In this episode of The Ty Brady Way, Gui Costin, founder and CEO of Dakota, shares his journey from a career marked by frequent job changes to building a thriving company that has raised over $40 billion for investment firms. Gui offers candid insights into entrepreneurship, sales process design, company culture, and the power of staying focused on what matters most.
Gui founded Dakota in 2006 as a capital-raising firm for investment funds. Over time, the company developed a proprietary investor database to support its fundraising efforts. In 2019, Dakota pivoted and commercialized the database—now called Dakota Marketplace—which serves over 1,300 investment firms and 6,000 fundraising professionals. The platform streamlines cold outreach by centralizing up-to-date institutional investor data, allowing sales teams to more effectively schedule meetings and drive results.
The conversation dives into Gui’s foundational philosophy behind The Dakota Way, a sales methodology he developed after realizing that informal, unstructured training wasn’t scalable. His four core principles are: (1) set clear expectations with leadership, (2) know who to call on by defining and executing on your total addressable market (TAM), (3) become a master messenger capable of clearly articulating your value proposition, and (4) have a killer follow up system using a CRM for systematic follow-up and accountability. These principles are designed to be simple, controllable, and highly effective, especially in complex, high-ticket sales environments.
Gui explains that a key component of Dakota’s sales strategy is “city scheduling”—having reps always plan meetings around five metro areas to create urgency and focus. This tactic, along with disciplined CRM usage, helps maintain momentum in a business where sales cycles often range from 9 to 36 months. He emphasizes that the best follow-up happens in the meeting—not afterwards—by directly asking prospects for next steps or a clear yes/no decision.
Another theme throughout the episode is culture and leadership. Gui distinguishes between being “nice” and being “kind,” noting that true kindness often means having tough conversations in service of growth. At Dakota, kindness is foundational—but it’s paired with high expectations and a strong drive for excellence. Gui believes that treating people well is the best way to retain top talent and preserve institutional knowledge, which is critical for sustained success.
The episode also touches on entrepreneurship, resilience, and the role of failure. Gui recounts how a failed content platform led to the creation of Dakota Live!, a weekly, now monthly, virtual series that evolved into a core part of their value delivery. That pivot exemplifies his belief in action over fear—a mindset instilled by his mother—and the importance of learning from setbacks.
Gui wraps by emphasizing that leaders have the opportunity to create meaningful, high-performing workplaces through intentional systems and compassionate leadership. His next book, Be Kind, will dive deeper into this philosophy, showing that high performance and humanity are not mutually exclusive.
