You will either step forward into growth or you will step back into safety.

( h/t Trent from The Simple Dollar )

What if I told you that the true path to financial success and freedom is the lotto?

The lotto.

Fuck 4-8% return every year, you’re a man. You want the big money. You want the thrill of risking everything on the long shot. Pulling out the win against all odds.

So what if the odds are stacked against you? Real men take them on and spit in their eye. And yeah, you’ll spend more money chasing the pot of gold than if you went the safe route, but you’re not in it for nickels and dimes. You want folding money. You wanna make it rain.

This is, of course, stupid. No one would ever tell you the path to financial independence & freedom is the lotto. Yet, every day hundreds of entrepreneurs are being given this same advice. Except it’s not “go for the lotto”, it’s “avoid creating a lifestyle company”.

A lifestyle company?

Around the tech startup / entrepreneurial community, it’s a backhanded label. It means that you have no interest in your company “popping”, hockey stick growth or any number of other bs euphemisms for striking it rich. You’re not thinking about your exit strategy. You’re not worried about how to get to a billion in revenue. You’re not in it be the man or to change to world. You just want to run your own company. As long as it pays your salary, you’re happy. “That’s a cute hobby” they’ll say.

A hobby

In reality, it’s a pat on the head and a “wait over there while the real men talk.” You’re not in Business (with a capital B), you’re in business (little b). It means you’re not playing the game. You’re content to dink and dunk your way to success using singles rather step up, grab your crotch, wink at the prom queen and take your swing, hoping for a home run. Like a man. LIKE A BOSS.

Except it’s still a lotto ticket. The difference is perception. It’s ok to fail at your moonshot company because everybody does! 9 out of 10 startups fail after all! Sitting around with the other lotto ticket holders, knocking back a few, talking about how tough a company is to run is the norm. Everyone’s dream, after all, is to start the company, blow it up and get out after 3 or 4 years. Next!

3-4 years? I’ve never understood having an expiration date on a company. Yet, for a lot of entrepreneurs, they do just that. The message is clear: I’m here for the time being until I can get out and get to where I really want to go. ( Most likely, it’s a beach & umbrella drinks. The standard founder destination. )

Again: I’m here for the time being until I can get out and get to where I really want to go.

What’s that sound like to you? To me it’s a layover in an airport. So from now on, that’s what I’m calling these companies.

Layover Companies

Entrepreneur: Following is an email describing my idea. Since you won’t sign an NDA, you agree that by reading beyond this paragraph you are agreeing not to share my idea with anyone, forward this email to anyone, or discuss the idea without my consent.

Me: I have not read past the end of the first paragraph (“”). I have permanently deleted this email from my inbox.

Entrepreneur: Why aren’t you willing to read my email?

Me: I’m unwilling to have an implied NDA applied to me via your email. You seem to be operating from a perspective of “implied suspicion.” I don’t work this way – I much prefer to operate from a perspective of “implied trust.” Since you clearly don’t trust that I’ll behave responsibly, then I don’t think I’m a good match for working with you.

Amen. Almost every single person I meet with wants me to sign an NDA. I either give them a flat out ‘No’ or I tell them they’re going to be paying for my time. The latter usually draws scoffs. However, if what you’re telling me is so critical to your company that you need an NDA to protect it, then my expertise is coming into play and I should be paid for that. Simple as that. Wanting to get an NDA to protect yourself, but not pay me just says that you want free consulting and don’t respect my time.

If you want to meet with me and discuss things, please don’t think that you’re doing me a favor. I’ll respect your time if you respect mine.

Step one: play good defense. Step two: don’t turn the ball over. Step three: run the ball effectively. Step four: dictate the tempo on special teams. Rinse, lather, repeat. It’s a simple formula — the Shredded Wheat of football philosophy — yet Virginia Tech is one of only a handful of programs that actually dedicates itself to the simple things, because it’s the simple things that win football games. And win, and win and win, to the tune of seven straight double-digit win seasons, three B.C.S. bowls since 2007 and annual national title contention. If it’s so simple, why can’t others do the same? There’s your big question, and I don’t have an answer. But coaches across the land, at all levels, would be wise to pop in a tape of Virginia Tech at work to see how it’s done. Few, if any, do the little things better.

I think the parallels to Apple here are apparent. Apple, just like Virgina Tech, does something so basic, so fundamental, that it’s a wonder why more companies simply don’t copy it. But therein lies the rub: never confuse simple with easy. Doing the things Apple does isn’t easy. Just like Va Tech’s persona, it requires motivation, dedication and the patience to see things through, despite naysayers. Not things are abundant in today’s society.

Most successful people, companies and teams understand this. That’s why simple, effective strategies are looked upon with some awe & mystery. They’re dismissed with a hand wave and blamed on something else ( luck, a certain person, whatever ) that other people don’t have. A nice excuse for why some people shine and over achieve and others falter.

