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

Alexia Tsotsis

Alexia Tsotsis is the co-editor of TechCrunch. She attended the University of Southern California in Los Angeles, CA, majoring in Writing and Art, and moved to New York City shortly after graduation to work in the media industry. After four years of living in New York and attending courses at New York University, she returned to Los Angeles in... → Learn More

Thursday, November 10th, 2011
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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.”


Company: Square
Website: squareup.com
Launch Date: February 2009
Funding: $341M

Square is making commerce easy for everyone. Starting with a free credit card reader for the iPhone, iPad, and Android devices, Square Reader allows anyone to accept credit cards anywhere, anytime, for a low transaction rate of 2.75 percent per swipe, with no hidden fees. Square Register serves as a full point-of-sale system for businesses to accept payments, manage items, and share menu and location information. Square Wallet, available in the US, is the most seamless way to pay,...

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Company: Twitter
Website: twitter.com
Launch Date: March 21, 2006
Funding: $1.16B

Created in 2006, Twitter is a global real-time communications platform with 400 million monthly visitors to twitter.com, more than 200 million monthly active users around the world. We see a billion tweets every 2.5 days on every conceivable topic. World leaders, major athletes, star performers, news organizations and entertainment outlets are among the millions of active Twitter accounts through which users can truly get the pulse of the planet.

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