Leading with Kindness: Building a High-Performance Culture Without Burnout with Gui Costin

In this episode of High Octane Leadership, Gui Costin, founder and CEO of Dakota, joins host Donald Thompson to discuss leadership, entrepreneurship, sales, culture, and the power of service. Gui shares his personal and professional journey, reflecting on how his early years bouncing between 14 jobs shaped the vision for Dakota, a company designed to offer lasting career paths, strong culture, and high-performance systems.

Founded in 2006, Dakota started as a capital-raising firm for investment managers and later expanded into a data-driven SaaS business. Today, its proprietary platform, Dakota Marketplace, serves over 1,200 investment firms and 7,000 fundraisers by streamlining access to institutional investor data and powering cold outreach efforts. Gui’s sales philosophy is built around a structured, repeatable system known as The Dakota Way, a four-principle framework for direct selling that emphasizes planning, defining a target market (TAM), effective messaging, and CRM-based follow-up.

Throughout the episode, Gui emphasizes a leadership style rooted in structure, clarity, and kindness. He explains how Dakota maintains a daily rhythm of accountability. 7:45 a.m. and 5:00 p.m. check-ins for sales teams, while giving employees freedom during the day to perform. Transparency and trust are key pillars of Dakota’s culture, supported by clearly defined core principles and an emphasis on internal consistency. Gui insists that “culture is how you treat people,” and shares that Dakota has no formal vacation or travel policies, reflecting his belief in adult accountability.

The conversation also touches on Gui’s upcoming book, Be Kind, which explores whether it’s possible to run a hard-charging, high-performance company while leading with compassion. Gui believes not only is it possible: it’s essential. He shares the insight that companies should focus on retaining their best people and that most talent loss results from poor leadership, not the organization itself. Words, tone, and behavior matter. Leaders must be intentional and self-aware in how they treat others.

Gui and Donald discuss the impact of in-person connection in sales, noting that meetings held face-to-face close at a rate three times higher than those on Zoom. Dakota leans into this insight with a national event series called Dakota Cocktails, held in top venues across major cities. These informal, high-touch events connect customers, prospects, and industry peers in a relaxed, engaging environment – offering real ROI through relationship-building.

Gui’s entrepreneurial advice to listeners is direct: “Get paid.” He discourages speculative startup models that delay revenue, emphasizing that sustainable businesses start by offering a valuable service people are willing to pay for, then evolve into products over time. His own journey from a failed startup in the early 2000s to building a thriving company with $20M+ in revenue reflects this path.

The episode is packed with leadership insights, practical sales frameworks, and genuine reflections on culture and service. Gui closes with a heartfelt message: treat people with respect, lead with kindness, and create environments where your team can grow—because that’s where long-term success begins.