People think entrepreneurs are risk-loving. Really what you find is
successful entrepreneurs hate risk, because the founding of the
enterprise is already so risky that what they do is take their early
resources, the small amounts of capital that they have, whatever assets
they have, and they deploy those resources systematically, eliminating
the largest risk first, the second-largest risk, and so on, and so on.
—Jeff Bezos
http://www.37signals.com/svn/posts/1516-people-think-entrepreneurs-are-risk-loving
//
As an entrepreneur all the decisions I have made for projects have not been too risky. It was always a risk I could manage and back-up with my own hard work and investment.
Dirty Coast began because I had all I needed to start it. I had the ideas for shirts, I knew the designers and illustrators through my work with Whence: the studio and we could built websites. The only risk I had to take on was 40k in up-front financing that was my own money. So no debt to a bank and no partners I had to answer to or who could direct the company creatively or financially. Thus I had complete freedom. But freedom also demands extreme focus and diligence. If the company fails it is all on you.
Make smart small decisions.
With Whence: the studio it started out of necessity. I didn't want to work for anyone else. So I started my own thing with my close friend Jason Melancon. I didn't know what I was doing but I was willing to learn and make mistakes (which there were a lot of in the beginning). Overtime I was able to establish a process, a team and confidence in how to manage and keep in the black my own company. The success and resources from Whence were then used to launch Dirty Coast and soon Humid Beings and The Canary Collective.
All of my projects have a starting point that is low risk and then prepare expansion plans designed to work organically based on cause and effect. If this happens we will do this, if this happens we will do that, if neither happens we will re-work the project based on a re-assessment of its failure or lack of success as we had envisioned it. This takes flexibility in thought and openness to allow the project/brand to go where it wants to based on the needs of your audience.
What I have learned over the past 7 years I will post here in my new section "Business/Economy" and this will shift over to the HumidBeings.com publishing platform on the 20th.
I hope it helps with your own plans to start your own venture.