It’s why the old dismissive of “If it’s so obvious, why doesn’t everyone else do it?” can be answered with “Because it’s hard.” People think radical, successful ideas need to be complex if they don’t understand them or can’t reproduce them. That’s because it’s a nice place to lay the blame on when things do work out.

As we’ve seen time and time again with companies, personal finance and, yes, even sports, dedication to a simple idea can reap incredibly huge rewards. After all, “The harder I work, the luckier I get” has never been more true.

Early on during the on boarding process, we had a call with the whole company, where the CEO at the time (Bill Coleman, or the ‘B’ in BEA) took questions from employees. The only one that stuck with me after all these years was this one:

Random BEA Employee: Bill, when are we going to go after IBM in public? I mean, their ads are everywhere. Hell, even my grandmother knows who IBM is, but doesn’t know BEA.

Bill Coleman: When your grandmother can write a $1.5+ million check for Java middleware, we’ll worry about advertising to her. Next question?

BOOM.

Slightly pompous delivery aside, Bill had a great point about business and who you should spend your time selling to. If you’re not talking to people who can write the check, you’re not talking to anyone.

I talk to a lot of entrepreneurs who are having good talks with this person or that person. Always claiming to be one-hop away from “the money”. I’m not sure these founders realize those people are there PRECISELY to keep them away from “the money”. “The money” is busy. They have stuff to do. If they talked to every single person claiming to solve all of their problems with their product, they’d cease to be “the money”.

Of all the things at the start of your entrepreneurial journey, learn one phrase: budgetary approval. Those who have it are your true customers. Find them, woo them, sell them. Everyone else you meet are, buffers meant to keep you spinning your wheels.

During the 80′s I was into metal / rock bands. Metallica, Def Leopard, Montley Creu and the like. As I became a teenager, I got more into rap music. The early 90′s was a golden era for rap, with Dr Dre, the Wu-Tang Clan, Nas, 2Pac and more all dropping their 1st or 2nd albums within 1-2 years of each other. In parallel, grunge music was washing over the country like a wave. Bringing this subculture into the mainstream were bands like Soundgarden, Pearl Jam, Alice in Chains and, of course, Nirvana. I had groups of friends who were into rap and groups that were into grunge, but very few into both. These being the two dominant music scenes in the country at the time, if you were of a certain age, you mostly found yourself identifying with one or the other. I was decidedly in the rap camp, but I respected most of the grunge music I heard and owned a few cds.

As many know, yesterday was the anniversary of Kurt Cobains suicide. You didn’t need to be a devoted fan of Nirvana to understand the impact this event had on the youth in this country. Here was a famous, well liked and talented musician leading the musical charge for a musical revolution and the generation it represented. Throngs of youths idolized him and he was one of the biggest icons of an entire generation. He had given a voice to a lot of disenfranchised youth struggling to find their place in a post-Reagan world.

And like that, poof, he was gone.

It was especially shocking because it was the first time people my age felt a real sense of loss outside of their personal lives. In fact, for many people, it was like losing a family member despite never even meeting him. The closest comparison I can come to for my parents is when JFK was shot. It’s not so much a sense of sadness, but a yearning for what could have been had they lived and the hope they represented.

When I arrived at school the first day after the news broke, his death was THE topic of discussion. I distinctly remember a malaise surrounding everyone. When we all finally got together for lunch and were able to talk about things, I heard someone, whom I thought was a friend, say the strangest thing when I asked about the suicide:

It wasn’t a suicide. My dad says it was a bunch of black guys who killed him & made it look like one. I be all you wiggers couldn’t be happier.

***record screeching….*** Wait, what?

I couldn’t believe what I was hearing. Here’s someone I thought was my friend, a guy like me, and he’s not only spouting off about his racist dad but simultaneously trying to denigrate me. As a kid of 13, I was really confused. That was first blatantly racist thing I’d heard anyone say around me, even without the second sentence. Even back then, I was happy-go-lucky and inclusive of everyone & everything, even if it wasn’t my cup of tea. Maybe I was naive, but that’s ok. Unfortunately, others didn’t share my empathy and sense of inclusion. That’s when I learned a hard lesson: you can be as nice and inclusive to people as you want, but don’t assume the same in return. Needless to say, me and this guy didn’t hang out after that.

That’s why every year when his anniversary comes up and gets a lot of press, I don’t just think of the day a generation lost a idol. I think of the day that I realized there are some shitty, angry people in this world and no matter how I treat them, it’s not guaranteed to affect how they treat me. It’s a cruel lesson to learn. In the end, however, it makes me strive to devote my time & energy on people that enrich my life.

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

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.

• Beer
• Coffee
• Sushi

I’m also not ga-ga over Rails. No wonder I have trouble fitting in.