Sitting at a small coffee shop in Sioux City, Iowa, Gillibrand parried a question about beating Republicans everywhere -- including conservative districts like the one she currently sat in -- by using her personal experience of ousting a longtime Republican member in a conservative district by taking positions on guns and immigration that are now out of step with Democratic voters.
"I first ran for office in 2006 in my 2-to-1 Republican district in upstate New York not unlike JD's district right here, a rural district, agriculture and manufacturing," Gillibrand told around a dozen Iowans, referring to JD Scholten, the former congressional candidate who came within a few percentage points of unseating controversial Republican Rep. Steve King.
Democrats seized control of the House for the first time in more than a decade in 2006, helped by a slate of moderate and conservative candidates and opposition to the Iraq war. They lost control four years later.
Gillibrand ran and won a House seat around Albany, New York, in 2006 by attacking her Republican opponent from the right on immigration and guns, calling securing the border "a national security priority" and touting an A-rating from the National Rifle Association.
Hours later, at a house party nearby, Gillibrand responded to a question about her previous position on guns by addressing the previous sterling rating.
"So, I had an A-rating as a House member," she said. "I only really looked at guns through the lens of hunting. My mother still shoots the Thanksgiving turkey. But when I became Senator, I recognized I had a lot to learn about my state and all of the 20 million I was going to represent."
And the next morning, at a coffee shop in Boone, Iowa, Gillibrand opened with a simple nod to her past.
"I represented a rural place in Congress," she told the audience at Livery Deli, a small coffee shop in the rural Iowa enclave.
Gillibrand's conservative record is one of the key criticisms her nascent candidacy receives from the left, but it shows how the 2020 candidate's early strategy is to face up to questions about her record, not run away from them, believing that embracing her story and evolution on issues like guns and immigration could win plaudits from caucus goers here in Iowa and convince them that she could win a general election against President Donald Trump by appealing to a spectrum of voters.
"My story is my story. And when I am wrong, I admit it," Gillibrand told CNN about not running from her more conservative past. "It is just who I am. And so that is why these stories are part of my story and it is what it is. It just defines who I am."
Gillibrand was quick to admit when she was wrong throughout this first trip to Iowa.
Asked by CNN why she took more than $1 million from lobbyists in her career, but is now swearing off super PAC and lobbying money, Gillibrand described her decision as a presidential candidate a "first step" and admitted she wishes she had done it sooner.
"Yeah, I do," she said. "And I think it is important to start somewhere and that is why I am starting here."
It was clear throughout Gillibrand's first trip to Iowa that few people on the ground knew much about her -- something even the senator recognized.
"I am not a national name," Gillibrand said on Saturday, "so the fact that you turned out is a blessing to my heart."
Some mentioned watching her announce her run on "The Late Show with Stephen Colbert" and a few more men and women said they watched her interview with Rachel Maddow earlier this week.
But Gillibrand's three-day trip to Iowa was mostly an introduction for both the senator (whose visit was the first time she had ever traveled to Iowa) and the people she met.
"We are just kind of lifting the veil today," Karen Heidman, a 72-year old Sioux City resident, said before meeting Gillibrand. "We want to see if she is street-able, if she can appeal to the kinds of people she needs to win in Iowa."
That unfamiliarity was clear in Ames on Saturday when State Rep. Beth Wessel-Kroeschell introduced Gillibrand by making the most common mistake about her: Botching her first name.
"Please join me in welcoming Senator," Wessel-Kroeschell said, before taking a long pause.
Gillibrand, familiar with this mistake, jumped in: "Kirsten!"
"Kirsten Gillibrand," a relieved Wessel-Kroeschell echoed.
Gillibrand's visit was also punctuated with clear references to the fact that her being the mother of two boys will be a common theme of her candidacy.
When she was asked about being the first Democratic senator to call for Sen. Al Franken to resign after a series of years-old allegations of inappropriate touching were leveled against him, she quickly brought up a conversation she had with her son, Theo, at the time.
"I am also a mom of boys and the conversations I was having at the time with Theo, who is 15, was 'Mom, why are you being so mean to Al Franken,'" she said in Sioux City. "And I had to be very clear with him as a mother: It's not okay to grope a woman anywhere on her body without her consent, it's not okay to forcibly kiss a woman without her consent, it's not okay for Al Franken, and it's not okay for you, and I could not be ambiguous about that."
She returned to her sons in lighter moments, too.
During a walking tour of Des Moines, Gillibrand agonized over what witty T-shirts to buy her two sons at RayGun, an iconic T-shirt and apparel store in the city's hip East Village. In the end, she bought them both sweatshirts and picked up an "America Needs Love" T-shirt for herself.
And she talked about how much her sons would have enjoyed a cookie baking session she attended with Jill Means at Kitchen Collage.
"Can I have that recipe?" Gillibrand asked as she rolled chocolate cookies and dipped them in sugar. "I have boys."
Gillibrand's maternal persona was on full display at almost all times on the visit.
When a tripod fell at a coffee shop, Gillibrand stopped her conversation to ask if anyone had fallen and hurt themselves. And at one point during the walking tour of Des Moines, the senator grabbed a reporter's arm to prevent them from stepping in something unseemly on the ground. And she was publicly worried about cameramen walking backwards in the snow.
"You are going to create anxiety," she said. "And we don't want anxiety."
Gillibrand is likely to be one of a handful of women running for president this election. Massachusetts Sen. Elizabeth Warren has announced an exploratory committee and both Minnesota Sen. Amy Klobuchar and California Sen. Kamala Harris are considering a run.
Gillibrand announced her candidacy by making clear that gender equality is central to her bid and that continued in Iowa, where she spoke to the Women's March Iowa event in Des Moines.
What was clear throughout all her events this weekend is that voters, particularly women, are eager to back a woman a few years after Hillary Clinton lost to Donald Trump.
"Men have had their shot," said Deb Mandicino, a 61-year old woman from Sioux City." Women do things differently and it's time to see that work out."
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