Cold Email Outreach With Jeremy & Jack

About this episode (#409): In this episode, Jack and Jeremy sit down with sales legend Josh Braun to explore how to start smarter, more effective cold outreach conversations. They break down Josh's "poke the bear" method, a way to uncover hidden pain points without triggering resistance, and share practical tips for making prospects pause, think, and actually want to talk to you. Key topics discussed: Why cold outreach fails when it starts with pitching or convincing How to "poke the bear" by asking questions that expose invisible problems Real-life examples from malls, car washes, and contractor bids that illustrate the method How to use emotional echoing to make people feel truly understood Why it's better to walk away from a bad fit than try to force a sale  How to tailor your message based on job titles and switching risks What Chris Voss taught Josh about silence, trust, and listening for truth The best cold outreach doesn't push, it creates a moment of reflection. Ask the right question, listen well,