The Exchanges

Q And out of curiosity, when you were doing these back channel references, what would you ask other founders, uh, to be able to, to better understand their experience with the investor that you're looking into?

A Yeah, my most effective question is one that I've actually adapted from, um, for candidates, but it works just as well for, for investors, which is I ask the person who I'm, I'm doing a back channel reference with. I ask them, let's say I take this money from NEA, and I tell you in, in six months, it didn't work out. What's your first instinct as to why? And, uh, and sometimes I'll even frame, like, let's say you and I bump into each other in San Francisco, and I turn to you, and hey, it just didn't work out. Uh, you know, I make it really real. I tell, I mean, I want them to feel the consequences of if they give me bad advice, uh, what it might feel like. 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, um, so that's one, probably my most effective question is, uh, this hypothetical of why wouldn't it work out in six months?

AI assessment note: “my most effective question is... let's say I take this money from NEA”

Q the business would be around for a while is the emphasis you put on spending time with investors and really In vet, uh, vetting investors and picking the right ones. Can you share, um, what were the most important criteria that you filtered for in choosing your investors and any questions that you asked to try to get responses that help you understand if an investor was right for you?

A It changed. It has changed for me over my career. I think early on, uh, when I was younger and I had my first startup, I really wanted more mentorship and guidance and, uh, Uh, you know, that's why we raised my last company, my series A, we raised from Benchmark, which has this philosophy of really being involved and helpful. Um, and, uh, not that I don't want investors to be helpful, but I also think I'm now more mature. I kind of have a better sense of, uh, where the company needs to go, and so I wanted an investor that first and foremost was aligned in values. You know, they were investing in me, and they put a lot of trust in me. They're not trying to, uh, replace me. They're not trying to, You know, um, exploit kind of the dynamic today. They see more of the value of the company being created in the future than the value been created so far. So that was first and foremost what I wanted. It was like sort of that values alignment, long term orientation, commitment to building a big successful company over the long term. And that's where references really actually play a huge role. You know, talking to somebody, um, is one thing you can ask. And investors are very good at selling. So you should be careful. There's very few questions you can ask an investor, uh, that you're going to get to the core truth. Uh, compared to talking to their references and, and certainly talking t…

AI assessment note: “I wanted an investor that first and foremost was aligned in values.”

Q I love that. Would you recommend the way that you raise this A to other founders?

A I would. And I think you should do it the right way. Um, you know, the framing your fundraise as a community round or putting out there publicly can have this maybe stigma that you're desperate. So you should find a way to do it that doesn't come across as desperate. Um, and I think the best way to think about it is to analogize, um, raising the way we did to online dating. Uh, you know, you could go to the local bar and, uh, find somebody that you might want to marry, um, Uh, that's possible. That's kind of how most people raise money. They go to the handful of best firms, and they go up and down Sand Hill Road, or maybe up and down their Zoom calendar, and they end up meeting with a handful of folks. But the reality is the world is big. There's a lot of great investors who might love your product for one way or the other, for one reason or the other, that you may not think to talk to, or maybe, uh, you don't get a sense to know until you kind of put yourself out there more publicly. And I think that's really the value of being more public in your fundraise, It helps you cast a wider net, which then you ultimately find the perfect match, the perfect marriage, and you end up, I think, um, really getting a sense for your market prices. That's the other thing that you benefit tremendously from is getting lots of offers and, and putting yourself out there. And the last thing I wou…

AI assessment note: “I would. And I think you should do it the right way.”

Q putting out these posts that were basically two liners. You had a statement about what first time founders do, and then you had a statement about, statement about what second time founders do. I want to talk through, um, The six or so of these that I've seen you put out, but before we hop into the specifics, why did you decide to start doing kind of these thematic posts?

A It came out of this realization that I would be so much better at my job if I took the version of me as a second-time founder and put me in the shoes of a first-time founder about 10 years ago, and I just reflected on how much I've learned. The reason I think these tweets went a little viral is because There's like some authentic truth to both parts. Like I made all of the mistakes, all the first time founders. I'm not, I'm not, you know, dogging on first time founders. I made every single one of these mistakes. And I also now learned as a second time founder, uh, the better way to do things. And so that's why I put it out there. It's just like, these are the kind of fundamental things I just learned by reflecting on what I could have been doing better if I'd known what I know today.

AI assessment note: “It came out of this realization that I would be so much better at my job”