Building A Community In Chicago

My first guest post is up over at Technori. I chose to write about my father, community building and the consummate entrepreneurial skill: listening.

For those unaware, Technori is a fantastic new source of information about Chicago & its entrepreneurs. Started by uber-mench Seth Kravitz, of fame, it celebrates both the technical and the non-technical successes here in Chicago, both large and small. Seriously, check it out.

The Problem With Not Shipping

It’s now been over 3.5 months since Cultured Codes first “State of Sync” post. This was meant to be the first in a series of posts explaining why the long awaited OTA sync was taking much longer than anyone first thought.

In that time, they wrote one more post 3 weeks after that and then nothing. In that last post, they even hinted at more details starting to trickle out, but so far nothing has been released. Cultured Code is now almost 3 years behind their biggest competitor in terms of OTA syncing, despite a few years head start. It’s now an official meme, complete with it’s own site.

There have been countless articles, tweets and blog posts asking just what is taking so long. Cultured Code is losing customers by the day as people get tired of waiting for the syncing equivalent of Duke Nukem Forever. With each month, the assurances that salvation is coming sound more and more like the pleading to give them more time.

When ( or if? ) Cultured Code eventually launches, their margin for error is so razor thin that any issues that come up ( and, as someone who’s shipped software for 12+ years, they will come up ) will be met with a resounding “THIS is what we’ve been waiting for?”. That will be followed by the last remaining believers limping over to their competitors, hat-in-hand & apologetic for staying with them for so long. Keep in mind that at that point, the majority of these users will be the ones that stuck with them through all of the delays. The faithfuls. Lose them and you’re really in trouble.

To say they have put all of their eggs in one basket is an understatement.

The worst part is that Cultured Code knows all of this. It will permeate every stand up meeting, every iteration retrospective and every bug report or feature request. The fear of launching too soon will give way to the fear of launching too late. It will calcify their team and make them unable to make an changes or improvements for fear of pushing things out more. It’s also forcing people to work on stuff ( code, bugs, documentation, etc… ) that is possibly months old. Bugs found today in code written a month ago are very, very difficult to track down. When everything is fresh in your mind, you solve problems quicker. When things go stale, the cost of changes goes way, way up. Everyone on the team will tense up, not just engineering, until there is some sort of cathartic release.

Also, god forbid something major comes along that threatens to screw up the release in a big, big way. Performance / scaling issues, architecture bugs or something else. Once you’re in the position Cultured Code is in, you HAVE to launch, even if what you’re launching sucks. Scrapping it, saying you made a mistake and you’re starting over is the same ( maybe worse ) than launching and bombing, so why not take the chance? This is how hacked up solutions of all sorts have made it live in applications around the world ( of course, I know from experience ).

Cultured Code has put themselves into a progressively worse position. As time has gone one, they’ve gone from needing their syncing solution to be a solid double to requiring that it’s a grand slam just to justify the past few years of excuses.

This, in a nutshell, is the problem with holding back until things are perfect. OTA Syncing by Cultured Code is, by far, not the first project to be in this position and it won’t be the last. The real answer isn’t to get better predicting what you need, thinking really hard about what the best solution is or to get more A-players.

It’s to get better a working in small units.

With small, chunks of work, you get something out the door quicker. You get it off your plate entirely and can move onto the next project, even if it’s within some larger project scope. Best of all, you get feedback quicker. You get to test your hypothesis quicker to see if you were right or wrong.

Most importantly of all, you practice shipping & finishing.

Update: Cultured Code times their 3rd blog post about sync perfectly with my post. Not only is the timeframe for the beta of JUST the mac-to-mac syncing more than a month out, but they’re removing the legacy Bonjour syncing.

Constraints As A Path To Freedom

Upon visiting the Museum of Contemporary Art in Chicago two weeks ago, I stumbled on this quote by Andrea Zittel:

The only way … you can be free from external rules is to create your own…rules that are even more rigid, but because they are your own, you feel… completely free.

