Nothing closes deals like a face-to-face meeting.ย
As the founder and CEO of Dakota, Gui Costin has helped investment firms raise between $25โ30 billion by perfecting what he calls The Dakota Wayโa sales process built on clarity, consistency, and, most importantly, human connection.
In this episode of Go To Market with Dr. Amy Cook, Gui talks about his journey from real estate to launching one of the most trusted platforms in the investment world. Listeners will hear how Dakota transformed from outsourced sales and marketing into a fully curated CRM used by over 1,200 firms and 6,000 fundraisers and why Gui decided to codify his process in his book, The Dakota Way.
But this conversation isnโt just about process, itโs also about mindset. Gui shares why cold emails are just the beginning, why you canโt rely on Zoom to build trust, and why younger salespeople should double down on authenticity and personalization. Along the way, he and Amy dig into the role of AI in sales, the power of culture, and why curiosity and kindness are non-negotiables for long-term success.
Here are some interview highlights:ย
Amy Cook: What inspired you to put your process into writing The Dakota Way?ย
Gui Costin: Thereโs no formal training for becoming a fundraiser. I wanted to codify the steps in a way thatโs simple and actionable. At Dakota, we focus on what you can control: setting expectations, defining your total addressable market, what you say in meetings, and how you follow up. Everything elseโthe stock market, the economy, even the weatherโis out of your control. The book is short, digestible, and built around that mindset.
Read More: AI, Authenticity, and the Art of Modern Prospecting
Amy Cook: That focus on control reminds me of how unpredictable markets can be. My husband actually worked at Lehman Brothers right before it collapsed. So, I know firsthand how volatile the industry can be.
Gui Costin: Exactly. Thatโs why being face-to-face is non-negotiable in investment sales. You canโt raise money on Zoom alone. Fiduciary responsibility requires you to meet clients in person. Cold emails open doors, but the magic happens when youโre across the table, simplifying complex stories into something memorable.
Amy Cook: Speaking of cold emailsโAI is everywhere right now. Many sellers worry it will replace them. Whatโs your take?
Gui Costin: AI can make us smarter and faster, but it cannot replace human connection. People crave relationshipsโfriendships, trust, belonging. AI can draft, organize, and speed things up, but it canโt shake someoneโs hand, read a room, or build a 25-year relationship.
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Amy Cook: What advice do you have for younger salespeople who think they can just work behind a screen?
Gui Costin: You have to grind through cold emails, yes. But the goal is always to earn a meeting. Once youโre face-to-face, your personality and authenticity can shine. Personalization is everythingโform letters donโt cut it. One of our young team members gets incredible results by tailoring every email to the recipient. That level of effort is what builds trust.
Amy Cook: What about the stereotype that millennials and Gen Z are โentitledโ in sales roles?
Gui Costin: Honestly, I donโt see it. At Dakota, our younger team members are hungry and smart. But I will say: the more life and business experience you have, the more valuable AI becomes. You know the right questions to ask, and that prompts deeper, more meaningful insights. AI favors experience.
