The LIFFFT team taking off…

Holy shit, I’m in the New York Times!

Wow, I’m humbled. Here’s my interview.

GigaOm airs my dirty laundry, web cries foul and calls me a liar.

Last month, I started talking to the editorial team at GigaOm about writing a guest post. I sent them a handful of posts I’ve been meaning to write. They were most interested in the one titled Everything I need to know about startups, I learned from a crime boss. 

It was fun, if slightly uncomfortable, to write. I had to tame down the initial draft quite a bit in order to share it with anyone other than a close circle of friends. Many people cried foul and accused me making things up anyway. Ah, the internet. 

Thanks to everyone who sent me positive feedback. Writing is inherently rewarding, but multiplied greatly by the appreciation of others. (Thank you.)

If you missed it, head over to GigaOm and leave a comment. :)

My Descent from Wunderkind to Flaming Disaster

This post is part of the Vittana “Make a Difference” blogger challenge. The contest asks people what education means to them, and how to make a difference in the world. The writer that gets the most retweets and donations in their name “wins” (though the real winners will be the recipients of the loans). 

If you enjoy this post, please retweet it and consider making a loan in my name (“Donald DeSantis”). Thanks for reading!

A sudden rapping of ruler on chalkboard jolted me back to reality. It was my math teacher. The entire class stared at me with looks ranging from bemused to annoyed. “Donald, I don’t care how good a writer you are. Close your notebook and pay attention!”

I loved songwriting. Unfortunately, my school didn’t offer creative writing classes. So instead of sticking to the curriculum, I created my own. Math class became writing class. Problem solved. I had no idea I would be doing this for the rest of my life, replacing formal curriculum with my own lessons. I was only twelve years old.

I sailed through high school in three years. I graduated with good grades. My teachers regarded me as a pain in the ass, but a bright pain in the ass. I continued focusing on music. I paid my classes the smallest amount of attention possible.

I entered the University of Washington in the fall of 1999. Barely seventeen, I was now making music with a mish-mash of backpack rappers whose eclectic style flourished during the late 90’s and early 2000’s. I helped promote shows alongside people who later came to symbolize Seattle hip hop. This included folks like Prometheus Brown and Sabzi (before they started Blue Scholars) and Meli, who went on to manage booking for many popular venues in Seattle. If I had put half as much time into my classes as I did into music, I would have been a very successful student. I didn’t.

It was the fall of my freshman year. Our math professor approached the lecture podium. “Overall,” he said, “you guys did quite well on the midterm. Someone, of course, got fifty points: a perfect score.” He stopped to let the 400 person lecture hall groan in unison. “The lowest score,” he paused dramatically, “was one point. One point out of fifty.” The very cute girl in the front row let out a pitying laugh. It was the kind of laugh you laugh when a hapless puppy falls off a chair, or trips down some stairs. It was the kind of laugh you feel bad for laughing, but the kind you can’t help yourself from laughing. I didn’t laugh because I knew what she didn’t: she was laughing at me. My stomach sank and face flushed a deep red.   

I ran after my professor when the class ended. “I’m the one,” I said breathlessly. “I’m the guy who got one point on the midterm.” He looked surprised, then reassured me. “I wouldn’t assume that. Wait until you get the midterm back.” “No,” I insisted, “it was me. I know it was me.” He looked at me, now quite seriously. “This was not a hard test. One point is basically what you get for putting your name on the midterm. Have you talked to disabled student services? You likely have a learning disability that they can help you to identify.”  
 
I stood gaping at him. The problem wasn’t a disability. It was neglect. But in that moment I realized my unwitting descent from wunderkind to flaming disaster. I’d like to say this wake-up call turned me into a model student, but it wouldn’t be true. The next quarter I barely passed Intro to Computer Science. I enrolled in Two Dimensional Design and the instructor gave me the lowest possible passing grade at UW: 0.7. (In a satisfying twist, design and software development are the two things I do best these days.)

After a miserable run at UW, I decided that leaving on my own accord would be better than getting kicked out. I had no desire to slow down on music and doubted my ability to focus on anything else. Around that time, I heard Western Washington University allowed some students to design degrees based on their interests. I transferred and began working with WWU faculty to create a curriculum. My classes ranged from recording arts to music theory, communications to web design. For the first time in years, I excelled.

