In Episode 19 of Startup School Radio,
a podcast that features stories and practical advice about starting,
funding, and scaling companies, our host Aaron Harris first sat down with Tyler Bosmeny, who talked about his experience going from the Harvard math department to co-founding education-oriented API platform Clever (YC S12). In the second half of the episode, Aaron interviewed Jason Freedman, who has co-founded two Y Combinator-backed companies: Flightcaster, which launched out of YC’s Summer 2009 class, and 42Floors, which launched out of YC’s Winter 2012 class.

You can listen to the episode on Soundcloud here, and iTunes here.

One interesting part of Jason Freedman’s interview is where he talked about how all of his startups have been born out of a problem that he had personally encountered, rather than from a desire to “start a company”:

Aaron: And the funny thing is, each of the ideas you’ve worked on, they weren’t things that you’d written down in a notebook somewhere that you were going to do at some point in life. It’s just ‘Hey, I just realized that this problem exists. Let me go fix this.’

Jason: You know, when you think of a startup career, I don’t have a startup career. What I’ve had is a succession of problems that have found their way into my life, and that I decided that I could figure out a way to solve.

Aaron: Yeah, it’s interesting, because from what we’ve seen, that tends to be the places where the best startups get started. It’s not the person going out and looking for a business to start or looking for a problem set that exists and to go create a startup against it. It’s, ‘Oh, wait, I’ve actually seen this. This doesn’t make sense. It’s in my life, let me fix it.’ Because you have so much depth of understanding and so much experience.

Jason: With 42Floors, we’re trying to make it easy for people to search for commercial real estate, and if I had started a startup to do that, I would’ve thought it would never work because it’s going to be way too hard and I didn’t really understand anything about commercial real estate. But solving a problem for myself, that I could figure out.

Aaron: It’s interesting how sometimes ignorance is the thing that actually lets you drive and start something.