Cold Email Outreach With Jeremy & Jack

About this episode (#407): In this episode, Jack and Jeremy break down a bold connection request on LinkedIn that skips the usual small talk and goes straight for the pitch. They debate whether this “go for the kill” approach ever works in cold outreach, and if so, under what conditions. Along the way, they define a framework for when pitching in a connection request might actually make sense and when it’s still a terrible idea. Key topics discussed in this episode: Why most people shouldn’t pitch in a connection request The rare exceptions where a direct pitch can work The role of curiosity, pain, and timing in message effectiveness What makes a product demo-worthy based on novelty alone Real-world examples of campaigns that broke the rules and won  The blurred line between “product-market fit” and compelling messaging When list-building and timing matter more than copy itself This teardown shows that even hard rules in cold outreach have exceptions if your offer hits the right nerve. Jack and Jeremy unpac