Jay Z + Me

I think it was Dustin Curtis who said something along the lines of “you can learn a lot about someone by their bucket list,” and he had posted his publicly recently. (Posting it is a great idea by the way, people will help you with it.) I began to think about mine, which was a little strange because I’ve been trying to move away from desiring things or experiences and just be more grateful in the present, but immediately a few music ones came to mind: have WordPress name-checked in a major hip-hop song, be in a rap video, and perform with one of my favorite artists (somehow).

It was less than a week later I got an email from a friend who was helping organize a hush-hush event where Jay-Z would sing his song Picasso Baby over and over 6 hours while interacting with various artists and an audience as a performance piece, and there might even be an opportunity to be one of the people he interacted with. My jaw dropped.

Continue reading Jay Z + Me

Naval describes the venture model while suggesting a way for firms to differentiate.

We help our customers but don’t tell them exactly how. Our core product is a commodity, yet we don’t disclose pricing. Even when we do, there are substantial hidden costs. It has to be bought in bulk, more than they want. We can take months to onboard a customer. We reject most of them but don’t actually give them a straight answer. They don’t get dedicated support. They don’t get to choose or replace their representative. We don’t commit to serve them in the future. We have hundreds of competitors with the same strategy. Now where’s my check?

Bookend Gifts

The news came out this weekend on Mercury News and the Chronicle, so it’s worth addressing here: The Bay Lights, a public art project that uses San Francisco’s Bay Bridge as its canvas, is a project I’ve supported since I first heard of it and the idea captured my imagination. I was happy to make the first monetary donation when the project got started, and as of last week I was able to make a closing bookend donation for the remaining amount they needed, a bit above $1.5M. It was an honor to chip in along with the thousands of other supporters who have already donated to make the project a reality.

The purpose of art is washing the dust of daily life off our souls. — Pablo Picasso

My hope is that over the next few years, and perhaps beyond that, the lights brighten people’s experience of San Francisco whether they see them every night or they’re one of the 16 million that visit the city every year. Hopefully that effect, however small, spreads to their other interactions long after the lights are off and the sun comes up. There are countless good causes around the world, some which I support regularly are listed on my about page, and I hope to have the opportunity to support many more in the future, but this close-to-home gift to a city that has given me so much seemed like the right thing right now.

If you haven’t seen them yet, here are the lights in action, more on the tech fixes happening to the lights on TBL, and photos I took climbing the bridge a few months ago:

Dear WordPress,

Has it really been 10 years? It seems just yesterday we were playing around on my blog, and the blogs of a few high school friends. Two of those friends are married, one isn’t anymore, two are still figuring things out, and one has passed away.

You were cute before you became beautiful. Wearing black and white, afraid of color, trying to be so unassuming. I know you got jealous when I wore those Blogger t-shirts. They were the cool kids at SxSW and I thought maybe you could grow up to be like them.

You wouldn’t have shirts of your own for a few more years. We didn’t know what we were doing when we made them and the logo printed ginormous. People called them the Superman shirt and made fun of them. But, oh, that logo — the curves fit you so well.

You showed the world you were growing up, and how much you cared about design and typography and other platonic ideals. You knew that open source didn’t have to be homely. I stretched myself too thin trying to get you there, and I did a stupid thing to pay for it. I hurt you, but instead of casting me away you held me closer, supported me, gave me another chance. I will never forget that. Akismet made me feel less guilty. I wouldn’t change anything, because the mistake made me understand how important it is to fly straight and take your time.

You’re so beautiful… I’m continually amazed and delighted by how you’ve grown. Your awkward years are behind you. Best of all, through it all, you’ve stuck with the principles that got you started in the first place. You’re always changing but that never changes. You’re unafraid to try new things that may seem wacky or unpopular at first.

I see you all over the world now, glowing from screens, bringing people together at meetups and WordCamps — you’re at your best when you do that. You’re my muse; you inspire me, and I’ve seen you inspire others. You become a part of their life and they become a part of yours. I hope we grow old together.

