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Our entrepreneurial adventure started six days ago in a brick building in Pioneer Square.  It was an appropriate setting to kick off GeekWire, since hundreds (if not thousands) of startup companies have launched their new businesses from this historic Seattle neighborhood.

But this time, it was different. We were taking the plunge.

We’ve decided to provide an occasional inside look at what’s going on behind the scenes at GeekWire, detailing the high and low points that we encounter as newbie entrepreneurs building an upstart media company.

Maybe there will be something to learn from our successes and failures. Maybe not.

This is the first installment in the series. We hope you’ll come along for the ride.

Making Changes on the Fly

Our entrepreneurial submersion officially started at 9 a.m. Monday, March 7, in the offices of Foundry Interactive, our very capable Web development shop. Foundry’s Bill Nordwall and the rest of the crew had spent the weekend prepping the site, making sure that the back-end plumbing was in place to handle a mid-morning launch.

Bill Nordwall works on GeekWire

It ended up being an important decision to get the new site — built on WordPress — launched quickly. But that wasn’t the original game plan.

We had intended to start with a pretty rudimentary splash page, allowing readers to sign up for our email newsletter, Twitter account and the GeekWire Facebook page.

But we scrapped that idea as we saw the actual come together quickly over the weekend — realizing it would be better to come out of the gate with a fully baked Web site where we could share our story, engage with the community and immediately start covering the tech news of the day. (“There’s just one chance to latch onto readers…” was the sage advice we got from more than one of our friends).

This strategy took more development horsepower, and some critical coordination on the back-end between Foundry and our hosting provider, Blue Box Group, over the weekend. Essentially we had to build a professional site in 72 hours, something that would have been impossible just five or 10 years ago. Todd and I also had to hustle to get some editorial content to fill the new site, including stories from the Emerald City Comicon convention. It was a busy weekend to say the least.

In retrospect, I’d say this was the most important decision we made in launching GeekWire.

Entrepreneurial lesson #1: Be nimble. Be quick. And don’t be afraid to change course at the last minute.

Oh Crap, We Just Launched, Now What?

With the WordPress installation complete and the site ready to go, all we had to do was push a button and GeekWire was born. I sat at Bill Nordwall’s computer, waiting for the green light. Our first setback was averted as Bill told me which button to push.

“Alright, go for it,” he said.

The site went live at about 9:30 a.m. Monday, but we decided to wait a little bit to tell the world about GeekWire.

The reason? We technically weren’t a business yet.

We had received our certificate of formation, but there were still some loose ends to tie up related to the business, including a legal document known as the LLC operating agreement.

Craig Sherman and David Wickwire of WSGR explain some last minute details to Todd Bishop, co-founder of GeekWire

From the depths of Pioneer Square, we voyaged to the tallest skyscraper in Seattle to huddle with our attorneys at Wilson Sonsini Goodrich & Rosati for a 10 a.m. meeting.

Now, I am a fast walker (Todd is often pleading with me to slow down).  But, even by my standards, I flew up the hill. By the time I arrived at the Columbia Tower, I was winded and sweating. I decided to take a breath, grab a glass of water and wait for our attorneys to arrive.

I logged onto the WiFi and started to make a purchase of a domain name that we’d forgotten to secure, (corresponding to our Twitter handle; more on that later). Realizing that I wasn’t going to have enough time to make the purchase, I e-mailed Bill Nordwall at Foundry and asked if he could buy it for me.

“Done,” he said.

The signing took about 20 minutes, and went off without a hitch. (This part of the day is kind of a blur).

We returned to the Foundry Offices to start our social media and PR campaign. (I actually jumped out of Todd’s car at a stop light on the way there, thinking I could walk faster than the vehicle could move).

I did beat Todd to the office, but my hyperactive mentality was not doing anyone any good. I cursed my new computer when I couldn’t log into (Why didn’t I load up all of my new passwords beforehand for the services I’d be using?)

Half-crazed, I ran around the office looking for the best spot to pick up the Wi-Fi signal.

Simultaneously, I caught Todd’s glance — and, because we’ve worked together long enough — I immediately knew I’d stepped over the freak line. (My wife encountered this earlier in the morning when I melted down because I couldn’t find two matching socks to wear.)

