“I’m all about investing in the individuals in front of me,” says CEO of Winning Margins and Community Groundwork, Michael Ceraso. “I get to watch people carve out their paths and change the world. It’s powerful!” Ceraso has grown up in politics. He served as New Hampshire’s Deputy Field Director for Obama, New Hampshire’s Deputy State Director and California’s State Director for Bernie Sanders, and New Hampshire’s State Director for Pete Buttigieg, but his political passion has shifted. Today, he’s on a mission to make political work accessible to everyone.
Ceraso finds confidence to join the political space
As a student working through community college, Michael Ceraso knew he wanted to be a part of politics, but he felt it was a space for Ivy League students. These insecurities plagued him right up to the unexpected death of his mother in 2007. “Her passing was symbolic to me,” he recalls. “She died too young to do everything that she wanted to do. It became clear I needed to start accomplishing my goals.”
Fueled by the clarity that followed his mother’s passing, Ceraso traveled to Iowa and knocked on doors during Senator Obama’s election. After volunteering in Iowa, Ceraso was hired to his first political position. He was off to change the world in Carlsbad, New Mexico as a political organizer for President Obama.
Ceraso’s new home was the smallest town he’d ever seen and in a remote, rural area. He was far from everyone he’d ever known, but he was following his passion. “As I campaigned in that community, I strengthened relationships, formed bonds, and built friendships,” he remembers. “I learned how to create a family from scratch in a short period of time.”
Ceraso’s first post was staunchly conservative. Even though he and his team didn’t flip the area, they did manage a massive increase in their party’s turnout.
Despite his success, Ceraso remembers feeling fairly “green” while working that first job. “I wasn’t totally organized as an organizer,” he admits. “But I was engaging enough that people listened to me.”
Years later, Ceraso has figured out the ropes and is still involved in politics. “It’s been fourteen years in the making,” he remarks. “Now I am CEO of a consulting firm called Winning Margins and a nonprofit called Community Groundwork. The things I’m accomplishing in my career right now are the things that I’m most proud of.”
Ceraso struggled to launch Winning Margins
In 2017, after Trump was elected, Ceraso was on a high after working on Capitol Hill for eight months. Compelled to do something grandiose, he met up in New Mexico with three close friends and started Winning Margins. “Our goal was to support underfunded state parties,” he remarks. “We went into rural and heavily Republican districts and found a way to support their Democratic candidates financially.”
A year into the venture, Ceraso realized the business model for his startup was flawed. “We wanted to change the world,” he recalls. We wanted to create something brand new and entirely outside of the system. It’s exciting, but it’s important to acknowledge there are many good things already in the system.
In 2018, Winning Margins failed and sent Ceraso into a financial tailspin. “I almost went bankrupt,” he says. “I believed so strongly in the cause that I kept putting money into it that I didn’t have. Working outside the Democratic Party can have its benefits, but I was competing with donors, strategies, and processes. I took stock, and it wasn’t good. I didn’t have much money, and the people I’d started Winning Margins with were going in different directions.”
At that low point, Ceraso started thinking about Winning Margins differently. He partnered with a friend in communications, and together they began representing candidates in the communications space. Then in partnership with Ceraso’s new nonprofit, Community Groundwork, they began training students to join Winning Margins as an internship.
“Winning Margins evolved to support underfunded candidates in underserved communities across the country and lift the voices of women of color as leaders around the nation,” says Ceraso. “Additionally, through Community Groundwork, we’re able to hire people from two-year institutions who may not have realized that they could have access to political opportunities. They come to work for us, and then they move on and do some really cool stuff. It’s cyclical, and it feeds itself monetarily.
Community Groundwork trains the next generation for political work
Community Groundwork brings Ceraso’s political career full circle. He started the organization after noticing a considerable underrepresentation of applicants coming across his desk from two-year colleges. “I think that lived experiences on a campaign are important,” he says, “but I just kept getting Ivy League School, Ivy League School, Harvard, Yale. My pool was pretty limited.”
As a former two-year student, Ceraso wanted to give back. He created a Go Fund Me page, raised $6,000, and started a pilot program in Long Beach training 25 students from Long Beach Community College. He partnered with a longtime friend, Elizabeth Emerald, to finalize the curriculum.
This nonprofit selects students attending two-year colleges, trains them for a career in politics, and matches them with jobs,” Ceraso says.
“Currently, we’re engaging with a swath of community colleges in the L.A. area,” Ceraso remarks. “There are around 600,000 community college kids in California alone, so it’s a great place to be an incubator. One by one, we’re helping community college students become engaged, effective, and equal citizens through careers in public service.”
Instead of organizing campaigns across the country, Ceraso has turned to organizing the next generation of organizers. “If I can empower people through Community Groundwork or hire them at Winning Margins, I get to watch them go out there, take those skills, and change the world.”
