Leadership traits of 5 successful startup founders

For some, these will come naturally. But it’s not congenital, it defiantly can be learnt.

Coatom
8 min readMar 23, 2014

Startups are inherently chaotic. Most startup founders carry a panic state of mind to get the product-market fit as early as possible. In pursuit of this, they seldom worry about building a culture within the organisation and aligns it to the success of the startup. Partly this could be due to ignorance, and probably the rest with investor pressure to grow faster and nothing else matters.

Although majority falls into this bucket, there are exceptions. Those are the ones which we call the successful entrepreneurs. Product features they built are mostly quoted for their success. But more than the product, their leadership traits had its major share in making them successful.

According to Wikipedia, “Leadership is a process of social influence in which one person can enlist the aid and support of others in the accomplishment of a common task”.

One cannot be leader unless he/she exhibits the qualities of a leader. There are numerous definitions on what are these qualities. But I would like to illustrate how 5 leadership qualities are exhibited by founders of 5 successful startups. Each one of them exemplifies one among these five traits.

  1. Determination
  2. Empathy
  3. Focus
  4. Simplicity
  5. Influential

Let’s take a look at each one of them in detail.

1. Determination

Drew Houston — Founder & CEO

Dropbox

In December 2009, the legendary Steve Jobs called Drew Houston to his Cupertino office and made a multi-million dollar acquisition offer. Jobs had been tracking Drew Houston who reverse-engineered Apple’s file system to tuck his startup’s logo elegantly inside Apple. Sources say that none of the Apple’s engineers had been able to do that. Besides, Dropbox’s initial success of surging to 50 million users in no time and one new user in every second, Jobs cannily saw it as a good strategic fit to Apple’s product line. But the bid was cut shorted by Drew Houston and said “I’m not here to sell my startup although you are my hero and what you offer is a lot for a 28 year old startup founder”.

Houston was determined to build a big company.

Replying to this, Jobs warned him that what you have is just a feature and not a product. Later when Jobs launched iCloud, he referred to Dropbox as a half-attempted effort to solve the biggest dilemma — How do you get all your files, from all your devices, into one place?

That was the real beginning the great success story of a startup founder who pushed aside a dreamy offer and wrote to his employees the very next day.

“We have one of the fastest-growing companies in the world,” it began. Many years later, in February 2014, it is valued as $10 billion as per this Series C fund raising announcement on TechCrunch.

If Houston was not determined in December 2009, no one ever would have heard about Dropbox and its coolest technology which apparently troubled the one and only Steve Jobs a lot.

2. Empathy

Ryan Carson — Co-founder & CEO

Treehouse

Ryan of Treehouse has been in the news for a while now. His claim to fame is byrolling out a work culture of 4 days a week. Yes, you read it right, the entire 35 member Treehouse team work 4 days a week (Mon — Thu, 9am — 6pm) and the weekends are very “looooong” for them, enjoying with their respective families. Ryan says “We think that information work isn’t like manufacturing. Another hour at the Mac Book won’t yield another $1,000 in profit. We believe that smart folks can get five days of work done in four days. Simple as that”.

If you think this is ridiculous and affects the performance of the company, you are completely wrong. They do $3M yearly revenue with high a growth rate and surprisingly profitable too!

A year later, they went further and removed all managers. They gave all employees 100% control of their time and let them decide what they work on each day. Although, this was not a new idea — GitHub, Gore Associates, Medium, etc — have already done & been successful with it, Ryan did a company-wide Q&A over a video just to ensure that he is on the right path. The votes flooded in and over 90% voted to go flat. What is more interesting is the reason for go flat.

He says “We started the company in 2010 and operated in the normal command-and-control structure. By 2013 we had grown to 60 people with seven managers and four executives. As we added more people to the team, we noticed something disconcerting: rumors, politics and complaints started appearing.”

As managers move up the ladder, they are getting farther and farther from the front line. They started applying their power on the team members, and finally lost trust from their respective team members. “I can’t count the number of times that people had really great ideas but were powerless to implement them.” Ryan says.

If you look closely at both these initiatives, you will notice that they acted as a motivation booster to all employees. 4 days a week and ultimate freedom at work. A heaven on earth!

This is the result being empathetic. If Ryan didn’t do this, Treehouse would have been just another company and Ryan, another mundane panicky CEO.

