Ever felt torn between career growth and your entrepreneurial aspirations? In this talk, I'll share my experience working as a Principal Product Designer at Yelp while successfully bootstrapping businesses. I’ll share stories from launching small businesses, growing them to 250k+ ARR, and getting acquired, all of while advancing my career at one of the world’s biggest tech firm. We’ll explore the advantages and challenges of this new work model, and how you can structure a career that works for you.