software startup

CTO dinner in Vancouver

For all it’s current acclaim, Silicon Valley has a problem.  While an abundance of capital, ideas, energy, and motivation is obvious, there’s also a growing shortage of engineering and design talent.  The Valley is becoming increasingly overfunded, but increasingly under-resourced – a condition which represents huge opportunity for Canadian cities.

This was why on Nov. 1st, we organized a CTO dinner in Vancouver.  Short flights to the Bay area, a high desire of Canadians and foreigners to live in Vancouver, leading technology institutes,  and an already existing and growing startup ecosystem all prime Vancouver to take it’s spot as a natural extension to Silicon Valley, and a consumer technology hub … and if that happens, it’ll be lead by designers and engineers … not MBA’s.

One challenges in achieving this vision is often not talked about:  Establishing a network of technology leaders / CTO’s  with experience building and scaling technology and teams.  CTO’s, unlike their CEO peers, don’t always have networking and socializing baked into their DNA’s.  This is obviously a hugely exaggerated stereotype, but they’re often builders, spending most of their current time, and certainly their past, hacking away building amazing product and technology.  Sharing war stories about scaling their technology and teams benefits the whole … experienced leaders, home brewed leaders, and new comers alike.  It’s something you see in the valley all the time … but not in Canada.  Hopefully we see more of this to come in Canada.

Please do celebrate fundraising

Not that long ago a tweet went viral that annoyed me to no end:

“Congratulating an entrepreneur for raising money is like congratulating a chef for buying ingredients.”

A blog post has been on the tip of my tongue since then, and recently, Mark Solon pushed out this beauty of a post which nicely summarizes the sentiments I was feeling.  http://towriteistothink.com/2012/09/18/celebrate-and-then-get-back-to-work/

I think the analogy of a chef (and the overall sentiment that raising money is insignificant) completely minimizes the significance of raising money.  Yes … I totally get it … raising money is only the beginning.  It’s a long journey, for which, raising money is only a small part.  But comparing it to buy ingredients … something that anyone can do with great ease … is misleading … and  is self serving to the person making the comment.  It’s what kids do in the playground when they name call.

Despite the impression people get from reading techrunch, convincing skeptical investors who are subjected to hundreds of pitches is hard …  damn hard.  Unless you’re a serial entrepreneur raising money on a deck (which rarely if ever happens), it represents many months, or years of sacrifice, hard work, iteration, and commitment, and if you are a serial entrepreneur, it still represents the hard work from the past bearing fruit.

In addition to the small validation you get for your effort by investors, there’s other reasons to celebrate and for congratulations.  Being able to tell your family that you’re working your tail off, making personal sacrifices, but at least not doing it for $0 is not insignificant.  Not having to lay off awesome, productive members of your team, that feel like they’ve become family is pretty awesome too.

Look, I get it,  You haven’t accomplished much yet.  You’ve just hit a single home run in the bottom of the first inning.  There’s a long way to go. I also get it that people want to discourage celebration because they want to discourage complacency.  I just don’t think that happens.  I’ve never met an entrepreneur that settles after raising money.  I think if anything its served as a motivator.  It’s added pressure and responsibility (in a good way).  You feel a personal obligation to return money to the individual investors.  I know that was the case with Attassa as I wrote about here.

So in parting … go dancing with your family, get a massage, drink wine with your partner, go to a movie, go go-karting with the team, and then as Mark says, get back to work.

Moving on from Yousendit

It was just over a year ago that Rod, Dwayne and I joined Yousendit after they acquired our startup Attassa.  After much thought, I’ve decided it’s time to move on.  There’s a lot of amazing people at Yousendit who’ve made me feel completely at home.  For that, I leave with nothing but respect and thanks to the people I’ve worked with.  In addition to leaving some truly great people, the hardest part is leaving a green card process.  The thought of trading permanent residency for the world of H1B’s, B1’s, E-2’s and ultimately the whims of USCIS is a little sad.  The US needs to take a serious look at immigration policy.  I dream that in 10 years, people look back at this time and view it as archaic and asinine.

Paul Graham would say that true “hacking” is not science, it’s not math, but rather, it’s art.  It’s creating things.  A hackers tools are a compiler and an IDE rather than a canvas and a paint brush.  Call it what you will (I like the artist analogy since it makes me look way cooler, hipper, and trendier than I really am), but whatever it is, I love it. I also believe that if you define hacking as “seeing a vision and implementing it”, it becomes something very hard to experience outside of starting up.

In larger organizations, it’s necessary to avoid disaster.  Only a very small number of programmers can actually envision and then design software;  and it’s super hard to find these people.  So … organizations gravitate towards designing by group thought, mostly lead by PM.  In this world, developers implement the design and vision.  And this works since for larger organizations to win, they just need to suck less than other big companies.  You could argue that strategically this is the way it should be.  You’d be foolish to pin the corporate strategy on the design and vision of a few hackers.  But for startups, the corporate strategy IS the design of a few hackers.  That’s your only choice.  Companies like Google used to get away with a hybrid by encouraging hack days, 20% time, and innovating from within.  Their revenue / employee afforded the luxury to innovate from within while still producing the bottom line.  That’s rare.

Most hackers can’t “hack” for a living; much like musicians can’t play music for a living; they mostly hold down day jobs at bigCo to afford their true passion to build what they want on evenings and weekends.  But I’m in the fortunate position to step back and hack full time again.  For all I know, I may be implementing someones vision in 4 months, and I’d be ok with that.  It annoys me to no end hearing engineers complain about working for bigCo and their lack of ability to engage their creative minds.  What a first world problem.  But for the time being I can’t wait to get started …

Lean startup – in Objective C

I felt like modeling some of the lean startup process in objective C – including when to raise capital.


Idea *idea= [[Idea alloc] initWithPassion];

Experiment *experiment;

while ([idea.market representsMassiveProfit]){

   experiment = [[Experiment alloc] initWithSomethingTestableAndIdea:idea];

   [experiment validate];

   if (experiment.addsValue){

      [idea addObject:experiment];

   }

   if (capital + idea == majorGrowth){

      if ([capital.source addsNonMonetaryValue] && [capital doesNotUnreasonablyDilute])

      {

         [capital accept];

      }

   }

   [experiment release];

}
Now if only someone would write an initWithPassion, addsMonetaryValue functions this whole startup process would be a breeze!

Tweetgab startup weekend project

Twitter is an unbelievable tool for getting the sense of what’s going and what’s being said at any given moment.  It truly is a tool for measuring “the pulse” of any event.”  One of the greatest things about twitter is that it’s completely free form.  There’s really no rules – as long as the content crams into 140 characters, it can be said.  As a result, the data within twitter has become very chronological.  A stream of unrelated tweets, with no real surrounding context.

No where is this felt more than at Conferences where organizers are beginning to use twitter to broadcast on projectors what the audience is saying.  This is great in theory, but there’s still no real structure of the data.  It’s just a stream of tweets, bound by a hashtag with no real context.

I attended a Startup Weekend in Palo Alto last week and formed a team which tried to solve this problem.  Here’s the presentation … Pardon the number of “Um”‘s … I really need to learn to speak better publicly.