#150 - Jason Calacanis Joins The Brainstorm To Talk Robinhood, Gambling and the Opportunities He's Investing In

**Sam Parr** (0:19)
All right, Jason, how are you?

**Jason Calacanis** (0:21)
Great.

**Sam Parr** (0:22)
So Jason's here on My First Million. We're gonna talk about ideas and stuff, and Shaan's gonna pop in in a second. But I heard you might be moving here to Austin. Is that true?

**Jason Calacanis** (0:30)
It's definitely being considered. I'll just tell you just straight up my thinking on it. I spent 30 years in New York and was amazing. 20 years in Brooklyn, just over 10 years in Manhattan. And then I moved to LA for 10 years and spent 10 years with my wife there. I got married, started a family, and then spent the last six years here in the Valley because I wanted to see if I could become the best angel investor of all time, which was sort of a goal, or one of the best, right? And so I moved up here for the deal flow, and I started the Accelerator, put 20 companies through the Accelerator, seven companies at a time, so 140 have gone through it in the last five years or so. And it's been wonderful. And then the pandemic hit, no founders want to come here anymore. San Francisco is getting more and more expensive, so probably two out of three startups we were investing in weren't here anymore. A funny thing happened, we didn't want to stop doing the Accelerator in the pandemic, so we moved the class online. When we moved it online, two or three times as many people wanted to come to the Accelerator. And so that was a very interesting moment of reflection for me. Then I thought I refused to have anybody on the podcast unless it was in person because I thought my superpower Sam was to be able to look people in the eyes and decide if I should invest in them or to look them in the eyes and be able to figure out what the next question was on the podcast. Now 100% of people have awesome setups, are totally accustomed to Zoom and don't want to come to San Francisco either to be on the podcast or to come to our accelerator. I have been investigating potentially moving to Austin.

**Sam Parr** (2:04)
Well, I heard a funny story and I thought it was baller. I don't want you to be embarrassed.

**Jason Calacanis** (2:09)
Okay, here we go.

**Sam Parr** (2:10)
You were talking to someone and he's like, yeah, I'm looking for a house here. Someone's like, well, if I see something, I'll send it to you. What's your budget? And you said something like, oh, there is no budget.

**Jason Calacanis** (2:19)
Well, I mean, relatively speaking, the houses in San Francisco, they're not and the wider peninsula, they're not comparable in price, right? I mean, in San Francisco, everything's $1,500 to $2,500 a square foot and Austin, it's $600 to $1,000.

**Sam Parr** (2:34)
I thought it was a baller move. I thought it was a baller move. Everyone says like this and that. And then the person told me, don't worry, he just said it in such a good way. He goes, oh, there is no budget. Anything I want. And I was like, that's a baller answer. That's a great answer. And I just thought it was cool.

**Jason Calacanis** (2:48)
Oh, there you go. Yeah, I've just been researching. I've been to South by a bunch of times since the late 90s. I went to the second South by Southwest interactive before they even had a... Before they were even using the convention center. I don't think the convention center was built. It was just all at that, whatever that weird hotel was on Sixth Street is where they used to host it. And there'd be 50 people per talk. And maybe there were 200 people there for South by Southwest interactive in 99, 2000 time period. It was very small.
And so, I love the town and I would be up for the adventure possibly. I'm looking at it, I'm investigating it and we'll see what happens.

**Sam Parr** (3:24)
So, Jason, you started a media company 10, how long ago was that?

**Jason Calacanis** (3:29)
Well, most people don't know that I started in the magazine business in the 90s. So, I started a magazine called Cyber Surfer, which was about online services and CD-ROMs. Then the internet happened and I started Silicon Alley Reporter, which was about tech companies in New York. I grew that to a $12 million business a year with 100 employees or so. And then the dot-com crash happened. I lost everything, sold that company for a couple of years' salary to Dow Jones, which then bought me out of my contract after two weeks, which was very weird. Yeah, then I started Weblogs Inc. and Gadget Autoblog, sold that 18 months or so after starting it for $30 million. That was considered an amazing feat or accomplishment at the time. Then I started Mahalo, which became Inside, and started Angel Investing, this is Akoya Scout, and it all started going in that sort of certain direction. Really, as a journalist and a publisher, you ask questions, and you try to get to truth, or at least you used to. Now you kind of, we could talk about late stage journalism, but back in the day, original journalism, you were supposed to be independent, and just ask really honest, fair questions, get the answer, double check that your facts were correct, and publish a story, and not put a link baiting headline on it. So that's where I cut my teeth, and after doing that for a while, I realized it really is the same thing as interviewing somebody and meeting with somebody about an investment.