In this episode of Founders Future, with host Zach Young, we’re joined by Jackie Pilossoph, founder of Divorced Girl Smiling. Jackie shares how a deeply personal divorce experience—paired with her background as a journalist, former Chicago Tribune columnist, and author—sparked the creation of a platform dedicated to helping people navigate divorce with clarity, dignity, and hope. What began as personal journaling evolved into a powerful community and media brand reaching millions through articles, podcasts, and trusted professional connections.

The conversation explores how Divorced Girl Smiling functions as both a support hub and a matchmaking platform, connecting individuals going through divorce with vetted attorneys, therapists, financial experts, and coaches. Jackie explains her hands-on vetting process, her commitment to personally speaking with users seeking guidance, and how long-term consistency—through years of content creation, SEO, and podcasting—has built lasting trust and authority in a crowded space. The episode highlights the value of perseverance, credibility, and human-centered support in building a meaningful, scalable business rooted in real-life impact.