Culture, Content, and the Future of Investment Sales

In this episode of Grow Your Business & Grow Your Wealth, Gui Costin, Founder and CEO of Dakota, joins host Gary Heldt for a candid and powerful conversation about building a sustainable business, transforming leadership, and navigating the evolving investment landscape. With over $40 billion raised since 2006, Gui shares how his early career, marked by 14 jobs in 17 years, sparked his mission to build a company where people could build lasting, meaningful careers.

Gui opens up about the rocky early days of Dakota and the leadership wake-up call that reshaped everything. In 2011, he shifted the company’s mission to focus on helping others get what they want out of life: a value now embedded in Dakota’s culture, hiring, and mentoring systems. Today, with over 80 employees and a high-retention, high-performance team, Dakota is proof that leadership is about how you treat people and how consistently you do it.

Throughout the episode, Gui unpacks his approach to mentorship, explaining that every employee at Dakota has a mentor, and that success starts with writing down your core principles and reinforcing them constantly. He shares how “Dakota-isms”, internal philosophies like "we grow apples for apple buyers", guide decision-making and clarify what good looks like in everyday interactions.

On the business side, Gui discusses the seismic shift from public markets to private investments, and how Dakota has evolved to support this trend through both outsourced sales services and its data platform, Dakota Marketplace. He also dives into the disruptive impact of AI, predicting a future where companies will manage teams of AI agents just like they do human employees.

For leaders and entrepreneurs, Gui’s message is clear: success hinges on clarity, consistency, and compassion. Whether you're scaling a firm or starting from scratch, this episode delivers practical, battle-tested wisdom on how to build a people-first company that thrives over the long haul.