How Cold Email Really Works Today with Adam Rosen

In this episode of The Rainmaker Podcast, Dakota Founder and CEO Gui Costin sits down with Adam Rosen, founder of an email marketing agency that helps startups, unicorns, and large enterprises generate sales through cold email. The conversation offers a practical, experience-driven look at how cold outreach has evolved, and why it remains one of the most effective tools in modern sales when executed correctly.Adam begins by walking through his entrepreneurial origin story, from studying sport management in college to discovering entrepreneurship late in his academic career. That pivot led to his first startup, a college recruiting platform that worked with major global brands. Despite making early mistakes, Adam credits cold email as the single most important driver behind acquiring customers, raising capital, and ultimately exiting the business—experience that later became the foundation for his current company.A major theme of the episode is how dramatically the cold email landscape has changed since the mid-2010s. Adam explains that tactics that once worked, such as sending high volumes of emails from a primary domain, are now actively harmful. Today, success starts with infrastructure: properly set up sending domains, inbox warming, and protecting domain reputation. Without that foundation, even strong copy and targeting won’t matter because emails won’t reach the inbox.The discussion then shifts to measurement and optimization. Adam cautions against tracking open rates in cold email, noting both deliverability risks and unreliable data. Instead, he emphasizes reply rates as the most meaningful signal of success, since a reply confirms both inbox placement and message resonance. Sudden drops in reply rates, he explains, are often an early warning sign of deliverability issues.Beyond tactics, the episode dives into the psychology of cold outreach. Adam and Gui agree that the biggest barrier to success isn’t technology, it’s mindset. Cold email doesn’t feed the ego and requires resilience in the face of rejection. Adam frames email as nothing more than a tool to connect party A with party B, arguing that professionals who can stomach direct feedback and rejection will consistently outperform those who avoid it.The episode closes with actionable guidance on email construction, from concise, relevant subject lines to short, direct body copy that clearly states purpose, value, proof, and a call to action. The takeaway is clear: when paired with the right infrastructure and mindset, cold email remains one of the most scalable and reliable ways to build pipelines.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.