11 Lessons Learned Launching Contextly on My Final Day at Wired

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What happens when you press this button? Credit: StevenDPolo/Flickr

Friday was my last day of work at Wired as a full-time writer and the editor of Threat Level. It was also the public launch of my editorial tools startup Contextly.

It turns out doing both *on the same day* is a potent combination, emotionally and logistically. I don’t recommend that anyone emulate it – unless, as in my case, it’s the best way to launch.

Contextly, whose current products help publishers increase page-views and time-on-site via related links and sidebars, got nice write-ups in TechCrunch, VentureBeat, The Next Web and Wired (yes, a little unfair there). I heard from a number of fantastic people via e-mail and Twitter, wishing me well. The launch led to a solid number of publishers signing up for our beta; headhunters calling; and in a fit of bad timing, unrelated to the publicity, I got a partnership inquiry I’d been hoping for for weeks.

That made for a crazy morning and day, trying to respond to all of them, while, at the same time, saying goodbye to colleagues and finishing out the day’s work, including editing articles that needed to be published that day.

Here’s what I learned (so far) from the day:

1. You’ll Always Be Behind: Wired publishes its morning update stories at 6:30 am EST. So I set the embargo on other publications to that same time. Unfortunately, that meant that the stories about Contextly would be published at 3:30 a.m. my time in San Francisco. I was up late with final work before the launch, so when I got up and online at 6 a.m., there were already a lot of e-mails and Tweets to deal with, before getting to the morning editorial meeting at Wired for the final time.

I think it’s a good lesson – there’s always going to be more than you can handle and you triage as best you can.

2. Connections Matter and People Want to Help: Many of the good wishes I got from friends, sources and colleagues I met over the last 10 years at Wired extended warm and useful offers. I now have a slew of coffee and beer get-togethers scheduled with entrepreneurs who are way ahead of me — and folks in D.C. and N.Y.C. that I’ll meet with when I get out there next. Some of these have been people that have known about Contextly for months; others just heard about it.

Find people you like and respect and stay in touch with them, even just on social networks. Be interested in what they do – you’ll make friends and learn things, which is much better on so many levels than just trying to connect with someone you think will be useful someday.

3. Semi-Stealth Works: Contextly has been in development for a while with a small team. I didn’t mention it on social networks and never tried to get publicity for it. But I did talk with publishers and other entrepreneurs about it, and we were hidden in plain site at the bottom of stories at a number of publications including Wired and Cult of Mac.

Why stealth? Contextly is competing with some very established companies, at least one with tens of millions in funding. Keeping a low-profile from them has been strategic valuable for a B2B company. It also helped with getting press, as the story and company were fresh. Surprise and secrecy can be great assets.

Don’t set strategy based on posts on Hacker News that proclaim that stealth is stupid — figure out what works for your situation.

4. Storytelling Matters: Though I have connections with the outlets that wrote about Contextly from my time as a writer, the process of getting coverage was *not* about calling in favors. I can’t emphasize that enough.

The story I pitched was very clear – a tech journalist is leaving to start a start-up. My twist is that I was leaving to make better journalism tools. There’s been quite a few of these, including Burt Herman of Storify used to be an AP reporter and Marshall Kirkpatrick of ReadWriteWeb is now running Little Bird. That was the story I pitched — not ‘Hey, do you want to write about how our related links widget is better than that other one’. That’s boring — the leaving story has some drama and surprise in it.

Getting press for features works when you are Dropbox or Facebook – but if you are a young company, you should be telling a compelling story if you want press.

5. You Can’t Control the News Cycle: Just a few hours after the stories about Contextly and my leaving appeared, Wired had an impromptu all-hands meeting, where Chris Anderson, the editor of Wired, announced to a shocked crowd that he was leaving to take over as CEO of his startup 3-D Robotics. Now that’s a story with drama. Chris Anderson is a marquee name and led Wired magazine for almost 11 years.

After getting over the shock, I first worried that my story would be overshadowed — but luckily, I’d been first by a good 7 hours.

And then I realized it was great – I was almost part of a trend story (by rule of thumb, it takes three to make a trend story). With luck, I’d get mentioned in the stories about Chris Anderson’s departure.

That happened – TechCrunch mentioned Contextly in its story on Chris Anderson, linking back to its earlier story. So two mentions on TechCrunch in a single day. And the Atlantic Wire even ran with a two-Wired-editors-leave-in-a-day story, with my picture next to his.

That was sheer luck. Chris Anderson’s departure was top-secret, until that morning. I’d originally planned to leave on Wednesday, thinking that would be a better news day than a Friday. But on Monday, I pushed it off until Friday, in part just so I wouldn’t have to make a special trip back in to Wired on Thursday for my goodbye party.

And, just as a sidenote, the sites that wrote about both departures could have easily linked their related stories, if they’d been using Contextly.

