As CEO and cofounder, Tyler Leonard focuses on building the relationships, team, and culture that allow Almost Always to do its best work. Drawing on a multidisciplinary background that spans strategy, production, design, and business development, he works closely with clients and internal teams to help ambitious companies navigate periods of growth, transformation, and reinvention. Tyler believes the best client relationships look less like vendor engagements and more like true partnerships—a philosophy that continues to shape the way Almost Always operates today.

Before cofounding Almost Always, Tyler held leadership roles at digital agencies where he helped scale teams, grow client relationships, and deliver digital products for organizations ranging from early-stage startups to global brands. Throughout his career, he has worked across industries including wellness, healthcare, hospitality, fintech, AI, and consumer products, partnering with companies such as Red Bull, MUD\WTR, Noble 33, and the City of West Hollywood. Known for his hands-on approach and long-term perspective, Tyler often serves as a strategic partner to founders, executives, and marketing leaders navigating periods of growth and transformation.

Tyler studied Marketing and Public Relations at San Diego State University. Outside of Almost Always, he invests in and advises startups, explores real estate opportunities, and is a partner in Library Ale House in Santa Monica. Most often, however, you'll find him coaching one of his sons' sports teams, spending time with his family at the beach, or catching a Lakers game whenever possible.