3. Focus

Joel Gascoigne — Founder & CEO

Buffer

For those of you don’t know anything about Buffer (very unlikely!), it’s an insanely simple tool to schedule tweets. Although, it provides awesome analytics which details the performance of your tweets (re-tweets, favorites, etc.) and suggests valuable content to tweet, the crux is its simplicity. Period!

An advocate & practitioner of the lean startup principles by Eric Ries, Joel is still busy tweaking his MVP — the one feature Buffer App — even after launching his startup two years back in January 2011. That’s focus!

Read through this blog post which he wrote soon after the product launch — Idea to paying customers in 7 weeks: how we did ityou will realize that focus along can take you to build a successful startup. In fact his MVP was just 2 page website. First page was to know how many people will sign up and the next is to find out how many would pay if they decide to use it?

Within 4 days after the launch, he got his first paid customer. In 3 years, nothing much has changed at Buffer. The focus is still on improving the scheduling feature.

Joel is a perfect example of a startup CEO who believe in one story and get the whole team to focus on building it till the time customers say “enough!

4. Simplicity

Evan Williams — Founder & CEO (Previously the Co-Founder of Twitter)

Medium

Medium is the simplest blogging platform ever created. This simplicity is garnering accolades from respected writers and designers worldwide. The early Facebook designer Julie Zhuo wrote “Medium is the best composition experience on the web, hands-down”.

New York Times tech columnist Nick Bilton also gives Medium a thumps up and wrote and email to TechCrunch journalist “I really like Medium — it’s one of the rare instances where the technology is truly in the background. I’d love to be able to replace WordPress with Medium on my personal site.”

You may be wondering why am I connecting the product’s simplicity to its founder’s leadership traits. Wait, you should know that Evan Williams — the founder of Medium– is also the co-founder of Twitter, the simplest micro blogging platform ever created. It’s not surprising that Evan founded Medium subsequent to Twitter as simplicity is what he believes & practices.

Guess how did he celebrate the Medium launch day with his team? With Cupcakes!

Medium tells us one thing clearly. If you are not inherently simple, you really can’t build insanely simple products for sure!

5. Influential

Dave Kerpen — Founder & CEO

Likeable Media

Let me quote from Dave’s and his Likeable Media’s — the most sought after social media marketing agency today — story. It began with a love story.

“When Carrie and Dave Kerpen decided to get married in 2005, they used their marketing backgrounds to create a promotional event and offset the costs of an expensive New York wedding. The Brooklyn Cyclones agreed to let the couple get married at home plate following a game, 1-800-Flowers.com supplied flowers, Smirnoff provided alcohol, Entenmann’s added desserts, and David’s Bridal sponsored the gowns. In July 2006, Dave and Carrie said their vows in front of 500 friends and family members and 5,000 strangers. The couple raised $100,000 from sponsors to cover the cost of the wedding, as well as $20,000 to give to the MS Society. Not only was this a dream wedding, but it was a dream promotion: Dave and Carrie generated $20 million worth of earned media for their sponsors. A few weeks later, they began getting calls from vendors asking what was next. Since they couldn’t get married again, they decided to start a company instead.”

Undoubtedly, Dave is one the most influential content marketers today. He has over 320K followers on LinkedIn and he gets an average 2000+ shares and 300 likes & comments on every posts. It’s hard to maintain this over the last many years, unless there is substance in his all articles. His influencing ability can be partly attributed to his media experience as he contested in a Fox reality show in 2003. He is also the author of a New York Times Bestseller in June 2011. He also contested for the position of borough president of Queens in 2003, bot left the race midway due to the entrenched strength of incumbent Helen Marshall.

All said and done, be it for his own wedding or his other publicity stunts, his influencing ability was the key driver.

It’s ideal for every startup founder to consciously attempt to work on these 5 leadership traits we’ve talked above. For some, these will come naturally but it’s not congenital, it defiantly can be learnt. A study by Fortune indicates, training alone improved leadership skills by 22%. When combined with Executive Coaching, improvement jumps to 77%. This means, you are bound to be successful 77% times more when you get this right. This is a stat that we can’t ignore for sure.

Like you, I’m also starting up soon. One thing for sure. If not all, I will try to practice atleast one among the 5 leadership traits I’ve introduced to you in this article and make it a successful venture. If you would like, you can follow me on twitter

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