Paddy Cosgrave co-founder of Web Summit at the opening talk of Web Summit 2015 — Photo via Forbes

6 Lessons Learned at Web Summit 2015

Yusuf Saber
Optima . Blog
Published in
7 min readDec 26, 2015

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A few weeks ago I was one of over 40,000 people who descended upon Dublin to be part of the Web Summit 2015. With over 20 specialized summits running in parallel, Web Summit offers something for everyone. As an entrepreneurial data scientist myself, I naturally gravitated towards sessions either by renowned entrepreneurs or by accomplished data scientists. As I sat there, I constantly slacked live commentary on the best bits back to my team in Cairo. A while later, we went through it all and selected our favorite highlights to share with you. This post spells out our six favorite entrepreneurship highlights. We will share what we learned from the data summit in a follow up post.

1. The path to success is only obvious in hindsight

Stewart Butterworth is CEO and cofounder of Slack. In a little over 15 minutes, he reflected on his experience building the fastest growing business app ever. He said “early on we used to go to people at other companies and beg them to try Slack”. That hustling seems to have paid off because now, he says “we don’t do any sales, people just start using the app for some reason”.

The path to success is only obvious in hindsight and is rarely glamours. Slack started out as a home made communication tool that the team built and used while working on an ill-fated game. Stewart said “it was very humiliating shutting down our game after 3.5 years of work. It was very stressful. Left us with lots of self doubt”. He reflected on the irony of his failures at making video games although he really worked hard to make one: The first time he tried to make a video game it failed and pivoted to Flickr. The second time he tried it also failed and pivoted to Slack. Quite some failure!

Most successful entrepreneurs would tell you that success can be as stressful as failure if not more so. Stewart said: “Now that we are successful, the stress is not a bit less, probably more”. He went on to say that he wakes up every day worried that this is the day he messes it all up and only by like 3pm that he can breath easy again!

2. Put yourself in challenging situations

Michael Dell took the stage to quite some applause. I was looking forward to some hard learned lessons. Unluckily, the interview was dominated, for good reason, with talk of the highly controversial EMC acquisition.

Success can have very humble beginnings. Dell started out with a mere one thousand dollars. Today Dell boosts cumulative earnings of nearly one trillion dollars over the company’s lifetime.

Maintaining a thriving innovative spirit is a significant challenge for a giant company. When asked how will Dell stay innovative, Michael said: “One thing we do is incubating smaller teams and letting them innovate in relative isolation on top of the capabilities provided by the parent company”.

High achievers tend to push themselves further than their peers. When asked what is your advise to aspiring entrepreneurs, Dell said: “Put yourself in challenging situations. You will discover that you have much more potential than you think”.

3. Work on ambitious projects

Ambitious projects inspire the best people to come on board and give them purpose and drive to see them through the toughest of challenges.

Mike Schroepfer, Chief Technology officer at Facebook, presented the three pillars of Facebook’s 10-year technological vision. The three pillars are:

  1. Availing internet connectivity to the yet unconnected regions of the world via a network of huge light weight solar powered drones that will fly for up to three months at a time and use laser to beam connectivity between the drone network.
  2. Breakthrough artificial intelligence in the form of Language Understanding and Photo Understanding. Focus was more on photos with Mike saying: “Imagine that you are one of the hundreds of millions of people with some sort of vision disability and you have trouble participating in the visual part of social networks and one of your friends, who just had a baby, posts a photo. We built a system that allows you to ask questions about a photo that it’s never seen before.” The technology seems to be quite good that it can identify the breed of a dog in a photo (which Mike demoed at the Facebook booth). Besides helping those with a visual impairment, photo understanding will make for a much more relevant Facebook newsfeed.
  3. Leveraging virtual reality (hence Facebook’s acquisition of Oculus) to offer Facebook users immersive content and more profound ways of connecting with people. As Mike puts it: “This is the ultimate technology for human connection because you can have this experience and build shared memories with someone else who may be miles away where you’re in a virtual space, you see your hands, you can point, hand each other things”.

