It’s difficult to imagine Jack Dorsey ever fitting the label of “small business owner.”
But as he points out, even the largest businesses had to start somewhere.
“We always start small, and I think there’s something really precious and unique and awesome about being small and then growing,” Dorsey, who co-founded social media service Twitter as well as mobile payments company Square, said in an interview after a small business forum on Thursday in Washington.
Dorsey now employs nearly 2,000 workers between the two companies, with Twitter boasting 200 million monthly active users around the world and Square quickly gaining traction in the United States and Canada. But as he points out, there have been plenty of challenges along the way for both ventures.
During a discussion with SBA Administrator Karen Mills to celebrate National Small Business Week, and in a subsequent interview with On Small Business, Dorsey shared some of the lessons he learned along the way.
1. Start with an idea
A common misconception, Dorsey said, is that successful entrepreneurs set out to be their own boss, and then they go searching for an idea. More often, he argued, businesses succeed when their founders take the reverse approach.
“It doesn’t start by you waking up and saying ‘I want to start a business,’ it starts by you waking up and saying ‘I’m really passionate about this thing and I’m going to do whatever it takes to make it work,’ ” Dorsey said, noting that he became interested in computer programming and digital communication long before he became interested in starting what became Twitter.
2. Keep a diary
Dating all the way back to high school, long before he was building companies, Dorsey was keeping a journal. Now, he calls it “probably the best thing I have ever done in my life.”
“Find a simple way way to track your progress,” Dorsey said. “You really get to see how you have grown, how your business has grown and how your own leadership has grown.”
He added that tracking that type of progress can help you decide whether you have the potential to grow beyond a local business into a larger enterprise.
3. Communication and cooperation are key
Dorsey recalled the early years at Twitter, when the site occasionally crashed due to miscommunications (or sometimes, a complete lack of communication) between his engineering team and his operations team.
“If you have two departments that are not talking, if you have two people who just can’t get along, that friction will manifest in the product itself, and your customers will see that friction,” he said. “You are putting your company’s issues before your customers, which is just rude and selfish.”
Correcting those communication lapses has been a top priority.
“We make sure we design and engineer the company and the organization as much as we do the product and the service we have built,” he added.
4. Build a transparent company
During every meeting at Square’s headquarters, someone takes notes, and those notes are then sent out to every employee in the company. The memos “keep everyone on the same page,” Dorsey said, but there are additional benefits, too.
“We also get all these new, diverse perspectives, and it makes people think in different ways, and that creates a lot more creativity in the organization,” Dorsey said. “Making sure that everyone sees that has been the most transformative for us.”
5. Sometimes, it’s okay to break the rules
When Dorsey’s father, Tim, was 19 years old, he and a friend started a pizza restaurant called “Two Nice Guys” in St. Louis, Mo. As one of the first rules of the business, the two business partners agreed never to date any of the wait staff they hired for the pizzeria.
“The first person they hired was my mother,” Dorsey said during the event. “My father fell in love with her, and he went to his best friend a week later and said ‘I broke the rules, I fell in love with Marcia, the business is yours.’ ”
“I was born 10 months after that,” Dorsey added with a grin.