The Ledger, every show

“Category three that people don't talk about. If they ask me, it will be uncomfortable for me to say no, so I will write them a check. I'll tell you that in my experience, this is up to 10% of the time. I am hoping the founder doesn't ask me for money. Because …”

“If you need a designer to build a slide deck, you're doing it wrong. And here's an even deeper, more important point. Your designer has no idea what the most interesting and important points of your pitch are. So if you hand them your pitch to design, they wil…”

“What's unfortunate is that they had just gone through this two year cycle where investors were basically screaming at them to burn and raise because investors were getting markups and they were raising new funds”

“I think that in general investors are allergic when we tell founders that there might be situations where their incentives and the founders incentives are not aligned perfectly.”

“They also always tell us like, hey, like we're funding your companies. Like you shouldn't be like, you know, like telling the founders not to have high burn.”

“An A investor gives you money, signs paperwork when you want them to, and shuts the fuck up. That's an A. There's a lot of room below an A. There's not a lot of room above.”

“Over the past two weeks, I've talked to a number of, kind of, directors of entrepreneur centers, and the constant thing that I'm surprised by is that they know these things that I'm talking about, but they still accept teams that don't abide by these rules. So…”

“And like, if you play the big company game, they will always beat you. You always have to be thinking about, what would you have gotten fired for at the big company? That should be your playbook at the startup.”

“The skill is often getting the thing taking off to take your money versus someone else's money, not picking amongst things that haven't launched yet and having feces about why one's going to do better than the other.”

“Well, I think that's what's so funny is because that's the, every successful YC story, that's the story in hindsight, right? It's like, everyone thought the idea sucked. It was off trend because it was off trend.”

“You need two different answers to what do you do. One that you give investors, and another one you give customers, and they're different. The words on the front page of your website are for customers. If you're using that for investors, more often than not, yo…”

“Your goal should be 80% accurate, a hundred percent clear, not a hundred percent accurate, 50% clear.”

“What most people don't realize about investors is that you're not really convincing an investor to invest. They're convincing themselves to invest. The more they can talk, the more they can talk themselves into giving you money.”

“It's really easy to say, well, you know, I can be in the game in Austin. I can be in the game in Seattle. There are investors there. There are people there. I can be in the game in New York. And I wish that we were more honest that like, yeah, you can play bas…”

“You know, one of the things that we say sometimes at YC is that don't make the investor your customer. But a lot of these conformists who are getting into startups, that's what they do. Like they want an idea an investor is going to like, they want to act the …”

“Literally, 40% of the last batch came in with just an idea. Most of them were working when they applied, were at work, working jobs when they applied.”

“Prices are almost exactly the same as they were during the last batch when it was like VC heaven on earth and money was flowing like crazy. We saw. 15 to 25. Some companies raised at 30. Almost no change from the last batch.”

“And what they didn't tell that founder is that every subsequent investor would say to themselves, huh, this investor put in a relatively small amount of capital, bought so much of the company that the founders are going to get so diluted that they're not going…”

“It shouldn't cost 50,000 dollars to a price round. Like you're just ripping off founders, pure and simple ripping off founders.”

“What I've also seen for second time founders is that oftentimes for an investor, it's more of a catch. It like helps you build your reputation in your firm, or it helps you get the deal approved. And like, so oftentimes there's like internal political reasons …”

“Spending more money allows product market fit to happen faster.”

“I think we see this in practice, too, because we will see founders who will pitch to investors, get no's, apply to YC, get into YC, and those same investors will say, now I want to invest in your company, and nothing has changed. No fundamental thing has chang…”

“When founders are fundraising, it's like the first thing, the first time they tell me there's a rejection and a why, I ignore it completely. If they've gotten like 15, 20, 25 rejections, I then ask, are the whys consistent? And only if then the whys are consis…”

“If they can keep you spending your entire salary, and if they can keep the money that you haven't vested yet larger than the amount of money that you have in your savings by like two to three X, you never leave.”

