Leadership did not get harder because markets turned. It got lonelier because scale removed the rooms where truth used to circulate across the startup ecosystem. Founders talk about velocity while quietly running on fumes. Operators ship clean products that feel hollow. Community became a feature, not a force. In that vacuum, isolation masquerades as focus and frictionless became a personality trait. The result is progress without pulse and leaders wondering why the climb feels quieter the higher it goes.
On January 29, 2026, Scott Heiferman steps into that silence with Michael Sippey for a conversation hosted by Jordana Stein through Enrich Events, bringing a slice of the startup ecosystem into a room built for honesty instead of performance. The framing says How I started Meetup, but anyone paying attention knows this is really about endurance. Sixteen years building a company that pulled sixty million people into three hundred thirty thousand communities does that to you. It sharpens your sense for what survives cycles and what evaporates when energy leaves the room.
Meetup was never about removing steps. It was about giving people a reason to take one together. Scott Heiferman learned early that fun and urgency beat elegance when the goal is connection, and that belief aged well while product doctrine chased efficiency through successive eras of the startup ecosystem. Michael Sippey brings the counterweight of a product mind that has lived inside Twitter and Medium, watching how small design choices either compress or expand human signal. This is not a fireside chat. It is two builders comparing notes on what actually holds.
The room matters because it is small. Roughly fifty curated leaders, filtered for intent, not applause. Enrich does not scale noise. It compounds trust. Jordana Stein built that instinct from experience, turning operator isolation into peer infrastructure with a referral rate north of seventy percent and an NPS that speaks for itself. This is enrichment in the literal sense, adding weight where leadership often feels thin.
What emerges here is not advice but permission. Permission to stop confusing low friction with high meaning. Permission to design for people who show up, not just sign up. Permission to admit that leadership without community is just decision making in a vacuum. Scott Heiferman has been inside that vacuum and built a way out. Michael Sippey knows the machinery that can either trap it or amplify it. The rest is what happens when the right minds share oxygen and let the conversation do the work, a quiet recalibration the startup ecosystem rarely slows down enough to allow.
