Ryan Howard on Sports Investing and MLB’s Labor Fight

The episode starts with host Jason Kelly introducing Ryan Howard, a former Major League Baseball star and MVP, highlighting his successful career and post-retirement ventures. Ryan has built a diversified investment portfolio, including sports and entertainment businesses, notably Batter Up, a baseball entertainment concept likened to Topgolf but for baseball. The hosts discuss Ryan’s background, his leadership in the sport, and his transition from baseball to entrepreneurship, emphasizing the importance of planning for life after sports and leveraging personal branding in the modern era.

Ryan Howard explains his company Batter Up, which aims to modernize the batting cage experience by creating a social, interactive environment similar to Topgolf for baseball enthusiasts. The business incorporates live pitching machines, entertainment, and a party atmosphere, intended to attract a broad audience beyond traditional players. Ryan shares his plans to raise a Series A round of around $15 million to open the first location in Phoenix, detailing his approach to investment, including the importance of founder relationships, brand positioning, and understanding the revenue model.

The episode explores Ryan Howard’s investment approach, which mimics baseball strategies—focus on the person behind the project, understanding the story, and assessing the potential for disruption and profitability. He emphasizes patience, perseverance, and the importance of backing ideas he personally enjoys and believes in. Ryan also discusses his investments in professional soccer and the Mexican league, highlighting the significance of global sports dynamics and the value of networks in deal sourcing.

The conversation shifts to the current state of Major League Baseball, particularly the labor negotiations between players and owners. Ryan offers an insider perspective, comparing the negotiations to politics, emphasizing the need for transparency and compromise. He advocates for a balanced approach that considers the interests of both players and owners, including potential benefits from adopting practices from other leagues, such as salary caps and revenue sharing, to grow the sport's economic value. The discussion underscores baseball’s cultural significance and the risk of losing momentum if disputes lead to a strike or lockout.

Ryan Howard reflects on the importance of engagement with fans and understanding local communities, sharing insights from his time playing in Philadelphia. He stresses that a blue-collar work ethic and honest effort resonate strongly with fans. The hosts discuss the broader challenges and opportunities in sports business, including franchise valuation disparities, revenue growth, and the need for innovative strategies to keep the sport competitive and financially healthy. The episode concludes with Ryan’s optimism about baseball’s future if stakeholders work collaboratively.