In this episode of the Orbit Marketing Podcast, Gui Costin, founder and CEO of Dakota, dives deep into the intersection of sales, content marketing, and leadership. Known for building one of the most respected fundraising and investor database companies in the investment industry, Gui shares how clarity, cold outreach, and content-led trust building have powered Dakota’s success.
Gui opens by framing Dakota’s business model—two core offerings: outsourced fundraising for investment firms and a SaaS-based CRM platform (Dakota Marketplace) used by over 6,000 fundraisers. He emphasizes that while warm referrals are ideal, systematic cold outreach has been the true engine of growth for both sides of the business. Dakota’s culture is rooted in core values like “Ask” and “Don’t Go Cowboy,” which guide team behavior and eliminate ambiguity.
A key takeaway is Gui’s philosophy that companies should never be in the “convincing” business. Instead, sales teams should focus on qualified leads—people already inclined toward their solution. This aligns with his insistence that teams must believe deeply in their product’s value; without that belief, outreach becomes awkward and ineffective.
Content plays a major role in Dakota’s strategy. Gui recounts the turning point in 2018 when Dakota turned its weekly sales call into a value-driven video series for clients—a decision born from a failed product launch. The lesson? Focus on delivering consistent value, not self-promotion. Gui believes good content answers the exact questions buyers are already asking, often before they ever speak with sales. He cites Marcus Sheridan’s They Ask, You Answer as a guiding influence, noting that nearly 70% of the B2B buying journey happens online before a conversation ever takes place.
Gui also shares why he’s a staunch advocate for hiring former Division I lacrosse players for sales roles. These athletes bring grit, resilience, and team-mindedness—traits critical in a rejection-heavy, high-effort sales environment. Their background conditions them to embrace structure and persist through cold outreach without getting discouraged.
As for leadership, Gui strongly believes that CEOs should never fully step out of sales. Instead, founders should create a structured, repeatable process (The Dakota Way) and lead by example. He describes sales as deeply emotional work and underscores the importance of empathy and presence in supporting sales teams. His daily check-ins, focus on activity-based metrics (like scheduling meetings in five target cities), and obsession with responsiveness reinforce this high-accountability, high-trust culture.
On the marketing side, Gui emphasizes simplifying messaging and storytelling. Buyers don’t need complexity—they need clarity. Whether through a blog post, email, or pitch deck, good marketing starts by making it easy for someone to retell your story.
The episode wraps with Gui’s reminder that process and principles—not heroics—are the foundation of sustainable growth. By focusing on what matters most, listening to customers, and refining your systems continuously, companies can scale with integrity and impact.
