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Leadership Edge with Paddy Cosgrave, co-founder and CEO of Web Summit and Collision

For my leadership series, I had the fantastic opportunity to sit down and interview Paddy Cosgrave. Cosgrave has been coined “master connector” by WIRED and “master of revels” by The Financial Times.

In less than ten years, Paddy has gathered hundreds of thousands of entrepreneurs, founders and CEO, political leaders, and cultural figureheads across Web Summit in Lisbon, Collision Conference in Toronto, and RISE in Asia.

Cosgrave has navigated his business through the global pandemic by moving his events online and building Web Summit’s proprietary conference software. In 2020, Collision hosted 32,000 people from 140 countries online, followed by Web Summit with over 104,000 people in December.

This April, Collision will be hosted online for the second year in a row and will gather 40,000 CEOs, tech giants, political leaders reshaping the world.

About Collision:

When Collision, North America’s fastest-growing technology event, moved online, the pivot to host thousands of attendees online was coined by the Sunday Times as a “pretty big experiment.” For the second year in a row, Collision will host attendees online on its proprietary software. After hosting 32,000 attendees at its first online event in June 2020, the Collision platform was called “the stunning future of online events” by Digital Trends. This year, the venue will host 40,000.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I’ve got to where I am today by being fortunate enough to get to work with great people. Media, very understandably, likes to simplify stories, and wrap the success of any company around an individual personality, and tell the tale from that perspective. I don’t believe that individuals build companies. It takes a village to raise a child, and it takes a team to create anything of note. I’ve been very fortunate to work with some fantastic people in my case, and I’m the first to tell you that I do not have any superpower.

One unique thing about me, however, is that I read a lot. The most common thing throughout my life, no matter what happens on a given day, is reading for five hours. Some days, easily 14 to 15 hours. I love to read compulsively.

But back to the company– we initially wanted to create a great tech conference for the community. We didn’t start with a huge aspiration. We just wanted to develop a fantastic place where people can gather and connect. Initially, we had 150 attendees, and over time, word spread. People started coming from outside of Ireland, and then eventually, over seven or eight years, we now have over 70,000 attendees from all over the world.

What drives you? What drives your company?

Our North Star is to create meaningful connections. Everything we do is about creating a gathering of people who will make meaningful connections. We are driven to create great products that people love. We build and implement software to try to make that possible. I believe that is the single biggest differentiator between what we do and other global event organizers. Our engineering team is the largest in the company, and we build things to make our conferences work for people.

I believe that in business, profit has to be secondary. I think that a lot of companies lose their way when they replace their mission with profits. You have to build a great product first, create happy customers, and then everything else will follow.

Is there a catalyst or inflection point that has shaped you into who you are?

Growing up, I was bathed in American culture. I loved going to the cinema. I loved everything about America. I went to high school in America for a few years. Within the first week of arriving in America, my high school organized a charity event where students fed the homeless that lived under the bridges of New York.

I had never been exposed to that level of just grinding deprivation and abandonment by society, and I think that is one of the most profound inflection points in my life. I was in one of the most elite high schools in America, surrounded by kids whose mothers and fathers were also some of the most important executives running America’s biggest companies. But they all seem to live a couple of blocks away from one of the most grinding deprivations that I’ve ever witnessed.

We have to be careful and skeptical and realize that not everything in the world is perfect. You can have the most successful and innovative and brilliant society on Earth. But you can also have great deprivation and abandonment right next to it.

Thank you for sharing that experience. How has that inflection point influenced Collision?

We try, wherever possible, to include voices of sometimes underrepresented or marginalized groups in different ways in our events. And that’s not just about minorities, or ethnic or gender, or other grounds; it’s also about including the representative voices of workers at business conferences. When we run a significant business event that brings together some of the most incredible companies on earth and employs thousands of people, it’s essential we consider the second-order consequences or unintended damage to workers, and not just on the latest innovation.

Can you share more about Collision? Is there something that you are working on that you are excited about?

The purpose of the software is to enable people worldwide to network with each other in meaningful ways. And a massive part of that is connecting some of the most interesting early-stage startups to some of the most successful and notable investors in the world. I love hearing stories of startups who reach out to us to share their excitement about the meetings they have with the top VC firms, and then in the weeks afterward, hear about the funding raised from those meetings.

What types of technology do you see evolving or thriving during the pandemic?

