Whew. Yahoo’s $1B acquisition of Tumblr has brought a lot of commentary, opinions and analysis out of the woodwork. It seems everyone has something to say about the event.

This will not be a top 5 list. I don’t have lists of top 5 things I’ve learned, or mistakes Tumblr made, or microbrews the engineers like. This is a meandering series of observations that I am trying to work out with myself — they’re lessons, yes, but they’re also the causes that effect me to view technology, product development and company culture as a petri dish of immense fascination.

It’s about being the only person to have worked at Yahoo, at Flickr and at Tumblr.

It’s seeing the ways that small actions can be a great force for right or wrong, how personalities can have an immense effect on a company, and in turn, on millions of users across the world, and how no matter what the press simplifies as the cause for major events, the reality is nuanced, given to movement in inches that topples the boulder rather than a Herculean push.

This is my first Medium post. I figured if there’s a place for introspective ramblings, it’s this platform.

I joined Tumblr as the 2nd wave of hires, as the 10th or 11th employee. I consider the 1st wave to be JacobPeter, and John as well as a few others. The first wave had helped David build Tumblr to be this gorgeous and addictive thing that was growing fast. Marco had just left to start Instapaper. Jared moved on to build GroupMe. And Meaghan had decamped to Kickstarter. There would be 3rd and 4th and 5th waves and so on. But in the early days, when it was 10 to 20 people, there was something really really special - we were on a rocketship changing engines in mid-flight..

SXSW house - picture by David.

I came to the job as a fan. I had emailed Tumblr on a whim, telling them of my admiration and absolute belief that it was going to be the next big thread in the social fabric of the Internet:

As I find myself discovering daily Tumblr awesomeness, I thought, “This is exactly the place where I want to help build and make better.”

A few months later, John called me on the phone while I was in Argentina and a few weeks later, I met David and the team and instantly felt at home.

I joined to take the product further, to help David execute his vision as he took on the large responsibilities of being the CEO. Tumblr was growing fast and David was needed to build out the engineering team, to scale operations, to manage fundraising and marketing and — basically, according to Marco — all the things he didn’t really like to do. And I was brought in to handle the one thing he did like to do, which was to envision the product and design. (Whoa!) I thought I was going to teach the guys a lot, having worked for years at building another pretty cool platform, Flickr. Instead, it was me to learned tons, mainly from David himself.

Walking from USV’s office because we ran out of meeting space.

It was humbling to work with David. And sometimes challenging to my ego. He has an incredible way of bringing you into his orbit. Even with all of the other things he had to worry about — the downtimes, decisions to bring in senior level management to control parts of his baby that he never had to worry about before, orienting Tumblr around creators instead of being a mass-market blogging tool, figuring out the international markets and growing community vectors like fashion, arts, music and so on — he was so on top of product that on most days it felt like I was two steps behind thinking through all the ways in which people would love or hate the features that we planned to push.

And important to me, we were all friends when the company was small. We went to lunch together, we played card games after work — the guys even went to my wedding in the middle of nowhere, Maryland. I was changing the world with a bunch of people I could go have drinks with — and we did! So many features and ideas came around the dinner table in those months. I got kind of fat.

Last hurrah at our wedding

More than anything, I loved the quiet hours, after everyone had gone home. David would sit on the couch and sketch in his notepad. Then he would walk by my desk and asked, “Hey, can we catch up on product stuff?”

Invariably, hours later, we’d both get stupid excited about the new stuff that we could build.

David was perpetually excited about Tumblr. I have never seen his enthusiasm wane . Everyone who worked at Tumblr were all in love with the product and used it every moment — but David had us all beat. He lived and breathed the product.

Matt Hackett & David Karp

Looking back, some of the things we built were awesome - and I’m glad to have added a bit of Flickr DNA to the features — kind of funny considering now Tumblr will be Flickr’s cousin in the Yahoo family.

The EXIF information attached to each photo - that was a refraction of my obessssion with an image’s contextual data. Having curators for the tag program - that was a reaction to Flickr’s Explore feature, where algorithmns can only turn up so many similar HDR images before human sensibilities have to take over. Reworking the photoset to show all the images instead of a lightbox photo - another reaction to the standard lightbox/slideshow experiences that were in vogue at the time. Starting a developer/API program - also a useful lesson I learned from Flickr.

There were some things that I wished I had done differently, had pushed for harder or done more forcefully. Controlling our own mobile destiny faster is one of them, and I’m happy to see Tumblr rolling out so many awesome updates on their apps recently. It’s also a measure of satisfaction to see so many items on the roadmap that we talked about getting shipped by a bigger, stronger and talented team of 200+ people.

Lunch on most days.

In the end, it’s hard to have two strong visions at play, and the way the team is structured now, with product engineering building things and product design visualizing things — makes a lot of sense for the company’s growth.

Tumblr - as with any company or product - isn’t about a featureset or even the numbers.. or in some cases, even the users. It starts with the people who dream up something different, who love what they’re doing and can’t wait to share with the world their crazy ideas. It’s the engineers and designers and support staff and salespeople and office managers and marketers who come to work each day to build something better. And at the heart of Tumblr is a founder who is also its hardest working employee.

Camp Tumblr, picture by David

David also gave me the itch to chase after my vision. And now, starting on my own journey to build something new, I’m even more amazed at what Tumblr has accomplished.

Building something new is hard.

Doing anything that you can to keep it growing and going and persisting is something else entirely. And I have high hopes for Tumblr’s place in the world.

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