The Power of Kindness

In this episode of As The Leader Grows, Gui Costin, founder and CEO of Dakota, shares his journey of building a values-driven organization focused on kindness, professionalism, and high performance. Costin reflects on founding Dakota in 2006, initially as a capital-raising firm for investment funds, and expanding it in 2019 to offer a subscription-based database used by over 1,200 investment firms. Throughout the conversation, Gui emphasizes that Dakota’s success is rooted not just in its services or sales strategy, but in its deep commitment to cultivating a strong, people-first culture.

Gui and host Ken Joslin explore how leadership rooted in kindness and intentional communication creates lasting impact. Gui distinguishes between being “nice” and being “kind,” noting that kindness includes having tough conversations that promote personal and professional growth. He explains that words matter, and leaders must be mindful of how they communicate to avoid diminishing employee morale or trust. Gui shares how Dakota’s culture is defined by treating people with respect, offering clarity, and developing employees through honest, constructive feedback.

He credits much of his leadership philosophy to two key mentors: Alan Breed, a long-time business associate who exemplified professionalism and thoughtfulness, and his uncle, Breck Costin, a life coach who helped him develop self-awareness and emotional intelligence. These influences shaped Gui’s belief that great leadership comes from vulnerability, consistency, and a genuine commitment to others’ success.

The conversation also covers how Gui balances a strong company culture with achieving ambitious business goals. He explains that Dakota maintains a focus on “what matters most” — whether that’s booking product demos or serving client needs — and eliminates distractions that don’t contribute directly to results. Gui believes companies can drive revenue while still promoting a healthy, empowering workplace.

Ken and Gui also discuss the challenges of managing team dynamics and handling difficult conversations. Gui emphasizes approaching tough feedback as a coaching opportunity — not a personal attack — and aligning it with the individual’s goals. He stresses that great leaders must cast a vision for what “good” looks like and communicate the “why” behind decisions to foster buy-in and accountability.

One of Gui’s most fulfilling moments came in 2011, when he redefined Dakota’s mission to focus on helping others achieve their goals. This shift created a more purpose-driven company, exemplified by Dakota’s community outreach initiatives and intern programs. He recounts how interns cited the company’s volunteer day as the most impactful part of their experience — highlighting the deeper impact of service and culture beyond business metrics.

Gui closes by announcing his upcoming book, Be Kind, which expands on the leadership principles discussed in the episode. His core message to leaders: treat people with compassion, be intentional with your words, and focus relentlessly on helping your team succeed — because when people feel valued and supported, performance follows.