An Afternoon with Jack Dorsey

A good speech inspires. It stirs emotion. It is simple. And sometimes a good speech comes disguised as something else. When Jack Dorsey, co-founder of Twitter and Square, visited Harvard Business School last week, his fireside chat with Karen G. Mills ’75, a past Administrator of the Small Business Administration, evoked emotions that only memorable speeches do.

After I left, I kept thinking about what Jack said. “You have to be in control of your own destiny,” he calmly stated. “Surround yourself with people who challenge your ideas” and “learn from serendipitous moments,” he insisted. As I was crossing the Charles River, these thoughts kept swirling in my head.

If I were not able to attend, I would appreciate if someone shared those remarks to the wider community. I want to share three things that stood out for me.

Every good speech consists of three parts. The first part is what I call the “The Appearance.” The speaker does not impress you first with his words, but with his appearance instead. President Bill Clinton, it is said, grabs everyone’s attention when he walks into a room.

What is his secret? He gives everyone his full, undivided attention. So did Jack. He made you feel he was there; his thoughts were collected. When a student threw him a curveball during the question and answer session, he stayed calm. He didn’t need to wear an expensive watch or a suit, instead preferring jeans, sweater, and simple shoes. He let his sincere interest shine through.

The second part is “The Story.” The speaker tells you his message, but he does not simply state what happened—he also tells you a story. Consider Martin Luther King’s effective messaging in his famous “I have a Dream” speech: “Five score years ago, a great American, in whose symbolic shadow we stand today, signed the Emancipation Proclamation, but 100 years later, the Negro still is not free. … America has given the Negro people a bad check, a check which has come back marked ‘insufficient funds.’

“And so, we have come to cash this check, a check that will give us upon demand the riches of freedom and the security of justice,” he exclaimed. A good story evokes emotions, and makes you listen more closely.

During the course of the chat, Jack kept telling stories. He told one especially humorous anecdote about his young father who opened a pizza restaurant with his best friend. In order to preserve the sanctity of the business, Jack explained that the two made a rule that they would not date any of the waiting staff. Naturally, the first person they hired was to become Jack’s mother. His father, having broken the rule, gave up the business to his best friend.

Jack shares one way he stays creative. He leaves his house every day at 7 a.m., only arriving at the office at 8:30 a.m. He walks to work, taking different routes each time. He says that observing ordinary life helps him to see things he would otherwise not see. At the office, his mornings are entirely scheduled. But his afternoons he leaves open to wander around in order to leave room for unexpected meetings or encounters that would otherwise not happen.

But you wouldn’t clap yet, because telling a story and appearing attentive aren’t enough. That’s why every good speech has a third part, the part I call “The Value.” A good story told in the right way is powerful. It makes for great entertainment. But it can be so much more powerful if the content is strong.

Jack said he sees technology fundamentally as a tool that should be used to make things more convenient and faster for a large audience. He emphasized how important it is to stay in control of one’s own destiny. He strongly insisted on enforcing transparency across organizations. Any notes of any meeting within Square are shared with everyone to promote team culture.

Most importantly, he said that it is important to build or work on something that one wants to see in the world. In another story, he explained how following your passion will lead you to your niche. And if you have passion, you will attract others, he noted. “Show, don’t tell,” he said. And when he pitched Square, he gave venture capitalists 140 reasons for not investing, and only 10 for investing. There will always be venture capitalists who don’t like your idea. Pitch your idea authentically and honestly.

That is it. Three simple lessons. Give your full, undivided attention. Tell your lessons through stories. And add value. What probably stood out most was Jack’s insight on constantly meeting the unexpected. That’s the reason he walks to work and walks around the office after scheduled meetings—to allow for things to happen that would otherwise not. Stay creative, stay serendipitous.

Patrick D. Daniel is a Visiting Fellow at the Graduate School of Arts and Sciences. Find him on Twitter @patrickddaniel.