Book Excerpt | Jason Calacanis

So that would be even better.

You know, it's like it took me 19 days to write the book, 2 or 3, maybe 3,000 words a day. And as I was writing it, I was like, this is really fucking hard. Like, it's hard, it's arduous. But then I was writing it with my best friend Brian Alvey. I was writing and he was reading it. Actually, he was like my coach. I wrote the whole thing. And HarperCollins was like, so we paid you this huge advance. We won the auction. There was an auction for the book. So tell us about what you think your process is going to be for writing the book. I was like, well, I'm going to write the book. They're like, that's great. When do you want to publish it? I was like, when it's a bestseller. They're like, awesome answer. We love that. Do you think you want some help? I was like, how so? They're like, well, you know, sometimes when people write books, we give them somebody to help them with the book. I was like, like a ghostwriter? Like, well, we call them like assistants or helper. I think, you know, it's like— I was like, fuck no, I'm writing this shit myself. I'm a writer. I'm not writing— and they're like, okay. And I could tell they're like really nervous because they paid me a lot of money and they're not sure if it's gonna come out well. And I said, I can tell you're kind of nervous about this. How about I write 5 chapters, you read it, you tell me if you like it? I write the first 5 chapters, and you read the book. I just said to myself, go full Jason, like 100% candid, just no filter, super candid. If you ever listen to my podcast, sometimes I get a little candid or blunt, or maybe you follow me on Twitter. And I said, I'm just gonna go for it. I'm gonna be super candid. It's worked for my whole career. So I wrote it, and Hollis emailed me, and she— then she called me. And it was, you know, whatever, 10, 11 o'clock at night in New York and 6 or 7 o'clock here. And she's like, I just want to tell you, I didn't think you could necessarily write a book this good. You have such a unique voice. It's a page-turner. Just finish the book. It's going to be amazing. I would never let a ghostwriter write anything for you. It's just like you have an amazing voice or whatever. It's so honest. I was like, great. Then I finished the book and then I get a phone call. Hey, we got the rest of the book. It's really good. I'm on the call with our general counsel, and our general counsel would like to speak to you. I'm like, okay. Well, there's about 17 people mentioned in the book in a derogatory or unflattering light who will probably sue you and us by extension. So what do you think we should do? I'm like, I don't know. I'm not a publisher, a publisher, but the stories are all true. Damn the torpedoes, let's go. I had to tell the truth. They're like, well, there is another option that we could put on the table other than fending off 17 lawsuits from people that you told terrible stories about. I said, what's that? They said, change the names. I was like, I'm not changing the names, no way. And so then I talked to my wife. She's like, Why would you want to go to war with 17 people when you could just change the names and make them a composite? It doesn't add anything to the book. You already have 7 active wars with people. Do you really need to have 25? I was like, God, you're right. Enemies accumulate, right? No, I agree. They just accumulate, right? And so I was like, okay. So then Brian and I went through the book. We changed everybody's name. We changed all the companies, we changed what they did. Stories are all true, and you read the stories.

Yeah, that's how it became Food Right Now.

There were some brutal stories in there. Which one is the most brutal, do you think? Let's see if she read the book.

The guy you called an asshole in Flatwood.

Okay.

Canceled on you.

Oh, that was brutal.

Yeah, I was like literally like, oh, okay.

And there was a few places in the book when they've just started like— This is in my crazy years. I'll tell the story briefly.

Oh, good.

So I was raising money for Mahalo, which is now Inside.com, and Sequoia, Kleiner Perkins, and Mark Cuban all agreed to invest. I had 3 term sheets essentially, so I went with Sequoia. No dig to Kleiner, just wanted to work with Sequoia, specific partner there, Roelof. And right as I'm about to close, one of my angel friends says, hey, Acme Ventures heard you have a term sheet, they want to talk to you. I was like, it's closed, I'm, you know, I'm signing the term sheets. He said, well, can you do me a favor? It's a good friend of mine, I'm an advisor, it'd make me look good if you took the meeting. Okay, I take the meeting. I take the meeting with Acme Ventures. That's not their name. Guy says, this is amazing. We'll beat Sequoia's term sheet significantly, like by millions of dollars, and we'll give you millions more. Will you just meet with our partnership? I was like, I don't know. It's great. Thank you. But I don't feel like going back to Sequoia and saying no. I already kind of verbally agreed, and that's my dream investor. They're the number one venture firm. They did Apple, Cisco. YouTube, Google, the list goes on, PayPal. And so he goes, just please come to the partner meeting. I said, okay, I'll come to the partner meeting. I was living in Los Angeles. This is before Uber, before Wi-Fi on flights. I come up on Southwest, I take the 6 a.m. flight because I got to get up at 4:30. I get to the airport at 5. You guys have done this. This is when I was hustling, not living the cush life I live now. I was like super hustling, you know, not watching any TV.

I think you're still super hustling.

I'm kind of— I kind of hustle, but I do go to Coachella and Burning Man now. I'm getting old. There's only so many Coachellas left in my future, or Burning Man. I saw Lorde and Lana Del Rey in the same night. I mean, kind of hard to beat that.

I don't listen to music either, so I have no idea what that is.

Anyway, so I land and my BlackBerry says there's a message, but I'm like racing to this 9 AM partner meeting. I get my Hertz. You know, this takes time at the airport. I'm driving. I'm, you know, so I plug my phone in, I put it on speaker. Hey, Jason, it's Joe from Acme Ventures. I hate to cancel on you same day, but I talked to my partners and they said, you know, it's not a fit for us. I am so embarrassed, but you don't have to come up today. I'm like, motherfucker. So I am just— and in my younger days, I was a little bit wild, so I do what any rational person would do. I go to his office after he says you don't need to come to the office. I show up at the office. I walk in. There's a big glass room. I mean, this is reception. There's a glass room. I walk in. I smile. I see the guy just like you right there. I look at him. He looks at me just like you're looking at me. All the partners look at me and then look at him. He comes running out. The woman says, do you have a meeting? I said, yeah, I'm meeting with Joe. She goes, "Oh, I don't have that here." Joe comes out. Didn't you get my message? I said, "Oh, I got your message." You are a beep beep beep beep beep. He's like, "I know I don't." I said, "Let me tell you how stupid you are." This is like as insane as I was. It's embarrassing, but I had this thing where if somebody was stupid, I felt it was my moral obligation to explain to them in detail how stupid they were. Now, if I meet somebody stupid, I'm like, oh my God, it was so great meeting you. I'm just looking at you like, I don't think you're stupid. Just picking a random person. I'm like, oh my God, it was so great meeting you. Let's keep the dialogue open. You have my email. Let's stay in touch. Put me on your monthly update or whatever. If you say, oh, let me know about deal flow. No, it's great meeting. And then I turn around and go, that guy's a fucking idiot. Lose my number. I would never say it to somebody's face. But back then, I felt obligated. So I said, let me tell you how stupid you are. You're so dumb that you didn't realize that you could have invited me to pitch the partnership, told me I am a brilliant founder, let me know that one of your partners is a complete curmudgeoned jerk-off and he refuses to invest because he thinks it's a conflict with this other company, even though it's not, or any number of excuses.

Mm-hmm.

But instead, you wasted my time as a second-tier venture firm that I was doing a favor to. You are a complete moron. I am going to tell. And I just like. And he's like, "Let me take you to sushi." I was like, "I wouldn't let you buy me lunch in ten lifetimes." I am going to tell every founder I meet what a colossal beep beep beep beep beep you are. And I walked out. And I saw the guy like a year later at like the D conference, and he came up to me and I said, no. And he said, okay, and he turned around and walked away.