The Ledger, every show

“When I was there early on, a lot of people valued. You got promoted by the sophistication of your technology, not by the problem it actually solves for a customer.”

“They just passively capture everything in a privacy sensitive way. It's stored locally. We don't have access to it. Only you have access to it.”

“Scribe was kind of an, and all kind of meeting bots are kind of nice to have. It's a vitamin, it's useful, you know, but like the idea that you could capture anything you've seen and never have to take notes again, that was a painkiller for some people.”

“Google has this, Sense of Googliness that you had to assess candidates by, but it always frustrated me that there was no clear definition of what Googliness meant, what it meant to be Googly. And I actually found that it tended to, on occasion, become weaponiz…”

“I think a lot of AI tools today are the sort of flash in the pan, exciting, cool demo. Well, cool. Isn't it amazing that technology can do this, but then nobody sticks around.”

“The switching costs are very high. And we also have everything you've seen that are heard up until you start, since you use our rewind. So even if tomorrow, Some big tech company launches what we do. You know, we've got a lot of users who say, well, why'd I sw…”

“You know, for us, the test I always use is if we were subpoenaed by the government, would we hand over anything useful or meaningful? No, like we never want to be in a situation where We have data about anything you've done that then we could hand over and tha…”

“I do think things like white collar knowledge work that is high paid, lawyers being one of them, is probably a good area. I think anything where today people are paying a lot of money and people are being paid by the hour that a machine could do as better, in …”

“And that's how I view this relationship with my investor. It's something I'm going to spend the rest of my life with. I'm going to be doing this for decades. I don't want to just meet the person I, you know, find at a bar. I want to cast a wide net and potenti…”

“In fact, we didn't, we had. 20 offers or more of a billion dollar valuation. We turned down.”

“I would hone it and use I hope I just doesn't offend anyone, but use like associates and VPs at firms that you don't want to take money on as practice. Cause you meet these people, their whole job is to meet with you and get deal flow. But like, actually, you …”

“We are hiring for hardware people so it's possible that down the line if we cannot, by the way, I'm very much a big fan of software. I don't know if you're if you've ever done anything hardware related, but software has many, many benefits of which I'm the big…”

“At Google, you know, they value sophistication of the technology more than they value solving a customer problem. And so that was a cultural thing that started from the early days that served us well, served Google well for certain products like search and pro…”

“And the way I see, you know, the next few years playing out is that in, in markets where there is a best of breed product that is a delightful product that practitioners and departments will decide to use and evangelize for, as long as those products integrate…”

“If I had to give myself advice to a past version of myself, I think a lot about that, and I think about optimization. I think that it would have actually served us better to be more narrowly focused on a set of customers and deeply empathize with their biggest…”

“We try to seek missionaries, not mercenaries. So people who are really focused on title as part of that process, ah, to me is a red flag. It means that they're about trying to make their LinkedIn profile look good, not how to make our customers wildly successf…”

“Looking back, what I would, wish I had done differently is, is have a small team of folks working on getting six reference customers who are using the product, paying for the product, and are willing to be public spokespeople for the product as a way, ah, to r…”

“I very much believe you should either be in fundraising mode or not.”

“When an investor asks, how much are you raising? More often than not, they're actually asking, how much do you think you're worth? Let's start the negotiation on valuation right now, because a 20% is what they want.”

“The caliber of person that I can hire today is far, far better than the person I could have hired, you know, when I started optimizing. So I do think that's a huge factor as well. You can hire much better if you, and certainly if your first company did okay, d…”

“Titles they're a bit weird because they're both kind of free to give in one sense, that it doesn't cost you more money, but they're expensive in that it creates this sort of, like, mutually assured destruction. You know, as soon as you give out that first VP t…”

“My very first Series A, I got, you know, I got benchmarked to agree to, you know, I think it was maybe eight percent or something.”

“They're often buyers at the IPO. They're not sellers.”

