Jack Dorsey at Startup School - Deepstash
Jack Dorsey at Startup School
Jack Dorsey at Startup School
Jack Dorsey at Startup School


117 reads

Jack Dorsey at Startup School

Startups are like artists

"The Art Spirit", by Robert Henri is about creativity through the lens of an art student. 

The book starts, "Art, when really understood, is a province of every human being. It is simply a question of doing things - anything. Well, it is not an outside extra thing. When the artist is alive in any person, whatever his kind of work may be, he becomes an inventive, searching, daring, self-expressing creature. He opens ways for better understanding."

Startups are interesting to others. They don't have to be painters to be artists. They can work in any medium.


27 reads

It's not just how important the end product is but the actual craft of doing the work, inventing within the work.

Few have the courage and stamina to see it through. You have to make up your mind to be alone in many ways. 


20 reads

Do what has not been done before

The old masters did know how they compose their pictures. Do not fall into the conventions they established. These conventions were right for them. 

It's easy to fall in the footsteps of others, to do what they do because you think it's the right way. You may think if they've had success, you can copy that success. Yet, you have to find your own path to be successful.


11 reads

Be a master of your own tools

An art student must be a master from the start. He must be a master of his own tools. That mastership is not a destination. It is a process and constant practice.

It is not enough to think of great things. What really matters is the work. To implement those ideas. Other's success seems like it happened in just a moment, but it takes years and years of patience.


10 reads

If you don't have purpose that is shared between everyone, you will not do anything that is timeless.

You must focus on building what you want to see in the world. When you have a passion for building for yourself, that' will draw other people to your cause and your team.


8 reads

Bill Walsh took a football team near the bottom and brought them to the top. He focused entirely on a new standard of performance.

The most challenging transition for an entrepreneur is going from individual action to leading a team. First, start with an idea and a philosophy of purpose, then find people to help you implement it. 


10 reads

  1. Start with a comprehensive recognition of reverence for identifying the specific actions and attitudes relevant to your team's performance.
  2. Be clear on your expectations of effort and execution of your standard.
  3. Let all know that you expect them to possess the highest level of expertise in their area.
  4. Teach your beliefs, values and your philosophy.
  5. Teach connection and extension. You don't want independent contractors, you want people who feel connected that can expand the organization.
  6. Make the expectations and metrics of competence.


5 reads

Habits of a leader

  1. Be yourself
  2. Be committed to excellence
  3. Be positive
  4. Be prepared to recognize fortunate situations and act on them immediately. Good luck is a product of good planning.
  5. Act professional. Push in your chairs, tuck in your shirts. If you build an organization that does that, you build an organization that cares about itself.
  6. Be organized.
  7. Be accountable
  8. Be near-sighted and far-sighted.
  9. Be firm
  10. Be flexible
  11. Believe in yourself
  12. Be a leader. Ensure to show and not tell.


4 reads

What not to do

  1. Exbihit paralyzing patience.
  2. Engage in massive delegating.
  3. Act in a tedious, overly cautious manner.
  4. Become best buddies with certain employees or play favouritism.
  5. Spend excessive time socializing with superiors or subordinates
  6. Fail to continue performance evaluations of long-time or tenured staff members.
  7. Fail to actively participate in efforts to praise and acquire new hires.
  8. Trust others to carry out your fundamental duties.
  9. Find ways to get out from under the responsibilities of your position.
  10. Promote a laid-back organisational environment.


7 reads

  1. Praise is more valuable than blame.
  2. Set expectations. Use every means before and after comment to tell troops what they're going to do and what they have done.
  3. Discipline is based on pride in the profession of arms, meticulous attention to detail, and mutual respect and confidence.
  4. Officers must assert themselves by example.
  5. General officers must be seen in the front line during action.
  6. There's a tendency for the chain of command to overload junior officers with excessive requirements in the way of training.


5 reads

  1. Formally celebrate and observe the momentous achievement and ensure everyone feels ownership of it.
  2. Allow pats on the back for a limited time.
  3. Be apprehensive about applause.
  4. Develop a plan for your staff that gets them back into the mode of operation that produced success.
  5. Address specific situations that need shoring up.
  6. Be demanding. Do not relax.
  7. Don't fall prey to overconfidence. Make change for the sake of change.
  8. Make hard decisions immediately after success.
  9. Never fall prey to the belief that getting to the top makes everything easy. It doesn't.
  10. Mastery is a process, not a destination.


5 reads

Keep daily notes

Keep a list of everything that you want to do every day and a list of things that you don't want to do. This will help to establish patterns for yourself. Every day for a week, wake up to this note. Check it throughout the day and before you fall asleep.

For example:


  • Stay present.
  • Be vulnerable. Show people your mistakes and fears.
  • Drink only lemon water and red wine.
  • Exercise.


  • Don't avoid eye contact.
  • Don't be late.
  • Don't set expectations for someone and not meet them.
  • Don't eat sugar.
  • Dont drink hard liquor or beer on weekdays.


5 reads


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