Whittemore grew up in Scarborough, Maine and graduated from Scarborough High School.  He attended the Northwestern University where he started the Center of Global Engagement and was a member of Phi Beta Kappa .  Whittemore studied abroad at The American University in Cairo .  He graduated with a BA in History in 2006. 
Early in his career, Whittemore was the Found Director for the Center of Global Engagement at Northwestern, which guides undergraduate students who want to make an impact on international issues.  At the same time, Whittemore was an Advisor and Editor of Social Entrepreneurship at Change.org and was an early content lead.   In 2011, he became the Principal at Learn Capital where he oversaw dealflow, content, and company building projects, as well as helped the fundraising processes. 
From 2012 to 2016, Whittemore was the Chief Marketing Officer at Partnered, a B2B platform that connected brands and startups.  In 2018, he started NewCo which focuses on strategies in the blockchain space.