43: Mario Gabriele - Reality is Story-Shaped
All links and transcript at dialectic.fm/mario-gabriele Mario Gabriele (X) is a writer, investor, and analyst. He is founder of The Generalist and Partner at Hummingbird. He aims to bring the rigor of investment analysis with writing quality and style that is closer to the New Yorker. His profiles, deep dives, and briefings are amongst the highest quality writing in the technology business, and he interviews practitioners weekly on his podcast. Recently, he wrote the definitive (and nearly book-length) piece on Peter Thiel’s legendary investment outfit, Founders Fund, and profiled Microsoft’s Satya Nadella. I spoke to Mario about stories and the truths they hold or reveal. He is a writer first, and it shows in his prose, style, and depth. We also discussed the evolution of The Generalist’s content and business model, both of which he has experimented with ruthlessly. The subscription counts 160,000+ readers / listeners and is currently ranked as the #7 bestseller in Substack’s business rankings. He is also an investor focused on the technology world’s heroes: founders. Hummingbird, which he joined earlier this year, is known for its obsessive approach to understanding the minds, motivations, and worlds of the entrepreneurs it backs. We dive into the under-discussed elements that shape world-beaters, including the notion that ambition almost always comes from some level of pain. Across the conversation, we talk about how authenticity and evolution run across his career, and how he is at peace as someone who doesn’t know exactly who he is becoming.
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Speaker A: The way to escape competition is through authenticity. Almost like staring at the sun. Yeah, it's like you can't really like look right at it. I'm curious how you have approached trying to get closer to it. Speaker B: I guess the things that have brought me closer to authenticity are doing things myself and putting myself in positions where there are few to no excuses that you can rely on. Speaker A: Um, that's so good. Speaker B: Founding The Generalist was like in many senses the most authentic thing I'd done professionally.
Have not seen someone who's so well adjusted and seems like full of ambition. Like, there's always something. People might tell you that's the case. There are founders you talk to who say, "Oh, I had a wonderful childhood," and then you'll find out 10 things where you're like, "You had a wonderful childhood?" Why are stories so useful? Stories are just like the hyper-effective version of language, in my view, because I think that's how our minds are so wired. Like, if I tell you something in a parable or a story, there's a reason that's like the foundation of all of our religions and political systems.
Speaker A: In one part of your professional and creative life, you are the one kind of observing and creating these stories, and another part in investing life, you're almost the one divining them or listening to them and interrogating them. Do you almost have like a skeleton key because you are a storyteller yourself? Speaker B: Wow, that's a really interesting observation. I hadn't put that together. Speaker A: Welcome to Dialectic, episode 43 with Mario Gabriele. Mario is a writer and investor. His primary focus for the last several years has been The Generalist, where he writes a subscription publication focused on technology, entrepreneurs, investors, the broader shape of the industry, and does so through a remarkably narrative lens.
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