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 unpack what it takes to earn a "yes" at first touch and how to craft messages people actually want to reply to. About the hosts: Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com

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“What did the council decide on item 42?” — answered with the speaker and the moment.

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