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.

Barry Johnson: Today’s discussion is about basic hurdle-clearing. That’s more for you, I think, because my project is still trying to reach escape velocity. I’m still all about testing the power of the rocket and its essential flightworthiness (I’m obviously a sucker for any metaphor from my Space Age childhood, such as “Launch Pad,” say!). Maybe we could start with a little exchange on the environment we are attempting to work within, though, because that’s a hurdle of sorts—and also an encouragement sometimes.

So, what do you think? Is Portland, Oregon, a good place to start non-profit journalism projects, and what special problems does it present?

Michael Andersen: I think the “hurdle” metaphor was mine, and it fits; you’ve been making NASA-quality preparations and I just decided to start sprinting.

With its mass transit and biking culture, I think Portland’s perfect for my transportation beat, at least. In Dallas or Seattle, money might be easier to find, but I’d probably have picked a different audience!

Do you pine for the wealthy corporate patrons that Portland lacks? Sometimes I do.

Barry: Well, our unemployment rate is quite high, that’s for sure, and we don’t have many Fortune 500 companies to tickle for money here. Our level of corporate philanthropy is low, therefore, and in the arts, which is where I operate, government support is very low, in the last decile, depending on what study you read.

Michael: That sounds like part of your pitch. All the more reason people should give you money, right?

Barry: Well, yes! Instead of trying to find money from a couple of big donors/corporations I’m trying to test the proposition that a lot of people giving a little can be enough to start and sustain a small, independent arts journalism group.

I’d describe Portland as relatively “transportation conscious”—is that what you’re finding? (Oh, and by the way, Seattle recently opened a light rail line to Sea-Tac airport!)

Michael: About time. Portland is definitely a town where rich and powerful people “get” the low-car concept, and that’s been useful.

I’d like to move on to some technical stuff, but is there any other wisdom you’ve picked up about working within a particular city’s culture?

Barry: I think Portland is a bootstrap sort of city. We seem to want big things to happen through hard work, not big investments. Sometimes that means we are so preoccupied with our own heavy lifting that it’s difficult to consider something new. And maybe the trick for a new journalism project proposal is to show how your existence will help them lift. Now, Mr. Science, let’s get technical!

Michael: Awesome. Mostly I just want to rattle through all the good, cheap software and web services I’ve found for this gig.

Barry: Useful! Like what?

Michael: To start with, there’s Google Apps for email and document sharing, OpenX OnRamp to serve ads, Mint to track expenses, e-Junkie to manage my shopping cart, PayPal Website Payments Standard and the amazing Square to process credit cards, Google Analytics and Quantcast to analyze web traffic, VerticalResponse to manage e-mail lists, Skype to make phone calls and Carbonite to back up files. That’s all in the cloud, and half of them are free at the basic level.

I also looked into using Recurly to auto-bill subscribers, but decided against it. And Mobify automatically renders your website for mobile platforms, but I haven’t set that up yet.

Then there’s downloadable software: OpenOffice for word and data processing, BambooInvoice for billings, Inkscape for graphics, GIMP for photo editing, Scribus (which I actually dislike, but the price is right) for desktop publishing, FileZilla for uploading files to the website, Notepad++ for editing web pages and Postage $aver for sorting my bulk mailings.

For managing content on the site itself, our designer stitched together the indispensable Wordpress (for the blog) and the flawed but powerful MediaWiki (for the wiki).

Barry: Sweet. But don’t you need an advanced degree in Geek to set these things up? And do you have the world’s biggest laptop? And how much of an investment have you made to date in software?

Michael: $29.50. It’s all open-source except the postage program. As a 501(c)3, we’re also eligible for discount software via TechSoup, but I actually don’t think it’s worth spending $24 for Microsoft Office these days.

As for the geekery, I think it’s mostly a matter of tracking down the right acquaintance. Any smart person (or even me) can figure out the basics of this stuff in half an hour with the right person on call to help.

Barry: $29.50? That’s highway robbery! And “smart person”—gulp.

Michael: Honestly, looking over the list above, the only applications that require any technical expertise (as opposed to patience reading the instructions) to set up are BambooInvoice, FileZilla, MediaWiki, and maybe e-Junkie. There’s never been a better time to start a company on the cheap.

Barry: I think you can write a “Dummy’s Guide to Starting Your Own Journalism Business” and live off the proceeds for the rest of your life. Did you have a “technical advisor” among your volunteers?

Michael: You’re on to my secret business plan.

The president of our board is a software engineer, so he literally has that advanced Geek degree. He’s been a big help during a few moments of panic. I was also fortunate to have spent a year as the online editor for a small daily paper, where resources were similarly scarce but there was an IT director willing to tutor me on this stuff.

Barry: How do you manage the transition from reporter or ad salesman to IT/web designer jockey? We’re used to thinking of these as specialized skills.

Michael: I came into this knowing design was a skill I don’t have. Portland Afoot’s biggest up-front expense was actually $2,400 to hire a gifted acquaintance to lay out the site and the print prototype. Once I had the templates, I was comfortable hacking at them. If a new company valued its founders’ time more than I’ve valued mine, it’d probably be more efficient to keep one or two trusted contractors on call.

What do you see as your biggest obstacle, technically?

Barry: My biggest concern is to come up with a really good membership management tool and then a great email service that will enable me to send those members eNewsletters that look great and that I can send to specific slices of the membership. Then it’s the content management systems—because I want to do audio journalism good enough for public broadcasting, for example, and video that’s television worthy. Fortunately, I’ll be working with other journalists who specialize in that technology. But some of what you’ve talked about—accounting and other business software—is absolutely critical, too. Each of the areas we are trying to “cover”—from admin to marketing—has its own set of specialized tools that we have to deal with, one way or another. All of them are obstacles.

Have we used up our allotted space? Time for re-entry from this high Earth-orbit? What will you be doing this week? And what are we slated to talk about next time?

Michael: Grab that parachute cord. Next week’s topic is “success”—how we’re defining it, and also the consequences of failure.

Once I get this month’s PDF to the printer (just a couple hours, Charles! I swear) I’m actually spending the week on freelance. I finally seem to be getting some traction as a transportation-reporter-for-hire, which is useful for paying my rent. What’s your mission?

Barry: Coincidentally, I’ll be working on a freelance gig, too. I also have a couple of meetings with potential arts group partners, and some more pesky stuff I’m labeling “admin.” Did I mention the vat of turkey broth? See you next week?

Michael: Aye aye, cap’n. Or whatever you astronauts say.

Barry Johnson has written about the arts since 1978, when he started writing about dance for the now-defunct Seattle Sun. He has edited arts sections at Willamette Week and The Oregonian, and recently finished a twenty-six-year stint at the latter by writing a general arts and culture column. You can find his up-to-the-minute thoughts on the arts at http://artsdispatch.blogspot.com. Michael Andersen publishes Portland Afoot, a ten-minute newsmagazine and wiki about low-car life in Portland, Oregon. He also writes about entrepreneurial local journalism on NiemanLab.org, oldforestnewtrees.com, and Twitter.

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