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Sam Lessin

Published podcast speaker

Claims
30
Episodes
1
Shows
1
Named items
3

Books, apps, and tools

The evidenced stack.

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app / built

Letter Meme

“I will say the thing that I've had the most fun with with AI and I find great is it actually is partially where the cartoons for this came from is I built a little personal news aggregator called Letter Meme”

Lenny's Podcast · 15 Jan 2026

Evidence receipt · Source ↗

book / uses

Hitchhiker's Guide to the Galaxy

“It actually reminds me, I'm reading one of my sons right now, the third book of Hitchhiker's Guide to the Galaxy.”

Lenny's Podcast · 15 Jan 2026

Evidence receipt · Source ↗

book / recommends

Lessons From History

“Ooh, okay. So let me pull up my list because I got to pull up my Kindle for this. One is I'm reading right now. I got to admit, I like to make fun of Marc Andreessen a lot, but he recommended a book called The Ancient City, which is fascinating. And so I'm in the middle of that right now. I'm really enjoying it. Man's Search for Meaning is great. I'm just going through. What have I read recently? You know what's great? Area 51, An Uncensored History: The Top Secret Military Base. Not very Erudite, great book. And then I honestly think the one serious one I'll make a recommendation on is Lessons From History is one of my favorite books ever. I would really, really, really recommend it. It's a short read, but Lessons From History by Ariel Durant is probably the most approachable, non-obvious book I love.”

Lenny's Podcast · 15 Jan 2026

Evidence receipt · Source ↗

Claim ledger

What Sam said.

30 transcript-backed records

01 / recommendation

Recommends Lessons From History.

“Ooh, okay. So let me pull up my list because I got to pull up my Kindle for this. One is I'm reading right now. I got to admit, I like to make fun of Marc Andreessen a lot, but he recommended a book called The Ancient City, which is fascinating. And so I'm in the middle of that right now. I'm really enjoying it. Man's Search for Meaning is great. I'm just going through. What have I read recently? You know what's great? Area 51, An Uncensored History: The Top Secret Military Base. Not very Erudite, great book. And then I honestly think the one serious one I'll make a recommendation on is Lessons From History is one of my favorite books ever. I would really, really, really recommend it. It's a short read, but Lessons From History by Ariel Durant is probably the most approachable, non-obvious book I love.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

03 / belief

There's even a point to like, there are lots of scenarios where I think an Irish goodbye is the best goodbye where you just kind of disappear.

“There's even a point to like, there are lots of scenarios where I think an Irish goodbye is the best goodbye where you just kind of disappear.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

04 / belief

If you're out in a situation, I think you kind of want to tip in my mind to the level of no one you're effectively paying for would bat an eye that you're being stingy is the way I would think about it.

“If you're out in a situation, I think you kind of want to tip in my mind to the level of no one you're effectively paying for would bat an eye that you're being stingy is the way I would think about it.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

05 / belief

Yeah, I think that's perfectly fine in terms of the way to do it. I just think the key is to make it easy for the person you're trying to do business with.

“Yeah, I think that's perfectly fine in terms of the way to do it. I just think the key is to make it easy for the person you're trying to do business with.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

06 / belief

I'm just saying it's quite a statement is my view that you've invested in your emoji pack or using special emojis people haven't seen before or it's like, again, it's a subtlety and you got to understand the room and the culture and what you're responding to, but I do think that people read more into that than people want to be read into it.

“I'm just saying it's quite a statement is my view that you've invested in your emoji pack or using special emojis people haven't seen before or it's like, again, it's a subtlety and you got to understand the room and the culture and what you're responding to, but I do think that people read more into that than people want to be read into it.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

09 / belief

Again, it shouldn't be 10 minutes. But again, I think the thing about it is imagine that the whole game in these social settings, again, is putting other people at ease, making them feel like you understand them and the room and you're a trustworthy person and on the same wavelength.

“Again, it shouldn't be 10 minutes. But again, I think the thing about it is imagine that the whole game in these social settings, again, is putting other people at ease, making them feel like you understand them and the room and you're a trustworthy person and on the same wavelength.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

10 / belief

There's a bunch of tips about, I think, generally famous people, but I think there's this thing which is not being sycophantic is what I basically say, but also not being ridiculous is almost the way I would frame it in this conversation, which the ridiculous is if you go up to Mark Zuckerberg and everyone knows what he looks like and who he is and you're like, "Hi, I'm Sam.

“There's a bunch of tips about, I think, generally famous people, but I think there's this thing which is not being sycophantic is what I basically say, but also not being ridiculous is almost the way I would frame it in this conversation, which the ridiculous is if you go up to Mark Zuckerberg and everyone knows what he looks like and who he is and you're like, "Hi, I'm Sam.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

11 / belief

I think part of my early attraction to the platform was it was the first time you walk around college and you're like, "I know these people, I just don't remember their names.

