Jake Roberts's Work | ContraWork by Jake RobertsJake Roberts
Premium ghostwriter for founders & executives
Chapter 10 of WHY DON'T YOU ASK QUESTIONS: Ask Instead of Assume. My mom feels a weird vibe, asks one question, and the whole story dissolves — it was never true. Most of the stories we create are heavier than reality. Part of the opening to my book, WHY DON'T YOU ASK QUESTIONS. One night, my girlfriend asked me why I never ask questions — and I couldn't stop thinking about it. Finishing December 2026. Underneath it: 200,000+ journal words since 2021. A spec newsletter issue, written in a founder's voice. Your happiest customers are lying to you politely — the one who quit taught us more than the one who sent a holiday card. Exit calls, minute fifteen, and the real reason people leave. A founder's seed-round post, before and after. Before: the announcement every founder writes. After: the same news as a story — the customer who quit, the six weeks fixing one thing, the two firms she brought back. Same facts. One gets scrolled past, the other gets shared.