After a splashy debut at last month's first Republican presidential debate, Vivek Ramaswamy has gone from an unknown to a contender who's now facing questions about his youth and lack of political experience, especially given his position as the first millennial to run for the Republican presidential nomination. He's being vetted over how he made his millions at the biotech company he started in his late 20s and frequent shifts in his foreign policy platform. He's also facing questions about how he would, if elected, enact his agenda and defend it from legal challenges.

One of the latest moments to illustrate this came last week when, a few days after a dinner with social media personality Jake Paul, he became the first of the major GOP primary candidates to join TikTok in an effort to appeal to younger voters, despite his concerns. Up until that point, he had railed against TikTok, calling it an addictive "digital fentanyl" and expressing an openness to ban it as part of his broader platform on curbing China's power.

"I'm a person who's always open to new arguments," he told reporters hours after he posted his first TikTok. "In this case, yes, I changed my mind."

The moment underscores a growing challenge for Ramaswamy and his campaign ahead of the second GOP primary debate: proving that his policy platform is substantive, even as it's constantly evolving.

Ramaswamy has gained ground in national and state polls, where he frequently places behind former President Donald Trump and Florida Gov. Ron DeSantis. A CNN/University of New Hampshire poll of Granite State voters released Wednesday showed him in a close race for second place with three rivals trailing Trump, who was the top choice of 39% of likely GOP primary voters surveyed. Ramaswamy, at 13%, ran about even with former South Carolina Gov. Nikki Haley at 12%, former New Jersey Gov. Chris Christie at 11% and DeSantis at 10%.

He's built his message around the idea that Americans lack purpose and meaning, and that the country needs someone like him -- young, unjaded and an outsider without the baggage of Trump -- to help restore the country's national identity.

"I think as a nation, we're all really just a little bit young, actually, going through our own version of collective adolescence, figuring out who we're really going to be when we grow up," he said at an event in Washington Wednesday, detailing his plan to cut 75% of the federal workforce. "Yes, we go through that identity crisis, that national identity crisis, but we can be stronger for it, once we get through it."

Critics have accused Ramaswamy of running to elevate his personal profile and described his on stage persona as "arrogant" or "annoying." But friends and allies describe him as intellectually gifted, radically ambitious and willing to debate with anyone and possibly change his mind or evolve his views. They credit him for a willingness to surround himself with people he disagrees with, including longtime friends and even his wife, head and neck surgeon Apoorva Ramaswamy. Most recently, the two publicly disagreed on Covid-19 vaccines -- he has regrets about taking it, she has none.

While some policy positions may change, those who know him say his core values -- American exceptionalism and the importance of free speech among them -- have not.

"To me, that's a sign of strength," Benjamin Zimmer, a friend of Ramaswamy's from college who later worked with him at Roivant, said of his updated stance on TikTok. "It's someone who's willing to be honest and open minded and doesn't come from some established dogma."

Mark Kvamme, a cofounder at Drive Capital who has donated to Ramaswamy's campaign and is helping him with fundraising, agreed.

"I've seen him digest information and look at things differently," said Kvamme, who met Ramaswamy when the two served on the advisory board of InnovateOhio, an initiative run by Ohio Lt. Gov Jon Husted to cut costs and expand the state's use of technology.

"He is constantly looking at new things, and he receives feedback," he said. "He may not agree with you 100%. But he receives it and looks at it and understands it and digests it, and then figures out where he stands on it."

Ramaswamy's open mindedness, which first appeared during on campus debates at Harvard College and Yale Law School, has helped propel his candidacy and exposed him to audiences including MSNBC and "The Breakfast Club."

But it's also caused problems, as he's adjusted his stances on issues including US military support for Taiwan, aid to Israel, the response to the Covid-19 pandemic and the importance of Juneteenth as a federal holiday.

Ramaswamy's campaign did not make him available for an interview with CNN.

From Harvard to Roivant

Ramaswamy's highly decorated resume resembles the last millennial presidential candidate and fellow Harvard graduate, Transportation Secretary Pete Buttigieg.

Born in Cincinnati, Ohio, to parents who emigrated from India, he graduated as valedictorian from the private Jesuit St. Xavier High School, where he also played tennis and was a member of the mock trial team.

At Harvard, he majored in biology, chaired the Harvard Political Union, where he moderated debates on issues like abortion rights, and moonlighted as a libertarian rapper under the stage name Da Vek. (Da Vek made an appearance in Iowa last month, when Ramaswamy rapped Eminem's "Lose Yourself" at the state fair. Eminem later asked the candidate to stop performing his song.)

"I consider myself a contrarian," Ramaswamy told the Harvard Crimson in 2006. "I like to argue."

From Harvard, he took a job at a hedge fund as a biotech stock analyst and worked there while attending Yale Law School, where he met his wife and befriended Ohio Republican Senator J.D. Vance. In 2014, he founded Roivant, the source of the bulk of his fortune. The company targets drugs that large pharmaceutical companies have shelved because they didn't fit into the company's business model. Roivant would buy the right to develop those drugs and share the profits with the original company. The "roi" in the company's names stands for return on investment.

