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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📺 Explore our curated playlist THE CAPITAL PLAYBOOK HERE: https://www.youtube.com/playlist?list=PLTJlaeHk03J3Csa1jytu1X1JKyZ_6qTQb
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Explore Strategic Growth & Investment-Ready Opportunities with GrowNLearn
GrowNLearn, led by Zorina Dimitrova, connects select VCs, Family Offices, and Strategic Investors with precisely matched, high-growth ventures.

We also support founders with strategic growth advisory—helping you transform your business model, increase valuation, and prepare for investment or exit.

🎯 No random pitches. No wasted time. Just targeted growth and curated deal flow.

📌 Want Curated Investment Deals?
👉 Book Your Private Briefing: https://grownlearn.org/
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🎧 Listen to the GrowNLearn Podcast
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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

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

Grownlearn is a dynamic and insightful podcast that delves deep into the world of business model transformation. Hosted by seasoned professionals with a passion for innovation, the podcast features engaging interviews with the foremost experts in the field. Each episode invites listeners to explore the strategies, challenges, and successes of businesses that have undergone significant transformations. From disruptive startups to established enterprises, Grownlearn provides a platform for the best minds in the industry to share their experiences, insights, and lessons learned. Whether you're an entrepreneur, business leader, or simply intrigued by the ever-evolving landscape of business, Grownlearn delivers thought-provoking conversations that inspire and inform. Tune in to stay ahead of the curve and discover the keys to unlocking growth and success through transformative business models.

New tracks tagged #leders