How Does Angel Investing Work? - Jason Calacanis - #154

**Chris Williamson** (0:00)
Oh yes, hello humans. Welcome back to Modern Wisdom. My guest today is Jason Calacanis, the man behind the This Week in Startups and Angel podcast, invested in Uber, Thumbtack, Wealthfront, Data Stacks, Robinhood, Calm and over 200 others. And I wanted to learn how angel investing and Silicon Valley works. I hear it on the news all the time, people making the millions out there in Silicon Valley, but I do not have a clue. I don't know what Series A shares are. I don't know about seed capital or any of that stuff. So I wanted to ask him, said, Hey Jason, teach me about angel investing. So today that's exactly what you're going to get to learn. But for now, please welcome Jason Calacanis. Jason Calacanis in the building. How are you?

**Jason Calacanis** (1:10)
What, what? How are you doing? Thanks for having me on the pod.

**Chris Williamson** (1:13)
You are in the most beautiful studio that I think I've ever seen.

**Jason Calacanis** (1:18)
Yeah, and you're in your bedroom.

**Chris Williamson** (1:20)
I am, that is true.

**Jason Calacanis** (1:21)
With a lighthouse poster.

**Chris Williamson** (1:23)
With a what?

**Jason Calacanis** (1:24)
With a lighthouse poster behind you.

**Chris Williamson** (1:26)
With a lighthouse poster, indeed. That is, but you know, we're all starting somewhere.

**Jason Calacanis** (1:31)
With a wave crashing around it.

**Chris Williamson** (1:33)
It's very, it's chaos, right? What were we talking about just before we started? There's some chaos going on here.

**Jason Calacanis** (1:38)
Chaos. Well, wait, where is that lighthouse?

**Chris Williamson** (1:41)
I'm not sure.

**Jason Calacanis** (1:42)
Do you have some specific meeting?

**Chris Williamson** (1:44)
No, I'm not.

**Jason Calacanis** (1:45)
What would Freud say about picking a lighthouse on the edge of human existence that's being pummeled by giant waves? What would that say about a man who puts that as the first thing he sees when he wakes up and the last thing he sees when he goes to bed?

**Chris Williamson** (2:05)
Can you tell that I'm an only child, Jason?

**Jason Calacanis** (2:08)
It does scream, I'm alone at the edge of existence, yes.

**Chris Williamson** (2:12)
Can you tell that I'm-

**Jason Calacanis** (2:13)
But maybe you're opting into it. See, that's the thing about lighthouse operators. They're opting into it. Nobody's forcing there. It's not a jail. So, there's a certain type of person who wants that solid, who wants that gig.

**Chris Williamson** (2:27)
Incredibly perceptive, my friend.

**Jason Calacanis** (2:30)
There you go.

**Chris Williamson** (2:31)
All right.

**Jason Calacanis** (2:31)
Well, welcome to This Week in Freud.

**Chris Williamson** (2:34)
Okay, go ahead.

**Jason Calacanis** (2:34)
For sure, man. Don't let me take it over in the first 30 seconds.

**Chris Williamson** (2:38)
That's fine. So, here's a question for you. I, podcasting as a host, which you are, do you find it odd being on the other side of the mic sometimes? You slip into host mode?

**Jason Calacanis** (2:48)
I do slip into host mode sometimes, and I do start thinking like, no, this is the question you should ask. And, you know, if you want me to answer that question, and you ask me four questions, just the second one is the winner. That's what the audience actually wants to hear. Or why didn't you ask me this follow up question? Yes, that does go through my mind sometimes. It happens, it makes it very hard for me to listen to other podcasts, because it becomes so obvious to me when the person who's conducting the interview doesn't know what they're doing. And then it really makes it amazing when you listen to, you know, Howard Stern interviewing Hillary Clinton or Joe Rogan interviewing Sam Harris, or Sam Harris interviewing anybody. You know, you start to realize, wow, some people are really great at this, right? And they all have different styles. And stylistically, you know, many different styles work. In some cases, it's very difficult for me when I know more than the subject. That was the thing I had to unlock as an interviewer. Sometimes I have somebody who is a guest and they know less about the topic we're talking about than I do. That doesn't often happen, but let's say it's Angel Investing or Media or something where I've spent a decade or two doing it and they're a young founder. They're actually deferring to me and sometimes they might say, well, what do you think? And that's problematic. In fact, Evan Williams, who is very good at media, but I think where he's more successful than I am having done Twitter and Medium and Blogger, but I created better editorial brands at him, certainly with Engadget and This Weekend Startups, like singular editorial properties. So we have long conversations. So when I interviewed him, every time I'd ask a question, I'd say, well, what do you think?