Special Episode: Jason Calacanis

**Jason Calacanis** (0:00)
Let me just make a little ad here. Hi, this is Jason Calacanis for Acquired.fm. Is that the domain name, Acquired.fm?

**Ben Gilbert** (0:06)
That is it.

**Jason Calacanis** (0:07)
All right, listen. You're listening to this. You're either a founder, an aspiring founder, an investor or an aspiring investor. For $100 a year, you're gonna get hours of content that's not available to everybody else. That's also known as an edge. You are in a competition with other investors, you're in a competition with other founders. You need an edge.
If I could tell you, you get one, two, three good insights a year, even one, would you pay $100 for an amazing insight that gave you an edge against your competitors? Of course you would, you'd pay $10,000. So why wouldn't you pay 100? Because it's content, you're thinking about it the wrong way. The LP program at Acquired.fm is not, it's not content, it's an edge. And it's an underpriced edge. So buy it for 100 now, before they raise the price to what it should be, which is 5,000 a year. This is Jason Calacanis, Acquired.fm.

**David Rosenthal** (0:59)
See you in the slack.

**Jason Calacanis** (1:01)
How's that for an ad, huh?

**David Rosenthal** (1:03)
You can have that. Mike, can you actually take your mic out of the stand?

**Jason Calacanis** (1:07)
You can literally have my ad.

**Ben Gilbert** (1:08)
I swear we did not ask him to do that, everyone.

**David Rosenthal** (1:10)
No, I just loved doing ads.

**Jason Calacanis** (1:11)
Thank you.

**Ben Gilbert** (1:23)
Welcome to this special episode of Acquired, the podcast about great technology companies and the stories behind them. I'm Ben Gilbert.

**David Rosenthal** (1:32)
David Rosenthal.

**Ben Gilbert** (1:33)
And we are your hosts.

**David Rosenthal** (1:35)
Acquired is all about stories. Ordinarily, we tell the story of a great technology company or a great leader or a great adaptation. Today, we are telling the story of someone who doesn't just have one story, he has a whole anthology across all of those categories, the one and only Jason Calacanis. So, just to give our audience a small sampling of all of the enterprises that Jason has started and is involved with across his career.

**Ben Gilbert** (2:02)
Yeah, David, I bet you can't do this all in one breath.

**David Rosenthal** (2:05)
No, no. Jason has founded four companies by our account, Silicon Valley Reporter, Weblogs, Mahalo and inside.com. Do we miss any?

**Jason Calacanis** (2:16)
No, those are them. Those are the four. And inside.com is the same captive which is the pivot of Mahalo, so arguably one.

**David Rosenthal** (2:22)
Did not know that.

**Jason Calacanis** (2:22)
People don't know that.

**David Rosenthal** (2:23)
We'll get into that. Three conferences, three podcasts, Angel, All In, and of course, This Week in Startups, which is now over 1,000 episodes. The YouTube channel around all of those, you were the first Sequoia Scout. You were literally the prototype of the Sequoia Scout.

**Jason Calacanis** (2:38)
Correct, and still the greatest returner.

**David Rosenthal** (2:41)
And still the greatest returner.

**Ben Gilbert** (2:42)
But who's counting?

**Jason Calacanis** (2:43)
It's not a competition, but I won.

**David Rosenthal** (2:46)
Maybe some time might have something to do with it. Well, anyway, we'll get into that. You've made over 200 angel investments in your career. You're a blogger, you're an author, you have a newsletter, you started the Launch Accelerator, the Venture Fund around that, the Syndicate around that. You are the self-provest. We have you on record as saying you are the either third or fourth best angel investor of all time.

**Jason Calacanis** (3:07)
For sure, yeah.

**David Rosenthal** (3:08)
We'll get into that.

**Jason Calacanis** (3:08)
For sure, Mount Rushmore. Chris Sokka, Ron Conway, obviously ahead of me, and then there's a bunch of people. Nobody knows who did incredible angel investments in Google and Apple, but they don't have like, they don't feel the necessity to put it on the cover of a book like I did.

**David Rosenthal** (3:26)
Speaking of, quote that we want to wrap this up with from your book. Most folks think I'm lucky. Some say I'm a complete fraud, and a handful think I'm a brilliant hype man. I don't agree with any of them. I agree with all of them. Jason Calacanis, welcome to the show.

**Jason Calacanis** (3:41)
Big fan of the show. Thanks for having me on, and David, thank you for doing that intro because your voice is so much better than Ben's. That is a radio voice you have, David. It's so soothing, and Ben and I are just like scratchy records, but Ben's got good insights, so I'm glad to be here. I'm a big fan of your podcast.