Nate Singer is the Managing Director of Mission Holdings, a father of two, and the guy who first got me interested in alternative education. We discuss his early struggles at boarding school, getting rejected to UC Berkeley (but successfully appealing the decision), working hard as a math major, second-guessing conventional teaching methods, creating a class about educational television (where he and I met), John Taylor Gatto, and encouraging Berkeley students to question mainstream pedagogy. After college Nate moved into the world of finance in a quest for broader impact and understanding the forces underpinning the school system. He talks about how he applied the self-directed learning ethos to investing, the importance of reaching out to strangers, why education is about “learning how to form and achieve a vision,” the irreplaceable value of entrepreneurial experiments, why to start a literal lemonade stand, and the challenges of raising kids in the San Francisco Bay Area. Nate's LinkedIn: https://www.linkedin.com/in/nate-singer-0078952/ Recorded on Nov 22, 2021, in Lisbon, Portugal.