From Seamless to Venture Partner: Fireside Chat with Wiley Cerilli


Startup Community

Startup Grind’s monthly fireside chat interviews features entrepreneurs, founders, innovators, and investors with incredible stories to share with the Startup Community. This month they welcomed Wiley Cerilli, a Venture Partner at First Round Capital and founder of SinglePlatform. Leading the chat was Peter Crysdale, Director of Startup Grind’s NYC Chapter.

Before venturing into the world of business, Cerilli wanted to be a teacher. Meanwhile, his parents were both entrepreneurs. His father, a real estate developer, taught him early on that entrepreneurs see the world differently than everyone else. In observing the way his father approached refurbishing an old building by commissioning an artist to paint what looked like huge bay windows on the side, Cerilli learned a lesson about entrepreneurship.

“Entrepreneurs see windows where others see brick walls,” he said.

Cerilli also talked about going to college to become a teacher. He tried a variety of majors, from psychology to history. A week into his sophomore year, he dropped out of New York University to join Seamless, the popular online food ordering service, which was only just starting out. He then went on to found SinglePlatform, an online marketing service for businesses, in 2010. He was CEO until 2012, when it was acquired by Constant Contact.

The idea of building a product and selling it, which is the common way of doing business, is a silly notion to Cerilli.

“Our motto was ‘if you sell it, we build it,’” he said.

Basically, ask the customer what they want and then build the product around it.

When asked about how many “no’s” could one take before taking a different approach to a product, Cerill isaid that “you pick what your idea says it’s going to be and what success looks like.”

After the chat, Crysdale took questions from the audience via Twitter.

The future of the startup and tech world: Silicone Valley or New York City?

“The benefit of being in San Fran or New York is that just like with anything in life, you have examples all around you of people who are doing really well,” said Cerilli.

He believes in the impact of success stories, which can be found in the NYC startup world.

“We just need a lot more stories and more entrepreneurs telling their stories to inspire people to say, ‘Oh wow, I can do that,’” he said. “We need more models, and entrepreneurs investing back into their community, encouraging people to do it.”

Cerilli said that he is focused on impact investing: that the greatest leveler of the world is education and technology. Building businesses at a lower cost is much easier, compared to the past. A distributive workforce is now possible, including having teams from different parts of the world working with you.

The move from Seamless to start SinglePlatform.

Cerilli said that he was “drunk off of the positive experience at Seamless.” He was with Seamless for ten years as Executive Vice President of Partner Sales and Marketing. It took him three months to build the product that became SinglePlatform, which was then funded by First Round Capital, the firm with whom he would eventually be a Venture Partner.

Cerilli admitted to initially being scared of the business failing, not because he might have made the wrong decision, but that he would leave his employees without jobs.

“I just felt like I had so much confidence that this idea was an idea that would work out and that made sense,” he said. “I knew I was going to get there at some point, but I just didn’t know if I was going to run out of time.”

But First Round’s support gave them the confidence they needed to continue.

Characteristic for a Team Member.

“Depends on what kind of superpower you’re hiring for,” said Cerilli.

As a Venture Partner, he always looks for someone positive and a team player. He also encourages entrepreneurs to consider people who have dealt with adversity, because they are excellent problem solvers.

For first time entrepreneurs looking for members to fill their team, Cerilli’s advice is to “learn how to tell a very effective story.”

When Seamless was starting out, there was no other company like it, so there was nothing to model themselves after. In order to encourage people to join them, they had to tell a unique story and sell that vision.

“Before you sail the sea, don’t gather a bunch of men and tell them to build you boat,” he said. “Teach them to yearn to sail the sea and they will build you that boat.”



About the author: Caithlin Pena

Caithlin is a recent graduate of Stony Brook University’s School of Journalism.  At  Stony Brook, she wrote for the Stony Brook Press as well as the Statesman.


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