I thought it was so amazing that I had to take a picture:


for use as my desktop. I’m completely overwhelmed at how concisely that quote sums up my own internal philosophy. Over the past few years, I’ve become addicted to the idea of self depravation as a key to unbridled freedom. It really ends up becoming an addiction of sorts. I feel a unbelievable sense of freedom after thumbing my nose at so many ideas and conventions once thought indispensable.

And to show the whole trip wasn’t all deep & philosophy-like, here’s an awesome Koons:


The Secret of Entrepreneur Zen-ness

warning: this post contains profanity. act accordingly.

There’s been a whirlwind of activity the past few days around Justin Vincents ‘Entreporn‘ (Ed: awesome phrase) post. Read the article, it’s pretty good. His main point is that there’s a sort of house of cards that the more public entrepreneurial community is built on. VCs, TechCrunch, etc… are all part of the same snake that feeds on it’s own tail.

Alex Payne decides to get a little self-righteous in his comment on HN, then retracts & clarifies his feelings in a lengthy, well written follow up. He argues you should go big with your ideas and try to change the world. Anything less is copping out like the guy who wouldn’t help Ralph Macchio in The Karate Kid 2.

I was originally going to write about how I totally agree with Justins approach and how Alex is espousing the same narcissistic, mid-life crisis POV that leads to more failure than successes. In the latter case, more often then not, you end up like guy Alex Baldwin makes fun of in Glengarry Glen Ross. “Yeah, I tried to change the world. Tough racket. *drinks*” Where’s the awesomeness in that?

Ironically, Thomas Fuchs, the husband of the target of some of Alexs barbs, Amy Hoy, is featured on the latest post over at The Setup.

The more I thought about it, however, the more I think both guys are wrong & right. Frankly, Daniel Jalkut offers up a middle ground POV in his post. A great piece of writing honestly.

Which brings me to my point and the secret I referred to in the title:

Stop giving a shit about what other people think about what you do with life.

That’s it. Want to try and convert the world to clean fuel? Go for it. Want to open a little ice cream stand on the corner by your house? Go for it. There’s room in this world for large, world impacting problem solving and small, hyper local problem solving. We need both. And guess what? Neither improves your sex life, makes you a better spouse or a better parent. You still have to live your life and do all of those things. If you can do something to make your incredibly short time on this earth more enjoyable for you and the ones you love, do it and get rid of anyone in your life that condemns it.

You can’t rely on acknowledgment from other people to validate what you do with your life. If you do, you’re setting yourself up for a big old shit sandwich. You’ll end up 50 years old, living someone else’s life, pissed off at your lot in life and wondering how you keep getting screwed over.

Besides, if the worst thing someone can say about you when you die is that “s/he made only 10 people incredibly happy”, you led a pretty damn good life.

Entrepreneurship And Making Your Bed

I haven’t worked from an office in almost 6 years. I wouldn’t have it any other way. Yet, I understand that working remotely or without the social interaction an office provides isn’t for everyone. Truth be told, it’s tough to keep focused or motived 100% of the time. There’s always one more hour of sleep to catch or one more web site to check out.

One of the ways that I keep myself on track is to have a simple routine that I follow everyday. It’s not a huge task list or anything, just little habits that I make sure to run through, with each one providing a little *oomph* during the day. To me, it helps to focus and gets me motived.

In addition to providing motivation, a side effect of having a routine is that it enforces discipline. There’s a snowball effect with everything you do during the day. So if you focus on doing small, positive things, they’ll aggregate together to have a positive effect on other areas of your life. The same is also true for negative things aggregating up into a larger, negative effect. It all really adds up in the end.

One of the easiest places to get started is where you start & end every day: your bed. I make my bed every morning. That’s it. It only takes a few minutes. But in those few minutes, I’m doing what I need to do throughout the day: following through with a task. In a nutshell, being able to follow through with something, without someone else making you do it, is a big part of entrepreneurship.

I’m always surprised at how much those few minutes mean over the course of the day. Once I started to do that every morning, I started to look for other little things to clean up, fix to take care of. Now I have half dozen or so things that I do before I start work. It gives me a great sense of accomplishment before I even really start my day. I sit down or head out, ready to tackle whatever I need to.

It make sound simple or childish, but it works. Now, I have to go and make my bed.