At 20 years old, I moved back to Seattle and opened a creative arts space. It was on 10th and Pike, next to what’s now Neumo’s on Capitol HIll. It was primarily a recording studio, though we had a large art gallery and event space. Prometheus Brown (who I knew from UW) came through. Macklemore would drop by and show off unfinished songs from Language of My World. Grieves was there constantly, hanging out and working on beats. This was where I met Kyle and where Mike Folden and I laid the foundation for a really amazing friendship.

Over time, I’ve become better at spotting my disinterest and bowing out early rather than persisting in obligation. This sounds obvious, but it took me years to understand and even longer to practice.

For “nontraditional students” like me, the future has never looked brighter. We have the Khan Academy and iTunes U in our pockets. Standford runs classes online and opens them to the public. Private companies like Treehouse and Code Academy teach us to code for less money than we spend on cable television.

This future may be bright, but it’s unevenly distributed. In 2007 I met a Spanish language instructor in Oaxaca. He had lived in the U.S. for ten years and only recently returned to Mexico. I asked him what he missed most about the states. He paused, then looked up and smiled. “The libraries. They were amazing. You would walk in and be surrounded by all of this knowledge. If you wanted to take a book home, they let you.” This response humbled me.

Most of the world doesn’t have broadband connecting them to Khan Academy and iTunes U. They probably don’t have a public library and community college in every town. They may face economic, gender, or religious discrimination. The greatest challenge I faced was my own single-mindedness (and it nearly sunk me).

However circuitous and humiliating, my education was important. It imparted the patience required to gain technical competence in a subject (recording arts) and the self-confidence to actually do something with those skills. And while my life in software appears very different than my life in music, the core is unchanged. I wake up every day and get to create whatever it is I can imagine. I’m incredibly grateful.

Education is a gift I took for granted and struggled to accept. Today I value it above all else. Here’s to the dreamers and underdogs, whether they’re following lesson plans or creating their own.

If you enjoyed this post, please retweet it and consider making a Vittana loan.

Trimming my worldly fat

I have a lot of stuff. We all do. It’s 2011 and this is completely normal. 

But I’ve become more suspicious of my stuff. Not any individual possession. The whole of it. There’s a school of thought that the more a person has, the more that person desires. It creates a cycle of dissatisfaction and unhappiness. I don’t feel like I’m suffering from that, but the idea makes me pause. Maybe I am, in small and barely perceptible ways, less happier (and more covetous) than I would be with less stuff.

I want to test this, and have decided to impose a cap on the number of things I own. This is neither novel nor new. Dave Bruno wrote a book on pairing his life down to 100 things. Just because it’s not novel, doesn’t mean it’s not difficult. We are attached to our stuff. I’m no exception.

Not wanting to fail due outsized ambition, I chose a conservative number: 300 things. If I can’t get down to 300 things, there’s something seriously wrong with me. And once I have hit 250, then I can target 200. We’ll see how I feel about continuing when I get to 200. :)

This comes with a few caveats: 

• I’m not dragging my understanding wife Adina into this (yet), and therefore excluding shared things like plates, cookware, furniture into this challenge. 
• I’m not going to get overly analytical about what a “thing” is. My rule is that if two things go together (like an iPhone and a charger or the case that came with my sunglasses) then they are one “thing”.

Rather starting with an inventory of my stuff, I decided to create a list of what I think I “need”. What I “need” is subjective of course - I need a snowboard, you may not. But I really enjoy snowboarding and paring down on possessions shouldn’t be an exercise in asceticism.  

I worked up this list of items I think I’ll need. Its length surprised me - on the favorable side. I could think of 109 things I need. This number will surely be going up as I actually start to get rid of stuff and realize how much more I need (or am reluctant to part with). I’m curious how much higher it will go, and how close my original estimate is. It makes me hopeful though, that I can easily hit 300. 

Take a look below. Anything I’m missing? 

