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In this March 7, 2015, photo, former Florida Gov. Jeb Bush is interviewed by host Bruce Rastetter, left, during the Iowa Agriculture Summit in Des Moines, Iowa. After a flurry of fundraising, formal speeches about economics and global affairs Bush got down to business this weekend appearing at the Pizza Ranch in Cedar Rapids, Iowa, after a stop at the Agricultural Summit.Charlie Neibergall/The Associated Press

Since announcing on Facebook his plan to explore running for president, Jeb Bush has courted high-dollar donors in private rooms and luxury resorts, and delivered weighty speeches in hotel ballrooms and city clubs.

This weekend, he was at a Pizza Ranch.

The former Florida governor arrived in Cedar Rapids behind schedule, a sign as strong as any that he is, in fact, running for president. Looking a bit dishevelled, with his open-collared shirt coming untucked, Mr. Bush took questions for more than 30 minutes at a location of the Iowa-based pizza chain that's as much a part of politics in the state as the caucuses themselves that lead off the state-by-state nominating contests in the presidential campaign.

Mr. Bush appears certain to get into the 2016 race with an early and dominating lead in fundraising. He's hired some of the best talent in the Republican Party and earned generally solid reviews at the early "cattle calls" where White House prospects gather en masse to address party loyalists.

But he acknowledged this weekend that winning over his party will depend just as much on his success at working the room and posing for pictures. Viewed by many as the ultimate establishment Republican, thanks to his family ties, he set out to introduce himself to voters, one at a time, in the "retail" politics that defines the campaign for president in Iowa and the other early voting states.

"A lot of people know me as George's boy or Barbara's boy or W.'s brother," Mr. Bush said, referring to family who have already lived at the White House. "But I've been on my own journey as well, and a lot of people don't know that."

Other likely candidates have for months headlined county party dinners or fundraisers for local politicians, but this was Mr. Bush's first trip to Iowa since campaigning in 2000 for his brother. He'll return after some retail politicking in New Hampshire next weekend and South Carolina later this month. The two states hold the first primaries of the campaign season after Iowa's caucuses.

Bush aides believe question-and-answer settings such as the one that took place Saturday night at the Pizza Ranch will showcase his personality – they call it a blend of the "guy next door" and a deep-thinking policy geek – better than formal campaign appearances. In the series of speeches Mr. Bush gave on the economy, foreign policy and his fiscal record in Florida in February, aides groaned quietly that he often rushed through the text, impatiently running over natural breaks for applause.

Some of that was on display this weekend at the agricultural policy forum hosted by Bruce Rastetter, an Iowa agribusiness magnate and Republican donor. Wisconsin Governor Scott Walker drew more applause than Mr. Bush, and New Jersey Governor Chris Christie earned more laughs.

But the crowd of roughly 1,000 responded with silence when Mr. Bush, leaning forward in his chair, answered a question about immigration by saying those living in the U.S. illegally "need to have a path to legalized status."

"I don't know him very well, but immigration might be an issue I have a problem with," said Gene Brodrecht, a Republican from eastern Iowa at Saturday's forum.

To sell his message that higher education standards in individual states and a robust legal immigrant work force are key to the nation's economic health, veteran Iowa strategist Doug Gross said Mr. Bush "has to say it over and over."

"I think he'd be making a mistake to kowtow," said Mr. Gross, a Bush supporter. "He needs to be who he is."

And there's no better place to do that than in one-on-one conversations.

"He's very down to earth," said Darcy Shaw, a Republican from central Iowa who met Mr. Bush at Friday's fundraiser. "He seems to be the personality he displays."

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