And during an interview with CNN on Thursday, as his team of staffers planned his first trip to Iowa on 2019, Hickenlooper appeared more resolute to make his unlikely story of geologist-turned-brewer-turned-politician include a run at the White House.

"I've been known to play a little cards," Hickenlooper said with a smile when asked about whether he enjoys betting. "Given that there is still uncertainty in the future, I probably would take the bet that I would run for President."

Hickenlooper will headline a house party with Iowa Democrats in Des Moines on Sunday afternoon and then travel to Court Avenue Restaurant & Brewing to mingle with staffers and patrons. The trip will further stoke 2020 chatter that Hickenlooper has done little to quell.

Hickenlooper is seen as a dark horse for the presidency, in part because he doesn't have the national profile that Democrats like former Vice President Joe Biden, Sen. Elizabeth Warren and Sen. Kamala Harris enjoy. But he was clear to CNN that he sees a window for him to upset big names like those.

"I play to win. I don't do something for symbolic benefit and I think a lot of what we have done in Colorado is useful for the conversation," he said. "If I run, I am going to run to win. It is not just going to be about making a statement."

The bravado isn't new for the Colorado governor, who tipped his hand -- arguably a little too far -- in late 2018 when he told a voter in New Hampshire that he was "going to run for President." Hickenlooper walked back the statement, even though it may eventually be true.

The former governor, who spoke at the US Conference of Mayors on last week about the need to empower cities and municipalities, not the federal government, recently traveled to Los Angeles this week to meet with top Democratic donors. He also staffed up his political action committee -- Giddy Up PAC -- earlier this year by hiring senior communications adviser Marie Logsden, finance director Dan Sorenson and adding foreign policy adviser Jeremy Rosner to a committee that already includes Brad Komar, Hickenlooper's 2014 campaign manager and someone who would likely assume a senior role in a presidential bid.

The moves come after months of behind-the-scenes operating by Hickenlooper's team, which included flying top Democratic operatives to Denver to meet the governor and interview for possible positions, according to people who talked to Hickenlooper's team.

Hickenlooper was also among the five candidates Hillary Clinton has met with to discuss 2020, according to a source close to Clinton.

Hickenlooper often tells his life story as one of hard work with a bit of luck. After receiving his master's degree in geology in the early 80s, he moved to Colorado and began his short-lived time as a professional geologist. After six years on the job, Hickenlooper was laid off when the commodities market tanked.

During that time, Hickenlooper traveled to California, saw a brewpub in Oakland and thought that concept would work in Denver. It led him to open Wynkoop Brewing Company in 1988, a large brewpub that went on to help reinvigorate the LoDo area of Denver and made Hickenlooper a wealthy man with enough money to fund, invest and run breweries across the country.

The success of Wynkoop -- and Hickenlooper's connections to Denver that grew out of that -- led him to successfully run for mayor of Denver in 2003, a position he held for eight years before serving two terms as Colorado's governor from 2011 to 2019.

The success in Colorado is the reason Hickenlooper garners some 2020 chatter, but that statewide appeal is also the reasons that those Democrats focused on taking back the Senate have been pressuring the former governor to try to oust Republican Sen. Cory Gardner from the Senate and forgo a presidential run.

It's clear after just a few minutes sitting with Hickenlooper, however, that spending time in the Senate does not sound appealing to him.

"It would be hard for me -- and I am not saying I couldn't do it and I am not saying my patriotic duty may compel me to do it -- but my character, what activates me, motivates me is building teams and surrounding myself with really talented people, taking big bites out of major challenges and then doing them," he said of a Senate run.

Asked if he believes tackling those challenges would be harder in the Senate, Hickenlooper doesn't hesitate.

"That's my point. You are one of 100," he said. "And my natural inclination is to go somewhere where I can create that team.

Hickenlooper describes his pitch to voters as a "unique" ability to "bring people together who have been feuding with each other and get them to find common ground and to create an environment where people actually listen to each other. He said he believes that voters want a candidate who rebuffs Trump with achievements and, if he runs, he plans to sell his ability to "achieve things."

The former governor, who has a record of accomplishing progressive policies but is far from a liberal firebrand, also rejected the notion that the Democratic primary electorate is hungry for someone willing to punch back -- and hard -- at President Donald Trump.

"I think there is a silent majority," he says, taking a pause, "a new silent majority that wants to elect people that get stuff done, stop fighting, stop hurling invective and roll up their sleeves and start working together."

The governor added that he intends for make his 2020 decision by the end of February or the middle of March, even as he works behind the scenes to lock in talent.

Asked why he is taking his time to make an announcement, Hickenlooper smiled.

"I am out of work," said the former governor. "I've got time on my hands."