In this episode of Innovation and Leadership, Gui Costin, founder and CEO of Dakota, shares how he built a high-performance business rooted in professionalism, structure, and kindness. Known for helping investment firms raise over $40 billion, Gui offers tactical insights into building culture, refining sales processes, and creating long-term value—for clients and employees alike.
Gui starts by introducing Dakota’s dual business model: an outsourced sales and marketing team for investment firms, and a subscription-based data platform, Dakota Marketplace, used by over 6,000 fundraisers. Initially focused on long-only equity strategies, the firm evolved in 2019 by commercializing its proprietary database, transforming it into a scalable SaaS product.
Jess and Gui discuss Dakota’s innovative use of media, including converting internal sales calls into a private, client-facing TV show. This pivot—born from a failed content platform launch—illustrates Gui’s entrepreneurial mindset: listen to customer feedback, adapt quickly, and find ways to add value, even when plans don’t work out as expected.
A central theme of the conversation is Gui’s belief that elite performance and kindness aren’t mutually exclusive. He describes Dakota’s cultural foundation as rooted in transparency, accountability, and respect—reflected in his long-tenured team and clear leadership philosophy. Kindness, Gui explains, isn’t about avoiding tough conversations—it’s about having them directly, compassionately, and constructively.
The discussion shifts to sales and fundraising strategy. Gui outlines the four pillars of The Dakota Way, his codified sales process: (1) Set clear expectations, (2) Know who to call on, (3) Know what to say, and (4) Have a disciplined follow-up system using a CRM. He emphasizes the importance of preparation, prioritization, and messaging that de-risks decisions for potential investors.
Jess and Gui also explore the emotional demands of sales—especially cold outreach—and the mental resilience it requires. Gui encourages fund managers and entrepreneurs to accept the “pedestrian” nature of outreach as part of the process and to develop confidence by focusing on their unique value. He stresses that great salespeople are both grinders and sophisticated storytellers—able to simplify complex ideas and build trust in high-stakes environments.
Throughout the episode, Gui draws parallels between business and coaching, referencing his time coaching a high school golf team. He learned to create platforms, not just teams—environments where people can thrive independently. That same philosophy informs Dakota’s culture and internal structure, where long-term growth and individual development are prioritized.
Gui also reflects on past leadership mistakes, particularly around communication and emotional control. These experiences inspired his third book, Be Kind, focused on leading with integrity and empathy. He openly shares a story about a “Bobby Knight moment” early in his leadership journey and how it shaped his resolve to lead differently moving forward.
The episode wraps with a discussion of mentorship, investor targeting, and strategic alignment—highlighting the importance of self-awareness, deep preparation, and aligning product structure with the right audience.
