The man behind Twitter and Square: Five Lesson Women Can Learned from Jack Dorsey

“I never wanted to be an entrepreneur. I actually wanted to be Bruce Lee.” — Jack Dorsey

If one asks a simple question about naming a modern-day corporate icon, Jack Dorsey’s name will not be far. The 44-year-old might not be a Steve Jacobs or Elon Musk but the serial entrepreneur founder of Twitter and Square is no less an achiever. The man is, in fact, a certified masseur who has also worked on fashion designing. So learn it from him! He is a multi-talented man who also has a heart for social causes. Dorsey recently pledged a whopping $1 billion to fight the Covid-19 pandemic. 

For many, Dorsey is unique because of his “unexpected” behavior. The man hasn’t been as regular to the headlines like some of his famous corporate colleagues but that hasn’t made the number of his admirers any less. He is a man who lives his life meticulously and has simple habits to follow, which makes his success story even more interesting.

Dorsey, who was born in St Louis, Missouri, on November 19, founded Twitter in 2006 (remained its CEO till 2008) and Square in 2010. Being at the helm of a social media platform which is never at peace, it is not new for Dorsey to experience phases in life that could be unsettling. Recently, he was at the receiving end of none other than President Donald Trump after the latter accused the platform of interfering in the November election after it blue-flagged one of his posts. With the exception of Facebook’s Mark Zuckerberg, no other corporate icon of today has to undergo that much of professional pressure. Dorsey manages it in style and it makes him somebody worth emulating.

Dorsey’s entrepreneurial qualities can serve as inspiration for not just male but even budding female business leaders. If we pick the man’s top five qualities that women entrepreneurs can learn from, here is the list (those lessons are not necessarily gender-specific for success is never determined by gender):

Keep it simple, it helps:
We all know how minimalist Twitter is. You have to express all your feelings in not sentences or words but just a few characters. This cuts out things that are unnecessary at the very outset. Dorsey’s love in taking on a complex idea and removing its “conceptual debris” so that the focus eventually falls on things that are important makes Twitter a favorite platform for those who think clean and clear. Dorsey’s father Ted acknowledges the man has always been a minimalist (he chose the smallest bedroom once the family moved into a new house) and that has turned out to be the man’s philosophy in business as well. For fresh women entrepreneurs who are still struggling to think clean about their road ahead because of lack of direction and proper advice, Dorsey’s example is something worth learning from. Be short and precise when you are still feeling that your communication is yet not that strong. Simpler things are easier to manage and master.

Look for ideas everywhere:
Meenakshi Rai is a small-town businesswoman in India. She assembles spring dolls and sells in local markets. One day, he found one of her friends, a homemaker, had tears rolling down her cheek as she was slashing onions. Anand was not happy to see this and while looking for a solution, Meenakshi learnt something from her little son. He opened up the drums of a drum-playing toy out of curiosity and put something else in its moving hands. Meenakshi placed a medium-sized knife in place of the doll’s hands and as she switched on the toy, it started moving the knife fast. She placed a piece of onion below the knife and the doll started slicing the onion! Such an innovation that went on to stop several women from shedding tears while cutting onions. 

Dorsey would have loved to meet Meenakshi because he too believes that ideas can come from anywhere. Speaking to the staff members at Square once, he said: “Ideas can come from anyone and they can come anytime. We all have various directions that we want to take the company and sometimes those ideas come during a shower, sometimes they come when we’re walking, sometimes they come when we’re talking with other employees at the coffee store.”

For those businesswomen trying to find a foothold, this is a priceless piece of advice from Dorsey. 

Follow a routine:
There are women entrepreneurs who are essentially multi-taskers. They may have a family to take care of besides running the show. For them, it is very important to follow a certain discipline in life, starting from getting up from sleep to ending the day. A well-maintained routine helps women entrepreneurs balance their highly demanding responsibilities in life and Dorsey can come handy for them in these circumstances as well. Dorsey, for instance, kicks off his day in an identical way: eat two hard-boiled eggs with soy sauce and the sides of berries. He takes a long walk to work everyday and also does meditation. Each of the days in a week is meticulously planned by the man, focusing on key areas of his ventures, namely, management, engineering, design, etc. He takes his day off on Saturdays. For all the women out there who aim to make it big in their business journey, that’s the way forward. 

Win trust of people through calculated risks:
When Dorsey started Square a decade ago, he had an understanding that there were more critics who wanted it to fail. He then played a mind game. As the founder, he himself presented 140 reasons why Square was destined to fail, coupled with his own rebuttals. The strategy paid off. Investors came rushing towards Square and it made a name soon in the world of payment processing. The reason that Dorsey could take such an audacious step is that he was confident about what he was doing because he had a thorough understanding of the field — the advantages and disadvantages. This is something that every business leader needs to take into account. They should be daring and ready to take a calculated risk to nullify any negative eventuality that could be there. Yes, it is always a chance but brave people do not hesitate to take this chance to come out as the winner. 

Take care about your looks, they should be presentable:
For many, this might sound out of place. Do women have to look good to be successful? No, that’s not the point. But if you are trying to pick a point or two of inspiration from Dorsey’s life story, then the looking thing commands importance. The man once sported disheveled hair and had a facial piercing but it changed after he became a top corporate figure. According to Dorsey, a presentable look of the leader is important for a company’s future and he now has a proper haircut and attire to face the world. To have an amazing haircut is now one of Dorsey’s 10 life philosophies for success. For those who idolize him, this is another crucial lesson to learn.