About
Charlie Graham is an entrepreneur, advisor, and investor who has spent the past 20+ years launching and scaling successful venture-backed startups. Charlie specializes in identifying market needs, rapid product iteration, growth through word-of-mouth, fundraising, and crafting compelling product strategies.
Charlie is currently the Founder & CEO of RivalSee (www.rivalsee.com), part of the Second Coffee LLC venture studio, focused on AI-first startups. RivalSee tracks and boosts your competitive position across AI search platforms, including ChatGPT, Claude, Perplexity, and Google AI. By uniquely creating personas representing your target customers, RivalSee reveals precisely when and how your content appears in AI-generated responses versus competitors—providing real-time share-of-voice metrics, source discovery analytics, and actionable recommendations.
Charlie is also currently the Founder & CEO of Second Coffee LLC, an incubator and venture studio dedicated to launching innovative AI-first companies including RivalSee, HuzzlePub, BetSee, YipYap and more.
Previously, Charlie was CEO & Founder of Hawku, Inc., the leading marketplace for utility and gaming NFTs, backed by Lightspeed Venture Partners, Multicoin Capital, Dragonfly Capital, Animoca Brands, and more.
Charlie also served as Founder & CEO of Shop It To Me, the premier online personal shopping assistant. Under his leadership, the company grew to over four million members, facilitating over $300 million in gross merchandise sales and earning numerous accolades, including a Top 50 Website by Time Magazine, a “site that revolutionized shopping” by Lucky Magazine, and receiving a Harvard Business School Alumni Growth Startup award. The company was successfully acquired in 2023.
Earlier, Charlie was co-founder and Chief Technical Officer of Hipbone, Inc., which provided enterprise-level chat and co-browsing solutions for Fortune 500 companies like American Express, Wells Fargo, Vanguard, and Office Depot. Hipbone received over $12 million in venture funding, won the 2002 and 2003 Crossroads A-List awards, and was acquired by Kana, Inc. in 2004.
Charlie is passionate about exceptional product experiences, behavioral psychology, A/B experimentation, distance running, puzzle hunts (such as the Stanford Game or MIT Mystery Hunt), dance parties, indoor home-run derbies, and spending joyful time with his wife, daughter, and son.
Charlie holds an A.B. with honors in Computer and Information Technology from Harvard University and an M.B.A. from Harvard Business School, where he graduated with high distinction as a Baker Scholar.