a SCK life.

I was on a panel earlier this week at the Churchill Club that I never quite caught the time to write about.   First, I want to thank Guy Kawasaki for inviting me on, it truly was a fantastic time.   This was my first experience on a big kids panel (ie Douglas Engelbart was in the audience).  To be invited to speak before such a fancy group as the Churchill Club truly was an honor.   Check out the video below (I think you have to fast forward a bit to get to the actual speaking…)

I’m always torn at such functions if its better to be brutally honest about experiences as a  young entrepreneur, or instead to create a thin wall, a façade that separates reality from the utopian existence we all claim to reside.

At the Churchill Club I chose honesty, telling a story about Zach sitting in the back of the infamous Ritual Roasters Coffee House , Ruby on Rails 101 opened on his lap,  convinced he/we could learn the complex programming skills necessary to get Triggit built.  Oh what fools we were.  Luckily we quickly realized there are a few more levels to programming then ‘Rails’ and moved beyond our stupidity,  somehow convincing Ryan it was in his best interest to come work with Triggit.  (That is another story entirely!)

Triggit didn’t start from some singular brilliant idea, sketched out to perfection from the beginning.  We didn’t release a magical application that instantly hit hockey stick growth, became profitable, went public and pours billions into the coffers of its stock holders to this day.  But then again, that reality is the fairy tale.   Even the most amazing products frequently struggle to truly succeed, especially financially.  Google went through 6 known iterations of its business plan, from licensing its search technology to the roaring success of Adwords. And Facebook sure can grab users, and claim high valuations, but they are far from turning a profit.

Reality for the majority of start-ups is that it takes a long time to build something that has real value, especially for first time entrepreneurs.   In the early days of building Triggit, without an established network in the Valley, and when we were first trying to figure out exactly how this all worked, we would just call people.  Anyone who would listen to us, who was in some related field (usually just anyone in tech) was liable to get a phone call from us. We rooted through our Alumni directories looking for ANYONE who would take our calls.  Looking back I just laugh at how serious we took this whole endeavor, but it was a step in getting us to where we are today.   Because the more phone calls we made, the more we vetted out ideas, and the more clear our eventual target became.

We went (and still go) to as many networking events as possible, just to talk about Triggit, see how people react, and come back to the office to iterate.  Then there are the days you just stare at your computer screen, trying to figure out exactly what it is you are supposed to be doing.  Bobby spent months trying to sell a product, before we actually had a product.  And then there are nights you wake up at 3am convinced you suddenly have it all figured out.   In every case, most time is dedicated attempting to execute a series of realities that most often fall flat on their faces. Failures sometimes bruise egos, loose money, and waste valuable time, but they also move us ever closer to the light at the end of the tunnel.   They also make the rollercoaster of a start-up one hell of a ride!    And the ideas that stick, that make it through the guantlet,  well, those are the really good ideas.   A few years after  jumping on a plane from beaches of Brazil to join Zach in pursuit of this crazy start-up, we may just have one of those really good ideas, and a truly fantastic product.

I hope I can always feel the freedom to write truthfully about my company and our crazy experiences; about the paths we should never have gone down, the silly moments wasted chasing elusive prestige.   But more importantly, the great times.  Like the time Zach rivetted an audience at the Web 2.0 Expo, making them full commited to the cause, and convinced that we can and will succeed.   And most importantly, the internal moments, not just becoming really good at foosball together, or getting drunk at Zeitgeist and inventing religions, but when we come together as a team, to execute on an idea, and watch it start to succeed.   Damn its a fun ride!

Take a look at the Churchill panel if you are interested (or just fast-forward to all the fascinating parts where I speak!).    And let me know what you think, I have learned a lot about myself in watching that clip, and I can’t wait to keep learning more!

I have no self-restraint.  After admiring Bobby and Ryan’s iphones for all of 3 days, I capitulated and bought mine today.  Of course, they are sold out at almost all locations, so I have to sit and wait for 7-10 days for its arrival.

The iphone truly is extraordinary though, and in so many ways just has me shaking my head in disbelief.   In the upgrade to the 3G network, the phone has become a personal mini-computer that is connected to the internet almost constantly.

