Five Cracking Lessons From Twitter CEO Jack Dorsey That Work For All
Jack Dorsey, a serial entrepreneur known for founding not one, but two immensely successful startups (Twitter and Square,) has led quite an exemplary life. From living life king size to working on his dreams with a one track focus, Jack Dorsey does everything in his power to make sure he puts out only his best foot forward. I’m going to share with you today five cracking lessons from Twitter CEO Jack Dorsey that will certainly slay you!
From high school dropout to founder of Twitter and Square, Jack Dorsey’s career path has been a wild ride.
He started as a programmer, and is now best known as the creator, co-founder and chairman of Twitter (now you may feel like you know him) and the CEO of Square (a company for mobile payments). Innovator of the Year Award for technology was given to him by The Wall Street Journal. He’s also one of the top 35 innovators in the world under the age of 35.
Jack Dorsey is a titan of technology.
As a leader of two of the most influential companies of our time, Jack’s calm, collected demeanor is no indication of the stress the man copes with on a daily basis. He is not what we would expect of a high-profile CEO, and as a self-proclaimed introvert, who provides thoughtful, controlled answers, he just might embody what we need from a lot more CEO’s today. Everything Jack Dorsey does, from his never-changing morning routine to his insistence on having “an amazing haircut” is meticulously considered — and his habits and attitudes are the backbone for his continued success.
While his tactics may seem unconventional, they’ve helped him develop some of the most desirable — and effective — corporate cultures in Silicon Valley.
He owns a BMW, yet commutes by bus. He does not have a separate work desk. His morning routine never changes but he often tries different hair styles. He is a brilliant masseur and has a dignified fashion sense. He loves to read and has developed a culture of presenting each new joining in his organization with “The checklist manifesto”. This is a great example of his unique management style and his unusual and extraordinary approach towards things.
Jack Dorsey’s leadership and entrepreneurial qualities can serve as inspiration for not just male but even budding female business leaders.
After having created billion dollar companies, he still takes the bus or bikes to work. So clearly he knows what he’s doing, both in life and in business, but also shows an interesting personality. And we can learn from his words and actions. Here are some truly riveting life and business lessons from the man who followed his dreams and made them come true.
Lesson #1: Look Out For Ideas
Jack Dorsey believes the biggest mistake an entrepreneur can make is to look at achieving their goals without a clear idea. More often than not, businesses succeed only when they are worked on with a clear idea in mind. “It doesn’t start by you waking up and saying ‘I want to start a business,’ it starts by you waking up and saying ‘I’m really passionate about this thing and I’m going to do whatever it takes to make it work,’” Jack Dorsey said.
While passion and dreams are all well and good, the route to success is only achieved when you have a strong and solid idea in place.
If you’re complaining about not having any ideas to work on and use it as an excuse not to have hobbies or build businesses, then you’re destined to fail. Ideas are everywhere around us, just like inspiration can be found in daily life. You just need to be open to them, to notice them and to actually take action once that happens. Every entrepreneur begins their career in the same way: with an idea. To succeed, however, that idea needs to be executed and made into a viable and durable project.
Successful people aren’t afraid to discuss ideas even if they may not sound good to others and make all attempts to try it out.
Twitter evolved when Jack Dorsey suggested the idea of a simple messaging system to be integrated into his dispatch software to a defunct company in Silicon Valley called Odeo. It’s co-founder Evan Williams and Biz Stone started a company called Obvious which became Twitter. Dorsey became its CEO in 2006. He composed the world’s first tweet — ‘just setting up my twttr.’ During the thought process associated to your idea, do not hesitate to discuss it with the people around you. By sharing your ideas you open yourself up to receiving constructive criticism regarding them. Other peoples’ thoughts and remarks, being from an outside perspective, are important for the development and execution of your project.
As with many ideas, necessity serves as the mother of invention.
Jack’s partner and co-founder Jim McKelvey is also an accomplished glass artist. But because he could not accept credit cards as payment, he was unable to sell his work to meets its true potential. Discouraged by the arduous and intimidating process of accepting payments via plastic cards, Jack Dorsey focused on developing a solution that worked for everyday people who also happened to run businesses of varying size and scope. Indeed, payment systems were in dire need of access and incorporation to keep pace with the evolution of commerce. Jack envisioned an idea where payment systems would become approachable, sociable and actionable. And thus, Square was born, ironically, next door to the old U.S. Mint in San Francisco.
