wiley cerilliA few weeks ago, 32-year-old entrepreneur Wiley Cerilli sat down with his wife. He told her an email company, Constant Contact, wanted to acquire his two-year-old startup, SinglePlatform, for $100 million.

The couple came up with a list of things to buy and do if the deal went through:

  • Get a new washer and dryer
  • Mount the TV
  • Buy new socks

"We couldn't think of anything else we really need," he said.

Last week, the $100 million acquisition was finalized—$65 million in cash up front with the ability to earn up to $30 million more over the next two years.

As a sole founder who had only raised $4.5 million from outside investors, Cerilli suddenly became a very rich man.

We met up with Cerilli and SinglePlatform's executive team on Wednesday night, just after the money hit their bank accounts.

We asked, "How does it feel to be absolutely loaded?"

"It doesn't seem real," he replied.

Here's Cerilli's story.

*            *            *            *            *

Cerilli grew up in Rhode Island and he was always a hustler.  He isn't a coder, he's a salesman, and Cerilli perfected his technique by selling flowers, lemonade and T-shirts to the Brown University community with his friend, Irving Fain.

Fain says they'd walk away some weekends with thousands of dollars in their pockets.

"If you can sell roses to people on a hot day during college graduation, you can sell anything," says Fain. "Wiley can sell effortlessly. He is the type of person who walks into a store to sell someone, and within minutes they're trying to sell him, asking to be his customer.

Cerilli learned a lot from his father, who died of cancer when Cerilli was 16. A real estate developer, Cerilli's father constructed multiple large buildings in Providence, one of which had no windows. He hired an artist from RISD to paint beautiful bay windows on it that could be seen from the highway. "I wanted to be like that and paint windows on my own windowless building," says Cerilli.

Cerilli went to Syracuse University for one year, but he quickly found he wasn't college material. He transferred to NYU where he could work and attend classes simultaneously. He says his first apartment was modest, with a blow-up mattress for a bed that frequently popped when he'd lie on it.

Cerilli dropped in and out of school at least five times. He never graduated but instead began his tech career. He worked alongside Meetup's Scott Heiferman at a startup called Rocketboard. Then Cerilli became an early employee at Seamless, a food ordering site created by Jason Finger.

When Seamless was acquired, Cerilli found himself a few hundred-thousand-dollars richer. Even then, Cerilli says he only splurged on socks.

Cerilli met his wife Allison on Match.com, although he was never hard-pressed to find a girlfriend. "It was an efficient way to meet someone and I was working all the time," he says. He says he thought his wife's profile was fake at first -- she looked too good to be true.

In 2010, Cerilli put his tech, sales and local restaurant experience to use. He founded SinglePlatform to help get small businesses online and manage all of their listings in one place.

Charlie O'Donnell, then of First Round Capital, was one of the first investors to notice Cerilli.

"Scaling local sales is hard and Wiley was one of the few people who had done it already," O'Donnell says of meeting Cerilli. "His experience at Seamless made him uniquely qualified in the space compared to the other people I had met."

First Round Capital contributed to SinglePlatform's initial $1.2 million round of financing, and followed up in a second $3.25 million round last summer.

Despite support from investors, SinglePlatform went through some rough patches. Fifteen months ago, Cerilli wasn't sure his company would make it.