2. Who Is Jack Dorsey?
• Co-founded dNet for dispatching couriers online,
but was kicked out in a disagreement
• Returned home and began studying botanical
illustration at Missouri Botanical garden; To him
illustrating flowers, like programming, was a
“perfect intersection of art and science.”
• Co-founded Twitter from the ruins of ODEO and
served as CEO for two years
• Fired from Twitter as an employee but remained
the group‟s chairman
• Co-founded Square, a company with many
parallels to Twitter despite operating in a
completely different category
• Spends 8 – 10 hours at both companies every
day = only 4 – 6 hours for sleep!
• Single, lives a few blocks from the office
3. How Does He Do It?
1 An usual ability to remain focused
• Jim McKelvey, today is Dorsey‟s partner in Square, recalls their first meeting in
1992. “I was sitting at a terminal entering all this data, and this kid walks up behind
me, with his arms straight at his sides. He was like [McKelvey speaks in a robotic
voice], „Hi, I‟m Jack.‟ I said, „Yeah, I‟ll be with you in a minute,‟ and I turned around
and completely forgot about him until I had to get up to pee. Jack was in exactly
the same position. He‟d been motionless for 45 minutes.”
2 Breaks up large tasks, and identifies areas of overlap
• Creates themes for each day: Monday is for management, Tuesday is product day,
Wednesday is focused on marketing communications and growth, Thursday about
developers and partnerships, Friday company culture and recruiting, Saturday he
takes off, Sunday is about strategy, reflection and preparations for the rest of the
week
Has a clear leadership vision, and a deep understanding of his
3
goals and motivations
• Sees himself as a craftsman than an entrepreneur – building a service rather than a
company
• Finds the common threads between the two companies; views both companies as
utilities, sees parallels in their goal, purpose and vision
4. How Does He Deal With Failure?
• Admits that looking back he was a flawed manager at Twitter and spent
a lot of time thinking about what went wrong
• Wasn‟t strong in his convictions because he felt inferior to Williams who
was the chairman and had funded the company
• Did a poor job explaining where he wanted to go and communicating his
vision to bring other‟s on board
• As Square‟s CEO, he bends over backward to be explicit, to
communicate and to guide. Hosts a “town square” company meeting
every Friday, where he talks about aspirations and values
• Has learned from mentors including Steve Jobs - organizes trips to visit
“beautiful things” to help his staff better understand why he considers
design so important
5. How Does He Integrate Work And Other
Domains?
• His first task every day is to text his
mother
• Has a black nine-inch tattoo, in the
shape of a thick S running down his
left forearm. The tattoo is said to
represent an integral – it symbolizes
integrating everything in his life
• Ultimate aspiration to be the Mayor
of New York City – what gets him
really energized is thinking about
activity within a city, seeing taxicabs
turn and the rush of energy that
courses through
6. My Takeaways
• Find your passion, your core strengths and pursue something that
allows you to utilize them to your full potential
• Find the common threads, the patterns and the areas of alignment in
your life
• Plan for the long term and articulate your leadership vision to others
from an early stage
• Identify positive attributes that you admire from people around you and
try to emulate them
• You can‟t have it all – there are always sacrifices to be made --- but
you can try to optimize and integrate your set up
• You need to be resilient and have an ability to bounce back from all set
backs – optimism is key
• Learn from your mistakes and use lessons to drive change
• Take breaks and learn how to disconnect
