A few weeks ago, I met a young operator for coffee in Boston. He works at an overseas co-living company operating in two cities. The business is real — hundreds of listings, established operations, real momentum. He reached out thoughtfully, proactively, trying to understand what selling into the U.S. might look like and whether there was a path forward. The Pitch Began — and So Did the Déjà Vu We sat down, ordered coffee, and started talking. He began explaining the product. At first, it sounded like property management software. I interrupted gently. The U.S. market has no shortage of…

Over the past few years, I’ve had countless conversations with people on the verge of a career pivot. Some were my mentees. Some were aspiring founders I met at accelerators. Others were professionals who pulled me aside after an event, lowered their voice, and said: “I think I’m ready to leave my corporate job and start something of my own.” Whenever I hear that, I don’t say yes and I don’t say no.I simply ask: Why? Because after hearing hundreds of these stories, one pattern stands out clearly:Most people aren’t actually struggling with their business idea — they’re struggling with…