When Charlie Kirk invited me onto his show, I hesitated. I knew little about him and had heard mixed opinions. Out of curiosity, I watched a few episodes. What I saw was a man I often disagreed with—but also someone earnestly searching for truth, and willing to listen with respect.
Charlie had read my book and wanted to talk about it. I agreed to go on his show on the condition that politics stay off the table. What followed was a terrific conversation. We spoke about cold showers, Stoicism, mindfulness—the deeper questions of how to live well. In those moments, Charlie wasn’t the political figure many love or hate; he was simply a curious human being who cared about more than politics.
What struck me most was this: Charlie understood that free speech isn’t singing kumbaya with people who already agree with you. It’s engaging with those you vehemently disagree with. He built a career on that principle—hearing, debating, and welcoming voices across the spectrum.
This belief resonated with me deeply. I grew up in the Soviet Union, where truth was whispered only in the safety of small kitchens. Reading the wrong books, holding the “wrong” opinion—it could cost you your job, your freedom, even your life. I know what real oppression looks like. I lived through it.
America, to me, was always the opposite—a place where disagreement was not only tolerated but celebrated. Where ideas competed openly, and freedom of thought was a birthright. But America feels increasingly fragile. The space for disagreement is shrinking, and fear of speaking up is growing.
Charlie understood this danger. He believed in the marketplace of ideas, especially when those ideas challenged his own. In that sense, he lived his values with rare courage.
After I shared these thoughts on X.com, my friend Guy Spier wrote something that touched me:
“Charlie Kirk had the rare courage to speak up for what he believed in, no matter the cost. How many of us were too scared? Afraid of losing our job, our investor base, our writing gig, our clients, our friends. The enemies of free speech only had a few high-value targets—and Charlie Kirk was one. But if more of us had spoken up and said what we know in our hearts to be true, then he would perhaps not have been such a lone voice. There would have been strength in numbers. How about more of us just develop a little more courage to stand our ground and speak our dangerous truth? That’s something I will do in memory of Charlie Kirk.”
Guy is right. Democracy doesn’t just die in darkness; it also dies in silence. It dies when fear keeps us from speaking honestly, when we retreat into echo chambers, when we reduce people to labels instead of listening to their ideas.
Chris Rock once said, “Anybody who says words hurt hasn’t been punched in the face. Words hurt when you write them on a brick.” Words themselves shouldn’t scare us. We should not be afraid to speak with those who disagree with us.
I disagree with my past self from five, ten, even twenty years ago—and I’m proud of it. That disagreement is proof of growth. In the Abracadabra chapter of Soul in the Game, I described how our words shape our thinking, and how true learning requires humility—the courage to treat every belief as a hypothesis. That’s why free speech matters: it forces us into the discomfort where real growth lives.
In memory of Charlie, I want to honor that courage. I refuse to stay silent. I love this country too much to bite my tongue. This newsletter will remain focused on investing, life, and music. But if you’d like to hear my unfiltered thoughts on everything else, you’ll find them here.
Rest in peace, Charlie.
What about free speech for Kimmel ?
While I cannot discount your admiration of Charlie Kirk’s “rare courage to speak up for what he believed in, no matter the cost”, I urge you to examine closely what he believed in. Without free speech, we would not know that Charlie Kirk believed:
* while gun deaths are unfortunate, the benefits of gun rights outweigh these costs. (‘costs’ as in mass killings, school shootings, shootings in places of worship, the availability of AR15s, no gun restrictions)
* increasing the number of armed citizens could reduce gun violence
* he was critical of the growing acceptance of the LGBTQ community, urging students to report professors who he felt promoted ‘gender ideology’ in educational settings
* In 2021 he established TPUSA Faith to unite churches against what he termed ‘wokeism’, reflecting his commitment to conservative Christian values and opposition to progressive ideologies
* he supported controversial immigration theories, including the Great Replacement Theory, which baselessly claims that immigrants are displacing white Americans and that Jewish communities are involved in this process.
* he often dismissed climate change concerns, claiming there was no scientific agreement on the issue and describing it as ‘nonsense’
* he was known for his influence on the hard right youth movement
Indeed, Charlie Kirk had the ‘courage’ to reveal himself and boldly proclaim his ‘dangerous truth’ and political direction. You are free to applaud Charlie Kirk and sing his praises, but be aware that your own experience might come true in America:
“I grew up in the Soviet Union, where truth was whispered only in the safety of small kitchens. Reading the wrong books, holding the “wrong” opinion—it could cost you your job, your freedom, even your life. I know what real oppression looks like. I lived through it.” Did the authoritarians you grew up under have the ‘courage’ of their convictions, their ‘dangerous truth’?
I disagree with most of what Charlie had to say too, but you’ve missed Kitaliy’s point. For you, does free speech mean people are free to say what they want as long as you’re OK with it?
No, I did not miss Vitaliy’s point. I got it, and I affirmed his friendship, his warm and fuzzy feelings toward Kirk. Actually, you missed MY point, Mike, which is this: listen closely to the words people speak, their ‘truth’, especially the words of those you love and admire. When the consequences and outcomes of free speech impact the rights and freedoms of others, it’s time to question and challenge those words. I did not read any challenging thoughts in Vitaliy’s article, and that scared me. For as many articles as there are wanting to canonize Kirk as a saint, there are an equal number of articles that bring to light his ideologies that are very, very contrary to the American way. Without free speech, most of us might never have become aware of Kirk’s brand and his influence. Thanks for your reply.
I appreciate this article about Charlie Kirk, but now is the time to do more than write about his ability to express free speech and to debate differences of opinions…we need to demand Congress to act like honorable professional elected leaders. So I have written my representative seeking a motion to censure those who participated in the booing of Representative Lauren Boebert yesterday (September 10th) while the session was trying to honor Charlie Kirk. That action was reprehensible and very unprofessional. Continued behavior such as this will only lead to more of it and perhaps even embolden their followers to seek violent ways to silence those who disagree. I urge you and your readers to be bold and courageous and express your disapproval of the Congress that stands by and allows members to act so dishonorably.