In 2012, Wiley Cerilli sold SinglePlatform, a startup he founded to help local businesses manage their online listings, to Constant Contact for $100 million. But, the day the sale went through was not the most fulfilling day of his life, he says. The best day of his life came two years later on Christmas Day when he gave his mother a three-bedroom house.
"Giving my mom a house, it was the final step in giving my mother what she had given me my whole life," says Cerilli.
Cerilli's mom was renting an apartment in a three-family house in New Haven, Connecticut. Earlier that year, a burglar had broken in during the middle of the night and she woke up as he was in her bedroom, stealing her iPad, Cerilli says. Shortly after selling SinglePlatform, he started looking for a house near where his sister lived in a quaint suburban town outside of New Haven. Finally, Cerilli found the right home. On Christmas Day, he gave his mom an ornament with something inside. She opened it up and found a picture of the home with a pair of keys and the words "This is for your new house" written inside. His mom started crying, he says.
At 16 years old, Cerilli's dad passed away after a three-month battle with lung cancer, he says. Cerilli's two older siblings were already out of the house and he had to grow up fast, he says. Suddenly, money was tight and he and his mom were struggling, he says.
Although she was hurting emotionally, Cerilli says his mother decided to start a business shortly after his dad passed away. It was the mid-1990s and women's health clinics were under threat from the pro-life movement. The Army of God, a domestic terrorist organization, was calling in bomb threats and a few members killed doctors who performed abortions. Cerilli's mom thought she could run a clinic that was safe and she wanted to stick up for women's rights.
"She would get death threats and people would send her envelopes filled with white powder, but she didn't give up," says Cerilli. "My mom taught me to stand up for people."
Unfortunately, after a few years, Cerilli's mom had to close the clinic. Cerilli dropped out of Syracuse University and decided to go to New York City, where he got a job with the founding team at Seamless. All throughout his career, his mom would give him advice, especially when he became the CEO of his own business.
After selling SinglePlatform and becoming a venture capitalist, Cerilli started a new business, mobile app food delivery startup Good Uncle Foods in late 2015. In January 2016, company raised $200,000 from Jared Kushner during the Good Uncle Foods's seed round. But during Donald Trump's campaign, Cerilli grew disturbed by the fact that Kushner would stand alongside of Trump and not speak out against what Cerilli viewed as racist rhetoric, says Cerilli. After Trump questioned a U.S. federal judge's ability to remain impartial because of his Mexican heritage, Cerilli says that was the last straw. In July, Cerilli called Kushner and said he was returning his money and divesting Kushner's equity in Good Uncle, says Cerilli.
"My mom taught me to build more bridges than burn, but she also taught me to fight for what I believe in," says Cerilli. "I saw this as my fight."