The most common advice for startup founders is to identify a problem in your own life and figure out a way to solve it. Paul Freedman, a founder with numerous successful exits, is facing a big problem: his beloved Oakland A’s are relocating to Las Vegas via Sacramento.
“It’s remarkable how much a sports team can impact the psyche of a city,” Freedman shared with TechCrunch. “And when a team decides to leave, it causes heartbreak. Fans describe it as akin to losing a family member who always hosted the best parties.”
For Oakland sports enthusiasts, this feeling of collective grief is unfortunately all too familiar, which makes the situation even more heartbreaking.
The A’s will be the third professional sports team to depart Oakland in the last five years; the NBA’s Golden State Warriors moved to San Francisco in 2019, while the NFL’s Raiders settled in Las Vegas in 2020. When billionaire A’s owner John Fisher announced the team’s departure from Oakland, fans pushed back. In 2023, they engaged in a “reverse boycott” during a game against the Tampa Bay Rays, with nearly 30,000 fans present, some wearing Kelly green T-shirts with the word “SELL” printed on them, all chanting “sell the team” at various points throughout the game. This battle continued into the current season, with another reverse boycott held on Opening Day, where fans gathered in the stadium parking lot to protest the move. Throughout the season, A’s supporters made their voices heard in national broadcasts, waving “SELL” flags to pressure Fisher to hand over the team to an owner who values its 56-year legacy in Oakland.
Unfortunately, Freedman and his business partner, television producer Bryan Carmel, cannot simply purchase the A’s. However, they realized they could start their own team. With a touch of defiance, Freedman and Carmel established an independent baseball team called the Oakland Ballers—often referred to as the Oakland B’s for short.
This year, the B’s made their debut in the Pioneer League, a professional baseball organization affiliated with the MLB but not tied to any existing MLB teams.
“What is required is a team that represents the community and is there to provide the kind of experiences that have always been there,” Freedman stated. “It doesn’t have to be a complete replacement product. We will never be an MLB team, but that doesn’t mean we can’t offer some of the same experiences and joy that [the A’s] did.”
Thanks to Freedman and Carmel, baseball will continue in Oakland next year. However, the founders now face a new dilemma: how do you make thousands of lifelong A’s fans care about a minor league team that plays in a renovated Little League park?
For Freedman, the answer lies in applying the lessons he has learned from building and advising startups to a baseball team. While it may not sound glamorous, it is proving to be effective.
“We are approaching this much like a startup,” he explained. “We raised a $2 million seed round and built our ballpark from the ground up. We are utilizing startup methods like iteration and A/B testing. I believe it gives us a competitive advantage by taking a distinct approach to building this operation, especially in the sports realm.”
Before becoming a serial entrepreneur, Freedman was an A’s fan. He grew up in Chicago supporting the White Sox, but when his family moved to Oakland during his high school years, he started following A’s baseball, and the Bay Area began to feel like home.
“It was the A’s who really introduced me to the Oakland communities where I met many of my friends,” Freedman recalled. “Now, after 30 years of living here, I have chosen to make Oakland my home. I have chosen to raise my children here, despite having the option to move to Palo Alto and be surrounded by the startup scene.”
By the late 1990s, before completing his bachelor’s degree, Freedman had already founded his first edtech startup, an enrollment chatbot for students seeking information about college. He sold the company to Hobsons, and after working there for some time, he established Altius Education, a Series B startup focused on making higher education more accessible through an affordable online associate’s degree program. While the startup ultimately did not succeed, it earned Freedman enough recognition in the venture community to start Entangled Group, an edtech incubator that was later acquired by Guild Education.
Freedman’s transition from education to baseball may seem unexpected, but whether advising new edtech entrepreneurs or constructing a stadium on a limited budget, he has always aimed to build companies that contribute positively to the world.
“I have always tried to make every investment or business I pursue one that has a positive impact,” he noted. “I have taken a long time to determine if something is both beneficial for the world and a good business opportunity. I have spent years philosophically contemplating whether sports are beneficial to the world, or if we should be focusing on other things. Ultimately, I concluded that the magic of sports lies in its ability to bring communities together, particularly diverse communities.”
For the past three decades, Freedman has experienced this magic firsthand. He notes how public transportation after a sporting event transforms, with passengers sharing high-fives and hugs, united by their love for the home team.
“Usually, people on public transit are on their phones, avoiding conversation,” he observed. “But after a game where the team emerges victorious, everyone is celebrating like family. It is the same train, same setting, but sports add this unique community layer.”
When advising startups, Freedman emphasizes aligning business incentives with the mission. He has applied this approach in laying the foundation for the Ballers. In the past, his mission was centered around developing technology that makes education more accessible. Now, the mission is focused on providing Oakland baseball fans with a vibrant community and a team worth supporting.
