In this episode of Sales Made Easy, Gui Costin, Founder and CEO of Dakota, joins host Harry Spaight to share the intentional, disciplined approach behind Dakota’s high-performing sales engine and values-based workplace culture. Known for raising over $40 billion through his investment services firm, Gui offers a blend of tactical sales insight and leadership wisdom, making this conversation a masterclass in combining outbound strategy with a human-centered business philosophy.
Gui begins by outlining why outbound sales, particularly cold email outreach, remains central to Dakota’s success. Unlike mass-blast tactics, Gui emphasizes that Dakota’s sales team sends personalized, one-off emails with precision: subject lines clearly labeled with meeting requests, concise messaging about who they are and what they offer, and specific calls to action like, “Can you meet May 4 at 3 PM?” According to Gui, this method executed consistently with 25–30 emails per day per rep, generates daily meetings and a healthy sales pipeline. Automation takes a backseat to real-time interaction because timing and responsiveness are key. Dakota’s team adjusts schedules in conversation with prospects to secure meetings, creating a more human and effective engagement model.
From there, the conversation shifts to Dakota’s evolution and product offering. Originally a capital-raising firm launched in 2006, Dakota expanded in 2019 by commercializing its proprietary database of investment allocators into a subscription-based SaaS platform. Gui explains that Dakota’s value is rooted in providing accurate, real-time data that investment firms can rely on to drive their outreach efforts. Their white-glove approach to client success includes five-minute response times and hands-on support across email, phone, or text. Gui underscores that the customer is always top priority, but just behind the internal team.
That distinction is critical to Dakota’s culture, which Gui describes as a blend of high performance and kindness. He believes a leader’s primary job is to create an environment where employees feel trusted, respected, and supported. There’s no room for passive-aggressive behavior, teasing, or office politics at Dakota. Instead, the focus is on clarity, directness, and mutual accountability. Kindness, to Gui, means delivering honest feedback that helps people improve, not sugarcoating issues. This ethos is reinforced daily, not through rigid policies but through behavior and example.
Competition plays a motivating role in this culture. Sales performance is tracked publicly on leaderboards, and compensation is tied to the number of meetings booked. Most reps are former college athletes, especially lacrosse players, hired for their grit, resilience, and coachability. While Dakota doesn’t offer awards like “President’s Club,” the team celebrates success informally and frequently, acknowledging hard work across all departments.
As a career salesperson himself, Gui reflects on the importance of structure, thoroughness, and responsiveness – traits he learned in his first role as a commercial real estate broker. He argues that these are more important than personality in driving consistent sales results. At Dakota, reps aim to respond to inquiries within five minutes, and demos are offered early in the sales process without needing extensive qualification because every prospect in their niche needs data. Rather than manipulating or chasing unqualified leads, Gui’s team prefers a “quick no” and asks direct questions like, “Do you think there’s an opportunity for us to work together?” This clarity avoids ghosting and allows reps to move on or follow up at the right time.
Gui closes by highlighting the competitive advantage Dakota holds: relentless attention to detail, founder-led ownership, and a culture that values accuracy, integrity, and speed. He invites listeners to reach out for a signed copy of his latest book, The Dakota Way, which outlines the firm’s four core principles for investment sales success. With his signature clarity and authenticity, Gui reminds us that outbound selling still works but only when it’s grounded in consistency, intention, and human connection.
