Startup Resources

Bootstrapping wisely means asking tough questions and prioritizing activities that are essential to your business development.

As oDesk VP Matt Cooper learned from his first startup experience, testing and feedback are steps that entrepreneurs ignore at their peril. “You’ve got to test whether the business you’re building is what customers want,” he wrote in a post for Inc. magazine last year.

Cooper describes his early efforts with Soggy Bottom Canoe and Kayak Rental — a venture started with his uncle in the backwoods of Mississippi — as “an unmitigated disaster.”

But it was an experience with valuable lessons that stuck, and he expands that list in the follow-up post, “More Lessons From a Bootstrapping Disaster.”

Acknowledging overly optimistic financial projections, poor understanding of the local market, and the tricky business of working with family, Cooper admits it was a poor business choice.

“I didn’t do my due diligence and knew very little about the location, competition, or anything else for that matter. As my father put it, the decision to help out my uncle, who was going through a rough time, may have ‘earned points in Heaven, but not on earth.'”

Despite the disappointment, Cooper says the memories were worth it: “Despite our long string of mistakes, when it was good, it was magical.”

Read more about Soggy Bottom and smart lessons for startups here!

feature image by Xavi Villalvilla on flickr (CC BY 2.0)

Matt Cooper

Vice President of International & Enterprise

Matt Cooper, oDesk’s Vice President of International & Enterprise, has more than a decade of executive operating experience in both start-ups and Fortune 500 companies. Previously, as a member of the executive team at Accolo, Inc., a recruiting services and technology firm, he grew the business from one employee into one of the top 50 companies on the Inc 500 list. He also co-founded a… read more