Yeah, a more cynical way to look at it is that Facebook is building technologies that would support the capitalistic urge to bring back growth to it’s saturating user base (and its stock). However, You have to admire Facebook for taking on such grandiose projects and for pushing the envelope this far.

4. Hold on to your values

“There is more to success than making money and shopping for boats” said Kickstarter’s CEO Yancey Strickler. “We have always approached Kickstarter from a very idealistic perspective. It’s who we are. From the very beginning we all vowed to never sell the company. To never try to go public. To try to preserve this as kind of a public trust as a space where new ideas can happen. We believe that a universe only driven by profit maximization can be poisonous especially to culture” said Yancey in justification to the company’s recent decision to turn itself into a public benefit corporation (PBC). Think of this as Kickstarter’s way of legally holding on to it’s values in the face of an ever mounting pressure to give in to optimizing solely for shareholder value.

Beyond holding on to it’s values, Kickstarter hopes to set a precedent for other entrepreneurs to follow. “I think there are other entrepreneurs, people like us, who want to do something more than just survive or get rich.” Yancey said. “There’s a lack of models to follow: if you look around the world of technology, there’s a lot of talk of valuations and growth rates and all of that, but there’s not as much talk about impact, about responsibility and things like that. We need to make ourselves example One”.

Kickstarter’s commitment to it’s values is inspiring. The fact that they invested the time to identify and internalize their values (which many entrepreneurs fail to do) to begin with is just as inspiring.

5. Appreciate your limitations

Phil Libin is the charismatic CEO behind Evernote (where this post was originally written). Phil took Evernote from nothing to over 100 million users and built the company up to 500+ employees in about 6 years .. and made productivity cool again in the process.

In July 2015, Phil left his position as CEO of Evernote to become a full time investor. When asked why he did that. He said: “I know my limitations I am not good at managing companies at their later stage”.

As an investor, Phil is looking for entrepreneurs who “think more of impact than flashiness”. Phil is on to a long term investment strategy: “In 10 years the tech industry as a whole will be worth much than it is now. That is why as an investor now, I am looking at a ten year time scale not a 6 month time scale”. If you have a good idea especially one that incorporates a conversational user experience, Phil wants to talk to you!

6. There is more to a startup than “get big or get lost”

David Heinemeier Hansson is partner at Basecamp, inventor of popular web development framework Ruby on Rails, and inspirational author of terrific books; most notably Rework.

David was scheduled to speak at Web Summit. He never made it though and instead posted his talk here. The thoughts therein stirred quite a bit of controversy: While they inspired many, they left others rather indignant.

The dominant philosophy in the tech startup world today is that you need to Get Big (t0 become the dominant disruptive unicorn of your industry) or get lost. The core of David’s message is: “Don’t just accept this definition of success because that’s what everyone is cheering for at the moment”. He encourages entrepreneurs to consider that “maybe the current atmosphere of disrupt-o-mania isn’t the only air a startup can breathe. That perhaps this zeal for disruption is not only crowding out other motives for doing a startup, but also can be downright poisonous”.

David goes on to list several motives for doing a startup that simply can’t exist in the cut throat atmosphere of a VC funded company seeking to get big fast. Those motives include being your own boss and not reporting to others, building a high quality product and selling it directly to customers, building lasting human relationships between colleagues and customers, and maintaining a healthy work life balance.

We see this not as excuse to aim low, rather a call to be realistic and to adopt a broader perspective on what life is, as David puts it: “This may sound soft, like we have a lack of aspiration. I like to call it modest. Realistic. Achievable. It’s a designed experience and a deliberate pursuit that recognizes the extremely diminishing returns of life, love, and meaning beyond a certain level of financial success. In fact, not only diminishing, but negative returns for a lot of people”. To sum it up, David’s advise is: “Curb your ambition .. Don’t take investor money if you can .. Live happily ever after”.

We are a team of data scientists and software engineers working to help enterprises makes the most out of their data. Our projects range from data analysis to extract insights, to predictive analytics to support decision making, to scalable production ready data products. Our focus areas are (1) personalization and (2) operational efficiency.

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