The Team. The more time that I spend building companies (Securemote, Linuxcare, Sputnik, Technorati, and now Offbeat Guides), the more I realize that the single biggest risk is in picking a great team. Get a great team that works together, and you can resolve almost every other problem - competition, product, market, financing, etc.

Pick a poor team, and you can have all the advantages in the world - lots of money, little competition, a killer product, a huge market, and the company will find a way to screw it up.

This was probably the biggest eye-opener for me when I moved from CTO jobs to CEO. It's all about the people, and how everyone works together. Learning leadership skills was incredibly important for me to be able to build and inspire teams.

I've seen both sides of this at all the companies that I started. In my experience, it's far and away the most important factor in a company's success or failure.

Management. The more companies I work for, the more I realize that coherent decision makers are the foundation of successful enterprises.

Strapped camera to head.. turned into company

Went to work for company started by guy who strapped a camera to his head ;-)

lol

Went to live in South America just because I was tired of Belgium, no job, no money. Turned out fantastic.

Gosh, I miss Belgium, spent 5 years there. Australian weather is great and stuff, but it's boooring...

Oz is boring? Im stuck in the UK and would love to be back in Oz because the UK is boring (and the weather is terrible)! My theory is that no matter where you live, it becomes normal (aka boring) after a few years.

Haha, so true!

Biggest risk : Not taking a risk, until now.

Going to start on my own from Oct 01, 2008. The current economic scenario makes that option seem more adventurous/challenging, making it my next biggest risk.

Nothing huge yet, but a risk I may be taking in a year or so is moving out of the province/country.

My goal is to move to Seattle with my girlfriend but obtaining a working visa trying to work at a small company/startup seems tough and basically start something new before moving back to Canada to start the next part of my life (probably a family)

It's a big risk to me because I'm currently in a nice cushy startup with great people, good money, and I really can't complain. But a man's gotta experience life you know?

Working at a corporation for a year. I guess it was worth it to know what it is like, but a terrible long term financial, educational, and health risk--not because of the company, but the domestication of relying on someone else over many years. Also, the opportunities I missed out on while working.

Got married.

Sold everything, moved from Australia to London.

Took up contracting

Wife worked on our startup while we bootstrapped instead of earning a salary.

In retrospect, it really doesnt feel like a risk at all, but I have significantly less hair.

Getting married.

Leaving a decent job where I worked with good people and was paid well. I left to go to grad school full time.

I have yet to complete my studies, but my feeling is that it has been worth the cost.

Not quitting my finance job.

Actually it was using 90k in credit card debt to finance my first business. It paid off.

quit my job, no funding, just own savings, each day of my personal freedom and a hard work is the best revenue I can get from this risk!

customer risk. assuming people know what they want.

specifically, do the potential customers who i interview really know how they want their information management problems solved

payoff: tbd

I wanted to study Medicine. I ended up working for Wall Street.