In this engaging episode of The Leadership Toolkit, Gui Costin, founder and CEO of Dakota, shares his leadership philosophy, business journey, and insights into creating a high-performing, people-centered organization. With Dakota having helped raise over $40 billion for investment firms since its founding in 2006, Gui reflects on the principles and practices that have shaped his approach to leadership and culture-building.
Gui’s story begins with early missteps in leadership — particularly around hiring and managing salespeople — which led him to develop a structured sales methodology called The Dakota Way. This four-part framework includes setting expectations, knowing who to call on, understanding what to say, and maintaining a disciplined follow-up system. He emphasizes that the CEO must own the sales process, especially in a startup or growing business, and cannot simply outsource that responsibility.
A major turning point for Gui came in 2011 when he began coaching a high school golf team. The experience taught him valuable leadership lessons that translated directly into business: set clear expectations, provide minimal interference, and create a platform where individuals can thrive. He stresses that effective leadership isn’t about control—it’s about building an environment that supports consistent, self-directed excellence.
One of Gui’s key insights is the importance of culture over control. At Dakota, there are no middle managers; instead, team leads collaborate directly with executives in a flat structure that emphasizes accountability and autonomy. Daily check-ins and regular “W Days” (What’s Working, What’s Not) ensure open communication and real-time problem-solving. The focus is on continuous improvement and team-wide engagement rather than top-down micromanagement.
Kindness, trust, and consistency are central to Gui’s leadership style. He distinguishes between being "nice" and being "kind," explaining that kindness includes delivering hard feedback with respect and compassion. Leaders must be mindful of their words, as one careless comment can undermine trust and morale. Gui believes that everyone deserves to be treated with dignity at work, given how much of life is spent in the workplace.
He also touches on resilience as a hiring filter—particularly for sales roles. Dakota prioritizes hiring former collegiate athletes for business development roles due to their proven ability to handle feedback, stay disciplined, and thrive in team environments. This approach has helped reduce turnover and cultivate a culture of performance without burnout.
The conversation closes with Gui’s reflections on mentorship, learning from failure, and his own journey through 14 jobs in 17 years before launching Dakota. He emphasizes that setbacks and detours are essential to growth and that a positive mindset and willingness to evolve are crucial in any leadership role.
Gui’s appearance on The Leadership Toolkit delivers actionable lessons in leadership, culture-building, and sales strategy—underscoring the value of consistency, humility, and human connection in building enduring businesses.