If there’s one word to describe Jameis Winston, it’s passionate. Whether firing up his team by eating Ws in a pregame speech, dancing through a postgame celebration while on crutches with a torn ACL, or, most recently, venture capital investing, the 2015 NFL first-overall pick throws himself wholeheartedly into every endeavor. “The easiest part of my day-to-day is being true to who I am,” Winston says. “When I go viral, I’m just being authentically myself.”
This mindset is shared by his business partner, serial entrepreneur and sports VC investor Danny Cortenraede. While most sports fans go wild for touchdowns and home runs, Cortenraede is almost giddy when discussing fan engagement solutions or data analytics. At his investment firm InStudio Ventures, Cortenraede has channeled his entrepreneurial energy into partnerships with professional athletes, including Winston, investing in sports technology, clubs and leagues, women’s sports, and youth sports. “We’re not your typical investment firm,” he says. “We’re entrepreneurs who have built companies and want to make a real impact on the sports industry.”
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Game plan for founder success
InStudio Ventures was born from Cortenraede’s recognition of a significant issue: nearly 80% of startups fail within five years. “That was just a crazy number,” he says. It prompted him to create a more systematic approach to VC investing. “This way, we de-risk our investments and increase the success rate for founders.”
His advice for aspiring entrepreneurs centers on securing substantial early-stage funding to cover the friends-and-family round, allowing founders to focus on growth rather than survival. Cortenraede stresses the importance of product-market fit, customer feedback, and key performance indicators like Net Promoter Score (NPS), customer satisfaction, and retention rates to gauge a product’s resonance with its target market. Effective cash flow management, scalability through process streamlining, and task automation are also critical.
All of that is great, but ultimately, Cortenraede believes success hinges on building a resilient, adaptable team aligned with the company’s vision. Winston echoes this sentiment: “We’re all ignorant to some things, so we have to take advantage of the resources we have on our team to help elevate us.”
From classmates to teammates
Before becoming business partners, Cortenraede and Winston were classmates in Harvard’s BEMS (Business of Entertainment, Media, and Sports) program, which Winston joined in the summer of 2023. Cortenraede went on to complete his executive MBA there. During a class break, Cortenraede seized the opportunity to introduce Winston to InStudio Ventures. Their first meeting outside of Harvard occurred in LA, with their entire families—kids included—present. “I’d already seen Danny in an intense learning environment, so I wanted to see him in an environment where he could let his hair down and be himself,” Winston says. Of that first meeting, Cortenraede says what really stood out to him wasn’t just Winston’s performance but “it was the kind of person he is.”
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While a professional athlete and a venture capital partner bring different skills to the table, Winston believes both roles require building genuine connections. “As a quarterback, you need to mesh with everyone, from the offensive line to the defense,” he says. In business, he evaluates his partners as he would teammates, but instead of physical attributes, Winston values authenticity: “If you’re giving off genuine energy, we’ll have a great conversation that hopefully leads to a strong relationship.” He adds that he and Cortenraede may live different lives, but they share a passion for sports and a common goal — “to be the best.”
Going deep
With a nine-year NFL career that earned him over $70 million, Money is no longer Winston’s primary motivation. Instead, he’s inspired by making a meaningful impact in sports, giving back to the game that has shaped his success. “My whole life, I’ve been taught to find ways to defeat my opponent schematically,” he says. Eventually, Winston realized he could apply those same skills to business. With the guidance of his manager, Winston learned the power athletes can wield by investing in technologies and media platforms that elevate both their brand and the industry as a whole — and make an impact beyond the playing field.
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“Yes, we will make great investments,” Cortenraede says. “But it’s about much more than that. It’s about doing something for the youth and improving the industry.” Winston has already lept into action, establishing the Dream Forever Foundation to support disadvantaged youth. “I want to learn from the best in entrepreneurship and venture capital so I can share that knowledge with young people who aspire to grow in this space,” Winston says. “I love learning and I love inspiring others to learn.”
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