Cheers to ten years, and here’s to a hundred more.

Love,
Matt

Automattic After-Market, Lee Fixel, and Tiger

One of the most striking shifts in entrepreneurship when I started Automattic seven years ago was the rise of the Founder Friendly VCs. The standard operating procedure at the time for VC-backed companies consisted of bringing in “adult supervision,” founders often taking largely-ceremonial roles like “chief architect” after the business had scaled to a certain point, aggressive financial terms around liquidation preferences, and a control structure that more often than not left founders with a minority say in the future of the company, especially if it went through rough patches. Folks like True Ventures (who Automattic has always been intertwined with) appeared as iconoclasts because they came out saying that founders were the best ones to grow a company long-term and structuring their entire practice and way of investing around that idea. It seems non-controversial now, but it was like Dylan going electric. Still in spite of their philosophical innovations, many of these funds were structured in similar ways to the ones of old, with 7-10 year fund lifetimes, for example.

Fast-forward to 2013 and there’s an even more founder-friendly class of investors rising, at least for companies that have made it past a certain exit velocity of growth and revenue. Most visibly pioneered by Yuri Milner and Facebook in 2009 there’s a breed of later-stage investors from largely financial backgrounds that come in with the ability to write checks larger than the entire size of most VC funds and a desire to align with founders so strong that they embrace things that even VCs from the founder-friendly cohort would balk at: forgoing board seats, assigning voting proxies to founders, taking very long term approaches to growth, and investing in (and seeking out!) companies outside of the California/New York bubble, from South Africa to Russia to Brazil. The most interesting thing to me about this new generation is how behind the scenes they are: forget about a blog or Twitter, most of these guys don’t even have websites for their firms. These are some of the smartest and most successful people you’ll ever meet and you’ll never hear about them… they like it that way. Asymmetric information is their core competitive advantage.

Anyway, wanted to get in front of the news that will inevitably come out in the next week or two: there has been a large secondary transaction in Automattic stock, about $50M worth. “Secondary” means that it’s existing stockholders, like the earliest investors or employees, selling stock to another investor versus money going into the company (“primary”). It was led by Lee Fixel at Tiger Global, one of the behind-the-scenes quiet geniuses that has previously invested in SurveyMonkey, Facebook, LinkedIn, Palantir, Square, Warby Parker… Automattic is healthy, generating cash, and already growing as fast as it can so there’s no need for the company to raise money directly — we’re not capital constrained. The minority of stockholders that elected to participate are holding on to the vast majority of their shares. We’re building an independent company that’s going to be a growing part of the fabric of the web for many years to come, so allowing early investors to lock in some returns releases any short-term pressure there might be on the company for a liquidity event and allows us to focus fully on the long road ahead.

As sometimes happens in with regulated financial things, I can’t answer every question about this, but will leave comments open. I hope to see some of you on Monday the 27th when I’ll be celebrating the 10th anniversary of WordPress alongside community members in over 500 cities. Also check out Toni’s post about all of the above. If you’re interested in living anywhere and working hard alongside people passionate about the same, Automattic is always hiring.

On Yahoo-Tumblr

It now looks pretty certain that Yahoo has pulled off a deal to buy Tumblr for 1.1B. The relationship between WordPress and Tumblr has always been pretty friendly: Tumblr’s own blog used to be on WP, WordPress.com supports Tumblr as a Publicize option alongside Twitter and Facebook, our Akismet team sends them daily emails of splogs on the service, and there’s healthy import and export traffic both ways. (Imports have actually spiked on the rumors even though it’s Sunday: normally we import 400-600 posts an hour from Tumblr, last hour it was over 72,000.)

News like this, whether from a friend or a competitor, is always bittersweet: I’m curious to see what the creative folks behind Tumblr do with their new resources, both personal and corporate, but I’m more interested to know what they would have done over the next 5-10 years as an independent company. I think we’re at the cusp of understanding the ultimate value of web publishing platforms, particularly ones that work cross-domain, and while Yahoo’s all-cash deal by some metrics, like revenue, is very generous, I think it’s a tenth of the value that will be created in these platforms over the coming years.

