Ep 07 - Building Dakota: From 14 Jobs to Purpose-Driven Leadership with Gui Costin

Summary

In this episode, Steven Clark interviews Gui Costin, Founder and CEO of Dakota, who shares his non-linear path to entrepreneurship and the principles that transformed his leadership approach. After cycling through 14 different jobs in 17 years, Gui founded Dakota to create a place where people could build long-term careers and "become the best version of themselves." 

Gui discusses how a failed platform pivoted into a successful database business, the importance of treating people with kindness rather than just niceness, and why cold outreach remains the foundation of effective fundraising despite technological shifts. Gui also shares insights on the evolving RIA landscape, private credit markets, and Dakota's commitment to community impact through its giving initiatives.

Takeaways

• Gui's career journey through 14 jobs in 17 years eventually led him to create Dakota to help others avoid constant "restarts"

• The Dakota culture emphasizes kindness while maintaining high performance standards - not "nice" but genuinely kind

• Cold outreach and being a "master messenger" remain fundamental to fundraising success despite technological changes

• The RIA channel continues to grow as advisors seek independence, creating ongoing opportunities

• Dakota Gives focuses on local, direct impact through carefully selected charities with an increasing focus on health, nutrition and youth sports

Chapters

01:00 Introduction and Early Career Path

06:18 The Founding of Dakota

13:25 Evolution of Company Culture

17:28 Leading Younger Generations

21:03 The Dakota Way of Sales

23:24 Trends in the RIA Family Office Channel

26:11 Private Credit and Investment Trends

30:56 Dakota Gives and Community Impact

33:46 Lightning Round and Closing