An Interview with Winston Elliott III

"Where a Passion for Liberal Learning Leads"

Winston Elliott III has always been driven. From his youthful engagement in politics, to his passionate pursuit of money, to his devotion to promoting free market constitutionalism, Elliott has done nothing with less than 100% intensity. For the past 15 years, his passion for liberal learning has led him to a Master’s degree from St. John’s College, to organizing hundreds of Great Books seminars, to founding a successful online journal of public discourse, to the board of Wyoming Catholic College, and finally to teaching the books he has come to love.

Winston became a reader partly as an act of rebellion from a family that had no interest in books. He enjoyed reading beyond his grade level -- The Godfather was a major achievement during his elementary school years -- but he never dreamed of discussing them with others until his 9th grade teacher arranged for weekly Junior Great Books sessions. “I had a lot of first dates after that, because I would always bore them by talking non-stop about some book I was reading.”

Two of those books determined the early course of his life. Allan Drury’s political thriller, Come Nineveh, Come Tyre, led him at 15 to found a Young Republicans group to fight communism. Ayn Rand’s Fountainhead inspired him more profoundly. He picked up Rand because an idealistic Congressman featured in the Washington Post named her as a favorite author. Her ideals captured his soul.

Elliott is not the first I have known to have been challenged or inspired by the secular, libertarian visionary. Elliott explained the fascination. “Rand’s heroes are like secular saints. They are completely devoted to being rational and productive. In their own way, they are virtuous men and women of high ideals, totally committed to achieving success and happiness through productivity. They don’t let any ties of family or romance hold them back. Atlas Shrugged ends with the formation of a community of such heroes -- how could I not want to be a part of that?” Elliott became an atheist evangelizer, even getting himself invited to church meetings so he could proselytize Christians. “Thankfully, I never succeeded with people who really had faith, only with those who didn’t, or who felt they had been betrayed by Christianity.”

Elliott went to a liberal arts college, but he later realized he hadn’t been liberally educated. “I majored in history, but really knew nothing about other branches of learning.” Immediately after graduating, he drove to Houston, whose entrepreneurial freedom would provide the perfect environment in which to pursue his Randian dream of making billions. Ten years later, he was well on his way, having founded a multi-million dollar computer company with 40 employees, while simultaneously completing his MBA. “The MBA helped a lot with my business. But it also made me realize that I loved the theory of making money more than the 80 hour weeks necessary to actually make it.” So he sold the company.

After a brief retirement playing tennis and reading Austrian economists, in 1992 Elliott became President of the Free Enterprise Institute, where he organized large and small seminars aimed at promoting libertarian constitutionalism to teachers. Yet he found himself most interested by the speakers who stepped beyond the boundaries of free market capitalism into broader issues of history, literature, the liberal arts, and culture. He began reading Russell Kirk, whose conservative vision was formed by the likes of poet and critic T.S. Eliot and religious sociologist Christopher Dawson. At the same time, he was questioning his Randian ideals. “I began to realize that, if I died, I would not want anyone that I knew to raise my children. Free market libertarians are smart and often succeed, but they are not nice. Rand preached and lived the ‘virtue of selfishness’; the world beyond her heroes consisted of the enemies of heroes and the despicable rest.”

Elliott came to Jesus while reading the “Genius of Christianity”, a chapter in Kirk’s The Roots of American Order over breakfast at Denny’s. “I freaked out when he described Augustine’s conversion. Tolle lege! I stumbled out into the parking lot, called Barbara (his future wife), and said, ‘You know that whole prayer thing you do. Can we do that now?’”

Kirk continued to form Elliott intellectually. “I hope our conservatism will be... a conservatism illuminated by the wisdom of our ancestors and inspired by a revived consciousness of the moral nature of society." Elliott began reading more broadly in the great books pointed out by writers like Kirk. Gradually he became convinced that discussing great books was the most effective way to learn. “As head of FEI, I brought in the best lecturers available. After 15 years, I realized I was just providing intellectual entertainment. So often, the more appealing the lecture, the less anyone remembered its content.” So he turned FEI’s programs into great books discussions. “Not only does the participant benefit from the reading, but through discussion its impact is felt and remembered long after they have returned home.”

Reading and discussing has had a great impact on Elliott himself: “To paraphrase the historian Will Durant:  We study great books as an encouraging remembrance of generative souls, a celestial city, a spacious country of the mind, wherein a thousand saints, statesmen, inventors, scientists,  poets, artists, musicians, lovers, and philosophers still live and speak, teach, carve, and sing.” Elliott evidently delights in passing that on to others, through FEI seminars, The Imaginative Conservative journal he founded in 2010, and now teaching his favorite books, like The Acts of the Apostles, at the Honors College of Houston Baptist University. “I make my students face the radicality of the ancient church. They don’t like that the early Christians sold everything and tried to live communally. But they need to see that Christians need to be 'all-in' on Christ.” Elliott certainly is.