The Entrepreneur Questionnaire: Josh Silverman, Former CEO of Skype

4 min readFeb 28, 2014


Josh Silverman is an entrepreneurial executive who has built and run a number of consumer businesses. He is currently President of U.S. Consumer Services at American Express. Josh joins American Express in July from Greylock Partners, where he is an executive in residence. Previously, Josh was the CEO of Skype, which sold to Microsoft for $8.5 billion in May 2011. Josh has also served as CEO of, held senior executive roles at eBay and was Co-Founder and CEO of Evite.

Why did you become an entrepreneur?

I started in politics thinking that was the best way to make an impact on the world. I got my degree in public policy and then went to work for [former New Jersey senator] Bill Bradley. After a while I realized I could reach more people and have a more immediate impact on the world if I joined the private sector. What I’ve learned is that to be an entrepreneur is to be a leader—you are driving change and getting people to join your dreams with their dreams.

What was your first paying job?

I had three jobs when I was 15. I mowed lawns, was an usher at a movie theater and worked at a Greek restaurant. After peeling hundreds of pounds of potatoes I was rewarded with washing pots and pans.

After years of running start-ups and spending time at Greylock, I imagine American Express will be a big change. What perspectives will you bring with you from Silicon Valley?

A real passion for customers and products, and that has to come from the top. In my time at Greylock I saw the partners investing in entrepreneurs who are passionate about customers and products and nurturing them to become great leaders. That’s the essence of Silicon Valley.

What are the big ideas behind the businesses you have run?

There is a common thread among all the businesses I’ve led. If you look at American Express and Skype, they both operate in massive, pervasive, critical industries that touch the lives of everyone on the planet. Financial services and communications are in the midst of major transformation and both Skype and Amex are well positioned to lead the charge. I’ve also enjoyed building businesses that bring people together: Ebay built a community of sellers; Evite helps people get together with people they love; Skype allows people to connect with each other even if they are on the opposite side of the planet.

Why are you excited about the future?

True global breakthroughs are happening at an unprecedented pace in a number of industries, including financial services and communication. Innovation in technology is empowering people to make change at a rapid pace while having a lasting impact on the world. Just look at the impact of social media companies such as Facebook and Twitter on the Arab Spring revolutions in the Middle East.

What was the most difficult lesson you have learned as an entrepreneur?

The most painful experience for me was laying off 60% of the workforce—50 out of 80 people—at Evite. Many of those people were talented, hard workers who had put in many late nights and weekends. It was extremely difficult but it forced us to focus. As it turns out a lot of the things we were doing were not that important. We became more nimble.

What has surprised you about being an entrepreneur?

I was surprised by how high the highs were and how low the lows were. Every entrepreneur needs a good internal regulator. Mine was my wife. You need to ride out the tough times. Really it just takes passion and drive. Being an entrepreneur is the ultimate equal opportunity.

What values are important to you as an entrepreneur?

Transparency and integrity. Treating people with dignity. A commitment to excellence. Teamwork.

What is the best business advice you’ve ever heard?

My friend Barney Pell once told me that when you try to do big things the world conspires to help. As it turns out, doing big things is not any harder than doing small things.

What are you passionate about?

I love building teams of great people, getting them inspired about a mission and then taking a hill together.

What motivates you?

The energy of the people around me. Direct feedback from the community about the products I’ve built.

What living person do you most admire?

He is no longer living but the person I most admire is Mahatma Gandhi. Not only did he change a country with hundreds of millions of people but he also introduced a new way of creating change.

If you could change one thing about yourself, what would it be?

I’m working on becoming more rigorous about how I spend my time.

What is the last book you read?

The Emperor of All Maladies by Siddhartha Mukherjee and Innocent Abroad by Martin Indyk.

What advice would you give on how to build a great business?

Learn to trust your gut. Persistence is important but you also need to know when to change course—the answer is rarely. Competitors will always continue to launch new products and you need to stay focused. At Evite we faced an onslaught of competition from Yahoo, Hotmail and AOL; as well as pure-play competitors like TimeDane, and Keeping the focus on our own game plan was key to our success. By the time I got to Skype I had already been through the onslaught so that when Google and Apple came at us, I was much calmer and better able to see our path forward.

Change comes at you pretty fast and you can’t let it become disorienting. People desperately need a steady hand at the wheel. Most of the external stimuli don’t matter in the end. The ability to discern what matters from what doesn’t matter is one of the distinguishing characteristics of great leaders.

-This interview was conducted by Erika Brown Ekiel




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