February 25, 2025 | 35 MIN

A Culture Of Success

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In this episode of the Market Insights Podcast, Gui Costin, CEO of Dakota, shares insights into leadership, workplace culture, and the evolving nature of sales and technology in the investment industry. Gui recounts his career journey, beginning in 1997, and how his passion for simplifying complex investment stories became the cornerstone of his approach to sales.

Gui emphasizes the importance of creating a workplace that fosters trust, longevity, and institutional knowledge. He believes employees thrive when treated with respect, kindness, and clear expectations. Dakota’s culture reflects this ethos, with no formal vacation or expense policies—a testament to Gui’s philosophy of trusting employees as adults. This approach minimizes bureaucracy and fosters accountability, allowing the team to focus on meaningful work without unnecessary constraints.

In discussing the competitive nature of the investment industry, Gui highlights the role of cold outreach and high-quality CRM data in identifying opportunities. Dakota provides clients with accurate, updated contact information, empowering sales teams to focus on connecting with qualified leads. Gui also underscores the significance of regular check-ins and structured meetings to ensure team alignment and transparency, drawing a parallel to the precision of football huddles.

Generational differences in the workplace are another area Gui explores. He debunks stereotypes about Millennials and Gen Z, praising their adaptability and tech-savviness. He encourages leaders to embrace the learning habits of younger generations, such as leveraging digital tools like YouTube for self-education. Gui also reflects on the evolving role of technology, emphasizing the need for businesses to adapt quickly to stay competitive in an ever-changing landscape.

Leadership, for Gui, hinges on vulnerability and the ability to connect with employees on a human level. He advocates for leaders to be mindful of their words and actions, fostering an environment of psychological safety. Gui’s leadership philosophy also extends to community outreach, which he describes as a cornerstone of Dakota’s identity. Employees consistently value opportunities to give back, highlighting the unifying power of shared service.

Gui concludes with advice for aspiring leaders: prioritize kindness, focus on results, and maintain a customer-centric mindset. He expresses optimism about the opportunities available in America, calling it a uniquely supportive environment for entrepreneurship and innovation. Through his leadership and business practices, Gui underscores the value of treating people well while driving high performance.

Podcast Experiences

  • Measure Success: Successful Sales Strategies That Actually Work

  • Mastering Institutional Sales with Allen Gray of Silvercrest

  • Driving Sales and Success with Brad Jung, Russell Investments

  • Democratizing Private Equity with John Bailey, OneFund Investments

  • Guantong (“GT”) Sun on Process-Driven Fundraising at Turning Rock Partners

  • Scaling Private Wealth with Doug Krupa, KKR

  • Michele Colucci on AI-Driven Healthcare at DigitalDx Ventures

  • Driving Distribution with Discipline – Daniel Noonan, Cohen & Steers

  • Earning Trust, One Deal at a Time – Drew Dolan, DXD Capital

  • Joe Grogan on Culture and Consultative Sales at WisdomTree

  • How Stacy Havener Built Havener Capital on Storytelling and Strategy

  • Capital Formation, Not Sales – Inside CAZ with Christopher Zook

  • Fundraising with Precision: Inside Optimizing Sales at LAB Quantitative Strategies with Shane McCarthy

  • Inside the Capital Formation Playbook of RMWC with Michael Rubenstein

  • Educate, Don’t Sell – Danielle Brown’s Fundraising Playbook at Altriarch

  • John Donovan on Building Trust and Transparency at TowerBrook

  • “Thinking Big” with Urban Standard: Seth Weissman’s Approach to Fundraising and Growth

  • Andrew Saunders on Building a Collaborative Sales Culture at Castle Hill Capital

  • Inside 65 Equity: Leon Brujis on Partnering with Founders for Growth

  • Inside Dundas Global Investors: James Curry & Andrew Brown on Hybrid Sales and Service

  • Culture, Content, and the Future of Investment Sales

  • The No Policy, Policy with Gui Costin

  • Sales Confidence, Culture & Connection with Gui Costin

  • Gui Costin On How To Create a High Performing Sales Team

  • How To Win More Deals with Effective Cold Email Techniques with Gui Costin

  • How to Build Unconventional Cultures That Thrive with Gui Costin

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

  • The Dakota Way

  • Mastering Sales with Data Driven Growth with Gui Costin

  • How Dakota Raised $30 Billion For Their Clients

  • The Dakota Way: Why it Matters with Gui Costin

  • What We’re All Missing to Be Successful at Sales and Like It with Gui Costin

  • A Culture Of Success

  • Words Matter: How Gui Costin Built a Culture of Kindness and ExcellenceNotable Leaders' RadioPlay

  • Mastering the Art of Fundraising: $40 Billion Raised Dakota CEO, Gui Costin

  • Unlocking the Leadership Code: Lessons from the Frontlines

  • The $40 Billion Secret: Gui Costin on Trust, Leadership, and Redefining Sales

  • Helping Investment Firms Thrive – Fastlane Founders with Gui Costin

  • The Power of Kindness

  • Sales Leadership in the Investment Industry with Gui Costin

  • A Modern Leader’s Guide to Sales Success with Gui Costin

  • Gui Costin’s Proven Formula for Coaching Sales Teams to Success

  • Capital Raising Campaign Strategies with Gui Costin

  • Embracing Accountability in Sales with Gui Costin

(610) 764-0539
Gui@dakotaLive.com

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