Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153

(instrumental music plays) I very much believe you should either be in fundraising mode or not. Always saying the highest price is almost certainly gonna be a mistake. 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 20% is what they want. If you say, you know, "We're worth... Uh, yeah, we're raising $10 million," they just take $10 million divide it by 0.2, and then that's what they think that you think your valuation is.

Ready to go? (instrumental music plays) Dan, I am so excited for this. We've gone back and forth on Twitter. I've obviously been a huge admirer of yours from afar for a long time. So, thank you so much for joining me.

Thank you. The feeling is mutual. I've been a bit of... a big admirer of the show and glad to be on it.

Now, I think great entrepreneurs are shaped by their early years. And so, I'd just love to go back. When you think about how your parents or how your teachers would have described the 10-year-old Dan, what do you think they would have said?

They would have been very, um, astute to notice that I was very into computers. So from a very early age, uh, we always had a computer around. And I owe my mom's boss, she was working as a secretary at Stanford, and her boss was Professor Hector Garcia Molina. And he had this amazing generosity where every time he would buy himself a new computer for home, he'd always have my mom buy the same one for herself. And then me of- me and my twin brother actually got to play with it a lot. So, uh, we'd always have the latest and greatest thing at home because of his generosity. And that, I think, propelled me to what I'm doing today, because I'm into computers, which is, uh, something I've been doing ever since I was 10 and even maybe younger.

I love that. What a great guy. What an awesome influence. Uh, along the way, we have many great yeses and many hard nos in life. And I find that they shape us, the highs and the lows. When you think about a great yes that you think really shaped you, and also a really shit no, what comes to mind for each, before we dive in?

Yes, uh, was about eight years ago when my now wife said yes (laughs) to getting married. Any other yes I've gotten from venture capitalists or employees or kind of pales in comparison to that big yes, so I can't really, um, compare. And then nos, there's one cl- there's one pattern of nos I've gotten that now my team knows is the, the most motivating no I get, which is the version of a no that starts with, "No, that's not possible." And I'm a big believer in technology's ability to do things that were thought of as impossible before. Um, and so I think since probably very young, 'cause I know this has been going on now for at least a decade, I'm very motivated when somebody has a cynical or pessimistic view on what technology can do. And there's nothing more motivating to me than hearing that and then trying to prove them wrong by showing them, by building the demo, by building the product, uh, by building the feature to prove that that is something that techno- technology can do. And in some ways, every version of every startup I've ever done is some, there's some seed of that idea that's said, "No, that that's not possible," that motivated me to persevere.