We are beginning to move past the pandemic globally, or at least, we are now very close to the end of that tunnel. People in certain parts of the world are beginning to emerge from a year of lockdowns and restrictions. I believe some amount of business tourism– where people work and travel 24/7 365 days a year — will be reduced, and that platforms like what we’ve built to help people connect before a real-world event will continue to have an impact.

Being able to meaningfully connect with people in advance of meetings and bring that interaction to actual in-person conferences is incredible. Technology that enables this will continue to evolve.

What is your blueprint to success?

Companies that are successful over time are because of the sum of small decisions and improvements made every day. Authors and the media love to write about a single, bold move that changed the direction of a company forever. In truth, I think those are outliers, and what matters is building a culture where incremental and continuous improvements become cumulative and leave a significant legacy over time.

As a business person, I don’t think my impact on the world will be all that significant. I don’t think business people leave legacies. I believe poets leave a legacy. And this may be one of the significant challenges for our generation.

For example, if you were an engineer 500 years ago, you worked on a bridge project. Your legacy is working on that bridge, and that bridge is likely to exist for decades, if not centuries. And that’s a tremendous legacy to leave. Most engineers these days are involved in continuous code deployment. The code that they write may very well be rewritten in weeks, if not days, later. I believe that businesses do not usually leave a legacy. They make short-term impacts. But legacies and long-term impacts are driven by ideas, and ideas come from literature, academia, culture, filmmaking, books, and writing.

Thank you! You mentioned literature, poetry, and filmmaking. Is there any specific work you would recommend?

Adam Smith and Condorcet, a contemporary in France, are two tremendous thinkers. Rosa Luxemburg from the early part of the 20th century, Noam Chomsky from the latter part of the century. And in mid 20th, Bertrand Russell. These are primarily philosophers, or what I would consider philosophers, and have left an incredible legacy and contribution to society.

Speaking of philosophers, what life philosophies do you live by?

A healthy skepticism for everything, including your thoughts, decisions, and beliefs, is essential. I try, whenever possible, to discuss and rethink what I know. Sometimes the exact moment when you need to question things is when you feel sure about something. I am generally skeptical of hierarchies, deference towards authority, and autocracy.

I am not a believer in autocracy or fascism. I think those are terrible things. But some of the disdain the West has for fascism or totalitarianism or dictators can, in some ways, be applied to corporate structure. Essentially, corporations are autocracies, or legalized autocracies, with very strict hierarchies. Anything we can do to reduce the amount of hierarchy inside a company will undoubtedly unleash innovation. The more gatekeepers you put between an idea and the execution of that idea, the more you slow down innovation.

I think that’s why I’m so drawn to startups. They lack hierarchy and are usually flat organizations that can move fast. When a company becomes submissive to authorities, it starts to kill a lot of creativity. In a sense, the internet is without hierarchy, and Wikipedia is a fantastic example of near-perfect human creation in the absence of hierarchies.

What do you want the readers to know?

I’m a massive believer that determining the ingredients of success is mainly outside the control of an individual. Gardeners understand that what matters is the soil within which plants grow and thrive, not the types of flowers. The key determining factor is the soil. You can’t expect people to flourish when they are essentially planted in damaged or poisoned soil.

If there are 100 people born into incredible deprivation, and in one of the world’s poorest countries, most of those 100 people are unable to do better than an average kid born in the Silicon Valley. The environments you tend to be in exerts tremendous probabilistic determination of your material success later in life. And if anyone is genuinely committed to increasing the likelihood of individual success, we need to address the overall structure.

You’ve got to look at structures and the systems and ask yourself, “What can be changed that will have a macro effect on increasing the likelihood of an individual’s success?”

I believe that one way to do this is to focus on increasing innovation and entrepreneurship in society. Read The Entrepreneurial State by Mariana Mazzucato. Mariana Mazzucato is an Italian academic, and her writing discusses the role that states should take in fostering innovation and entrepreneurship to lead to economic and individual growth.

I also recommend reading Ha Joon Chang, a South Korean academic at the Cambridge University. Ha Joon Chang is the world’s leading expert on why certain economies succeed and why certain economies fail. His original book is called “Kicking Away the Ladder,” and it’s about the traits common to all of the successful economies that exist on Earth today and the policies pursued by those who have not. It’s truly not just down to the individual. The soil has to be fertile, and the people have to be nourished with the right support and education.

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