Despite his formidable success, Jack Dorsey can offer would-be entrepreneurs a relatively simple formula: keep pushing ahead without ever feeling as if you’ve made it.
If there is one thing I’ve noticed across every successful person in the Valley, it’s that they are action-oriented. They realize that if they keep their ideas inside their minds or limited to mere conversations, the ideas will get pulled in too many directions and never materialize. Jack Dorsey explained that the initial prototype or version doesn’t have to be perfect, but it will at least provide a base off which to build. This stands in stark contrast to the approach some other companies have taken in trying to secure large amounts of funding before building a solid customer base or even having a product.
Lesson #2: My Routine Smells Cocaine
While people think living the startup life is all about haphazard lifestyles and irregular patterns, Jack Dorsey thinks otherwise. According to him, only when you have a clear routine for your everyday life, can you really work toward being successful. Without structure and discipline, everything falls into chaos and chaos has never been man’s best friend.
The shocking number of hours Jack works daily would be impossible if he wasn’t using an interesting technique — theme days.
He plans out his week in advance and focuses on one thing each day, in both companies. That helps him stay concentrated, get things done and move forward in a certain area every single day. A well-maintained routine helps entrepreneurs balance their highly demanding responsibilities in life and Jack Dorsey can come handy for them in these circumstances as well. 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 people out there who aim to make it big in their business journey, that’s the way forward.
Ever wonder why Steve Jobs wore the same thing to work everyday? It was so that he could focus on what needed to get done instead of worrying about what he wore to the office.
Planning a week’s worth of wardrobe, meals, and workouts ahead of time save you stress and precious minutes (not to mention money). Sure, it may seem a little OCD at first, but at least you know you won’t have to stand in front of your closet for 20 minutes trying to piece an outfit together. And think of all that cash you’ll save by bringing your lunch to work! Jack has built that particular early routine because it can be achieved anywhere…there is no excuse not to achieve it. He can meditate anywhere, all he needs for his 7 minute work out is a wall and a chair, and he can walk anywhere. So no matter whether he’s at home or traveling there is simply no excuse.
The first step in achieving extreme efficiency is, according to Jack Dorsey, to lose the food.
The businessman said he eats just one meal per day at dinnertime between the hours of 6:30 p.m. and 9 p.m. as opposed the usual three to six small meals recommended by health experts. His dishes typically consist of a protein (chicken, steak or fish) with vegetables (salad, spinach, asparagus, or Brussels sprouts.) This practice of condensing all meals into a short period and fasting for the rest of the day is referred to as intermittent fasting. When it comes to the weekends, Jack Dorsey said he cuts out food completely, fasting from Friday through Sunday evening, and only drinks water for those three days!
Right now, some of you might be thinking: Routines and structure are restrictive and limiting, how can they be beneficial?
Of course, if we were to treat our daily schedule with an iron-clad rigidity, our regular routine would limit the types of things we’re able to do. But, we’re NOT talking about treating our routines like rules. By using our routines for the majority of situations and still allowing exceptions to exist, we get to choose what serves us best in the moment. The point is that or daily routine is beneficial the majority of the time because it builds structure and helps better manage our time. And in exceptional circumstances we can choose to use a different approach. Routines help busy people succeed by giving a standard structure to every single day. Especially when things are changing, structure reduces your feelings of overwhelm because your routine helps you know exactly what to expect. Routines ground you and help you feel more in control when things are uncertain or unpredictable.
Lesson #3: Don't Be a Jerk
For Jack Dorsey, a good leader is someone who guides the people in their organization so that they can make the big decisions–not someone who issues decisions down from on high. “If I have to make a decision,” he says, “we have an organizational failure.” With this kind of perspective, the health of an organization depends not on the power of its leader, but on the power of its members.
Hierarchical, power-based, and distant leaders create fear, compliance, and helplessness.
