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Three Years at 10up: The Untold Stories

Yesterday marked my three year anniversary at 10up. I joined as the team’s first Senior Web Strategist, recruited to support both new business development and project execution for a then scrappy team of 5 full timers (including me) and a few specialized freelancers. Today I oversee project delivery and drive organizational planning for a team of 90 (and growing) web professionals representing a spectrum of talent from design to UX to monetization strategy to enterprise-class engineering.

It’s been an intense, unpredictable, fulfilling journey that’s given me the opportunity to grow not only as a professional, but as a person. With the support of a top-notch team, and a boss who’s given me the leeway to learn, I’ve worked with dozens of clients to design and build publishing systems, engaging interactive content experiences, and sustainable business solutions / processes that affect the bottom line in real ways. You can read about most of this on our website or in a transcript of one of Jake’s business talks. As special as it is, this story feels a little tired and too shiny, maybe even “done” in the preteen apathetic sense. Definitely not OG, as Helen would say. So instead of going on about where I (we) are, I’ll take you back to a few of the places I’ve (we’ve) been and reintroduce you to the special ones that helped me (us) along the way…

What do you mean you thought the background color would change once we went live?

This is a real thing I said just days before Helen and I launched one of our first websites together. Even though she’s not a designer, Helen graciously “fixed” the background while talking me off the ledge for probably (definitely) the 12th time that week. A few days later I stayed up the entire night before launch, watching the site with an irrational fear that if I didn’t something would fucking break again. There was really only so much Helen could do for me back then.

Jer-Bear and Dr. Tollman

Known to most of you as Jeremy Felt and Zack Tollman. These two taught me everything I know about how things are made on the internet with WordPress (Sorry, Helen, but you know we were usually talking about much less productive shit back then). I will be eternally grateful for the deliberate and patient explanations you gave me about all the things, reassuring me that questions were good and I should always ask them. You made me look awesome in that first year when I’m sure I was at least (mostly) mediocre, covering my ass on countless occasions and teaching me that no migration is simple, particularly the people ones.

Have a sec? / Go to bed, Carl…. Seriously though.

The Carl Danley introduced himself to me outside the WordCamp Miami after party in 2012. I have no memory of this, but apparently it happened. Jake had lunch with him the next day and he was our 8th full time employee a couple of weeks later. Legend goes that he stayed up the entire night before that lunch engineering his first WordPress plugin. The kid was a different kind of hungry. For about two years I had the privilege of watching Carl’s brain work. At least once a day I’d receive this Skype ping — Have a sec? — followed by an immediate Skype voice call and screen share of something insane (out of scope) he’d been toiling on for a client project. It was hard to contain that kind of raw talent and it always felt a bit wrong for even trying. But seriously, he needs sleep! Carl, if you’re reading this, go to bed right now.

And he has flowing locks…

This was how I first described Vasken Hauri to a fellow 10up leadership member after interviewing him for a Director of Engineering position. I’m a real asshole, guys. But this guy, he really gets it. His appreciation for and mastery of data-driven decision making is the daily slap in the face this manic, at times process-averse, (recovering) project manager needs. Vasken challenges me to prove my instincts, articulate them into processes, and trust others to succeed within them. I’m not great at being wrong, but he’s made me better at it. Oh, and for an entire year he forwarded me, tweeted me, and otherwise harassed me with materials that emphasized my childlike appearance / behavior.

Classic Moments from All Company Meetups

  • Where’s Jess? / She’ll be here.
  • Miss, you’re going to need to quiet down… / Jess, seriously, you’re so loud…
  • Cards Against Humanity
  • Zach Brown tries (is forced) to keep up with Jess. Hilarity ensues.
  • Did he just throw up on those people?
  • Tours of the Vegas Strip from Grant Landram
  • Screaming inappropriately during any competitive activity
  • Cigars
  • Dancing in the streets of Portland
  • Okay, I’m just going to make a decision.

Trekking the Country with Jake

  • in my 1995 Toyota Celica
  • on a Southwest flight
  • on a train
  • through a red light
  • running late
  • making plans
  • finalizing presentations
  • laughing

Here’s looking forward to another 3 years, a few hundred more 10uppers (Do you hear me, Paul?!), and even more stories along the way.

