My guest this week is Max Nussenbaum. Max is the Program Director for the On Deck Writers Fellowship. In this episode, we take a look at his fascinating journey to where he is today.
He started his career as an 18-year-old applicant, and 19-year-old contestant, on Who Wants to Be a Millionaire. He then joined Venture for America where he worked with Andrew Yang and got involved in real estate in Detroit. After that, he started his own company called Castle which became one of the stars of Y-Combinator, grew extremely quickly and flamed out as quickly as well. You will hear Max talk about this struggle with a lot of great self-reflection on the lessons that he learned.
Max has a beautiful philosophy that life should be fun and a wonderful self-deprecating sense of humor. This has definitely served him well in this career that started with Who Wants to Be a Millionaire through Venture for America and now running the On Deck writing fellowship.
- Max on being called a Polymath. (02:05-02:54)
- Max talks about how he got on Who Wants to Be a Millionaire. (04:55-07:42)
- The biggest lesson he learned from his experience being on Who Wants to Be a Millionaire. (08:10-11:25)
- Max talks about his philosophy “It is better to be interesting than good”. (09:00-09:51)
- How does Max strike the balance between just being interesting and being interesting and good? (11:25-14:01)
- Max talks about one of his core philosophies: “Life should be fun”. (14:15-16:00)
- Max on shit-talking for fun and how he finds it important. (17:05-20:00)
- What is Venture for America? (20:05-21:31)
- What drew him to join Venture for America? (21:31-23:50)
- Max talks about what Venture for America has done well. (23:53-28:21)
- Max talks about his previous company, Castle. (28:24-31:30)
- The lessons he learned from starting Castle. (31:30-35:40)
- What he could have done differently in running Castle. (35:40-39:10)
- His opinion on the housing challenges in New York. (39:12-41:26)
- Max’s approach to learning different skills. (43:19-46:20)
- Max talks about a side project he is currently working on. (46:20-47:22)
- Why is having a side project important? (47:23-49:48)
- Max talks about his role in On Deck and the lessons learned which he is applying in his current role. (50:03-54:30)