The 10 Year Strategic Plan for Wildwood

If you want to build a successful business, you have to be ready to work 24/7/365 to have a shot at success… or do you? Both Natalie Nagele and DHH bootstrapped their internet businesses to millions in revenue, yet they took different paths to get there, with DHH only putting in a small number of hours vs Natalie who ate, slept, and breathed her job as a founder in the early days. In this episode we discuss whether or not DHH's approach is truly repeatable for others trying to get their businesses off the ground, the limits to human productivity and happiness, and the role that society and hustle culture in  shaping how we feel about our work as founders.