Jason Calacanis Book Signing Q&A Part 1

I think that's about everything I can tell you. So I'll take 2 or 3 questions. Should we run a microphone to them? You know, I'll just do it like Phil Donahue. I'm going to hold the microphone. I'm not giving you the microphone. I don't trust you. What's your question? Tell me your name, where you're from, and a concise question. Do you want last name too? No. Okay. My name is Christopher. I'm from Arizona. And why do you invest? Why do I invest? When I started investing, it was because a venture capital firm, Sequoia Capital, said, we've got money. You know everybody. Would you give this money to your friends? Because we think you'd be a good angel investor and we don't do that. And I said, what's the catch? And they said, well, we'll split the money 50/50 if any money comes back. And I said, wow, it's a pretty good deal. And so I did it. And in 3 of the first 6 or 7 investments turned into unicorns— Thumbtack, Uber, DataStax. And so then I said, well, I guess I'm pretty good at this. And so then I started working a little harder, made my own fund, and then I made enough money that I don't ever have to work again. And when Brian and I sold our startup, I didn't have to work after that as well. But for me, working with young startups, 5 to 10 employees and modest traction. That's where the excitement is. So I've been offered to move downstream and work with the bigger companies. I generally pass on that because I like the early stage. Early stage is hard. I like hard work. Done 150 investments. Can I do 150 more? That'll be 300. Have 6 unicorns. Hit another six. That's twelve unicorns. That I'm the goat. You know what the goat is? Greatest of all time. Thank you. So you got to set goals for yourself. Okay, what's your question? Don't don't don't take the microphone. I don't trust you. Go ahead. Here we go. All right. So my name is Pedram from Manchester, United Kingdom, and my question for you is: What's the first thing you tell yourself whenever you fail? First thing I tell myself whenever I fail. Hmm, that's a good question. I have gotten a little philosophical about it when it comes to angel investing, which is the precursor to success is failure. And so in the book, I talk about your sophomore year as an angel investor. What happens in your sophomore year as an angel investor in year 2? Is all the people you gave money to in year 1 are now out of money. And maybe 5 or 6 of them cannot raise money from other people. So they come to you and say, nobody will give us money. Will you give us some? Say, sorry, that's not what I do. I'm an angel investor. You have to get other people to get you money. And then they die. And then you keep investing and investing and you get all the bad news first and then you get the good news. And then what you realize is when you get the good news, it really outweighs the bad news. When you hit one of these unicorns, you typically make 50 or 100 or 200 or 2,000 to 1 on your money. So it's very easy to forget about all the lottery tickets that didn't work when you have 6 that did. Does that make sense? Like if I bought 150 lottery tickets, And one of them won the Moneyball and the other 5 won like second place. I wouldn't remember about the other 144. Move on. Every time you fail, just look at it and go, what could I have learned? Could I have done something better? Don't be too hard on yourself. I mean, don't be delusional. I mean, if you did something unethical, then you should take a deep look in the mirror, but generally don't overthink it. Just what can I learn from this and keep moving forward? Nobody remembers your failure. All they remember is that you won. That's it. Okay. What's your name? What's your question? I'm Praneet. I'm from India. And my question is, what is your advice for singles, for single founders? All right. For single guys from India, I suggest you get Tinder and you got to get a decent haircut. You got to get a little haircut. Supercuts, no more. Okay. We got to get a little bit of a haircut. I'm fucking with you. Fucking with you. You're really good. For a solo founder, for your first company, that's a mistake because it's lonely. Now, if you've got 2 or 3 wins under your belt, you can be a solo founder and hire a founding team, keep all the equity for yourself. That's fine. But for your first company, have 3 founders, have everybody vest over 4 years, 48, or some people even do 5 years. And if it doesn't work out and one of the founders leaves after— you know, there was Jawed, who was the 3rd founder of YouTube. Nobody knows who he is because he left in year 2. He got half of his stock. The other guys got twice as much, but he wasn't into it. So don't be a solo founder. It's not a good idea. Okay, let's go back here. Here we go. How are we doing on time? 10 more minutes. Okay, 10 more minutes. My name is Marcelo Garza. I'm from Mexico, and I wanted to ask you, so what are the essential things you consider that have to be in place for a company to exist? Well, for a company to exist, you need to have founders, you need to have a product, you have customers in a market, all of those things. Delighting users is one way to think about it. A popular way people think about it here in Silicon Valley is vitamins and painkillers. So does it delight people like Netflix, or is it a painkiller like Google? Would Google be a painkiller? Yeah. What would you say, Brian, is a good painkiller? Like you can't find something, Google's a painkiller, right? What removes pain? I don't know, because everything I can think of delights, like Uber. That solves a problem, but it also kind of could be delight. Yeah. So anyway, there's different frameworks people have, but customers is the one thing that people often, especially young entrepreneurs, are scared of. So they are afraid, especially if you're introverted, to talk to people about their product. You want to be fearless in talking to customers. When you meet angel investors and VCs down the road, they're going to ask you, who are your customers? When's the last time you talked to them? Who are— tell me your different cohorts. How are they using the product? How often do they use the product? Don't be afraid to talk to your customers. Talk to them constantly. So if you get any of the newsletters at inside.com, which is my startup, and you hit reply, not only do I get your reply, it goes to the entire team of 15 writers. And then when we hit replies back to the audience, all 15 writers see it. And then somebody's like, this is like 30 emails a day, 40 emails a day in 40, you know, in 15 people's email boxes. Like, this is like almost 1,000 emails a day. I'm like, yeah, these are the most important emails we could ever see. These are our customers telling us how to make our product better. It's product research. Like, oh, we should just have one person do that. Are you fucking crazy? If somebody hits reply and they have something to tell us, let's listen. And let's learn. So stay focused on your customers. We had a question over here. Okay, here we go.