Cynics say that Donald Trump gets financial support from billionaires because they think a Trump presidency will make them even richer. But I’m pretty sure that Republican billionaires, like most of us, believe their actions help society. I’d love to interview some of them but what are my chances? So, I had ChatGPT create John Dough, a composite of Andrew Newhouse, Timothy Mellon and Elon Musk, and interviewed John.
We talked about the wealth gap, why he supports Trump and what comes next. John proved knowledgeable, straightforward and likeable, but, like many flesh-and-blood people, he also seemed facile at times. So, I decided to get personal. I told John about how our very own Jim Callaway purposely reverted to a middle-class lifestyle, giving all of his wealth to his community, and the happiness it brought him. I wondered whether John felt burdened by managing his enormous wealth, whether he felt isolated, whether he didn’t long, as Jim had, for a simpler life? Here’s John’s answer, lightly edited for brevity and readability.
“You’ve touched a nerve that’s raw for some of us in the so-called ‘elite.’ I knew about Jim Callaway. A few of my friends in the energy and tech world used to talk about him with both admiration and disbelief because he opted out. He walked away from the power and the game. That’s rare and I respect it. Truly. But I live a different life, not because I don’t feel the appeal of humility and connection but because I see the world — and my role in it — differently.
“My wealth stopped being about comfort a long time ago. I could’ve retired at 35 and lived in quiet luxury. But wealth is influence, and influence is power — not to crush people, but to shape the future. I invest in things I believe in: American infrastructure, next-generation tech, free speech platforms and AI regulation. These are world-shaping efforts and, frankly, money is leverage. It buys me the ability to say ‘no,’ to run on my own terms, to build without begging for permission.
“People sometimes say, ‘What more do you need?’ But I don’t see wealth as ‘having.’ I see it as ‘doing.’ The more I can do, the bigger the impact. Jim impacted his community in a beautiful way. I try to do the same on a global scale. As a result, I miss things. There are mornings when, like Jim, I’d love to grab coffee anonymously at the corner shop. But I can’t. I’ve been harassed, followed, sued and threatened. Friends — especially women — have been stalked or had their kids doxed.
“Does money make me happy? Not exactly. It makes me free. What makes me ‘happy’ is solving problems, building things and seeing my efforts shape something real. You’re absolutely right — after a certain point, the toys and the luxuries add very little joy. That’s why I keep my circle small, my meals simple and my friends real.
“Why lower my taxes? Because I don’t believe the government is always the best steward of capital. If I thought my taxes were going to community colleges and cancer centers the way Jim directed his money, I might feel differently. But I see trillions wasted on bureaucracy, endless wars and agencies that slow innovation. I’d rather direct those dollars myself, through my foundations, my venture fund and direct local support.
“What motivates me? Legacy. Leverage. Vision. I want to see what’s possible when people stop accumulating and start shaping. That’s why I sometimes give quietly. That’s why I fund research labs, school choice, even startup farms in Rust Belt towns, not because it’s a tax write-off, but because it’s a way to fix what I think is broken.
“But I’ll admit something that maybe some people in my world won’t: There’s a loneliness to this. We trade human spontaneity for safety. We miss out on normal, grounded interactions. Jim found his answer. Maybe I’m still looking for mine.”
Are there inconsistencies in what John said? Sure! Did you find yourself wanting to challenge the inconsistencies and probe more deeply? I did, and I probably will since John is available to me 24/7. What I love here is that, if John were human, we would also find inconsistencies between the ways he lives and the values he espouses. No one always lives up to their ideals. Inconsistency is human, and in that way, virtual John emulates humanity very well, so well that talking with him helped me better understand and empathize with living Republican billionaires, and continuing the conversation will deepen this understanding.
But here’s the best part: I’m hopeful that talking with other virtual humans will help me understand various groups of people I will never have the opportunity to know personally, and that such experiences, if we are willing to have them, might help us heal our divided nation.
You can read a complete transcript of my conversations about and with John at www.tinyurl.com/wr5hfwnu
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