Alexander has taught all humanities, coached, and dorm-parented for nearly 20 years at Dartmouth College, The King School, Kingswood-Oxford, Philips Andover and The Taft School. He is an expert at the college application process, including college essay writing and standardized test preparation. He has tutored hundreds of adolescent teens and young adults from middle school through college level on all spectrums, behaviorally and academically. He attended Philips Exeter Academy and received an undergrad degree from Kenyon College and a Master's Degree from Dartmouth College. He lives in Middlebury, CT with his three rug rats and wife, Alexa.