I needed to slow down. Breathe. Think. Plan.

We had created a list of things to accomplish on launch day, and I turned to that in order to make sure everything was getting done. Thankfully, the site was performing well, and there were only a few minor glitches that Bill quickly fixed.

Nonetheless, there were times during that first day when I felt like a deer in the headlights. There was so much coming at us (media requests, business formation questions, Web development issues, editorial decisions, advertising inquiries) that an uncomfortable paralysis hit. (It didn’t help that I forgot to turn off the email alert in Twitter, which notified me every time a new follower joined @geekwirenews).

The paralysis was not unlike that horrible feeling of writer’s block, something any journalist has encountered during his or her career. Thankfully, I’ve dealt with this before.

I fell back on some advice that my mom — a former journalist herself — once gave me: “Just get something down on paper.”

We had to do the equivalent, just knocking off task after task.

This paralysis has hit a few times during the week, and it’s something I am sure most entrepreneurs have dealt with at some point. How do you prioritize when you’re juggling 100 things? (I’d love to hear your tips.)

Entrepreneurial lesson #2: Relax. Think. Execute. And rely on a trusted co-founder to help identify and root out unproductive behavior.

It’s All About the Community

As the day continued, we were humbled, emboldened and energized by the reaction from the technology community. That’s you, our readers.

More than 100 people commented on the initial launch post, most wishing us well in the new venture. Our Facebook page exceeded our wildest expectations, finishing the week at more than 1,000 followers. And we got our first stories picked up on TechMeme and Slashdot, the massive technology news aggregation sites. (Here are the stores in case you missed them: “Microsoft idea: Dating service for people with a ‘source of shame’ … like comic books.”; and “Microsoft seeks to toss Apple ‘App Store’ brief, says font too small“.)

This is just the start.

Todd and I are in our best form when we can focus on journalism, delivering hard-hitting or fun stories that we think the community will want to read. And by mid-week we were starting to hit our groove again, with a critical look at the new “King of the Web” venture; news of a Seattle techie’s involvement in an Ashton Kutcher-backed startup; and our “person on the street” interviews with Apple fanboys and gals waiting in line to buy the iPad 2.

The platform was humming and our editorial juices were flowing. It felt good to be in business, with only ourselves to blame if things went wrong.

Entrepreneurial lesson #3: Tap existing communities and networks to help spread the word, and quickly get back to the core part of the business that you love.

Setbacks and Disappointments

All things considered, we couldn’t have been more happy with our first week. But there were some disappointments, too. In addition to the entrepreneurial paralysis that I mentioned above, one of the most notable issues involved Twitter, the platform we use to help spread content to the masses.

Long line at the Apple store. A missed opportunity

Despite applying for a trademark for the GeekWire name, we’ve been unsuccessful so far in obtaining the @geekwire Twitter account. (The user of the account has never posted a message, that we can tell, and our attempts to get in touch with her haven’t yet worked). We’re still hoping we can secure that, but at this point — despite our attempts — it is looking like a dead end.

I am perfectly happy using @geekwirenews, but from a branding perspective it would have been nice to nail down the other account.

We’ve also missed some pretty nice marketing and branding opportunities, an important factor for any new media business. The biggest occurred on Friday as we were covering the launch of the iPad 2.

Basically, we need business cards. That might sound silly in this high-tech age.

But with hundreds of geeks lined up around the Apple store at the University Village, most just sitting there with nothing better to do, we could have started to spread the gospel of GeekWire and given them a physical reminder to check the site when they got home.

We considered running over to Kinko’s at the last minute to print off some flyers, but decided it was better to just focus on the story. There will be other branding opportunities to come, and we’re not going to miss out on those.

Entrepreneurial lesson #4: Mistakes and setbacks happen. Learn from them, and move on, quickly.

We’ve been working hard over the weekend to catch up with email and line up stories for the week ahead. We’re focusing, as well, on advertising and sponsorship for the site. And we’ve got some exciting news of our own in store. It all should make for an interesting story for GeekWire Week #2.

Thanks again to everyone for tuning in, and for joining the GeekWire community.

John Cook is co-founder of GeekWire. This is an occasional look at what’s going on behind the scenes at the new technology news site. You can follow us on Twitter: @geekwirenews.

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