As someone who came of age during the rise of the personal computer (I have a picture of me playing on my first computer at the age of 3), it has been an unreal ride.  In the early days when we were kids we had what we thought was a pretty sweet DOS machine.  My older brother James was a whiz at it.  I figured out enough commands to play tetris, command and conquer, and power up Q & A to write my elementary school papers.    Every week Zach and I would rollerblade down to the local college to pick up a copy of Computer World so we could get the updated list of phone numbers for the BBS’s so we could dial-up and play Risk ‘online’.   Then came windows, and AOL and Prodigy.  I got really good at scamming as many free discs as possible and was right constantly canceling accounts and opening new ones as to take advantage of all the free minutes.

My family’s first laptop was this big white brick made by a company that doesn’t exist anymore.   Windows sort of worked on it, but man did it take ages to load.  I think I did a demo for science class on it once though, I thought I was pretty cool.

And now I’m getting an iphone.  I suppose it’s a cell phone (which is a different discussion then above for sure, as my family had an early car phone that I think was as big as my head.)    But truly it’s a computer that is infinitely more amazing then that old white clunker of a laptop.   I’m a bit terrified of becoming even more connected then I am now, but more then anything I am thrilled for my new toy.  And of course, I am super excited for it to become obsolete and surpassed with something even more rad in the hopefully very near future.

WSJ: Men write Code from Mars, Women Write More Helpful Code from Venus

If only this was more then just anecdotal evidence! But I find the discussion interesting regardless. I actually predict that we are going to see a whole new generation of young female coders in the next decade. Girls that grew up online and hacking the Internet along with their friends and brothers.

 There is a lot of mundane shit in a start-up. How do you find alpha users that fit your target audience? If you have a start-up like Triggit, you search through Google, and Technorati, and blog directories, and any source for users. Then you have to find all their contact information, which is another pain in the ass. Here we sit, with all these really innovative ideas for development, and marketing, and design and we need to spend hours upon hours searching blog directories for users.

So what does a bright, ambitious, probably a little egotistical (we are after all entrepreneurs) company do to solve this problem? Obviously we find cheaper talent to do the shit work. We would not actually want to hire someone in the US, because that would require tax documents, or employment forms, or really just a lot more cash then our stingy and frugal lil start-up can deploy. We’ve got to keep the burn low! So we turn to Asia, and Outsourcing.

When I first started looking for outsourced talent, I was a true believer in the commoditization of a particular skill sets. I read all of the articles I could get my hands on about the subject, and they all endorsed the view that simple tasks could be simply outsourced. I scoured the various outsourcing sites: Rentacoder.com, getafreelancer, elance, odesk, freelancenow. I was thrilled! Look at all of this cheap talent! $3/hr, sweet!

Marcos lived in Corodoba, Argentina spoke great English, and only cost $6 and hr! We were stoked, he seemed to be able to code okay, so we set him up to do feed integration for us, a tedious task that is also profoundly precise. For a while we rationalized that his average work was worth the cheap price, but then users started to complain that the matching wasn’t great, clients begun to wonder what was taking us so long to get them into the system, and Marcos kept vanishing every couple of weeks to take vacations with his new fiancé. Marcos sure was cheap, but his price reflected his work.

We have since gone through a series of outsourcers for various projects. From lead generation to simple CSS alterations and basic pages. And the results have been uniformly the same. The talent is cheap, but the results are marginal at best, and reliability is non-existent. My favorite was when one of our better guys, Prem, wrote us an email saying “Sorry, Couldn’t work on your Project for the Past 2/3 days due to complete Power shutdown during Day time & also problems with Internet Connection.” Needless to say about half our projects fall flat on their face.

I no longer fear for the job security of quality engineers in the developed world anytime soon. The need for quality and reliability is a massively hard problem even when you have the talent sitting at the desk next to you. Outsourcers have little incentive to produce anything more then the minimum requirements as typically even the best individuals and firms are balancing multiple projects at once. Loyalty is almost impossible as each fights for better ‘feedback scores’ so they can obtain more, better paying work. But if you set your expectations low, and realize a lot of your projects might fail, outsourcing has the potential to be a great, if frustrating experience.

Wow, I have quite randomly appeared in Exec, an international website geared towards business executives, in an article entitled Women in Enterprise. The article uses me as an example of “steller female talent” from Silicon Valley to discuss the emergence of entrepreneurial women worldwide. I find this honor a bit silly as women like Nina Bianchini (CEO and co-founder of Ning) and 23andMe co-founders Linda Avey and Anne Wojcicki, are really breaking ground and kicking ass in Silicon Valley.

