Guest insights
Five guests on starting over
A chef, a VP, a planner, a librarian and a radio journalist on what it actually felt like to begin again.
Starting over comes up in almost every conversation we record. Here are five moments from recent guests that we keep coming back to.
Ravi Shah — “Lean on what you already know”
Ravi left professional kitchens to become a software engineer at 35. His advice: don’t hide your previous career. His experience running a kitchen made him calm in production incidents in a way his colleagues found remarkable.
Hannah Brooks — “Run the experiment quietly”
Before leaving her VP role, Hannah spent a year testing her new business on evenings and weekends. By the time she resigned, she already had three clients.
Lucas Meyer — “Pick the number in advance”
Lucas decided exactly how many paid subscribers he needed before leaving his job. When the moment came, the decision had already been made.
Grace Kim — “Start with people, not product”
Grace’s bookshop began as a reading group of eight. The community came first; the business followed.
Jordan Hayes — “Write the honest email”
Our own co-host closed his first startup with a long, candid email to customers. Several of them became the first users of his second company.
Maya is a former product lead and a coach to first-time founders. She brings a researcher's patience to every interview and has a habit of finding the one story a guest has never told on air.