“I think part of my early attraction to the platform was it was the first time you walk around college and you're like, "I know these people, I just don't remember their names.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

13 / belief

" Most of the time, that is not an invitation saying, "I'd love one too and follow them to the bar." So I just think you have to recognize the signs effectively when the moment is passing or it's time to move on, et cetera, and then respect it is what I would say.

“" Most of the time, that is not an invitation saying, "I'd love one too and follow them to the bar." So I just think you have to recognize the signs effectively when the moment is passing or it's time to move on, et cetera, and then respect it is what I would say.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

14 / observation

The reason is, but it's at least enough plausible deniability of semi-bad etiquette that leverages the social situation to be a better etiquette, that it's a useful thing to think about as a small queue.

“The reason is, but it's at least enough plausible deniability of semi-bad etiquette that leverages the social situation to be a better etiquette, that it's a useful thing to think about as a small queue.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

15 / observation

You want to basically let people feel respected as much as anything else. So if you're too overt about it, even if everyone kind of knows what's going on, the key is to give them plausible deniability to themselves and the community effectively that we've wound down this conversation.

“You want to basically let people feel respected as much as anything else. So if you're too overt about it, even if everyone kind of knows what's going on, the key is to give them plausible deniability to themselves and the community effectively that we've wound down this conversation.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

17 / belief

Again, I think the thing I keep in mind is especially in an age where everyone's used to being in front of computer screens and looking at six different windows at the same time.

“Again, I think the thing I keep in mind is especially in an age where everyone's used to being in front of computer screens and looking at six different windows at the same time.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

18 / belief

I think the answer is find someone in your universe who you think dresses well. And again, ask them for help and what makes sense from that perspective.

“I think the answer is find someone in your universe who you think dresses well. And again, ask them for help and what makes sense from that perspective.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

20 / belief

I'm not saying you should be totally cut and dry, but it's kind of, I would say emojis almost feel like jokes to me, which is like, tell them at your own risk and they're probably not worth it.

“I'm not saying you should be totally cut and dry, but it's kind of, I would say emojis almost feel like jokes to me, which is like, tell them at your own risk and they're probably not worth it.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

21 / preference

Yeah, this is a big thing in general, which is I think people are afraid to ask in all sorts of situations down to which forks should I use?

“Yeah, this is a big thing in general, which is I think people are afraid to ask in all sorts of situations down to which forks should I use?”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

22 / recommendation

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.

“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.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

23 / evaluation

If the storytelling of Elon allows SpaceX, which by the way, I love, I think SpaceX is an awesome company, but if all of a sudden that actually can be worth $1.

“If the storytelling of Elon allows SpaceX, which by the way, I love, I think SpaceX is an awesome company, but if all of a sudden that actually can be worth $1.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

24 / preference

For me, I think I'm really interested in the cultural implications of AI or the new businesses that need to exist because it is a force in the world.

“For me, I think I'm really interested in the cultural implications of AI or the new businesses that need to exist because it is a force in the world.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

25 / recommendation

If you're the less senior person, if you are the less busy person, you should let the other person tell you when they're free and then make it work on your end, is what I would say.

“If you're the less senior person, if you are the less busy person, you should let the other person tell you when they're free and then make it work on your end, is what I would say.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

26 / evaluation

You don't want to tell a dirty joke in the wrong room. But I think the thing about humor is there's this interesting subtlety to why it's so useful in social settings, which is one, it kind of shows you the ultimate mastery of a social situation.

“You don't want to tell a dirty joke in the wrong room. But I think the thing about humor is there's this interesting subtlety to why it's so useful in social settings, which is one, it kind of shows you the ultimate mastery of a social situation.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

27 / commitment

I will say that there is probably in January or February going to be a, what we've internally been calling the fem etiquette course because my wife and other women have said, "This is good, but there's a bunch of other stuff that women need to know.

“I will say that there is probably in January or February going to be a, what we've internally been calling the fem etiquette course because my wife and other women have said, "This is good, but there's a bunch of other stuff that women need to know.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

28 / recommendation

Again, I think the thing for us is I'm kind of a ship early, ship often guy. So V1, you should buy it now and study it because it's good and it's going to be a limited edition.

“Again, I think the thing for us is I'm kind of a ship early, ship often guy. So V1, you should buy it now and study it because it's good and it's going to be a limited edition.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast

29 / evaluation

It's not a huge podcast. It's big enough, but I actually think the thing that's been most surprising to me about it is that even though we don't really have growth strategies and we're not trying to blow it up and we don't get paid for it, it's like weirdly useful is what I would say.

“It's not a huge podcast. It's big enough, but I actually think the thing that's been most surprising to me about it is that even though we don't really have growth strategies and we're not trying to blow it up and we don't get paid for it, it's like weirdly useful is what I would say.”
Speaker
Sam Lessin
Publisher
Lenny's Podcast
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