In this episode of Scaling Up, Not Giving Up, host Richard Lee sits down with Jeremy B. Shapiro, a serial entrepreneur and author of Your Business Growth Playbook, who shares invaluable insights on moving beyond the daily grind to build a truly self-sustaining business (0:04). If you’re a founder caught in the uncomfortable middle stage—past the initial hustle but not yet free—this discussion offers practical strategies to break through plateaus and achieve entrepreneurial freedom.
Jeremy delves into crucial topics such as recognizing early signs of founder burnout, why continuous hustle is not a sustainable long-term strategy (11:57), and how to effectively time-box your strategic efforts (23:56). He also introduces the concept of an org chart method for gradually replacing yourself (37:57), allowing you to scale without becoming the bottleneck, and even explores what a real business sabbatical can look like (43:41).
The episode emphasizes building businesses that don’t depend on you for survival (0:21), focusing on systems that support sustainable growth and mindsets for cultivating optionality and time freedom. Tune in to learn how to transform your business from a trap into a vehicle for true liberation, with actionable advice to help you get unstuck and back to exciting growth.
Read More: https://yourbusinessgrowthplaybook.com/scaling-up-not-giving-up-podcast-richard-lee/
Listen on iTunes: https://podcasts.apple.com/us/podcast/the-business-shouldnt-need-you/id1804985577?i=1000741546239
Listen on Spotify: https://open.spotify.com/episode/39DBURdX4EBxLGz4mLJRLk
Watch on YouTube: https://www.youtube.com/watch?v=Xe0fFp2s-gQ