The subject of Women Entrepreneurs always fun to explore.This Exec article suggests that more women are becoming entrepreneurs and challenging traditional boundaries. Over the last couple of decades the percentage of small businesses owned by women has climbed past 25%. But these numbers are deceiving as one look around the tech landscape demonstrates that women aren’t entering every entrepreneurial space in equal numbers. This was especially obvious at the Google I/O event last week as I think women were outnumbered 20-1.Women simply are not around starting companies in certain industries, usually around the math and sciences and related to tech, engineering and finance. The few women that do appear in the space are most frequently in PR or marketing.

One major thesis on this drought is because girls have not historically entered the maths and sciences at the level of boys. The leaders of the tech industries today were the ham radio gurus and computer hackers of yesterday. We need to encourage our young girls to build things, write code, be geeky! As a kid everyone always referred to me as a ‘tomboy’, I just thought sports, and woodwork, and playing war with elaborate forts to construct were the cool things to do. Its neat to be called ’steller talent’ even on a random international site, but the Exec article is a bit ahead of its time. Women aren’t quite sprinting to call themselves entrepreneurs quite yet.

Can you spot the single women in this photo?

Via Marc Andreessen, whose blog.pmarca.com is phenomenal.

Sleep is Queen. We all know this fact, but I frequently forget how miserable life gets when Queen Sleep gets mad at me and leaves me restless night after night.

Last week was brutal.   For four nights in a row I was rotten.   I would feel exhausted and fall asleep the moment my head hit the pillow, but there I was an hour or two later, wide awake, counting goats, rice kernals, anything! if only I could sleep!

After a few sleepless nights I finally gave in to this restlessness and popped my computer open at 2am. I worked until 6am and then passed out hard. I woke up actually feeling refreshed. Beat to shit, but refreshed.

During those 4 hours of late-night work, I did the one project I had been neglecting for the past week. The one that was just sitting staring at me with its sullen eyes. Daring me to forget, daring me to try to move on.

As an entrepreneur on a very small team there isn’t much direct transparency into my day-to-day activities. But there is always Queen Sleep. And she is always watching.

Triggit had our first conference booth this past week at Ad:Tech.  It was a great success and everyone seems pretty excited about what we are up to.

Flow: The Psychology of Optimal Experience.

Mihaly Csikszentmihalyi

It’s the moments that hours feel like minutes, when you miss a date because you were so immersed in an activity that everything around you seems inconsequential.  That is Flow.  In a fantastic book stemming from years of research and study, Mihaly Csikszentmihalyi provides a convincing framework for identifying, and achieving moments of this optimal experience.   In evaluating how we structure of our lives, our daily activities, our upbringing, Csikszentmihalyi suggests that by keeping your mind attuned to the idea of Flow, this state of pure experiential happiness is obtainable as a end, not just an abstract.

We live in what I believe is one of the scariest, and most amazing times to ever be alive.   We’ve time, money, health, and resources to navigate our world in ways that have never been possible before. Yet so many people see discontent with their daily existence, and yet frustratingly fail to ever do anything about it.  I really enjoyed how this text explores the questions of what is happiness? What is optimal?  Its something I think about a lot as I attempt to confront all of today’s paradoxes and weave together a reality that will let me sit in my rocker on my centennial birthday and look back on life with a shit-eating grin my face, just giggling at how delightful it has all been.  Fantastic stuff.

All the coffee was French press. They used to make it so thick and delicious that when you were finished there would be a film of grounds stuck to the bottom of your cup. But for a dollar fifty, you could sit and get wired and just work…work…work. Triggit started amid the ardor of those tables, Zach took me there to work the day I moved to San Francisco, and Ryan was met, befriended, and recruited from those days (although let it be noted he never actually enjoyed working there…). Roasters was Triggit’s coffee shop. These days they take away the power sockets on the weekend so people don’t nest for to long, and the coffee has gone the wrong direction (they are attempting to master the art of roasting), but when you walk in the door, Ritual Roasters Café still emotes raw, vibrant, energy. It was wonderful to be able to move into our own offices, but Roasters provided many a great day to Triggit. Its great to see them getting some loving from the New York Times, they have created an amazing atmosphere, and really are kickin ass.