In this episode of The Marketing Stir, Gui Costin, founder and CEO of Dakota, shares the story behind building a people-first company that has raised over $40 billion for investment firms while launching a fast-growing SaaS platform. Gui speaks candidly about leadership, culture, marketing strategy, and the power of clear systems—anchored in the principles outlined in his new book, The Dakota Way.
Gui opens by describing his role as “keeper of the culture,” ensuring that Dakota’s values—especially kindness, accountability, and focus—are consistently reinforced across the organization. Founded in 2006, Dakota began as a capital-raising service for investment firms and expanded in 2019 with the launch of Dakota Marketplace, a subscription-based investor database that helps sales professionals find institutional capital more efficiently. With over 65 teammates supporting the platform, Gui emphasizes how culture and clarity have been critical to sustaining growth.
At the core of The Dakota Way is a four-step framework for successful sales and fundraising: (1) set clear expectations with leadership, (2) define your total addressable market (TAM), (3) master your messaging to simplify complex ideas, and (4) use a CRM to track and scale outreach. These principles, Gui explains, are easy to understand but emotionally challenging to implement—yet they consistently produce results.
A recurring theme in the episode is Dakota’s intentional culture, particularly the distinction Gui makes between being “nice” and being “kind.” True kindness, he explains, involves difficult conversations and accountability, all delivered with empathy and respect. It’s a philosophy that supports hard-charging professionals while retaining top talent—a priority Gui links directly to maintaining institutional knowledge and competitive advantage.
The conversation also explores the limitations of the CMO role in today’s complex marketing landscape. Gui argues that most companies misfire by hiring a “unicorn” CMO to solve ill-defined marketing problems, when what’s actually needed is clear alignment with sales strategy, deep analytical skills, and cross-functional leadership. He emphasizes that marketing is fundamentally about demand generation, and the best marketers think like salespeople—obsessed with ROI, message clarity, and understanding the buyer’s journey.
On sales, Gui reinforces that everyone is in sales in some form, but mastering cold outreach remains one of the most valuable, and underappreciated, skills. He shares insights from his own early career bouncing between roles before learning how to systematically acquire customers—a turning point that shaped his leadership style. Today, he still joins sales check-ins, onboarding calls, and stays closely connected to Dakota’s sales engine.
The episode wraps with a look at Dakota Gives, the company’s community outreach initiative focused on supporting micro-charities in the Philadelphia area. Gui shares how giving back—through mentorship, career days, and health education—has become one of the most fulfilling and culture-strengthening aspects of the company.
Through stories, strategies, and honest leadership reflections, Gui’s conversation offers a compelling blueprint for building a resilient, high-performing organization—rooted in clarity, culture, and service.
