Measure Success: Successful Sales Strategies That Actually Work

On this episode of the Measure Success Podcast, host Carl J. Cox welcomes Gui Costin, Founder and CEO  of Dakota, a sales and marketing firm serving investment companies. Since its founding in 2006, Dakota has helped raise billions for clients, but Costin’s deeper mission has always been about people development—particularly giving young professionals in Philadelphia a stable career pathway and the training he himself lacked early in his career.

Costin begins by reflecting on his unconventional career path—14 jobs in 17 years—driven by his strong sense of independence and restlessness. While he admits this instability hindered long-term growth, it inspired him to build Dakota as a place where college graduates could find structure, mentorship, and the opportunity to grow. Central to Dakota’s success is a focus on hiring resilient individuals, often former Division I athletes, who are accustomed to rejection and relentless practice. Costin notes that these individuals bring a team mindset, perseverance, and an ability to thrive in challenging sales roles.

The conversation moves to Costin’s leadership philosophy, heavily shaped by his sons’ lacrosse coaches and his own experience coaching high school golf. From them, he learned that real leadership balances discipline, accountability, and deep care for people’s development beyond short-term wins. For Costin, “caring” in business means providing upward mobility, being compassionate in the face of setbacks, and creating an environment where individuals can thrive both professionally and personally.

Costin highlights the importance of focusing on what matters most, which he calls Dakota’s guiding principle. In practice, this means relentless clarity on priorities, asking “why” repeatedly until the true purpose of an action is uncovered, and building structures—like daily 7:45 a.m. check-ins for his sales team—that enforce discipline and consistency. These habits, he argues, are what transform difficult tasks like cold outreach into long-term success and resilience.

A significant portion of the discussion also centers on Dakota’s product: a comprehensive, accurate CRM database that eliminates wasted time on research, bad contacts, and missed opportunities. Costin stresses that the real value for clients is having the right contacts readily available, ensuring sales teams can focus their energy on building relationships and closing deals rather than data gathering.

The episode also explores Costin’s writing journey. His first book, Millennials Are Not Aliens, challenged generational stereotypes. His second, The Dakota Way, distills the firm’s four core sales principles. He is now working on Be Kind, a book on leadership and culture, which he describes as far more emotional—drawing on personal experiences, mistakes, and lessons learned over decades. Unlike The Dakota Way, which is practical and process-oriented, Be Kind is meant to capture the heart of Dakota’s culture and the values that sustain excellence.

When asked how he measures success, Costin emphasizes team growth, continuous optimization, and personal relationships. Professionally, success is about developing his 80-plus teammates and optimizing processes across the company. Personally, it is about family, health, and maintaining the energy to serve his team and customers. For Costin, leadership is ultimately an act of service—creating the conditions for others to succeed, both inside and outside the company.