CJR’s “Launch Pad” feature invites new media publishers to blog about their experiences on the news frontier. Past columns by Michael Andersen, founder of Portland Afoot, and Barry Johnson, who is at work on an arts journalism project, can be found here.

Michael Andersen: Hi, Barry. The two of us are finishing this stint at Launch Pad HQ after next week’s installment, but we didn’t think any discussion of entrepreneurship would be complete without talking about the twin engines of free enterprise: success and failure.

I read once that capitalism without failure is like religion without sin. As I got into this crazy endeavor, the idea of failure has definitely been lurking behind me, pushing me to work longer hours, write better copy, take smarter risks.

You left behind a much sweeter gig than I did to join the news-startup world. How have you approached the idea that everything might fall apart?

Barry Johnson: Like everyone else in the journalism biz, I’d been watching things devolve, and I had some ideas about it all that I wanted to test. I thought that it was going to become increasingly difficult for the big, general interest newspaper/TV news show to find readers/viewers because the information they delivered was so easily obtainable elsewhere, and they were failing to deliver the specialized information/analysis/commentary that the increasingly fractured public wanted, whether it was business news or in-depth arts criticism. So I wanted my newspaper to respond by turning itself into linked but discrete little businesses, each supported in different ways by different audiences and advertisers. Needless to say, no one thought that was a very good idea. But Oregon Arts Watch, which is still gestating, is a chance for me to conduct that experiment in a limited way.

The only way it would “fail” would be if I didn’t conduct the experiment in a rigorous and aggressive way. I want to know if this idea works or not. If it doesn’t, fine, I’ll move on to something else. But I thought this idea gave Portland its best chance to maintain and even extend its cultural journalism as it became more and more culturally complicated. I guess what I’m saying is that I didn’t really think in terms of the project itself succeeding, just whether or not the experiment was rigorously conducted.

Michael: An experiment The Oregonian wasn’t willing to conduct, because they had more to lose if they failed?

Barry: I’m not sure why, exactly, but I’m guessing that it was a far more aggressive response to the problems we faced than they thought necessary or that the newspaper culture in general was willing to consider. I think there’s still a residual feeling that somehow we’re going to get over this and things will get back to normal. I don’t think that’s the way the economy, the advertising world, and the culture are breaking, so I thought it prudent for someone to try a different approach.

Michael: I totally agree with your read on the marketplace.
Back when people were warning me not to quit my day job, I seriously considered taking the template to my mid-size suburban daily’s publisher and suggesting that they give me my $33,500 annual salary to use however I liked. I’d cut my pay to $20k, launch a business with the difference, and let the Campbell family take home any money we could make off the enterprise.

I decided against this for two reasons: One, I didn’t think they’d give me creative control, which I knew I wanted; and two, I didn’t think I would do a good job if I knew I could easily fall back on my old one. Again, I thought I needed the failure.

Barry: Maybe not the failure, [but] the possibility of failure, right? As a spur?

Michael: Exactly.

Barry: How does it feel to own the possibility of failure? I’m betting it feels better than watching others decide your fate for you…

Michael: I guess I don’t feel qualified to answer yet—hopefully neither of us will be! Which brings us to the flip side: success. You posed a smart question when we were planning this debate. What does “success” even mean? What would it look like?

Michael Andersen and Barry Johnson are news entrepreneurs in Portland, Oregon.