The list is growing of those who bet on their ability to create something totally new, without the benefit of a college education

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here is a new status symbol in Silicon Valley — having dropped out of Stanford or Harvard or MIT. According to Sean Fischer, writing in the Free Press (“Generations Dropout”), “a new generation is leaving elite schools in droves, convinced that the future belongs not to the credentialed but to the self-taught.” Dropping out is now a résumé item.

In part, that trend of leaving school prior to graduation is driven by sharply rising tuitions, which have doubled since the 1980s. There is currently $1.5 trillion in student debt. And in part by the realization that a humanistic education, apart from one’s specific major, is no longer to be had: Culture war orthodoxies have overtaken the exploration of the great questions of existence.

Since 2010, venture capitalist Peter Thiel has been offering $200,000 fellowships to young people who want to “build new things instead of sitting in a classroom.” And the 1517 Fund, headed by Danielle Strachman and Michael Gibson, who helped start the Thiel Fellowship, invests only in companies started by students or college dropouts. The Fund’s founders seek to free students from the credentialing paper belt of higher education.

Among the 200 attendees at a Dropout Graduation ceremony in an old San Francisco movie theater this past summer were a number who raised millions of dollars for startups while in college, prior to dropping out, and several who did so while still in high school and then decided to skip college altogether.

HISTORICALLY, THE MOST FAMOUS dropouts have been concentrated in high tech — Bill Gates, Mark Zuckerberg, Jack Dorsey, Steve Jobs. But the list is growing of those who bet on their ability to create something totally new, without the benefit of a college education. Charlie Kirk spent a few weeks in college before deciding it was not for him.

In just 13 years following his graduation from high school, he built a nonprofit organization, Turning Point USA, with a thousand employees and $150 million in annual revenues. And that is apart from his three-hour daily radio podcast. TPUSA is widely credited with getting out sufficient young voters in seven swing states to provide the margin of victory for Donald Trump in 2024. In short, he changed history.

At his funeral, Kirk, 31, was eulogized by President Trump, Vice President Vance, and Secretary of State Rubio. Every member of the cabinet was in attendance.

Ben Shapiro recounted how Kirk, then a gangly teenager, first introduced himself at the annual donor weekend for the David Horowitz Freedom Center — “Hi, Mr. Shapiro, I’m Charlie Kirk.” He had already raised the seed money for TPUSA.

Shapiro’s description of Kirk, even at 18, dovetails fully with all those that appeared after his assassination. Above all, boundless, nonstop energy. In addition, eager, aggressive, and whip-start. After their first hour-long meeting, Shapiro turned to his friend Jeremy Boreing, cofounder of the Daily Wire and said, “That kid is going to be the head of the Republican National Committee one day.”

But as he admitted later, that was selling Charlie short. He achieved much more than that in just a few years — building “the single most important conservative political organization in the country.”

Over the next 13 years, Shapiro adds, Charlie became better and better at every aspect of his craft — as a speaker, debater, organizer, and fundraiser. And he grew intellectually as well. He did not skip college because he was uninterested in ideas, but rather because he was so intellectually curious, and doubted that his curiosity would be sated on most campuses today.

He read constantly, the kinds of works that once formed the spine of an education in the humanities and which are today read by only a smattering of undergraduates — Plato, Aristotle, Aquinas, Augustine. His speeches and debates were peppered with book titles that he recommended listeners read.

UNLIKE CHARLIE KIRK and the Silicon Valley dropouts mentioned above, Bari Weiss finished college at Columbia University. She and a group of friends were even the subject of a documentary, Columbia Unbecoming, which addressed the anti-Israel and anti-Semitic effusions rampant in Columbia’s Near Eastern Studies department, particularly those of Professor Joseph Massad, and the harassment suffered by Jewish, pro-Israel students, like Weiss.

But like those mentioned above, Weiss bet on herself in a very big way when she resigned from her position as an editorial page editor and columnist at the New York Times. She did so after the forced resignation of editorial page editor James Bennet, in the wake of the publication of an op-ed by Senator Tom Cotton advocating the use of the military to quell rioting after the death of George Floyd, if local police forces were inadequate to do so. That publication set off a revolt of younger staffers at the Times, and senior management caved.

Weiss had originally been hired by the Times to widen the scope of op-ed contributors, after the shocking results of the 2016 election revealed that the paper was out of touch with the country it purported to be covering. And she responded with daggers drawn to the apparent constriction of the editorial page after the dustup over the Cotton op-ed.

“Twitter is not on the masthead of the New York Times,” she wrote in her resignation letter. “But Twitter has become the ultimate editor. Stories are chosen to satisfy the narrowest of audiences rather than to allow a curious public to read about the world and then reach their own conclusions.”

The fact that Weiss had been repeatedly asked by colleagues whether she was “writing about the Jews again”; that others had posted ax emojis next to her name on the company’s internal Slack channels; and still others had called her a racist and a liar on Twitter, also contributed to her departure.

