"If it's Valentine's Day and I still haven't heard from him I'll be surprised," Jeff Kaufmann told the Wall Street Journal
While Bush campaigned for 2014 candidates last year, he didn't hit the early primary states like Iowa and New Hampshire, which hold the first two nominating contests and where other potential presidential contenders have already made frequent visits.
The former Florida governor last month went to South Carolina, which holds the first-in-the-South primary, to speak to graduates at the University of South Carolina
, but he hasn't engaged in the traditional, on-the-ground retail politicking that's expected in some of these early states.
Bush only recently announced
that he's "actively" exploring a presidential bid, and his team and supporters have quickly started organizing behind the scenes to form political action committees
that will help him travel to meet with voters and donors as he also campaigns for non-presidential candidates.
His leadership PAC, Right to Rise, held its first fundraiser Wednesday night in Greenwich, Connecticut, which was attended by former high profile figures in the administration of his brother, George W. Bush.
GOP strategist Ford O'Connell said now is the time for Bush to focus on doing the behind-the-scenes action like securing financial commitments and organizing his team so he can be better positioned to ward off other potential GOP contenders.
"You got to convince these donors that you're serious, and you have to have a pre-campaign vehicle to do it," O'Connell said, referring to the leadership PAC.
Bush has declined to attend a social conservative gathering in Iowa later this month that will feature a hoard of other potential candidates, like Chris Christie, Mike Huckabee, Scott Walker, Ted Cruz, Rick Perry, Ben Carson and Rick Santorum.
Steve Deace, a native Iowan and conservative radio host, argued it's a mistake for Bush to skip the Iowa Freedom Summit, which is hosted by Rep. Steve King and the conservative group Citizens United.
"If you're not willing to speak to a conservative group that even Chris Christie is willing to speak to, you're probably in the wrong party," Deace said in an interview.
"If you don't come here and let people see you--this is true in both parties--and let them rub elbows with you, you're not going to win," he added.
The former governor, however, already has an advantage over the other candidates thanks to name recognition and ties to the Bush family donor network. A recent CNN/ORC International Poll
indicated Bush was the frontrunner of the crowded field of possible GOP candidates, with 23% support.
Republican strategist and Bush supporter Ana Navarro, who's also a CNN contributor, said Bush is focused on fundraising and organizing but added voters can expect Bush do some public events in the coming weeks.
"Jeb has got his groove back," Navarro said, adding that the former governor is "working long hours" and working hard to build his team.
She stressed a similar line from the announcement of the PAC
, saying that he won't "cede an inch of territory" on issues or demographic groups.
Bush's spokeswoman, Kristy Campbell, did not respond to a request for comment from CNN about his travel schedule. Campbell told the Wall Street Journal that Bush "will travel to states around the country in the coming months to support conservative candidates and causes."