[shingen]

I think it's entirely possible to be both throughout a lifetime. I've been frighteningly ambitious and conservative at different points in my life and with different ideas.

When I was 21 / 22, I decided I was going to take on eBay. The premise, circa 2002, was to wipe out fees and shift the monetization to information and reselling (provide analytics & data to the sellers, and a re-selling channel in which they could contact buyers and attempt to generate repeat business). Basically sell tools and productivity to the sellers, instead of just slapping them with fees; at the time eBay was borderline retarded when it came to analytics and data provided by the marketplace.

I built the service, launched it, got modest early traction, took no venture capital, used guerrilla marketing, and then a really bad event struck my life that was outside my control. Shit happens and all that.

My latest venture is more modest, and I'm older and wiser. The odds of success are radically higher in this venture.

At 30 (no kids yet), I find my threshold for frighteningly ambitious projects is now primarily dependent on my personal finances. At 21 I didn't give a shit, at all. When I add another layer of financial security, I'll chase the dragon again - I really can't wait.