In her final salvo, Weiss quoted the promise of Adolph Ochs's upon purchasing the Times in 1896 “to make the columns of the New York Times a forum for the consideration of all questions of public importance and to that end to invite intelligent discussion from all shades of opinion.” A noble idea, Weiss wrote to publisher A.G. Sulzberger, Ochs’ fourth generation descendant. But such ideas “need a voice. They need a hearing. Above all, they must be backed by people willing to live by them,” Weiss concluded. And in that regard, the great-grandson had been found woefully lacking.

As for Weiss, she was now without a prestigious job and without a clear next step career-wise. But she had hinted to a vision in her resignation letter. She continued to believe that “Americans still hunger for news that is accurate, opinions that are vital, and debate that is sincere. I hear from these people every day.”

Above all, she felt there was a large audience of those who reject the notion that “truth is an orthodoxy already known to an enlightened few whose job is to inform everyone else” — a view she found prevalent at the Times.

Within just over a year of leaving the Times, Weiss had started a Substack newsletter under the title Common Sense, and a year later expanded that into a full-fledged online media company, the Free Press. As of late December 2024, the Free Press already had one million subscribers, and currently has a revenue stream of $15 million annually. David Ellison, who owns CBS through his Skydance Media company, has been widely reported to have offered Weiss well north of $100 million for the Free Press, and to install her as editor-in-chief of CBS News.

So, on a financial basis, Bari Weiss’s bet on herself seems to have worked out beyond all expectations. But I think there is another crucial sense that she bet on herself and has come up a winner: She bet that there are many who share her intellectual curiosity and would pay to join her for the ride, as her growing readership and revenue stream has allowed her to nurture a growing stable of talented young writers and gain access to virtually anyone whose thought interests her.

Two hints on this point. In addition to building the Free Press, she was a founding trustee of Austin University, a four-year college created in response to the crisis in American higher education, and based on the idea that the pursuit of truth is ennobling, liberating, and productive. (On the productivity point, one of the college’s major financial backers is Jon Lonsdale, cofounder, along with Peter Thiel and Alex Karp, of Palantir Technologies.)

The college is organized around 15 core courses taken by all students in math, science, literature, history, and philosophy, and it boasts that all courses are taught by senior faculty (not teaching assistants) in small groups of not more than 12 students, and that there will be no grade inflation.

Second hint: While at the Times, Weiss popularized the term “the intellectual dark web” first used by Eric Weinstein, a theoretical physicist by training and managing director of Peter Thiel’s venture capital firm. Eric’s brother, Bret Weinstein, a professor of biology at Evergreen State University, was forced out for refusing to comply with a “no whites allowed” day organized by black students on campus.

The term refers to a group of thinkers who resist easy classification, but who in general see themselves as left-wing or who at least started there, but who found that there was much greater willingness to entertain their ideas among conservatives. They are resolutely opposed to identity politics and almost everything that passes under the label “woke,” and staunch opponents of censorship and cancel culture.

I have been an avid reader of the Free Press from its inception in its Common Sense days, and have consistently found it the most stimulating journal out there, with the only competition being Tablet magazine, founded and edited by another very bright Jewish woman, Alana Newhouse. (Bari Weiss worked at Tablet early in her career.)

One of the Free Press’s most attractive features is Bari Weiss’s interviews with anyone about whom she is curious. Because she is curious, she listens attentively and always comes well-prepared. She scored an interview with Dr. Marty Makary the day after President Trump linked autism with taking Tylenol in pregnancy, in a press conference with Health Secretary Robert F. Kennedy Jr. Other skeptics of the Covid regime, who now hold senior health positions, Stanford professor Jay Bhattacharya and Dr. Vinay Prasad, wrote for the Free Press prior to their appointments and have been interviewed by Weiss.

Other recent interviewees include University of Chicago philosopher Agnes Callard, Yale constitutional scholar Akhil Reed Amir, and the Times’ Ross Douthat, on the case for religious belief. If there is a thinker whom you follow, he or she will almost certainly turn up on the Free Press roster eventually. Jonathan Haidt comes immediately to mind as a recent example. Economist Tyler Cowen, a sharp critic of the Trump tariffs, economic historian Niall Ferguson, political philosopher Yuval Levin, and journalist Abigail Shrier are other examples

Very little of the content is small-bore politics, and much is not political at all — e.g., a current series of authors, most not previously known to me, reflecting on the joys and challenges of growing old; a weekly series with Douglas Murray on great speeches, from antiquity to Churchill, that he has found worth committing to memory. The Free Press has also sponsored debates around the country, the most recent of which on whether the United States still needs to police the world.

The Free Press also engages in investigative journalism, much of it in defense of Israel. One recent article exposed how the 18 most frequently shown photos of starving Gazan children all failed as proofs of starvation. “How Qatar Bought America” is the subject of another recent long piece.

Amity Shlaes argues in a recent National Review piece that the crucial determinant of the ongoing competition between China and the United States will be whether the spirit of entrepreneurship continues to flourish in America — i.e., people willing to bet on themselves and take risks. The dropouts from elite universities, Charlie Kirk, and Bari Weiss all reflect, in one way or another, the continued vitality of that spirit.

(Originally featured in Mishpacha, Issue 1082. Yonoson Rosenblum may be contacted directly at rosenblum@mishpacha.com)