Donald Berwick, a former administrator of the Centers for Medicare and Medicaid Services under President Barack Obama, joined an advisory group for Roivant after being recruited by former Democratic Senate Majority Leader Tom Daschle, another member. The group would meet two to three times a year, including when the company suffered a major blow after an Alzheimer's drug it developed failed.

"He spoke of the social responsibility of the company, which was interesting," Berwick said. "Pharmaceutical firms have really not been doing a great job of social responsibility in pricing. It really bothers me a lot, and he seemed to be willing to be more responsive, more thoughtful and more progressive."

Fighting 'woke' companies and investing

By 2020, Ramaswamy had started popping up in conservative media spaces, including the Wall Street Journal op-ed section and Fox News, railing against "stakeholder" capitalism, which generally argues that companies have a responsibility to everyone who has a stake in a company, not just people who hold shares. Shareholder capitalism argues the goal of companies should be to maximize returns for shareholders.

"Speaking as a CEO and a citizen, I don't want American capitalists to play a larger role in defining and implementing the country's political and social values," Ramaswamy wrote in a February 2020 Wall Street Journal op-ed. "I think the answers to these questions should be determined by the citizenry -- publicly through debate and privately at the ballot box."

Ramaswamy targeted large asset management companies like BlackRock, which have embraced ESG -- environmental, social and governance -- initiatives. Larry Fink, the chief executive of BlackRock, said in June he would stop using the term ESG because it has been politicized.

Ramaswamy expanded on that premise in "Woke, Inc.: Inside Corporate America's Social Justice Scam," in which he argued that companies and activists work together to "steal our shared American identity" and advance a left leaning agenda that would be difficult, if not impossible, to pass through Congress.

"Woke culture posits a new theory of who you are as a person, one that reduces you to the characteristics you inherit at birth and denies your status as a free agent in the world," he wrote.

Ramaswamy's insistence that company leaders shouldn't get involved in politics was tested twice during the pandemic: In 2020, Ramaswamy struggled to respond when Roivant staff demanded that he make a statement in support of Black Lives Matter after George Floyd's murder. He eventually declared Juneteenth a holiday and spent the day in reflection, he wrote in "Woke, Inc." In early 2021, Berwick and other advisory group members ended their relationship with Roivant over his conservative comments, including a Wall Street Journal essay condemning social media companies for their response to the January 6, 2021, riot at the US Capitol. He stepped back as chief executive of the company in January 2021 to become executive chairman.

"Since then he's gone much, much farther in his presidential statements," Berwick said. "He seems to be willing to say anything he needs to in order to win over the most extreme of the Republican base. I no longer know, at all, what he really believes."

During the pandemic, he and his friend and former high school debate partner Anson Frericks started talking about their issues with corporate activism. Frericks, a former Anheuser-Busch executive, had been frustrated by the backlash to the 2021 election law overhaul passed in Georgia in response to Trump's false claims of widespread voter fraud in the 2020 election.

The two debated starting a portfolio of companies that wouldn't engage in the culture wars -- an alternative to Coca Cola, an airline company, or a social media rival to Twitter, prior to Elon Musk's purchase of what is now called X. Instead, they settled on forming Strive, an asset management firm.

"It's hard enough to create one company, let alone a portfolio of companies," Frericks said. "So we ultimately decided on why don't we go upstream and actually compete against BlackRock, which was sort of almost like the fountainhead of this stakeholder capitalism movement."

The company, which has received investments from billionaire tech mogul Peter Thiel, has more than 40 employees and $1 billion assets under management. It has also faced some hiccups, including two lawsuits from ex-employees. Frericks said the company is "defending ourselves vigorously."

Frericks said Ramaswamy's decision to run for president this year came as a surprise to him, given how recently they started Strive. "I agree that we are somewhat lost as a nation, that we're searching for a cause," he said.

Ramaswamy announced his campaign during an appearance on Tucker Carlson's former Fox News show, where he had been a frequent guest. Frericks wasn't the only person caught off guard by the timing -- Ramaswamy's parents were surprised as well and his wife told The Atlantic that he didn't seriously talk about running for president until last December.

In the months since, Ramaswamy has done dozens of TV interviews, campaign rallies and podcast appearances, including hosting his own podcast. By August, he'd gained enough donors and poll support to make it to the center of stage at the first, Trump-free debate. There, former Vice President Mike Pence called him a "rookie," Haley said he lacked foreign policy experience "and it shows," and Christie said he "sounds like Chat GPT." Ramaswamy hit back by calling his opponents career politicians and "super PAC puppets."

In the weeks since the debate, Ramaswamy appears to be entering a new phase of the campaign aimed at fleshing out his platform. This month he laid out the legal argument behind his plan to conduct mass layoffs at several federal agencies at America First Works, part of a network of groups founded by former aides to Trump, and gave a speech about his plan to combat China's growing global influence.

"I think we did the thing where I explained the broad vision to the country and engaged in, I would say, the introductory conversations, which was a fun phase of the campaign," he said at a sit down with reporters last week. "But now we're getting to the really serious phase of the campaign where we talk about not just the what, and even the why... but the how."