How Dakota CEO Gui Costin Turned Weekly Sales Meetings into “Dakota Live” and Deal Flow

25/09/2025 21 min
How Dakota CEO Gui Costin Turned Weekly Sales Meetings into “Dakota Live” and Deal Flow

Listen "How Dakota CEO Gui Costin Turned Weekly Sales Meetings into “Dakota Live” and Deal Flow"

Episode Synopsis

Legendary operator and author Gui Costin (Founder & CEO, Dakota) breaks down how a failed content bet became a growth flywheel: Dakota Live—a weekly sales meeting turned show that shares real investor intel and creates trust at scale. We get into raising from RIAs, sales coaching (his 4 principles of fundraising), and the “no-policy policy” that built a high-trust culture. Gui also shares why kindness + clear expectations outperform, how hiring for culture compounds, and how to convert content into pipeline without the gimmicks.

Host: Zorina Dimitrova
Books referenced: Millennials Are Not Aliens, The Dakota Way, and Gui’s new leadership book Be Kind.
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Chapters
00:01:12–00:07:11 — Dakota’s Pivot to Live Content
00:07:12–00:09:13 — Marketplace Momentum
00:09:14–00:14:48 — Kindness, Clarity, and the No-Policy Policy
00:14:49–00:20:06 — Data, Demos, and Who It’s For
00:20:07–00:27:30 — Mentorship that Changes Trajectories

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