… for the gate is wide and the road broad that leads to destruction, and those who enter through it are many.
— Matthew 7:13
EVERY TRAVELER STARTING A JOURNEY MUST decide what road to take. The road well traveled seems like the obvious choice. The same is true in the search for startup success: Following a path of common wisdom—one taken by scores of startups before—seems like the right way. Yet for most startups, the wide road often leads straight to disaster. This chapter looks at how and why this is so.
Let me begin with a cautionary tale. In the heyday of the dot-com bubble, Webvan stood out as one of the most electrifying new startups, with an idea that would potentially touch every household. Raising one of the largest financial war chests ever seen (over $800 million in private and public capital), the company aimed to revolutionize the $450 billion retail grocery business with online ordering and sameday delivery of household groceries. Webvan believed this was a “killer application” for the Internet. No longer would people have to leave their homes to shop. They could just point, click, and order. Webvan's CEO told Forbes magazine Webvan would “set the rules for the largest consumer sector in the economy.”
Besides amassing megabucks, the Webvan entrepreneurs seemed to do everything right.
The company raced to build vast automated warehouses and purchased fleets of delivery trucks, while building an easy-to-use ...