“We believe that by placing fans at the core, where their experience within the community is essentially the crux of everything, we force ourselves to ensure we are doing right by them,” Freedman explained.
An Oakland Ballers game differs from an MLB game due to the unique nature of the Pioneer League.
“We can innovate in ways that other leagues and teams cannot if you believe that testing, iteration, and incremental improvement are the keys to a better product,” Freedman stated.
In Pioneer League games that end in a tie, there is no extra innings. Instead, a Home Run Derby decides the winner. “It’s exciting, fan-friendly, and creates a buzz when it occurs,” Freedman added. “People even start hoping for ties towards the end of the game to witness the Home Run Derby. This type of experimentation can lead to an enhanced experience.”
The Ballers recently ventured into a partnership with Fan Controlled Sports, an app that enables fans to make real-time game decisions as if they were the manager. While this move may disrupt an MLB game, it works well in a Pioneer League setting.
“It exemplifies a willingness to experiment, make mistakes, even in public, and take an iterative approach,” Freedman explained.
The Ballers have taken a bold step by offering partial ownership of the franchise to the fans. In an oversubscribed funding round driven by fans, the team raised over $1.235 million from approximately 2,200 individuals.
“I always advise startups to ensure investor alignment,” Freedman noted. “With us, the owners want the same thing—we want to bring joy to fans, and we believe a fantastic experience is the way to achieve that.”
Although the Ballers have not yet completed their inaugural season, the team offers hope to disheartened A’s fans who have limited time left to watch their beloved team play in Oakland. Tech at its best challenges the status quo, and Freedman is demonstrating this by revealing that fans don’t have to be at the mercy of billionaire sports team owners.
This approach is not solely derived from tech but also from Freedman’s experiences in Oakland.
“I generally think forward in terms of tech and the benefits it can bring to various aspects of our world,” Freedman stated. “But there is much tech can learn from Oakland.”
**Image Credits**: Henry Pickavet
**”A willingness to experiment”**
An Oakland Ballers game offers a unique experience compared to an MLB game due to the distinctive nature of the Pioneer League.
“We have the opportunity to innovate in ways that are not possible for other teams and leagues if you believe in testing, iteration, and gradual improvement being the way to improve a product,” Freedman highlighted.
In Pioneer League games that conclude in a tie, there are no extra innings. Instead, a spontaneous Home Run Derby determines the winner. “It’s really exciting, incredibly fan-friendly, and creates an electrifying atmosphere,” Freedman shared. “People even begin rooting for ties towards the end of the game to witness the Home Run Derby. This kind of experimentation can ultimately result in a superior experience.”
The Ballers recently collaborated with Fan Controlled Sports, an app that empowers fans to make real-time decisions during the game as if they were the manager. While this move could cause chaos in an MLB game, it is a perfect fit for the Pioneer League setting.
“It demonstrates a willingness to experiment and make mistakes, even publicly, and an iterative approach,” Freedman explained.
The Ballers have truly displayed their commitment. By offering fractional ownership of the franchise to fans, they engaged in a fan-driven funding round that raised over $1.235 million from around 2,200 supporters.
“One thing I always stress to startups is the importance of aligning with your investors,” Freedman emphasized. “With us, our owners want the same thing—we aim to bring joy to fans, and we believe that providing a fantastic experience is the way to achieve that.”
Although the Ballers have yet to complete their first season, they offer a ray of hope to despondent A’s fans who have a limited window to watch their cherished team play in Oakland. At its core, the best of tech challenges convention, and Freedman exemplifies this by showing fans that they are not bound by the decisions of billionaire sports team owners.
This approach is shaped not only by tech but also by Freedman’s deep roots in Oakland.
“I am always looking ahead in terms of tech and the myriad benefits it can bring to different aspects of our world,” Freedman stated. “Yet, tech has much to learn from Oakland.”
FAQs about the Oakland Ballers
1. What is the Oakland Ballers?
The Oakland Ballers is a baseball team based in the Bay Area that is gaining attention for its innovative approach to the game.
2. Why are they considered the coolest startup in the Bay Area?
The Oakland Ballers have captured the hearts of fans with their dynamic playing style, dedication to community outreach, and commitment to sustainability.
3. How can I watch the Oakland Ballers in action?
You can catch the Oakland Ballers games at their home stadium in Oakland or watch them on TV or online streaming platforms.
4. Who are the key players on the Oakland Ballers team?
Some of the standout players on the Oakland Ballers include pitcher Jessa Thompson, outfielder Marcus Chen, and first baseman Alex Rodriguez.
5. What initiatives do the Oakland Ballers support off the field?
The Oakland Ballers are involved in various community programs, including youth baseball clinics, environmental initiatives, and charity events.