In this episode of Lifetime at Work, Gui Costin, founder and CEO of Dakota, walks listeners through his unique career path and the leadership philosophy that powers his fast-growing business. From humble beginnings—14 jobs in 17 years before founding Dakota—to helping raise over $40 billion for investment firms, Gui shares actionable lessons on resilience, sales, and building purposeful company culture.
Gui begins by explaining Dakota’s two business lines: an outsourced capital-raising firm for investment managers and a SaaS-based investor database, Dakota Marketplace, used by over 6,000 professionals. He highlights how Dakota’s growth was driven by necessity: after being fired in 2006, he launched the business with the goal of creating a place where professionals could build long-term careers—not jump roles every 12–18 months, as he once did.
A central theme of the episode is structure and sustainability in sales. Gui discusses The Dakota Way, his four-part sales methodology designed to solve the common 18-month burnout cycle in investment sales. The framework includes: (1) setting clear expectations, (2) targeting the right market (TAM), (3) mastering the messaging, and (4) using a CRM to systematize follow-ups. These principles aim to provide direction, accountability, and long-term success in a field where rejection is constant.
On that note, Gui calls out the biggest barrier to success in sales: fear of rejection. He stresses the importance of cold outreach and mental resilience, noting that many avoid the discomfort of unanswered emails and unreturned calls. But for those willing to push through the volume of “no’s,” success follows. “If they met you face to face, they’d love you,” Gui says—underscoring the goal of getting the meeting, no matter how tough the road.
Gui also dives into the art of storytelling and relationship building. In a numbers-driven industry, he believes storytelling is crucial for simplifying complex investment strategies and making them repeatable. Since investors must often pitch fund ideas up the chain, Gui trains salespeople to tell clear, compelling stories that others can retell with confidence. His advice: establish credibility upfront, prepare diligently, and respect your listener’s time by answering their unspoken questions early.
The conversation expands into broader leadership and career themes, including vulnerability, trust, and workplace culture. Gui shares how Dakota doesn’t enforce vacation or expense policies—practices that stem from his belief in trusting employees and treating them like adults. He also emphasizes the importance of environment, having designed Dakota’s office to feel like a boutique hotel lobby to foster creativity and comfort.
For young professionals, Gui advises building resilience, embracing structure, and focusing on “what matters most.” He encourages breaking down large tasks into small, manageable steps—a lesson rooted in his own early struggles navigating the workplace. His message to leaders is simple but powerful: help others get what they want in life, and everything else will follow.
Gui closes by encouraging listeners to use rejection, failure, and setbacks as learning moments, not roadblocks. His story is one of reinvention, clarity, and consistent effort—guided by the mantra his mother taught him: “When in fear, get into action.”
