The 100th mailbag episode highlights seven special contributors to the podcast, sharing personal stories and reflections on their investing journeys. From success stories with investments like Shopify to the impact of the podcast community on personal growth and financial decisions, the chapter emphasizes the importance of starting early and being part of a supportive network. The episode also features conversations with retired investors, reflections on life-changing moments, and aspirations post-COVID, making it a celebratory and insightful milestone for the podcast.