Ryan Petersen: Building Flexport

Build the system behind the system. Flexport founder Ryan Petersen shows how to turn messy, multi‑party operations into a simple, scalable system that compounds growth without sacrificing trust. He explains: The iPhone clue: using public shipping data to predict launches—and create pull from zero Retention is destiny: the equilibrium math that caps growth (and how to bend it) Full‑stack or bust: customers buy outcomes, not point tools 108 steps to scale: structure the workflow, then automate or offload 90%+ Freight whiplash playbook: win share at $600 rates, keep trust at $20,000 The YC clarity rule: say it simply, make upside legible, accelerate yes Crisis ops at speed: repurposed jets and 500M masks during a global shutdown The confidence gap: why stepping away was rational—and what evidence made the comeback inevitable Choosing bottlenecks: sequence capability buildouts so quality scales with volume Automate vs. outsource vs. in‑house: a deci...