Thing | type | quantity

• neckties, accesories, 2
• casual belt, accesories, 1
• dress belt, accesories, 1
• sunglasses, accesories, 1
• backpack, camping, 1
• tent, camping, 1
• stove/pot combo, camping, 1
• dish, camping, 1
• spork, camping, 1
• camping pillow, camping, 1
• sleeping pad, camping, 1
• sleeping bag, camping, 1
• headlamp, camping, 1
• camping chair, camping, 1
• underwear, clothing, 5
• socks, clothing, 5
• shirts, clothing, 12
• jeans, clothing, 2
• sweaters, clothing, 5
• workout top, clothing, 1
• casual shorts, clothing, 2
• running shorts, clothing, 1
• sweat pants, clothing, 1
• rain jacket, clothing, 1
• soft shell, clothing, 1
• warm jacket, clothing, 1
• hat, clothing, 1
• sport coat, clothing, 1
• road bike, cycling, 1
• helmet, cycling, 1
• cycling shorts, cycling, 1
• cycling 3/4 pants, cycling, 1
• cycling waterproof pants, cycling, 1
• cycling gloves, cycling, 1
• bike tool, cycling, 1
• cycling socks, cycling, 2
• cycling lights, cycling, 2
• cycling computer, cycling, 1
• bike mounted snack bags, cycling, 2
• cycling shoes, cycling, 1
• workstand, cycling, 1
• lock, cycling, 1
• mountain bike, mtb, 1
• camelback, mtb, 1
• shorts, mtb, 1
• pads, mtb, 2
• gloves, mtb, 1
• shoes, mtb, 1
• toothbrush, personal items, 1
• hair clippers, personal items, 1
• razor, personal items, 1
• wallet, personal items, 1
• water bottle, personal items, 1
• coffee cup, personal items, 1
• coffee maker, personal items, 1
• backpack (city), personal items, 1
• duffel , personal items, 1
• dress shoes, shoes, 1
• athletic shoes, shoes, 1
• casual shoes, shoes, 1
• sandals, shoes, 1
• boots, snowboard, 1
• snowboard, snowboard, 1
• snowboard socks, snowboard, 1
• pants, snowboard, 1
• goggles, snowboard, 1
• gloves, snowboard, 1
• jacket, snowboard, 1
• leg base layer, snowboard, 1
• core base layer, snowboard, 1
• helmet, snowboard, 1
• snowboard bag, snowboard, 1
• laptop, tech, 1
• laptop sleeve, tech, 1
• ipad, tech, 1
• headphones, tech, 1
• iphone, tech, 1
• external hard drive, tech, 1
• packable bag, travel, 1

Apparently Sunday is a good day to post to Hacker News

Yesterday, my buddy John Cook featured a few of my thoughts as a guest post on Geekwire. The post is called What being hopelessly single taught me about pitching tech celebs and compares the challenge of approaching stars in the startup world to approaching attractive strangers at bars. I wrote it with a local audience in mind - Seattle folks are known to be a little reserved/shy. I was hoping to inspire a few more wallflowers to take a deep breath and share their story with an investor, blogger, or whoever will listen. 

My buddy Ian posted it on Hacker News where it quickly hit the front page (slow news day I guess). Paul Graham, the Afrika Bambaataa of tech startups, even chimed in on the discussion. 

Good times. :)

Coming soon to a web app near you…

Working on some new UI styling for FlickMob, Giant Thinkwell’s latest creation. 

Taking a break from coding on Friday to dip in the Puget Sound.

How to get on TechCrunch with a few lines of JavaScript

A few weeks ago Giant Thinkwell was gearing up for the launch of Mix n Match, a Facebook game featuring Sir Mix-A-Lot. We had lots of media targets, but cutting through the noise is always a challenge. 

One of the best lessons I ever learned about marketing was to latch onto larger stories and use them to get press you otherwise would never get. Although confident we’d get coverage on gaming and social media sites, we wanted to have an ace up the sleeve to guarantee buzz. My personal measure of success was a write-up on TechCrunch, an outlet that otherwise felt like a longshot for this launch. 

Grasshopper’s David Hauser talks about great PR as not one specific instance of great press, but rather creating the feeling that “you’re just everywhere”. People can’t help but hearing about you. Our own seasoned marketer-in-residence, Adam Tratt, claims there’s actually a term for this: ambient marketing. 

So what did we deem buzz-worthy? How about Sir Mix-A-Lot dj’ing on the new tech-hipster darling, Turntable.fm? What if we did something no one had done yet - create a custom avatar for Sir Mix-A-Lot? That seemed like the right order of magnitude.

A few lines of JavaScript later we had a janky, but working, bookmarklet that swapped Sir Mix-A-Lot’s normal avatar for an custom one.

With about 45 minutes lead time, we shot over an email to TechCrunch that told them about the live DJ set and our game, Mix n Match. In short order, we had a write-up talking about both Sir Mix-A-Lot’s DJ set as well as his new game. As a side note, is that this DJ set has been referenced several times as a key point of traction for Turntable. We think Turntable was on its way to glory with or without us, but it’s always interesting to see the residual impact of a single event like this.

Kav and I had a lot of fun making this happen. Check out the video below for our moment of victory at about 4A.M. on day of launch.