Jack Dorsey: “The Hardest Thing For Any Entrepreneur Is To Start”

Twitter and Square co-founder Jack Dorsey took the stage at the GigaOm Roadmap conference to talk about his experience being well, basically a jack of all trades (rimshot).

Dorsey revealed that both his own and his family’s experiences with entrepreneurship were inspiration for his two current startups — both of which remove friction from human communication and industry, a process Dorsey described as “getting rid of the ‘conceptual debris’.”

Dorsey has long identified with the struggles of entrepreneurs; He brought up the example of his mother, who ran a small coffee shop in St. Louis, “Starbucks came and it didn’t go so well,” he said.

Then he brought up his dad, who co-founded “Two Nice Guys,” a pizza restaurant also in St. Louis. When Dorsey’s dad and his co-founder began to hire people, Dorsey said, they promised each other they wouldn’t date any of the wait staff. “First person to get hired is my mom,” Dorsey went on, “And so my dad had to leave the business and I was born.”

Before quickly relating these stories, Dorsey said that companies need to start quicker and iterate more; “The hardest thing for any entrepreneur to do is to start.”

One of his favorite things about Square, he emphasized, is that it helps companies start, “It is amazing, you are in business right away, in terms of anyone being a retailer. The line between consumer and retailer, the counter blurs. You see this at Apple, people don’t wait in line, don’t wait behind a point of sale system, there is no counter. It takes the friction out.”

Dorsey said that Silicon Valley’s culture of mentorship also appealed to him because of its frictionless quality, “Any entrepreneur can come up to me and discuss and idea. As people who are also just getting started, we need to make sure that we’re always accessible to people who want to start something new.”