A Wondrous GIF Shows the Most Popular Baby Names for Girls Since 1960 — The Atlantic

Such a great example of using color to effectively communicate trends. And, yes, Jessica was the most popular name in the US when I was born.


Turning Points

In life you rarely see turning points coming. There are no cautionary yellow signs with bold markers alerting you to what lies ahead. The signs are subtle and chances are you’ll be oblivious to them until you take the unmarked exit off the freeway of status quo, changing direction forever.

Taking the turn feels different for everyone. Some of us cruise through life at a moderate pace, easily decelerating to calibrate for the exit’s change in direction, then accelerating quickly on the path forward. Some of us live in the fast lane, barreling forward until we notice the exit, sliding over 4 lanes to make it, and then jacking on the brakes to avoid smashing into the guard rail.

The last two years have been the longest off ramp of my life. A relationship, five moves, three hairstyles, a new job, two bad habits, and four pant sizes later, I’m finally starting to reach for the gas pedal again. Sure, I’m a bit scratched up from the guard rail, but the engine still runs, the paint looks decent, and the merge hasn’t been as big of a bitch as the turn.


After spending a couple of months in Central Florida with my dad this summer, I relocated to Milwaukee in August. Why Milwaukee? It’s affordable, most of my family lives here, flights to the Coasts for work aren’t unbearably long, it’s on a lake, and the people are nice. An unexpected perk — the people watching. Just ask me about the time I saw a drunk volleyball girl eat it on the bike rack outside McDonalds.

Team 10up has doubled in size again this year. I’m on my way to our second annual meeting in Las Vegas and I can hardly wait to see this team for the first time in person. We’re no longer a mostly homogeneous group of engineers, but a diverse, multidisciplined team of strategists, creatives, systems engineers, monetization specialists, and storytellers. I have what many would (and do) consider a dream job.

I’ve been single for four months. Which seems unremarkable until you consider that my longest streak prior to this was two months, crammed in between a series of relationships that spanned seven years. Unsurprisingly, people, things, and places look entirely different when you view them through your own lens, unclouded by another’s perspective. For me, they’re clearer, prettier, freer.


The left lane is always tempting, but the pursuit of balance is more compelling and sustainable, so I’ve found a nice pocket in the middle lane to cruise in. Don’t get me wrong, I fully intend to use the fast lane for its intended purpose — sometimes you just gotta get shit done, but for now I’m happy just to be enjoying the drive again.

I’m at WordCamp Providence Today!

I will be speaking in the beginner’s track at WordCamp Providence today debuting my “Writing Tools for WordPress” talk. In addition to highlighting tools that can help any publisher bring life back to their blog or website, we’ll be getting a bit interactive with an in-session brainstorm and a little WordPress mobile application action to get the Providence crowd publishing on the spot.

If you attended my session, please post a link in the comments of this post sharing what you learned at WordCamp today and any goals you have for your site now that you have… no more excuses!

Rockin’ the new WordPress application…

Really loving easy access to posts, pages, and comments with the new Facebook-esque navigation in the new WordPress application. (I guess Facebook can’t be doing mobile totally wrong if we are seeing UI copycats, right?)

The constant prompting to link my .com account to the app is kind of strange though, particularly since I use the application to manage my self hosted WordPress site. I guess this integration has been around for awhile, but it’s much more noticeable now. Would have been nice to include a setup wizard to guide users through the process with this new major release.


On Tuesday I started my 36 hour journey across New England with stops in Providence, NYC, New Jersey, Philadelphia, and Boston (+1 brief pit stop in Detroit to catch a connecting flight). I helped demo an amazing VIP project with Helen in NYC and played nice with a new potential client in Philly. I played Wii Boxing and Angry Birds with Elisio. I successfully made each of my trains, flights, and cabs. All in all it was a successful tour.

Today I’m feeling more than a little exhausted and my brain is still trying to grasp the fact that it’s somehow Thursday already. Almost feels like spinning in circles. Maybe because I did.

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Things I love about Vermont

Almost a year later and I’m back! Currently kicking it in Vermont until the end of April and then back to the Boston area. Here’s a few awesome things about Vermont:




Slippery Slopes



Silly Ski Clothes