Cold Email Outreach With Jeremy & Jack

About this episode (#405): In this episode, Jack and Jeremy run a two-part teardown of real cold outreach messages. They start by analyzing a LinkedIn message that pitches AI agents for lead generation, then break down a clever follow-up email from a SaaS tool the recipient had signed up for months earlier. You’ll hear what worked, what didn’t, and how to write outreach that actually gets replies, whether your audience is ice cold or just cooling off. Key topics discussed in this episode: Why vague or generic subject lines instantly signal cold outreach - The dangers of pitching without credibility, proof, or a clear ask How to use curiosity properly in cold messages (and when it backfires) Why offering value or reciprocity makes outreach more effective A teardown of a SaaS follow-up email that used a “you never used your free credits” angle The difference between cold, warm, and “lukewarm” outreach (and why lukewarm might be your best audience) How small, specific asks can increase reply rates This episode