June 05, 2025 | 23 MIN

Mastering Sales Targeting & Outreach with Gui Costin

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In this insightful episode of SalesPOP!, Gui Costin, founder and CEO of Dakota, joins host John Golden for a candid conversation on the state of modern sales—and what fundamentals still hold true. Drawing from decades of experience building Dakota into a leading fundraising and data platform for investment firms, Gui breaks down his no-nonsense approach to cold outreach, preparation, and professional discipline.

Gui begins by emphasizing that while sales technologies have advanced, the core challenge remains the same: booking meetings with qualified buyers you don’t yet know. He challenges the notion that cold outreach is outdated, arguing instead that it’s a critical skill that too many salespeople avoid due to emotional discomfort. His message is clear: success comes from embracing the discomfort, not avoiding it.

A cornerstone of Gui’s sales philosophy is intentionality—especially when it comes to cold emails and calls. He outlines a precise structure for outreach, including a clear subject line, a short, punchy introduction, and a direct meeting request. He also stresses the importance of professionalism in every interaction—sounding polished, anticipating objections, and treating every call as a chance to build trust and credibility.

Preparation is another recurring theme. Gui explains that the best salespeople take extensive notes, come to meetings with clear objectives, and ask thoughtful, strategic questions. He encourages reps to view meetings as conversations between equals—not as performances or pitches—and to be confident enough to ask the tough questions, including, “Is there a fit?”

Much of the episode is rooted in Gui’s structured sales framework, The Dakota Way, which centers on four things every salesperson can control: setting expectations with leadership, knowing your target buyer, preparing your message, and managing your CRM and pipeline proactively. He argues that consistent reporting and upward communication aren’t just about accountability—they’re about empowering your manager to advocate for you internally.

Throughout the conversation, Gui reinforces the value of curiosity, consistency, and culture in sales. He believes great salespeople are always learning, always refining, and never relying on shortcuts. His advice is both practical and mindset-driven: focus only on what you can control, eliminate distractions, and build systems that reinforce discipline.

Gui’s appearance on SalesPOP! delivers a compelling blend of tactical advice and strategic perspective—highlighting how preparation, intentionality, and emotional resilience remain the bedrock of sales success in an increasingly tech-enabled world.

Podcast Experiences

  • 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

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