Miles Deamer is a Vice President at Crossover VC, an early-stage venture fund that invests in the operator-led pre-seed and seed funds that are the first call of today’s best founders as well as select direct investments at the Series A and B. Miles has spent more than a decade in Silicon Valley designing and implementing business strategies in the fintech and proptech verticals. Prior to joining Crossover, Miles spent seven years as an early employee of multiple venture-backed startups including Kiavi, Sundae, and AlphaFlow, where he led initiatives relating to capital markets, operations, and business development. Miles received a BS from USC, where he was also a member of the D1 National Championship water polo team. Outside of work, you can find Miles early on Sunday mornings cheering on his hometown soccer team Fulham at a local San Francisco pub.
EVCA: How does Crossover's focus on working with the "modern athlete and entertainer" impact the fund's investment philosophy?
Miles: While the bulk of Crossover’s investor base is made up of traditional LPs, we also count ~45 pro athletes and entertainers as strategic investors in the fund. These investors look to Crossover to serve as a trusted onramp into the private technology sector and enable them to access opportunities beyond those traditionally associated with their brand. We use the term “Modern Athlete and Entertainer” because today’s talent is smarter, wealthier, more powerful, and more motivated than prior generations to leverage their platform to achieve success beyond the field of play. With a tip of the hat to people like LeBron James, the Williams Sisters, Kobe Bryant and many others who set an example for the next generation, we view Crossover’s role as one of trusted guide and provider of access to the traditionally gated technology sector.
We are big believers in the power of community and that excellence inspires excellence. This is reflected in the programming we curate that brings together the founders, investors, and talent in our ecosystem. However, when it comes to our investment philosophy, we are purely focused on delivering top tier returns by investing in the best early-stage technology opportunities.
EVCA: What is the most important factor you consider when evaluating pre-seed and seed-stage focused funds?
Miles: The key factor we look for when underwriting a new fund is assessing what the GP’s superpower is, and how that unique advantage will produce outsized returns. We review dozens of funds each week, and you’d be surprised at how many times a manager either fails to articulate true competitive differentiation, or to draw a through-line between past investing or operating experience and their fund’s investment model. As a new manager, it’s incredibly important to recognize your competitive differentiation and ensure that you can communicate an investment strategy – backed up with data – that supports this advantage and the ability to execute against it.
EVCA: What is one piece of advice that you would give to other operators who are looking to break into the investing ecosystem?
Miles: First and foremost, it’s important to have an honest conversation with yourself about why you want to become an investor and what unique advantage you can bring to the table in an ecosystem flush with capital. Becoming an investor is more than just meeting founders and writing checks– a significant amount of your time will be spent on firm-building activities, admin and reporting, LP relations, fundraising, and more. It’s challenging and lonely work, and too often we see new managers jump into fundraising before really understanding what they are signing up for. Remember this is a ~12 year commitment when taking into account extensions.
But for those who are ready to make that commitment, opportunity abounds. I encourage new managers to identify their own superpower, formulate a compelling and focused thesis, and lean into your unique advantage, such as sector-specific specialization or tapping into unique networks of connectivity that produce top emerging talent
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