Headshot of Ryan Wilson

Ryan Wilson

President, FiveFifty

Internet entrepreneur and digital marketing expert Ryan Wilson has spent his career mastering the art of programmatic media. He understands the nuances of data-driven advertising and addressable media, informed by decades of experience pursuing his interest in the way technology can represent people. As the founder and president of digital marketing trade desk FiveFifty, Ryan has developed a team of similarly adept digital marketing experts, with technical aptitude for the minutiae of activating consumer data as well as passion for the continuous learning required to remain relevant in the field.

Ryan grew up in a Navy family, moving from state to state and forming an adaptable nature along the way. When a mentor suggested exploring technology in order to understand the future of business, Ryan took the advice, earning dual degrees in Marketing and Management Information Systems at Florida State University. “That small suggestion started me on the path to digital marketing, and decades later, I’m still moving deeper and deeper into the same intersection of psychology, commerce, and technology.”

Ryan entered the workforce at the height of the 2000s-era dot-com bubble, cutting his teeth in database development and business intelligence as an IT consultant with Accelerated Consulting Group and later as a Software Development and Product Manager with Affinity Group, Inc. “Companies were all trying to build models around their databases, in order to understand customers better. What interested me were the links between customer data, how the relationships between data points worked. I remain fascinated by how technology can conceptualize what a customer looks like, and how that customer can be activated.” Around the same time, Ryan and a friend started their own ecommerce website, Star City Home Decor—one of the earliest web retail sites selling furniture entirely online. He also went back to school, earning an MBA from the University of Colorado Denver as well as an entrepreneurship certificate from the Bard Center for Entrepreneurship. In 2006, Ryan co-founded Intela, where he was instrumental in the design and launch of the company’s lead generation business. “As a performance media agency, we didn’t make money unless we helped the client sell something. That pressure creates a deep connection with the performance aspects of advertising: If you don’t figure it out, you don’t get paid. I learned how to truly connect with an advertiser, and how to understand what the media is doing on a more nuanced level.” During Ryan’s time there, Intela grew to employ over 100 workers. He left Intela in the summer of 2012, when he and his wife had their first daughter.

In August, 2012, Ryan founded FiveFifty, a Denver-based digital marketing trade desk that specializes in addressable media. “I wanted to reach out to a wider range of clients beyond the scope of performance media. I felt the same concepts should be applicable to a larger community of brands.” Named after Colorado’s US 550 “Million Dollar Highway,” FiveFifty focuses on digital media buying and campaign optimization, delivering cutting-edge programmatic audience buying at scale across digital media. FiveFifty was acquired by and became an in-house trade desk for Booyah in 2022, now offering programmatic media buying services to clients across the portfolio. “Booyah is like a bigger version of FiveFifty: We share a similar focus on performance, and we both value strategy and tech innovation.”

Beyond work, Ryan’s life is centered around his family. Whether it’s a weekend ski trip, sight-seeing in Japan, or a cross-country road trip in the camper van, he’s always on the lookout for new ways to explore the world with the ones he loves most. His wife, who’s a healthcare rock star, is a constant inspiration, and his two kids keep him humble. “Sometimes I come home from work feeling big after a successful work day, and my kids quickly remind me who’s really in charge. That sense of perspective is a lovely thing.”

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