Opinion
Lessin says Y Combinator founders pitch investors like 'animals'
“We're a little bit making fun of the fact that YC founders do come out a little bit like animals, right? There's like having met with many of them, I guess not their fault. They're like young kids. They've been holed up in a room coding and that's all they've …”
Prediction Not checkable as stated
Lessin: Seed VCs backing AI companies will lose an 'impossibly large amount'
“I think that the venture capital, the seed venture capitalists who invest in companies that are branded as AI companies are going to lose an impossibly large amount of money in the coming years.”
Opinion
Lessin: AI empowers incumbents rather than creating great startup opportunities
“AI is a powerful tool. It's incredibly powerful for existing businesses and existing structures. It's not a great startup opportunity.”
Opinion
Lessin: Startup founders wearing a Rolex watch is 'very classless'
“Like, you shouldn't have a Rolex, right? It's like very classless, if that makes sense, to like show up as a startup founder with a Rolex, right?”
Opinion
Lessin: Only 0.1% of startups have breakthroughs powerful enough to ignore etiquette
“It is true that if you bring manna from heaven, right, like you invent something that is literally the next Google or whatever out of pure thought, That sometimes none of this stuff matters, right? Like if you just, if you fully, that's it, you know, it's like…”
Insight
Lessin: Founders should always offer to pay the bill with VCs
“Within reason, always offer to pay. Now, you should be turned down, right? If you go out with a VC, right, and you're like, you know, you put a card down, 99% of the time, they'll be like, I got this, like, please, like, this is, don't worry about it, right?”
Insight
Lessin: Pushing humor right to the edge signals social mastery
“The thing about humor is it kind of, there's this interesting subtlety to why it's so useful in social studies, which is one, it kind of shows the ultimate mastery of a social situation. If you're able to tell a joke, Which is right up to the line or even push…”
Assertion Not checkable as stated
Lessin claims his anti-Calendly diatribe drove most of the company's monthly growth
“I actually, I think I am not overstating it when saying there was a period with Calendly where I personally had driven most of their growth for the month. I got messages from the board because I went on this diatribe about how much I hate Calendly and how disr…”
Insight
Lessin: Less senior professionals should never default to sending Calendly links
“The default, I really strongly believe the default should not be Calendly. The default in most situations, especially if you recognize the power hierarchy, the busyness hierarchy, if you're the less senior person, if you are the less busy person, You should le…”
Insight
Lessin: Using emojis in business communication is risky and rarely worth it
“Emojis almost feel like jokes to me, which is like, tell them at your own risk and they're probably not worth it.”
Insight
Lessin: Vibe coding does not really scale
“But then vibe coding also doesn't really scale. And so the reality is after a certain point, I had some friends who are great engineers just take it and like up level in a few ways that I honestly ran out of time to work on.”
Insight
Lessin: Seed investing does not work in capital-intensive businesses
“Seed investing does not work in highly capital intensive businesses.”
Insight
Lessin: ChatGPT chat histories are ideal data for matchmaking apps
“If we're really trying to match up humans, like, call it Tinder T.O., one of the best sources of information to do that is their ChatGPT histories.”
Insight
Lessin: Ordering the priciest menu item signals cost insensitivity to investors
“In general, it's, don't, Order the most expensive thing on the menu. Does it really matter? Especially, like, an investor, do they really care? No, they don't really care, but they do notice, and you're like, ah, you're the type of person that, like, is truly …”
Insight
Lessin: Putting an assistant before a CEO in emails signals wrong hierarchy
“If you're sending an email and the first person on the email is the assistant and the fourth person on the email is the CEO, you've probably done it wrong.”
Disclosure
Lessin: Early attraction to Facebook stemmed from familial name-face blindness
“I actually have such a clinical problem on name face recognition that's actually runs in our family. I have this whole backstory, which is part, you know, I worked at Facebook for a long time, was really into it early on. No kidding. I think part of my early a…”
Insight
Lessin: Greet people with 'nice to see you' to prevent awkward repeat introductions
“If you go around saying nice to see you to everyone, they're like, there's a small percentage this person doesn't remind me who I remember who I am, right? And there are other ways are key, but like, that's okay. Like that's part of the etiquette dance to some…”
Insight
Lessin: Professional etiquette requires having a completely unnoticeable personal scent
“Your scent should not be noticeable, is almost the way I would put it you know, in any direction. It's not, you're not, there's no advantage to that, is basically what I would say.”
Insight
Lessin: Professionals must honor committed meetings even if booked with wrong person
“That's not a thing to call out, by the way, from an etiquette perspective. Once you're committed to the meeting, you're doing the meeting, even if it's the wrong person.”
Insight
Lessin: Saying 'I'm grabbing a drink' is an exit, not an invitation
“If someone says to you in a conversation, they'll wind it down. It's like, I'm going to go grab a drink. Most of the time, that is not an invitation to say, I'd love one too, and follow them to the bar.”
Sam Lessin