In this insightful episode of SalesPOP!, Gui Costin, founder and CEO of Dakota, joins host John Golden for a candid conversation on the state of modern sales—and what fundamentals still hold true. Drawing from decades of experience building Dakota into a leading fundraising and data platform for investment firms, Gui breaks down his no-nonsense approach to cold outreach, preparation, and professional discipline.
Gui begins by emphasizing that while sales technologies have advanced, the core challenge remains the same: booking meetings with qualified buyers you don’t yet know. He challenges the notion that cold outreach is outdated, arguing instead that it’s a critical skill that too many salespeople avoid due to emotional discomfort. His message is clear: success comes from embracing the discomfort, not avoiding it.
A cornerstone of Gui’s sales philosophy is intentionality—especially when it comes to cold emails and calls. He outlines a precise structure for outreach, including a clear subject line, a short, punchy introduction, and a direct meeting request. He also stresses the importance of professionalism in every interaction—sounding polished, anticipating objections, and treating every call as a chance to build trust and credibility.
Preparation is another recurring theme. Gui explains that the best salespeople take extensive notes, come to meetings with clear objectives, and ask thoughtful, strategic questions. He encourages reps to view meetings as conversations between equals—not as performances or pitches—and to be confident enough to ask the tough questions, including, “Is there a fit?”
Much of the episode is rooted in Gui’s structured sales framework, The Dakota Way, which centers on four things every salesperson can control: setting expectations with leadership, knowing your target buyer, preparing your message, and managing your CRM and pipeline proactively. He argues that consistent reporting and upward communication aren’t just about accountability—they’re about empowering your manager to advocate for you internally.
Throughout the conversation, Gui reinforces the value of curiosity, consistency, and culture in sales. He believes great salespeople are always learning, always refining, and never relying on shortcuts. His advice is both practical and mindset-driven: focus only on what you can control, eliminate distractions, and build systems that reinforce discipline.
Gui’s appearance on SalesPOP! delivers a compelling blend of tactical advice and strategic perspective—highlighting how preparation, intentionality, and emotional resilience remain the bedrock of sales success in an increasingly tech-enabled world.