Bryan leads Craft's New York office and is a partner on the investment team. Prior to joining Craft, Bryan built Reddit's New York office and revenue team, growing revenue over 10x to $100m+ in annualized revenue while managing sales, customer success, and creative strategy for the East Coast. During his time at Reddit, Bryan built partnerships with brands including Google, Microsoft, Target, Coca-Cola, P&G, and HBO.

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Bryan was an early member of Twitter's New York team, where he worked on acquisition marketing with then-emerging startups such as Harry's, Bonobos, Peloton, Warby Parker, Casper, and Dollar Shave Club, while contributing to the build-out of their direct response ads offerings. Bryan has been an active investor both personally and via Riverside Ventures, which he founded in 2017. His investments include Carta, Citizen, Bonobos, Slack, Robinhood, DocuSign, and Dapper Labs. In 2018, Bryan was named to Forbes 30 Under 30 list for Marketing & Advertising. He was also recognized by Ad Council for championing nonprofit advertising that builds awareness around mental health and diversity & inclusion. In 2021, Bryan was named to Business Insider's Top 100 Seed Investors and The 50 Most Important VCs in New York.