The Ledger, every show

“Today we have companies that are worth four and a half to five trillion dollars. If you give it another five to 10 years, those companies continue to compound. It will be worth 10 trillion or more.”

“We then did this analysis and this is the type of analysis I really enjoy doing, like, let's take our best customers, and let's take our worst customers, and look at their return rates, and it turned out our best customers at the highest LTVs return the most”

“DoorDash won because they did have a differentiated strategy, which is focused on the suburbs. They were, had a differentiated strategy on focusing on the merchants as well and on selection. So those were two prong on the strategy that were quite different. An…”

“You see companies today going from zero to ten million in ARR in very, very fast, ah, time frames, which we have not seen in the past.”

“Oracle, the last time I checked, still exists. If you think that they're a legacy company, I don't know why OpenAI would want to leverage their balance sheet and their and their tools to be able to run data centers.”

“The top five to 10% of their engineers shipped three times more than they did last year.”

“In probably two or three years, we will not call them AI companies. Just the same way that internet companies over time, yeah, there were native internet companies, but over time, every company became an internet company. Every company became a mobile company.”

“The whole idea was we're going to go out to Rwanda. We're going to prove out that we can do this. And then we can bring back all of the safety records to the U S and eventually be allowed to fly in the U S which is what has happened now.”

“Tony invested ten million dollars of his own money, but most of it was financed through being very, very creative, figuring out how to get merchants that we ordered from to give us credit and to increase the credit line. We had a, eventually got a line of cred…”

“They didn't think this was a, this is a high margin business. They thought of it as like, ok, this will be a low margin business too, and we like low margin businesses.”

“They decided, like, these merchants are going to be hurting, and we need to help them, and so they proactively went out and uploaded menus from different merchants onto DoorDash and said, hey, I know you guys are hurting. The only thing you can do is delivery.…”

“The Series C that Sequoia decided to lead was quite hard. I think the company had thought that because it had doubled or tripled GMV, and the unit economics was getting better, that the valuation from the B to the C would be double or triple, and in fact, it e…”

“He slashed commissions for a period of time that totaled over a hundred million dollars during that time.”

“And I'm sure in a few years we'll be looking at ten billion dollar gains or more.”

“They called it before all of the other national media outlets.”

“There's the reason why small towns, there's a main street where everything happens, and so then you start realizing that the density problem is not as complicated as you might think, and they won because they were able to take the profits of the suburbs to go …”

“The solution to pick back and ship in four hours was to solve a operations flow issue and not batch the operations, which I don't think anybody else figured out in e-commerce back then besides Amazon.”

“I think we changed the whole industry, and it originally was just a competitive response. We had a liberal return policy in 30 days, other people copy 30 days, then it was 90 days, other people copy 90 days, and then we made it three 65 days.”

“At Zappos, it was, what do we do after nine-eleven when sales went to zero, what do we do during the financial crisis when credit became very, very difficult, and we were borrowing sixty million dollars, and we had sixty million dollars that we did nothing wro…”

“You have a business that went from a business that was growing 2030, 40% a year to a business that declines and you lose 80% of your revenue.”

“We have three billion dollars of capital on the balance sheet at Airbnb, but we have three billion dollars or four billion dollars of customer deposits.”

“They grew very fast, they probably grew too quickly their unit economics wasn't great, they had a few hard fundraising rounds for the C and D, they fixed the The unit economics. So in 2019 it was a walled oiled machine”

“Other things that, you know, I'd say we try to avoid is things that are roadkill along the way of a company like OpenAI or Google or Amazon or Meta. So, small refinements into what the model doesn't do well today. That's just gonna be real cool along the way.”

“Right now there's a different example where lots of, there's a lot of test revenue, but the churn is very high because people don't stick, so there are a lot of things where You see very, very fast adoption, but the churn rate is very, very poor.”

“The only restaurants that would be on Grubhub's website were all the companies that already had delivery staff available. So what DoorDash did was to expand the market. And by expanding the market, they were very focused on that problem.”

“Tony's whole notion was not just food delivery, right? He wanted to build the FedEx, his initial pitch was the FedEx of local, and he wanted to deliver almost everything, but he was going to start out in food, because if you can deliver a pizza before it gets …”

“We broke it down into from GMV to retention, to the cohorts, and the cohorts were just really sticky, even at the early days. We don't see that very often. I've seen that in very few companies where that's the case.”

“I had to write three memos for DoorDash investments.”

“I wrote four memos and got four no's for a Kaoshi investment.”

“A company that is used to growing 30, 40% a year went to losing 80% of its revenue.”

“Clay, I'll just use Clay as an example, where they started out as trying to bring programming to the masses. They built something and there were no, there are not enough users who thought that this was something that they wanted. They didn't know what to do wi…”

“That's pretty consistent to how many companies and how many founders we have to see Before we make one investment on typically we see about a thousand companies before we make one investment.”

“And so when they first started, it probably took 18 months to launch their first event. And now it takes a matter of hours.”

“Zipline, they started out with this idea of building a mobile platform for robotics where the iPhone was going to be the brains. And what they ended up with was what Keller would say was kind of like a toy and people would play with it. They had fun with it. A…”

“We had fifteen million dollars in revenue. You can kind of tell that we were in a bubble when someone would be willing to buy a company that had fifteen million dollars in revenue for two hundred and sixty-five million dollars. But also, you know, it was the t…”

“When we, on any given day, the orders that we had, 80% of it was from repeat customers, and we grew the business, some with marketing, but the majority was by providing great customer service, having high repeat rates, having high LTV, and having customers bas…”

“Tony Hsieh had this experience at Link Exchange where we didn't define the values of the company. We started hiring people that were conventionally right for the positions in the job, and one day he woke up and realized the company that he had founded and buil…”

“At tell me networks, when we're burning sixty million dollars a quarter, how do we get through that, and how do we pivot the company from a consumer business that wasn't working into an enterprise business?”

“We're going to raise money, and we're going to do it in a way that doesn't burden previous investors. So we're not going to raise money at a low valuation. We're going to raise debt.”

“He knew that restaurants wouldn't survive. They had less than 30 days of cash. And, you know, that's less than 30 days of cash when they actually are running at full speed.”

“He had a fairly easy series A raise in my opinion, because he had five term sheets and we were competing with five term sheets and I had a jump on the competition, but it happened fairly quickly.”