The most cliche advice for startup founders is to identify a problem in your life and find a way to solve it. A founder with multiple exits under his belt, Paul Freedman, has a big problem: His beloved Oakland A’s are moving to Las Vegas by way of Sacramento.
“It’s interesting how much a sports team impacts the psyche of a town,” Freedman told TechCrunch. “And if a team ever makes the decision to abandon the town, it creates heartbreak. Fans have described it like a death in the family, and the death is the family member who threw all the parties.”
For Oakland sports fans, this collective grief is familiar, which makes it even more devastating.
The A’s will be the third professional sports team to leave Oakland in the last five years; the Golden State Warriors of the NBA moved across the Bay to San Francisco in 2019, and the NFL’s Raiders set up shop in Las Vegas in 2020. So when billionaire A’s owner John Fisher announced he was taking the team out of Oakland, fans fought back. In 2023, they participated in a “reverse boycott” at a Tuesday night game in June against the Tampa Bay Rays. Nearly 30,000 were in attendance, some wearing Kelly green T-shirts with the word “SELL” emblazoned across them, all chanting “sell the team” at various points throughout the game. That fight carried through to this season. On Opening Day, another reverse boycott was held, with fans this time gathering in the stadium parking lot to protest the move. Throughout the season, A’s fans made a statement in the backgrounds of national broadcasts, waving “SELL” flags to pressure Fisher to hand the A’s off to a new owner — one who cares about the team’s 56-year legacy in Oakland.
Unfortunately, Freedman and his business partner, television producer Bryan Carmel, can’t just buy the A’s. But while they may not have $1.2 billion to throw around, they realized they could start their own team. So with a dash of spite, Freedman and Carmel founded an independent baseball team called the Oakland Ballers — the Oakland B’s for short.
This year, the B’s made their debut in the Pioneer League, a professional baseball organization that’s partnered with the MLB, but unlike the minor leagues, it’s not tied to any existing MLB teams.
“What is needed is a team that represents the community and is there to provide the kind of experiences that have always been there,” Freedman said. “It doesn’t necessarily have to be fully a replacement product. We’re never going to be an MLB team, but it doesn’t mean we can’t provide some of the same experiences and some of the same joy that [the A’s] did.”
Thanks to Freedman and Carmel, there will be baseball in Oakland next year after all. But now, the founders are faced with a new problem. How do you get thousands of lifelong A’s fans to care about a glorified minor league team that plays in a renovated Little League park?
For Freedman, the answer is to take what he’s learned in building and advising startups and apply it to a baseball team. It may not sound glamorous, but it’s working.
“We’ve approached this very much like a startup,” he said. “We raised a $2 million seed round, and then built our ballpark literally from the ground up. And we’re doing things that startups do, like iteration, A/B testing … I think it’s a competitive advantage because we’re taking a very different approach to how you would build this thing typically in sports.”
Before Freedman was a serial entrepreneur, he was an A’s fan. He grew up in Chicago, cheering for the White Sox, but when he was in high school, his family relocated to Oakland. When he started following A’s baseball, the Bay Area began to feel like home.
“It’s really the A’s who have brought me into the Oakland communities where I’ve met a lot of my friends,” Freedman said. “Now, I’ve lived here for 30 years, and have chosen to live in Oakland. I choose to raise my kids in Oakland, even though I could have moved to Palo Alto and been with everybody else doing startup stuff.”
By the late 1990s, before Freedman had even gotten his bachelor’s degree, he had already founded his first edtech startup, which was an enrollment chatbot that answered students’ questions about college. He sold that company to Hobsons, and after working at the edtech giant for a few years, he founded Altius Education, a Series B startup that sought to make higher education more accessible through a low-cost, online associate’s degree program. The startup flamed out, but it earned Freedman enough respect in the venture world to found Entangled Group, an edtech incubator that was later acquired by Guild Education.
Freedman’s transition from education to baseball is a bit out of left field. But whether he’s advising new edtech entrepreneurs or constructing a stadium on a tight budget, Freedman has always wanted to build companies that make the world better.
“Every investment or every business I’ve ever tried to do, I’ve tried to make it an impact business. I’ve taken a long time to decide: Is this both good for the world and a good business?” he said. “I actually spent a long time philosophically deciding whether sports was good for the world … should we be doing other things? What is it about sports? And then ultimately, we came to the conclusion that the magic of sports is the way it brings communities, particularly diverse communities, together.”
Freedman has spent the last 30 years of his life reveling in that magic firsthand. He thinks about how it feels to take public transit right after a sporting event, when everyone in the train car is united by their shared love of the home team.
“Normally when people are on public transportation, they’re on their phones, they’re not talking to anybody,” he said. “But you take that same train and you put it after a game where the team won, and everyone’s high-fiving and hugging like it’s their family. It’s the same train, same context, but sports creates this community layer.”
When Freedman builds and advises startups, he tells founders to align their business incentives with their mission. He’s taken this same approach when laying the foundation for the Ballers. In the past, his mission has been to build tech that makes education more accessible. Now, the mission is to give Oakland baseball fans a thriving community and a team that’s worth cheering for.
“We believe that if you center your fans, and you know their experience in the community is fundamentally what the whole thing is about, then you kind of force yourself to make sure you’re doing right by them,” Freedman said.
“A willingness to experiment”
An Oakland Ballers game looks a bit different than an MLB game because the Pioneer League itself is a bit different.
“We can innovate in ways that other leagues and other teams can’t, if you believe that testing and iteration and incremental improvement is the pathway for a better product,” Freedman said.
When Pioneer League games end in a tie, they don’t move on to extra innings. Instead, there’s an impromptu Home Run Derby to decide the winner. “It’s really cool, it’s super fan-friendly, and it’s electric when it happens,” Freedman said. “People even start rooting for ties at the end of the game to see the Home Run Derby. That kind of experimentation can ultimately lead to a better experience.”
The Ballers recently took a big swing and partnered with Fan Controlled Sports, an app that allows fans to make real-time decisions about the game like they’re the manager. It’s a move that would wreak havoc in an MLB game, but works in a Pioneer League setting.
“It demonstrates both a willingness to experiment, and a willingness to make mistakes, even if in public, and an iterative approach,” Freedman said.
The Ballers have indeed put their money where their mouth is. They opened up partial ownership of the franchise to the fans. In an oversubscribed, fan-driven funding round, the team raised over $1.235 million from about 2,200 people.
“One of the things I always advise startups on is to ensure investor alignment,” Freedman said. “With us, it’s like, do your owners want the same thing? And fan owners, we believe, want exactly the same thing — what we want to do is bring joy to fans, and we think the way to do that is to create a great experience.”
The Ballers haven’t even finished their first season yet, but the team offers a glimmer of hope to forlorn A’s fans who have less than a month left to watch their lifelong favorite team play in Oakland. At its best, tech challenges the status quo, and Freedman is doing just that by showing fans that they don’t have to live by the whims of billionaire sports team owners.
This isn’t something Freedman only learned from tech, though. His focus on his mission comes from spending most of his life in Oakland.
“I’m generally a tech-forward thinker and think that there’s a lot of benefits that technology can have to most elements of our world,” Freedman said. “But there’s a lot tech can learn from Oakland.”