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10 Entreprenurial Lessons From CEO Jack Dorsey

10 Entreprenurial Lessons From CEO Jack Dorsey

Jack Dorsey is only 36 years old but is already responsible for founding two multi-billion dollar companies as well as creating a net worth estimated at $1.1 billion.

Dorsey (@jack) was one of the founders and CEO of Twitter. The lessons he learned starting and running the company would play a large part in his business philosophy for his next business Square.

It is Square, more so than Twitter, which demonstrates that Dorsey is a true business visionary. While he is still relatively youthful he has a lot of experience under his belt and a unique business mind. Dorsey spent much of his early twenties discovering what he wanted to do. Among his pursuits was a brief period as a fashion designer and a botanical illustrator, starting a web based dispatch company and computing programming.

To help understand what guides Dorsey’s business decisions at Square, below are ten of Dorsey’s key business principles. They offer a glimpse into the minimalist but highly effective way that Dorsey runs his company. They also suggest how we can manage our own businesses so that we achieve our goals.

#1 Transparency is Key

In the early days of Twitter it was a common experience for the site to go down because of traffic surges. Being unable to use the site was something that upset a lot of Twitter users. Jack Dorsey said that Twitter failed to communicate to its users why the site was having trouble with its down time. He said that he learned a valuable lesson about being transparent with its users and the technical challenges the site faced. As an added bonus by being open about the technical problems with the site, Twitter ended up attracting additional engineering talent.

#2 Conversation with Your Customers Creates Loyalty

Once Twitter had made the decision to be more transparent it found that one of the greatest benefits was increased customer loyalty. Because users felt that they were part of the development of this new technology they had a deeper level of engagement. Making your customer a champion for your brand is an important part of the marketing strategy for both Square and Twitter.

#3 It Is Crucial That All Employees Are Heading In the Same Direction

Jack Dorsey says that the greatest threat to both Square and Twitter does not come from his competition. Instead he most concerned about ensuring that everyone in the company is heading in the same direction towards a common goal. He believes that in order to achieve this employees must be educated about not only what the company’s goals are but why they are doing it. It also means that there must be open communication through out the company about what other employees are doing. In order to help achieve this, in Square whenever three or more people are having a meeting the notes of the meeting must be recorded and freely shared around the company.

#4 Record and Analyze Everything

One of the mistakes that Twitter made, Dorsey says, was not to track and analyze the performance of its system. At the beginning it had no way of tracking the usage patterns of its users, and thus no way of improving it. From the beginning with Square Dorsey was careful to log and track all information about the business. All aspects of the business are tested and measured.

#5 Become a Good Story Teller

Jack Dorsey says that one of the best skills he has learned is how to become a better story teller. What he means by this is that you must understand your product from your customer’s perspective and tell a story around that. For example when he tells the story of Square he pictures a person from the city of Chicago and how they go to have a coffee and how Square is part of that experience. The great thing about using a story is that it is something that anyone at any level of the company can relate to. This helps everyone from Engineers to marketing staff to be moving in the same direction.

#6 Minding the Team Dynamic Is One of His Most Important Tasks

Dorsey says that making sure that he has an optimal team working towards the company’s goal is one of his most important jobs. By this he means bringing in the talent that the team needs and removing those elements which are distracting or not working well with the team.

#7 Minimize the Mechanics of Your Product

When designing a new product Dorsey aims to minimize the amount of mechanics that are required in order to use it. When something takes fewer steps to use, more people will use it. With a system such as Square which requires a larger user base in order to be successful, this simplification of use is crucial.

#8 Make Sure That You Do Everything Perfectly but Limit the Number of Details

Dorsey believes that everyone in the company should focus on a limited number of crucial details. Once they understand what these details are they should make sure that they do them perfectly. He says if you can do that and understand at a higher level how they fit in with the overall goal of the company then you cannot help but succeed. For Dorsey as CEO of Square those details are recruiting, internal and external communication and financing.

#9 The “Magic Moment” Is When What We Create Intersects With Our Lives

Jack Dorsey tells a story about how the new owner of his father’s old pizzeria tweeted at him one day. He told him that the pizzeria was now using Square in order to process its transactions. For Dorsey this is the “magic moment” when what we have created naturally intersects with our lives.


#10 Expect the Unexpected

There is a Linda Barry quote that Jack Dorsey likes to try and live his life by. That quotes says “Expect the unexpected, and whenever possible be the unexpected.” As entrepreneurs we should expect that many things that we cannot predict will occur. How we manage these events will in a large part dictate our success. However reacting to the unexpected is by itself not enough. We must also be a force of innovation doing things that others cannot yet imagine.

This post was made by Tom Jones of