Update: Some people are reading too much into the import numbers — I don’t think there will be an exodus from Tumblr. For more color read the comments on this post.

Jawbone UP vs Basis

Jawbone UP I’ve always been into personal analytics. From Wakemate to the Nike Fuelband I’ve tried pretty much every device that’s come on the market to help you become more self-aware of your activities, and hopefully improve them as well.

Lately I’ve settled on two that I think are really high quality: the Jawbone UP and the Basis watch. I would recommend either above the Nike Fuelband or Fitbit, but let me share some brief thoughts about my experiences with each:

The UP is beautiful — it’s easy to wear with pretty much any outfit, even with formal wear I find I can move it up my arm a little bit inside my sleeve above my shirt cuff thanks to the flexible nature of the band. The social app they have for it is cool, though it can be a little weird to see your teammate’s minute-by-minute sleeping habits (“Hey! I noticed you were up between 3:32 and 3:50 AM last night. How ’bout them Giants?”).

I'm very proud of my sleep.
I’m very proud of my sleep.

The battery life is over a week so you never have to think about it, but you do have to carry around a proprietary connector for it which I keep losing leaving me (like right now) with an uncharged and useless device. To sync you plug the band into your phone’s headphone port and the sync takes a few seconds, it’s a fun process I do usually first thing in the morning to see how I slept the night before and it’s also fun to demo to friends. The first one I had was in their “mint green” color and I ended up wearing it out — it started to look dirty and I broke it where the headphone jack comes out making it difficult to charge and sync. That said, I was pretty rough on it. My new one is blue and I like it much better. My only big complaint about how the whole thing works is it doesn’t detect when you go to sleep, you have to press and hold the button on the end to put it from wake to sleep mode, which I would frequently forget to do. I really like the idea of the smart alarm and power nap features even though I never used them.

Basis B1 BandThe Basis is a bit clunky and retro looking, but functionality-wise it provides some really cool data: it tracks your heart rate, skin temperature, perspiration level, steps, and sleep. It detects automatically when you’re asleep, no buttons to push. The data is presented in a really cool web app that lets you compare some of the data points and that I learned cool things from, like my heart rate jumps about 20 beats per minute when I wake up, and I’m most warm about two thirds into my sleep cycle. There don’t appear any social features that I’ve seen in the software, though its habit formation tracking seems pretty slick. The way the “buttons” work on the device is pretty cool, the silver dots in the corners are touch-sensitive. There’s a button on the side that I haven’t figured out what it does yet. Syncing and charging is much worse than the UP — it’s got an even clunkier proprietary USB thing that both syncs to your computer and charges, but because the display can show you how you’re doing as you go throughout the day I don’t feel the need to synchronize it as often. The heart rate tracking is by far my favorite feature. It’s comfortable to wear, but doesn’t disappear like the UP. Finally, as an added bonus, it tells the time. (Surprising useful.) If it somehow merged with the Pebble I’d be in geek heaven.

If I had to pick between the two I’d just use the Basis. The awkwardness of the device is outweighed by the richness of the data it provides. For right now I’m not choosing: I wear one on each wrist and compare the data. (It’s always within a few % of each other for things they both do.) If I were hiking in the woods for a week I’d probably just take the UP as its battery would last the entire time. It’s really illustrated for me what a silo each of these systems are, they don’t talk to each other at all and it appears unlikely they ever will.

Long-term I think we really need an open source package you can run on your own servers that can ingest the data from all of these services, say from back when I used to use a Wakemate sleep tracking to today’s Fitbit Aria scale, the meals I track in the UP app with my Basis heart rate data and Runkeeper and Hundred Pushup logs, and provide you with a single data store for all the personal analytics you generate across various services. I think there’s going to be a lot of competition in this space in the next few years.

Dave Winer tweeted this on Saturday:

One of the things I love and admire about him is that many, many years after he doesn’t have to anymore he’s still learning, hacking, and taking free time on a weeknd to make something new.