“In many ways, this is a defensive tactic to warehouse talent. Out of the fear that maybe someone else can use you in a way that can hurt the company.”

“A structural advantage with a product that's good enough can win. And man, it really helps when some startups specs the whole product for you. Right? Like Microsoft's move is to not innovate the good enough product. It's to copy it. Maybe five to 10 years late…”

“What we did is that after 10 minutes of people watching free, free live video, we just put up a big thing that blocked the video that said, your ISP is not doing a free peering relationship with us, so we can no longer serve you video. If you'd like to call to…”

“I think sometimes counterintuitively investors who know slightly less about your space can be a little bit more grasses greener, like, optimistic than folks who know more about your space.”

“Too often, genius is mistaken for discipline. It's just like, you know, a lot of people think, oh, this person out executed all their peers because they were smarter, and it's like, that assumes the peers were actually working on the thing they said they were …”

“The vast majority of the best investors have invested in whole dozens of companies you've never heard of who've died. And so it turns out that because you raise a check from a famous name, or because you're able to raise a lot of money, almost has nothing to d…”

“When success happens, it's gonna punch you in the face. And you're not going to be able to confuse it for anything else. If you're not getting punched in the space with traction, you're not succeeding, and you don't need all those people.”

“Usually our guidelines for B to B companies is trying to be in the 150 to 250 K a month range. That, and close to profitable. That puts you typically in the maximum leverage category, which significantly increases the chance that going out and raising a series…”

“In reality, two things are different. Investors, I don't think for a good reason, significantly bias for second time founders. Significant bias towards second time founders. And there's something you have to understand. Second, if you've been in the valley for…”

“So strangely, starting with a higher price or a price is almost always better than starting free. Almost always better.”

“The kind of community of startup people and or investors usually don't have the problem that you're solving. So if you're using investors as a trigger for, am I solving the right problem? Or like, Do they find this useful? It's almost never the case. I'm almos…”

“An A investor, grade A investor gives you money quickly, signs the paperwork quickly, shuts the hell up. That's an A investor. There are very, very few A plus investors in the world. There are very, very many less than A investors.”

“The most hyped investment on Demo Day is often not the best one. Very, very often. I think what's interesting is that the crowd on Demo Day is just not as smart as it appears”

“So I would say that it's extremely rare that an investor can have truly big impact.”

“I think investors believe that having the skill to network to an investor is an important characteristic of a good founder, and I think, ah, kind of YC's core position from the beginning is that it's not.”

“I could say that if you're not going to a top five school, You are not technical and you want to get into tech startups. It makes no sense to me why you wouldn't try to get a job in an early stage company in a startup city.”

“People do not see the NBA as a startup. What is that called? It's not seen as like a positive resume item.”

“The strategy that got them to this school, that got them the meta job, that got them the Ivy league degree. Is not going to be the strategy that actually gets them to be successful as a startup founder.”

“You start having conversation with the founder, and you'll actually feel like you're talking to an investor, to a VC. And you're like, but what about your passion? Like, what, what's your opinion? Like, what do you care about? And it's all kind of like, contri…”

“Well, and I think what's interesting is that when we try to be smarter, we make mistakes. When we try to be smart about markets, or when we try to be smart about comps, We make mistakes because, one, we haven't studied those markets closely, and two, because s…”

“I also think that if you come from a big company, either in product or engineering, more often than not, you've never solved your own problem. Like you're working on other people's problems. And so I think that your instinct when you start a company is like al…”

“When rockets are reliable, you can go anywhere in the world in 45 minutes. Like, we could commute to Tokyo.”

“If you really care about those problems, you have to be optimistic to try to solve them. And like some of the people who are like the biggest social critics or the biggest revolutionaries or the biggest change agents in our society were default optimistic.”

“I couldn't find tech and co-founder, so I just moved to the next challenge. I hired some engineers, or I got a dev shop, and, like, nothing will keep me Well, hold me back. And what's so sad about that way of thinking about it is that like, one, the percentage…”