Baratunde Thurston is the CEO and co-founder of Cultivated Wit, a design, media, and technology company. I came across Baratunde’s book, How to Be Black, in a used bookstore last summer. It caught my eye because the title is so funny, and because I recognized his name, probably from his days as Director of Digital at The Onion, his column in Fast Company, or his more than 10 years as a standup comedian. His book is so engaging and has a really smart approach to discussing race, culture, class, and much more. When I heard him discussing his educational experience on WTF with Marc Maron and heard about his participation in out-of-school activities such as Higher Achievement and the DC Youth Orchestra, I knew I had my hook for inviting him to be a guest on Please Speak Freely. We had a great conversation about his experience going from public schools in Washington, DC to the prestigious Sidwell Friends School, then to Harvard University, and the many adventures he had along the way.