Throughout his career, Jack Dorsey has operated with a laser focus on the power of fast, simple, and effective communication. Reaching well beyond his work in founding and serving as Twitter’s first CEO, Dorsey has applied his passion for good communication to his other business ventures, as well as his personal management philosophy.


In the past two decades, he’s taken full advantage of the potential of technology for sharing and coordinating knowledge and data, and has founded a number of successful companies while building his personal wealth to a net worth approaching $7 billion. His career, starting as a teenager, reflects a considerable technical talent that made this possible, while the management skills he’s developed in the past decade largely continue to drive his ongoing success today.

Early entrepreneurship

While he’s best known for founding Twitter, Dorsey began his journey as a professional programmer when he was in high school. Fascinated by the complexity of coordinating vehicles in real time in an ever changing traffic environment, he built a program to help businesses track and manage taxis and delivery vans. The software, now over 25 years old, is still being used by some taxi companies today.

Dorsey’s complicated rise as an entrepreneur

While Dorsey’s personal success is undeniable, his career at Twitter is rather controversial. Acting as Twitter’s first CEO and cofounder, he oversaw its initial rise, and rightfully deserves credit for his hand in its success. In 2008, however, he was ousted from his position and given a position as a passive chairman with a silent board seat. This was, according to sources at the time, largely due to his poor relationships with investors.

During his exile from Twitter, Dorsey moved on to found Square, an online payment management company that allows businesses and individuals to accept cashless payments with a minimum of tedium. Square quickly became successful and grew, giving Dorsey the opportunity to develop and further define his management skills, while avoiding many of the issues that plagued his time at Twitter. Buoyed by his success, Dorsey returned to Twitter as executive chairman in 2015, where he has remained since. Today, he is a well recognised entrepreneurial figure that strongly evokes the image of Steve Jobs, who mirrors his own journey to a notable degree.

Leading with employees in mind

Unlike many of the founder-CEOs we’ve discussed, Dorsey does not believe in tightly controlling information, or micromanaging the decisions of employees. Rather, his approach is significantly more hands-off, focusing more on delegating important decisions to the proper experts, and ensuring that employees have the information they need to make good decisions.

Unlike more traditional CEOs, Dorsey also seems to prioritise the development of company culture and internal ideology over the interests of investors. This has led to an unemotional and risk-averse approach to change management, which caused significant bad press for Dorsey in 2015 and 2016, after his return as CEO failed to turn the company around in any spectacular fashion. Despite this, the approach appears to be working, as Twitter announced its very first profits on 8 February 2018.

A likely reason for this success is that, as a part of Dorsey’s management strategy, employees are strongly encouraged to think and act independently, and to take responsibility for their decisions. In a similar situation, CEOs like Elon Musk or Steve Jobs might have simply changed the direction of their company by personally taking over the jobs of their employees and restructuring the business under their own power. Dorsey, on the other hand, relied on Twitter employees to do the work. As a result, Twitter boasts a workforce that is meticulous, responsible, and creative where other teams rely heavily on top-down direction.

What we can learn

For business owners, Dorsey’s journey is educational in a number of ways. His personal technical skills and vision ultimately made him a great entrepreneur, while his management style lends itself to long term success, even as it might slow short term growth. Conversely, his relationship to investors constitute a clear blind spot that has plagued him throughout his career.

How not to treat investors

Not respecting his investors ultimately cost Dorsey his initial position as Twitter’s CEO. Worse, it has continued to adversely affect the growth of his companies. By neglecting to prioritise short term investor returns, Dorsey made a number of enemies out of people who should have been his allies. These, in turn, dragged his and his companies’ names through the mud, which likely depressed share prices further.

Despite his relationships with investors, Dorsey’s entrepreneurial success is undeniable. Dorsey’s approach to management promotes the growth of a strong team that isn’t reliant on a single charismatic leader. That depth makes it more resilient, and protects the future of the business beyond Dorsey’s tenure there. Beyond that, it’s important that both Twitter and Square have reported profits this year. This profitability lends both companies greater resilience, and somewhat helps to reduce their reliance on investors going forward. While controversial, Jack Dorsey’s career is a success story that provides a lot of ideas for entrepreneurs to think about, and to incorporate into their own businesses.