September 18, 2025 | 29 MIN

Building a Culture ofKindness and HighPerformance: LeadershipLessons from Dakota

Listen Here:

Download Transcript

Episode Summary | Download Summary

In this episode of Imagining Bridges to Better Leadership, Gui Costin, founder and CEO of Dakota, joins host Dr. Kevin Neal to share his journey of leading with empathy, grit, and intentional culture.

Gui reflects on founding Dakota in 2006 after working 13 different jobs, and how those experiences shaped his mission to build a company where people can grow, stay, and thrive. Dakota has become a standout in the finance and technology space by focusing not just on performance, but on people.

Gui and Kevin dive into the mindset that drives leadership excellence — one rooted in problem-solving, emotional self-awareness, and what Gui calls “getting to yes.” He discusses how trauma and upbringing shape leadership tendencies and highlights the importance of healing, kindness, and clarity in how leaders treat others. Through Dakota’s unique core values — known as “Dakotaisms” — like “Don’t go cowboy,” “Throw your hat over the wall,” and “Ask,” Gui has cultivated a culture where creativity, honesty, and hard work are non-negotiable.

Throughout the conversation, Gui shares personal stories, including the bold risk he took in launching Dakota after being fired for pitching an idea — a decision that ultimately led to his biggest breakthrough. He explains how building a culture of kindness and high standards isn’t just a philosophy — it’s a daily practice. At Dakota, culture is upheld through clear communication, mutual respect, and surrounding the team with high-
performing “A players” who align with the company’s values.

Gui also speaks candidly about the responsibility leaders have to create opportunities for their people and why upward mobility should be a core principle, not an exception. He emphasizes that great leadership requires both high expectations and deep compassion, and that success comes from helping others get what they want out of life.

He concludes by offering listeners a free signed copy of his book, The Dakota Way, and shares that his upcoming book, Be Kind, will further explore the intersection of leadership, culture, and service. His message to leaders is simple yet powerful: when you lead with clarity and kindness, you don’t just build a company — you build a legacy.

Podcast Experiences

  • Building a Culture ofKindness and HighPerformance: LeadershipLessons from Dakota

  • Mastering Sales Targeting & Outreach with Gui Costin

  • 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

GUI SIGNATURE-3