Why Leaders Need a “Third Space” - Christine Song on Building 5 to 9 Society

What if “networking” is broken - and leadership is lonelier than we admit? In this episode, Christine Song (Founder, 529 Society) breaks down why big conference rooms and name tags don’t create real relationships - and why she believes leaders need a third space outside of work to talk honestly, pressure-test decisions, and build trust without politics. Christine shares how a single LinkedIn post led to 600 applicants in 30 days, why she chose to keep 529 Society intentionally small (and vetted), and how she designs intimate, high-trust dinners and operator-founder-investor cohorts across Canada. We also dig into what founders often miss when they only spend time with other founders, how “character” becomes a business advantage, and why IRL connection is becoming more valuable as online trust erodes. If you’re a founder, exec, operator, investor, or builder who’s tired of performative networking and wants a more real peer network - this one will land and you'll probably want to join her community.