Here at the DEMO conference in Santa Clara, VentureBeat’s Matt Marshall asked Twitter founder Jack Dorsey about his regrets, “What can the 67 companies here learn [from your experiences with Twitter]?” Marshall asked.

Dorsey, who is still Chairman of Twitter, put context around his answers, “Twitter has some interesting scaling issues, massive spike around an event” and then went on to bring up the following more relatable points.

• We were a company built around communications, but we weren’t communicating with our users, not letting them know why we were going down. Once we started blogging about it, we engaged users.
• We were very poor internal communicators in the beginning. The product needs to have well-defined goals.
• We were flying blind on analytics, had no data about what was happening. We didn’t take the time to build systems that could track what was going on, and once we did, we found holes.

“The hardest thing for an entrepreneur to do is get started,” Dorsey continued, “Twitter was an idea that had been evolving since I was 15 years old.”

Dorsey then talked about those mistakes in the context of Square, “We’re not at risk of losing 140 characters, we’re at risk of losing a sale … We’re dealing with actual people’s money, so we can’t make mistakes.”

About Twitter’s forthcoming announcement, “It’s a great turning point in a company when you can have a press event in your company, so I’m going to allow them that glory.”

About his future plans after Square, which is now giving away 10,000 of the black Square credit card readers a day, Dorsey said, “Healthcare, There’s nothing more precious to us than our health.”

Crunchbase

• SQUARE
• JACK DORSEY

Company: Square

Website: squareup.com

Launch Date: February 2009

Funding: $141M

Square is a revolutionary service that enables anyone to accept credit cards anywhere. Square offers an easy to use, free credit card reader that plugs into a phone or iPad. It’s simple to sign up. There are no extra equipment, complicated contracts, monthly fees or merchant account required. Co-founded by Jim McKelvey and Jack Dorsey in 2009, the company is headquartered in San Francisco with additional offices in Saint Louis and New York City.

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Person: Jack Dorsey

Companies: Twitter, Square, Ustream, Fancy, Thrive Capital

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