How to Build Unconventional Cultures That Thrive with Gui Costin

In this episode of Strategic Counsel, Gui Costin, Founder and CEO of Dakota, joins hosts Anne Candido and April Martini for an in-depth conversation on building unconventional cultures that thrive. Gui shares how he built Dakota’s high-performing yet deeply human workplace, one that combines structure, accountability, and kindness to achieve remarkable business results.

Gui begins by explaining Dakota’s evolution, from a capital-raising firm to a thriving SaaS business with over 1,500 investment firm subscribers. With over 65 employees, Dakota’s success is grounded in a cultural philosophy that prioritizes how people are treated – starting with leadership.

Gui emphasizes that culture is defined at the top. Leaders, through their words and actions, set the tone for how people behave and treat each other. His approach centers on creating an environment where team members are treated like adults – with trust, autonomy, and respect. For example, Dakota has no vacation or expense policies. Instead, employees are empowered to manage their responsibilities responsibly. But that freedom comes with accountability: underperformance or misalignment with company values results in direct, honest feedback rooted in kindness, not judgment.

The team dives into Gui’s concept of Dakotaisms, core cultural principles that guide behavior across the organization. These principles are prominently displayed in the office and reinforced through daily routines and onboarding practices. One example is “Walk the 8 feet,” a reminder to encourage collaboration and knowledge sharing across teams. Another is “Don’t go cowboy,” which discourages siloed work in favor of transparent communication.

A core component of Dakota’s hiring strategy is finding cultural fit. Gui shares that the company looks beyond resumes to evaluate character, mindset, and shared values. Many of Dakota’s BDRs are former Division I lacrosse players, a decision rooted in their resilience, competitiveness, and ability to handle rejection. These individuals, Gui notes, are used to rigorous coaching and bring an unmatched work ethic. Traits critical for cold outreach and client development roles.

The conversation highlights how culture drives performance, especially in sales. Gui explains that Dakota’s business depends on consistent cold outreach, and without the right team in place, the company wouldn’t function. By setting clear expectations, celebrating resilience, and providing a path to growth, Dakota turns what’s often a high-turnover role into a launching pad for career success.

Accountability is maintained through regular feedback and open dialogue. Gui distinguishes between being “nice” and being “kind”, with kindness meaning you care enough to deliver tough messages in a constructive, supportive way. He sees it as his job to remove obstacles and help people succeed while maintaining high standards for performance and behavior.

Gui closes with a message about the power of intentional culture: it must be defined, lived, and reinforced constantly. Leaders have to model the behavior they expect, and companies must be relentless in hiring and retaining people who align with their values.