How to find an angel investor for small startups w/ Jason Calacanis

I'm excited to release this interview with Jason Calacanis during the launch of his new book, Angel: How to Invest in Technology Startups-Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000.

I've been a super fan of Jason since coming across his show This week in Startups when he produced it on set with black curtain backdrops and large wooden dining room tables. A lot of people give GaryVee credit for the foresight of thinking like a media company -- but Jason got to it first.

Behind the bravado is a kid from Brooklyn that worked his tail off to get to where he's at, challenged with lessons of success & failure weaved into the fabric of his story. Today, Jason leads Inside.com with the same burning passion to take on the big platforms as he did with his first startup, Silicon Alley Reporter. 

Sit back and enjoy this episode with Jason, as he walks us through the mind of an angel investor and how to start thinking scale in your small software business.

Listen the episode

Interview transcript

Hey, everybody. Welcome back to the Matt Report season five. We're winding down season five. In fact, folks who were listening, now you should have heard the last episode of season five. But I get a bonus episode with one of my favorite people on the internet, Jason Calacanis. Jason, welcome to the program.

Jason C.: Hey, thanks for having me.

Matt: Creator of Weblogs, Inc sold to AOL. Early investors in Uber, Thumbtack, created a company called Mahalo and fought Google at every turn and corner. Created another company that I originally found you through is This Week In, the sort of all the YouTube stuff and live video stuff you were doing. Now you're running Inside.com, news and entertainment delivered via email. I am a huge fan of that as well. You run LAUNCH Incubator and events, and now you've written the book, the book of angels as it were. It's angels-

Jason C.: Yes, of angels. I like that.

Matt: Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned 100 grand into 100 million buckaroos. Jason, welcome to the program again. Did I miss anything?

Jason C.: It's-

Matt: I probably did.

Jason C.: Probably. Well yeah, it's one of the great things about history is like people only remember the victories if you have them. Then they forget all the losses. But you brought up Mahalo, so that was great, my PTSD started triggering. Mahalo, we basically pivoted into Inside.com, so the story ended up well. But we're working like dogs, get a return for those Mahalo investors. I never give up. It's one of my either charming or stupid qualities depending on the situation that I never give up.

Matt: Obviously, want to talk about the book. For me, I'm not a super heavy book reader. I got it, I got an early copy. I did a little Jason Calacanis of my own, I just contacted your publishers. I sort of worked my way in through the backdoor and I said, "Hey, I'd love to talk to this guy."

Jason C.: Hustle.

Matt: I definitely want to talk about the book, but real quick. This Week In network, I mean god, you had This Week In Web Design, of course This Week In Startups. You had I think This Week In Movies as well. Do you think that you were just so early, like the technology wasn't there?

Jason C.: Yeah, for sure. What we did was we tried to do a network of shows seven years ago. It was a little experiment. Me and a couple of my friends put 100k in each. We got to the point where it was making some money and there were two breakout shows, Kevin Pollak's Chat Show and Th