“Are you raising money? And my answer almost always is, is never yes or no. They want just a yes or no. Usually it's some version of, well, no, but if over the next week we get a term sheet you can't say no to, we're probably going to take it. So that's somethi…”

“Last year, when we did this fundraise, I we did this kind of in public. We put the deck out, and then for any of the people we felt were good finalists, we gave them a calendar link for the first meetings, and those meetings are all one week, so no more than o…”

“When you have like, 30 back-to-back associate investor meetings where you're practicing your pitch and tweaking the deck every single meeting, by the end of that, you have this really, really honed product, like a stand-up meeting.”

“Oftentimes, especially I found this too, when you very quickly can tell the person you're meeting with, they just, they have an inclination. They want to invest almost from the beginning and all of their questions you'll find out. I actually, I think are often…”

“I think it helps with recruiting. I think that's probably the biggest benefit. You know, great, great talent can work anywhere, and if they had the choice between a company that's got, you know, great marquee investors who, you know, who've done their homework…”

“Never take more than One X non-participating preferred liquidation preference.”

“I think the most important thing to do if you're an investor today is find founders who are obsessed with problems, not solutions.”

“The best CEO for a AI customer agent is somebody who started their career answering customer support calls.”

“I've never seen a situation where we'll ship a little feature and we're done. It's always like, oh shoot, now there's this edge case we didn't think about it. And then, oh, this other person wants to do this other thing. So you, it's like opening a commitment …”

“I tried to buy Amplitude when there are four people. In fact, they were about to raise their, I remember we're sitting at, I think at Chipotle and Soma with Spencer. And I, to this day, I'm so impressed with, I just, I was offering him insane amounts of money,…”

“That is the one where in that moment I should have just said, okay, we're going to crush them and do product analytics. I think too much of my ego is associated with that. I should have been more Zuck like and just said, okay, they didn't accept our offer. Let…”

“Another example is segment. That's something, another area where it was adjacent to what we're doing. We tried to acquire them. They were later stage. Then they said, no, they ended up being successful.”

“I probably should have. I kind of regret not doing it. I think I was maybe too much pride and ego that I didn't need it. But YC has a lot of gifts to keep on giving, even if you're a second time founder, like work at a startup like office hours. So I am very i…”

“Technology doesn't get better by itself, by the way. We could look at, you know, here's a good analogy, we could look at AI today the same way that Before SpaceX, people looked at the Space Shuttle. Like, hey, we had the Space Shuttle, then we retired it, and …”

“NEA is known to have 15 year fund life cycles as opposed to the traditional 10. Very often they're buyers at the IPO. They're not sellers.”

“Investors are very good at selling. So you should be careful. There's very few questions you can ask an investor that you're going to get to the core truth. Compared to talking to their references and certainly talking to back channel references are very, very…”

“I think founders will be really honest with other founders. So don't be afraid to, you know, you're thinking about taking a term sheet from an investor. Look at, you know, all the other people they're on the board with and just reach out to the CEOs of those c…”

“And usually when you ask somebody their first instinct, and you ask them in this hypothetical, you get to some truth that you might not otherwise get when you ask about strengths and weaknesses.”

“And because the good news is we have six years of runway. We've got plenty of time to live up to the big valuation.”

“If I look back at the things that I did at Optimizely, my last company, the vast majority of my time and effort was wasted. What really mattered was like getting two or three things right. That ultimately led to our success.”

“They actually wouldn't want me to just blindly follow their point of view. They want to be heard. They want to know that their point of view matters, that I'm hearing it, but more than anything, they want to make sure that I'm following my gut. I'm making the …”

“First-time founders think that the best way to get their team to follow them is to be liked, but really second-time founders recognize that the best way to get their team to follow them is to win, so that's more important than being liked in the moment, and th…”

“Again, a good reason why bootstrap founders probably are successful is they're not surrounded by these people. You know, you end up just, you're forced to talk to users because you probably haven't hired that customer support person, and you hear the pain from…”

“So many technical founders, especially people who've worked at big companies, end up making the mistake of thinking that the value that they're creating is in the sophistication of their technology, not the problem it's solving.”

“If you're forced to write that demo script before you start building, it makes you think about the use cases, the demos or that, that, that would demo nicely. And I think that clarifies, that focuses you back to the main thing. It focuses you on what actually …”