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AnecdoteVideo · 27:04 — 34:28
The most impressive ultra-successful people are genuinely curious — they take silly ideas seriously, make others feel important, and their humility and interest in others is a true superpower, not an act.
Shawn recounts meeting an extremely wealthy, reclusive billionaire founder at a dinner who was unassuming, curious about Shawn's projects, and shared how their firm used AI for microsecond trading decisions. The billionaire made Shawn feel good rather than intimidated. Sam connects this to Dale Carnegie's principle that people want to feel important, and reframes the skill as genuine curiosity rather than manipulation. ✦ AI generated
Shawn · My First Million · 2026-07-31 · original ↗
starts at this moment · 27:04
I sit next to this one guy, and he's very unassuming, and I start talking to him, and he's very nice. He's kind of like Dharmesh Shah, the the one of the founders of HubSpot, like very low-key. He's like, 'How are you using AI?' And I'm like, 'Well, I made a Chrome plug-in that helps you select like which jeans fit you if you go to a store, if you like jeans.' [He says his name and] the guy runs maybe one of the most, if not like the top three like financial services business in the world, and he's extremely multi-billionaire. [He was] so epic and so world-class at what they do, they made me feel He made me feel better than him in a weird way. [Sam:] He had true true charisma then in that he was genuinely interested in other people, not based off of like, you know, some weird power rankings. And when you're interested in people, that makes them feel great. And that's a gift. That's a that's an amazing gift. [Shawn:] And I've noticed that with a bunch of really successful people, the ones that I truly like, they are so curious. They are curious to the point where they will uh think about silly ideas very seriously and take them serious. [Sam:] Dale Carnegie, How to Win Friends and Influence People, he says, 'The root of everything that you read from me is basically people want to feel important.' And if you understand that, then like life's cream cheese. Like life's good. And if you make people feel important, then then that is how you win friends and influence people. [Shawn:] To all the up-and-comer up-and-comers listening like Quinton, be humble and be nice and make people feel important. And that is like kind of a key to life. [Sam:] I would say, be curious. If you're genuinely curious or interested in in people, curiosity's like one of these um you know, like those like grandma's remedies where it's like, 'Oh, I have uh pneumonia.' And it's like, 'Put some whiskey in the pancakes and that'll do it.' It's like, 'What? That doesn't make any sense.' And then it like works. It's curiosity's kind of like that where almost all these unrelated problems can be solved with curiosity.
verbatim transcript · starts at 27:04
Transcript · around this moment
26:46So yeah, I'm a I'm a big believer in that. My kids are really little right now, but I I do similar things." >> That's awesome. Okay, let me tell you another story about someone. You and I, we get invited to some stuff that occasionally is interesting. Most of the time, we both say no, but I decided to go to one of these dinners, and it was in a beautiful apartment, and clearly
27:04some guys there were like total ballers. But I sit next to this one guy, and he's very unassuming, and I start talking to him, and he's very nice. He's kind of like Dharmesh Shah, the the one of the founders of HubSpot, like very low-key. He's like, "How are you using AI?" And I'm like, "Well, I made a Chrome plug-in that helps you select like which jeans fit you if you
27:27go to a store, if you like jeans." >> John, look at my ass right now. [laughter] Tell me that these don't fit like fit like they were fitted by AGI. Three cities don't have water right now because these pants fit so well. >> [laughter] >> And uh I was like, "How about you?" "What are you doing?" And he like starts explaining some stuff, and it's kind of blowing my mind, and
27:48I'm like, "Wait, who are you?" And he says his name, but he doesn't really say what he does. And the guy runs maybe one of the most, if not like the top three like financial services business in the world, and he's extremely multi-billionaire. And he's the founder of >> Extremely multi-billionaire. >> Yeah, extremely. Like, [laughter] he's so extreme, and I thought I after he I start talking to him like, "I
28:12recognize you. You have articles written about you. It's where it's like this mysterious billionaire." >> Wait, say his name, and then we'll bleep it. >> Okay, so he's the founder of >> Yes. Okay. >> So, one of the most like sophisticated financial services business, arguably potentially some of the one of the most profitable in its field, making like tens of billions in profit. >> That's that's almost an intimidating
28:32person to meet. It's almost like, have you ever Do you You know, I used to have this old Dell laptop that when it really when you when you opened up a few too many windows, the fan would kick on, and it would start heating up. I feel like that dude's brain must just be like that. Is was there just heat exhaust coming off of them? >> I'm I'm closer to a homeless guy in
28:51terms of like accomplishments and brain power than I am to this guy. And it was so awesome that this guy walked into this room. He was one of the most quiet guys. He probably talked the least amount. >> you describe his calves and stuff, what did he say about AI? He said he was blowing your mind a little bit. What did he say? >> Uh I have to be somewhat vague. He was
29:09saying He was just explaining like how they do it for like trading and like making financial decisions. But he frankly he was using He clearly was trying to talk my level, but it was so hard without using like the jargon that he had to use. But like at one point I was like, "So, is your company cool? Uh why is it cool?" Uh he's like, "Well, I think we have a good culture. We pay
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