These leaders treat their people as resources, to be used. A role in a set of tasks. The best leaders, on the other hand, build human relationships that are about the whole person, going beyond just the role they occupy or the resource they represent. Why do they do this? Because if you build human relationships, your people will feel that you actually care, and they will be more likely to connect, collaborate, and perform. The quality of your relationships determines the quality and sustainability of results. If you see each other as people, warts and all, you can build the trust needed to freely discuss ideas, problems, clarify misunderstandings, and most importantly, help each other when needed.
Always be in touch, be accessible and approachable.
Be one of the team, don’t set yourself above them, or ask them to do things you wouldn’t. Make time for them, make it clear that you care about their ideas and experiences at work, that you value their work and their input. Never pass the blame down the hierarchy to try to appear infallible — whether they’re brave enough to say it or not, your team will know if something was your fault. Don’t lose their respect by shirking responsibility; show them how to own mistakes, learn from them and move forward.
A workplace without respect is usually fairly easy to spot.
People probably don’t contribute many ideas, they may not speak up when problems arise and they may be constantly searching for a way out. When leaders do not treat their employees and peers with respect, the entire foundation becomes wobbly, putting the organization at risk. If we want to influence others to work with us or to complete projects for us, it’s important to remember the old English proverb, ‘you catch more flies with honey than vinegar’. When we are polite and respectful to others, people will be more willing to work with us, and even to take risks with us. A sour, disrespectful boss will only accumulate empty chairs as people move on to better opportunities.
Don’t tell your employees that respect is an important part of the culture and then violate that value by expecting them to work 60+ hours a week.
I’ve seen this culture and style of leadership many times over the past two decades and can say categorically that it does not work; at least not for long. Good employees get burned out, then they become frustrated and resentful. Then they disengage and leave. Remember, good leaders help their people become better employees. But the best leaders encourage their employees to become better people. And becoming our best requires balance. As a leader, learning to connect with respect is one of the most powerful strategies you will ever develop to help create a culture where you employees will not just survive, but thrive. And the best part is, you will be setting a powerful example that leaves a legacy of future leaders to help grow your organization long into the future.
Lesson #4: Fail Openly
For Jack Dorsey, his career was a huge roller coaster ride. Before twitter, he started a company to dispatch couriers, taxies using the web. He founded twitter in 2006 but was asked to move out of his own company in 2008. Even this did not deter him. Instead, because of his persistence, he made a historic comeback. He also founded another successful startup Square in 2010. Success was not served to him in a platter, he worked very hard for it. Winning is not coincidental, it requires passion and persistence.
When Jack 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. As a leader, you 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.
It’s important to look at failure as a jumping off point, not an end.
Don’t let failure push you down. It’s all in how you view it. Use failure as a way to bounce back rather than a sign you can’t do something. One key is to quickly jump back into the game after a setback. Admit your mistakes and move on with a focus on improving upon them. It’s that combination of resilience, grit and determination that helps you bounce back. Successful people see temporary failures as steppingstones to success. It’s time to stop thinking that you’re only successful when you’re perfect — perfection is an allusion.
There are millions of people, every single day, who are messing up.
In fact, you can pick up any successful person’s memoir, and guaranteed, that person has a story in there about failure. What they won’t have, though, is a story about giving up. Honestly, failure is normal. If you could do anything and everything you wanted with trial and error or practice, you’d be superhuman. But you aren’t, and you aren’t expected to be! Life is about figuring out who you are — a lot of that comes from falling flat on your face. When you try something new, you probably not going to be good at it at first. That doesn’t mean you don’t have the potential to be, it just means you need to keep working at it.
Fear of failure is a very real thing and it stops people from taking risks that might lead to success.
It is important to change your mindset when it comes to failure, so you can see it as a learning experience, and more of a turning point rather than the end of a venture. Success is reaching a goal or aim, but it doesn’t necessarily mean reaching that goal or aim on your first try. Failures are the different stepping stones on your journey to success. For some, this journey might be longer, but it is just as worthy, and the success is just as valid. If fact, the longer it takes you to get there, the more endurance and strength you’ve proven to have because you have resisted the urge to give up along the way.
