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Sam Lessin: recommendation

15 Jan 2026 Lenny's Podcast How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin

“There are limits to this, but if you go out to a normal dinner in a normal situation, you don't offer to split it, you just offer to pay for it. And then you should be declined on that, but there is a little bit of a risk there because someone might not decline you and then you kind of are on the hook for it, but that is, I think, the polite thing and the polite way to approach it.”

— Sam Lessin

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Speaker
Sam Lessin
Attribution
Verified speaker
Claim type
recommendation
Recorded
15 Jan 2026
Publisher
Lenny's Podcast

Transcript context

…Yeah. Awesome. And look, I think I would say in terms of this, which I always think is important is like, look, within reason, always offer to pay. Now, you should be turned down. If you go out with a VC and you put a card down, 99% of the time they'll be like, "I got this. Please, don't worry about it." And that's the right vibe on it. You do not need to do this if it's a $10,000 dinner, if they've ordered a super expensive bottle of wine. There are limits to this, but if you go out to a normal dinner in a normal situation, you don't offer to split it, you just offer to pay for it. And then you should be declined on that, but there is a little bit of a risk there because someone might not decline you and then you kind of are on the hook for it, but that is, I think, the polite thing and the polite way to approach it. What if they're just a billionaire? I just had dinner with a very successful VC and I did not feel like offering to pay made sense, would you still-…

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