To start, Elmendorf went to the white board and asked the crowd of about 100 what they wanted to know. People shouted out about a dozen questions including “what was your first entrepreneurial experience, what didn’t you like about school” and “what was your biggest failure?” He wrote down their questions and then spent the next hour answering them and telling stories.
Elmendorf’s first entrepreneurial experience was with his brother selling Xeroxed space invader game sheets for a quarter.
He came from an entrepreneurial family with a lawyer dad and a mom who ran her own catering business. So he thought that was the way of the world.
Elmendorf also worked a whole summer for a company and didn’t get paid. He learned early on about the importance of contracts.
“Lesson number one write shit down and get it signed” Elmendorf said.
When he met Richard Yoo, another co-founder of Rackspace, he presented him with a four-page contract outlining the duties Elmendorf would perform.
In 1998, Yoo, Elmendorf and Pat Condon, all students at Trinity University, formed a web hosting company that became Rackspace. Graham Weston and Morris Miller met with the three later on at a burger joint and they agreed to invest in the company.
Today, Rackspace is a publicly traded company with more than 4,000 employees. Its stock, traded under the symbol RAX, closed at $44.02 share Friday on the New York Stock Exchange.
Back to his crowd-sourced talk, the thing Elmendorf didn’t like about school was it’s linear instruction.
“I can learn non-directionally all the time,” he said. “I’m a pathological learner.”
He loves Reddit and the Internet.
Someone asked him what he does when he is bored. He cooks. He once took a three-day class in meat fabrication.
What is his most important startup advice?
“It’s a team sport. It’s never just one person,” he said. “Even at the most primitive level it’s a team sport.”
It’s important to like the team you work with at a startup, Elmendorf said.
“If you don’t like them now, it’s not going to get better,” he said. “It’s like parachuting into a bad marriage.”
Elmendorf got along with Rackspace’s core team so well that he still likes them after 13 years of working together.
Also, it’s important to know what you’re good at, Elmendorf said.
“I’m not a good manager,” he said. He likes coding. “The code doesn’t get mad.”
Today, Elmendorf has a new startup, r26D, which created TruckingOffice.com, a small fleet management system. The company has 1,000 customers.
“I like projects that are targeted at small businesses,” Elmendorf said.
He advised the crowd to find a startup that customers like and are willing to pay for its products.
“You do know you can’t buy your own products,” Elmendorf said. “You need to ask yourself who is the customer and how do I serve them?”