Lesson #5: Keep Things Simple
140 characters. That’s all you get on Twitter. Just like writing a haiku, there’s no room for unnecessary syllables — and Jack wouldn’t have it any other way. Dorsey loves to take a complex idea and begin removing the conceptual debris, so you can just focus on what’s most important.
Jack Dorsey believes in the simple joys and ways of life.
Extravagant things tend to fail because there isn’t anything else to back up what you have achieved so far. Furthermore, the more you do, the more people expect and that is never a good thing. Jack not only lives this way, but has also instilled this rule into the way he functions at work. Take Twitter, for example. People say so many things with such limited characters, giving readers and followers something truly meaningful to look read. If there was too much text, one would simply ignore the message or even miss it, right? In life and in business those who choose less over more succeed in the long term. And Twitter is one of the greatest modern proofs of that. All your messages have to be short. So no fluff, repetitions or complex sentences. Just simple thoughts.
Simpler things are easier to manage and master.
His 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 entrepreneurs who are still struggling to think clean about their road ahead because of lack of direction and proper advice, Jack 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.
Simplicity is the best policy — in your offering, in your operations and in your organization.
Trends are changing at an ever faster pace. Customers’ demands never stop growing. And the market is becoming an ever more confusing place. No wonder there is a growing yearning to dial down the complexity. Indeed, I believe that simplification is just what companies need: With a business characterized by simplicity, you can be as close as possible to your customers while simultaneously operating at maximum efficiency. And you have the greatest chance of business success even in turbulent times. Successful companies frequently operate in networks within their organization. They often have rather boring org charts based around centers of excellence. But they work in multi-functional teams that are constantly being adapted to suit new circumstances. Rather than changing the underlying structure, they change their operating script. Simplicity at all levels also means fewer meetings, targets instead of processes, and principles in place of structures.
In the professional life, over-complicated things might be a sign that things are unclear.
As a manager, I find it important to make sure everybody has a clear and shared understanding. Spending time on reformulating in a simple way is a good management practice. If I don’t understand something easily, why should other people do? We live in a world where being smart is not understanding better or faster than others but leveraging collective intelligence to grow better together. Simple is not synonymous for easy. And complex is not synonymous for clever. It’s pretty much the opposite. Being able to share complex things in a simple (but not over-simplified) way requires maturity and clear understanding of the situation. Making things complex can be a sign of uncertainty or sometimes contempt and leads to confusion.
So that’s how you become a successful tech startup founder. You have to be purpose-driven, find what works and do more of it, be passionate about the work you do and willing to hustle more than the average person. But you also need to get out there and do some things differently. And if you can’t think of anything, there’s already so much powerful advice you can follow from those who are where you’re heading.
Jack is not alone in his humble demeanor and lead by example mentality.
We are unfortunately bombarded with the outspoken garish leaders that dominate news stories of today, but the softer hands are all too often ignored. It’s leaders like Jack Dorsey, Jeff Winner, Bill Gates that the younger generations should aspire to, and there are leaders all over the world that embody the same values but never get the chance to highlight the importance of those values. We are lucky to have those big names show what a true leader is, and it’s time to make a more focused effort to bring the others into the spotlight.
Jack Dorsey believes that a strong team is not formed when you hire stars, but when you develop your own people.
His business is about people. He delegates lots of tasks, so he believes that you need to invest in a team. One of the most important contributions he makes to his companies is getting out of the way so employees can get the job done. And Jack is also not afraid to show his vulnerability. He says that if people see your fears and mistakes, they feel close to you. Indeed, Dorsey’s leadership style utilizes visionary skills and a steadfast demeanor to help navigate change and chaos well. But at the same time, he has consistently fostered cultures of engagement, so others are comfortable with change as well. He believes in transparency, trust and serendipity.
Entrepreneurship is all about going that extra mile to reach the place where magic happens. So, pick a few tricks from this charismatic, unconventional entrepreneur and define your own trade.
Jack Dorsey’s life is one everyone wants to lead and when you see a man like him succeeding because of the lessons he lives by, you know your life is going to be a success as well! So what do you like the most about Jack Dorsey? And what else can you learn from him? If you have learnt other things from Jack Dorsey’s inspiring life, comment and let me know!
Digital Dandy. Hacker From Heart. Workaholic. Coding Artist. Self-made.