6. Be a Source, Not a Supplicant: There was no news restrictions on Chris Anderson’s announcement. I knew it was big news, so I immediately reached out to a couple of journalists to share the info – nothing more than what would go out in a press release. I didn’t push to be included in the story – though I had hopes Contextly would get mentioned.

The point was to be someone who can be relied on for info, NOT to store up karma to be able to call in favors for coverage later. You just want your emails to be opened and your calls to be taken when you have a story to GIVE to a reporter. You want to build up your credibility and relationships. I can’t say it enough, but it’s never about banking favors to call them in later.

You likely know more than you think you do – and you can help reporters understand the world. For instance, in June, Paul Graham wrote that startup funding and valuations were going to become very tough. Well it’s been five months. Any company that’s fundraised since then has great info to share. How tough was it? Did investors push back on valuations? What metrics seemed key? If you can coordinate with a couple of other recently funded companies, and one that raised before then, you could pitch an AWESOME story to a reporter (find one who covers the VC community and wrote about PG’s letter.). It’s not going to focus on your company, but you will get mentioned.

And even better, you are helping others understand the world, while building up your credibility as a source and a person to talk to.

7. Prepare More: I didn’t prepare nearly as well as I could have before launch. I created lists of people I wanted to contact by e-mail to tell them personally about the new adventure – people who I’d known well and those who were supportive early on when Contextly was just a gleam and some rough code.

I should have pre-written individually ahead of time, and used something like Boomerang to time them. I probably should have scheduled Tweets and had enough done so that I could have been up at the time we actually announced.

Instead I ended up sending a set of impersonal mass e-mails and then when people responded, I replied with something personal. That was okay, but not ideal.

One thing I did do right was to have a pre-written draft blog post that I shared with reporters, along with screen shots and a head shot. You want to make it easy for people to write about you.

There are other things that should have been done ahead of time, but you get the point.

8. Have a Great Team: The Contextly crew is small, but dedicated. We rebuilt our API and our WordPress plugin over the last month or so, and I ran into an odd bug Thursday that had to be fixed by launch. I went to sleep Thursday night, and it was fixed by the time I got up. I’m lucky to work with a team that loves the challenge and loves building tools that millions of readers a day will see.

I also had amazing support from my family, who encouraged me to pursue my dream, rather than trying to persuade me to stay with the guaranteed paycheck. Evan Hansen, the editor of Wired.com, has also been invaluable in supporting Contextly and providing advice — even though doing so meant losing an employee.

9. Leaving A Day Job is Hard But Leaving Can Be Right: Wired is filled with smart, dedicated and perfectly cynical journalists, and it’s hard to emphasize enough how much they taught me and how rewarding it was to be part of that team.

That job shaped me and my identity, so leaving — not just there, but also the profession — was deeply sad and really emotional for me. Even the morning bike commute Friday felt special; seeing the Bay Bridge framed from atop a narrow hilly street and passing a cable car – something I’ve done for years and often failed to appreciate.

But it was also time — perhaps past time. I’d been stretching myself thin balancing Contextly and Wired, and for Contextly to bloom, it needs my full-time attention. For instance, scheduling calls with publications before work hours or during lunch is pretty tough — especially since news can break at any time and you are forcing clients onto your schedule.

The ride home Friday wasn’t full of exhilaration from throwing off shackles, but it felt right and purposeful.

10. Health care is Sadly Still an Issue: I ran into Chris Anderson in the supply room Friday afternoon as I was throwing old expenses reports into the shredder bin, and he wisely asked, “What are you doing about health care?”

The answer for now is COBRA, but that’s going to be very expensive. Applying for private insurance is an awful experience that makes you feel like a bad person for seeing the doctor when you’d gotten sick or hurting yourself while playing a sport. We’re bootstrapping – by choice – but we quickly need to get to a place where we can join a healthcare cooperative.

It is my single biggest monetary fear about starting a start-up. I’ve no doubt I can make enough money to pay my rent and live cheaply — but not being able to afford decent insurance could lead to devastating, long-term financial problems. I know there’s no easy solution and this isn’t intended to be political, but it’s a real problem, and not just for aspiring startup founders.

11. There’s A Lot to Do: Launch day was fun and exciting, but it hopefully just leaves you with more to-do. There are potential customers to talk with, blog posts to write, features to spec and build, potential partnerships to explore, bugs to crush, and roadmap decisions to be made.

When a co-worker at Wired asked on Friday what I’d be doing come Monday morning, I tried to explain but ended up sounding like I’d be having leisurely days working from cafes. But I know the answer really should have been “More than I think I can do.”

I’m sure there’s much more to be learned from launch day as I’m still overwhelmed by it, but hopefully there’s a sliver of wisdom in here that will be useful for other founders.

If you are a publication, a company or a startup with a blog, you should give Contextly a try – we are making online publishing better for writers, readers and publishers, big and small.

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