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

Download file | Play in new window | Duration: 00:44:23

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 Thi...