That'd be a great point if I hadn't started Windy Citizen with $3k to my name and $100k in student debt. I moved into subsidized housing in Chicago so I could save money.

> I moved into subsidized housing in Chicago so I could save money.

Not sure how I feel about that. Section 8 is supposed to help people who are struggling, not subsidize early-stage startups.

I guess it's probably a net gain for the economy, but you should strongly consider giving back and donating some of your money to groups that help underprivileged families in Chicago.

He had 3k to his name and 100k in debt. That's not struggling?

Honestly? No. That's just being a fresh grad from Princeton.

If you're in a position where you could easily go get a high paying job, but instead you choose to go on public assistance so you can focus on your startup, I'm not sure why I as a taxpayer should be subsidizing that.

Because as you said yourself it's a net gain for the economy, a good investment. By now he'll have paid back many times more in taxes than he took in those early days. Hell, one of the arguments in favor of having some kind of social welfare safety net is that it encourages people to be entrepreneurs instead of just staying with the safest job they can find.

I would sure as hell rather subsidize a startup entrepreneur than the people who would, statistically speaking, otherwise be occupying that Section 8 housing unit. Does that make me a bad person? So be it.

Were you a solo-founder when you started it? How did you build your team and find a cofounder?

I was more or less a solo founder. It took me 4 years to find a proper co-founder. I had to fire my first co-founder and my second co-founder. I had to generate significant revenue and traction before my current co-founder felt secure enough to leave his job and join up.