teddy bear that can be configured to tell a short story about virtually any topic, or play a parent’s recorded voice. It gets its signals from a mobile app on a nearby parent’s phone. With the change of a T-shirt and programming, it can become "Hawkeye Bear," (for the University of Iowa mascot), "Army Bear," "Bible Bear," or anything else.
Given his financial success, presidential politics is something of a hobby. Grubbs declined to say what his two companies generate in annual revenue, although he didn’t disagree with the $22 million reported in a 2012 story by Inc. magazine.
Doug Stafford, the Kentucky senator’s top political strategist, introduced Grubbs to Paul. They’d worked together on state elections. This past spring, Stafford asked Grubbs if he’d be interested in a senior role with Rand PAC, a leadership committee laying the groundwork for a White House bid.
Grubbs and Paul took a corner table in a crowded Capitol Hill restaurant in June. Grubbs was told to ask any question. His two main lines of inquiry: money and commitment. Could Paul raise enough cash to win? And was he willing to dedicate about 50 days, the average in 2012, working the small towns, fairs, town hall meetings in Iowa?
“I also wanted to get a sense of whether I would like him personally and I came away very much knowing that I would enjoy working with him,” Grubbs said. “When I called Doug Stafford the next day, I told him that Senator Rand Paul was one of the most thoughtful people I had ever met from an intellectual view.”
Grubbs said he also factored in Hillary Clinton, who he expects will win the Democratic nomination, in his decision-making about Paul. “I think his dynamics work against her,” he said. “She is very beatable.”
Clinton, for now, is a distant target. Paul would first need a strong showing in the Iowa caucuses, which Grubbs calls “the most complicated election in the United States,” and one where "every yard you gain is hard."
Many caucus voters expect to personally meet the candidates—at least once and sometimes multiple times. The voting is held in the dead of winter when people would rather stay in their homes. And the field is at its most crowded, since Iowans make the first cut.
In addition, the low-turnout contest can’t be easily swayed by television ads alone. Former Sen. Rick Santorum of Pennsylvania narrowly edged out eventual nominee Mitt Romney in 2012, after campaigning in all of Iowa’s 99 counties in a pickup truck.
Grubbs knows Iowa politics as a voter, strategist, and candidate. He served in the state House in the early 1990s, unsuccessfully ran for U.S. Senate in 1996, and was chairman of the Republican Party of Iowa during the 1997-98 election.
Those connections could help Paul soothe old wounds among the state party’s hierarchy, many of whom were infuriated when loyalists to his father took over the party’s leadership after the 2012 caucuses. After a counteroffensive led by Governor Terry Branstad, the Ron Paul loyalists were kicked out earlier this year.
Whether the younger Paul is capable of bringing new voters to the caucuses—as Barack Obama did in 2008—is the crucial question.
There are three significant voting blocs in Iowa’s Republican caucuses: religious and social conservatives, traditional “country club” Republicans, and Libertarian-leaning “liberty” voters. To win, Paul would need to draw heavily from the latter two groups, and perhaps add on some independent voters. His call for party activists to “agree to disagree” on social issues is a deal-breaker for some Evangelical voters, who represent a good chunk of the party’s base.
To win, Paul and Grubbs will have to broaden the electorate. The hypothetical math looks favorable for this. In 2012, only about 121,000 Republicans caucused in a state with 620,000 registered Republicans.
They're looking to younger professionals as their prime targets. Calling the senator a “conservatarian”—part conservative, part libertarian—Grubbs said Paul’s get-government-off-my-back leanings could have a strong appeal among younger workers. “The under 30 crowd is very ‘live and let live,’” he said.
So far, Paul has spent a lot of time talking on college campuses, discussing cell-phone privacy, and raising his profile on social and mobile media. Technology is certain to be at the heart of any appeal, and the political medium will be the message. "Senator Paul believes in a populist campaign where his supporters are able to use the tools of technology to reach out to voters without waiting for a centralized campaign to tell them what to do," Grubbs said. "This is a campaign vision that a lot of people talk about, but he is determined to make happen."