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PODCAST

Dakota Rainmaker Podcast

The "Dakota Rainmaker Podcast," hosted by Gui Costin, CEO of Dakota, offers a unique look into sales strategies from top industry executives. Each episode explores the inner workings of successful sales organizations, from philosophy to execution. This podcast is essential for sales professionals seeking wisdom from the best in the field.

business management

All Episodes

22:50

Be Kind and Win: Gui Costin, Dakota

Dakota Rainmaker Podcast ·

2026/03/03

In this special episode of The Rainmaker Podcast, Gui Costin is interviewed about his book Be Kind. He reflects on early leadership missteps marked by volatility and ego, and the turning point that reshaped his approach to culture and accountability. Gui challenges the belief that high performance requires harshness, arguing instead that kindness and hard standards can coexist. He draws a key distinction between being “nice” and being “kind,” emphasizing direct, respectful feedback over avoid...

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51:04

Michael Sidgmore on Winning the Wealth Channel

Dakota Rainmaker Podcast ·

2026/02/17

In this episode of The Rainmaker Podcast, Gui Costin sits down with Michael Sidgmore, Partner and Co-Founder of Broadhaven Ventures and Founder of Alt Goes Mainstream, to unpack one of the most important structural shifts in asset management today: the convergence of private markets and private wealth. Michael begins by walking through his path from growing up outside Washington, D.C., to studying at the London School of Economics, where he first gained exposure to private markets by leading ...

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19:15

The National Squash League: Reinventing Pro Squash

Dakota Rainmaker Podcast ·

2026/02/10

In this special edition of the Rainmaker Podcast, host Gui Costin sits down with Spencer Lovejoy, Co-Founder and CEO of the National Squash League (NSL), and BG Lemmon, co-owner of the Philadelphia Lightning, to unpack what it takes to build a modern sports league from the ground up, and why squash is uniquely positioned for a team-based reinvention. The conversation opens with Spencer’s journey from junior squash in New Haven to competing professionally on the global circuit, and ultimately ...

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32:45

How Cold Email Really Works Today with Adam Rosen

Dakota Rainmaker Podcast ·

2026/02/03

In this episode of The Rainmaker Podcast, Dakota Founder and CEO Gui Costin sits down with Adam Rosen, founder of an email marketing agency that helps startups, unicorns, and large enterprises generate sales through cold email. The conversation offers a practical, experience-driven look at how cold outreach has evolved, and why it remains one of the most effective tools in modern sales when executed correctly. Adam begins by walking through his entrepreneurial origin story, from studying spor...

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35:33

Why Discipline Matters in Fundraising With Larry...

Dakota Rainmaker Podcast ·

2026/01/27

In this episode of the Rainmaker Podcast, Gui Costin sits down with Larry Pokora, Managing Director on the Investor Relations team at Tilden Park Capital, to unpack a 30+ year career spanning traditional asset management, alternatives, and institutional fundraising. The conversation moves from Pokora’s blue-collar upbringing in Pittsburgh to his hard-earned perspective on what actually drives long-term success in fundraising. Pokora begins by tracing his career back to an unconventional start...

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34:29

From Operator to Investor: How Nate DaPore Built Roo...

Dakota Rainmaker Podcast ·

2026/01/20

In this episode of the Rainmaker Podcast, Gui Costin sits down with Nate DaPore, Founder of Roo Capital, to explore how an operator’s mindset, disciplined sales execution, and hands-on value creation have shaped a differentiated venture capital platform. DaPore’s story begins with early exposure to sales and entrepreneurship out of necessity. Paying his own way through college, he convinced a car dealership to give him a trial selling cars over the summer, quickly outperforming expectations a...

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38:04

Andrew Fentress on Building a Risk-First Private...

Dakota Rainmaker Podcast ·

2026/01/13

In this episode of The Rainmaker Podcast, Gui Costin sits down with Andrew Fentress, Co-Founder of ACRES Capital, to discuss his career path, the formative experiences that shaped his leadership style, and the lessons he carries forward from multiple market cycles. The conversation blends personal background with practical insights on sales, investing, and long-term platform building. Fentress begins by tracing his early life in the Washington, D.C. area, where he grew up surrounded by compet...

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34:47

Building Trust at Scale: Brian Willer on Leading...

Dakota Rainmaker Podcast ·

2025/12/16

In this episode of the Rainmaker Podcast, Gui Costin sits down with Brian Willer, Senior Vice President and National Sales Manager of Institutional Business Development at Federated Hermes, to discuss leadership, communication, and the operational discipline required to scale an institutional sales organization. Willer begins by reflecting on his early background growing up in Maine with no direct exposure to investment management. His interest in financial markets was sparked by curiosity ra...

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31:21

Mark Tower on Consistency, Connection, and Leading...

Dakota Rainmaker Podcast ·

2025/12/09

In this episode of the Rainmaker Podcast, featuring Mark Tower, Senior Institutional Sales and Marketing Professional at Asset Management One USA, delivers a comprehensive masterclass in relationship-driven sales strategy, leadership, and career longevity within the asset management industry. With 25 years of experience, Tower offers a mix of practical advice and personal anecdotes that emphasize the importance of consistency, adaptability, and authenticity in building a successful sales care...

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27:53

Karl Engelmann on Building Sarmaya, Selling with...

Dakota Rainmaker Podcast ·

2025/12/02

In this episode of the Rainmaker Podcast, host Gui Costin welcomes Karl Engelmann, co-founder and COO of Sarmaya Partners, to share the story behind the firm’s rapid emergence and his philosophy on sales, leadership, and entrepreneurship. With over three decades of experience in financial services, Karl offers listeners a rare, behind-the-scenes look into launching an asset management firm and the strategic thinking driving its success. Karl begins by tracing his unconventional career path, f...

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26:36

Ryan Williams on Mastering Sales with a Lean Team and...

Dakota Rainmaker Podcast ·

2025/11/18

In this episode of the Rainmaker Podcast, Gui Costin sits down with Ryan Williams, Director of National Accounts at Swan Global Investments, to explore what makes a lean, non-channelized sales team thrive in a competitive asset management environment. Ryan shares his journey from internal wholesaling to leading Swan’s distribution relationships, offering a rare look at the mindset and discipline required to succeed in investment sales today. One of the central themes Ryan discusses is Swan’s ...

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35:22

Leading with Transparency and Bazooka Content: Manish...

Dakota Rainmaker Podcast ·

2025/11/11

In this episode of the Rainmaker Podcast, Gui Costin sits down with Manish Khatta, CEO and CIO of Potomac, for a candid and insightful conversation about building and scaling a modern asset management firm through transparency, technology, and content. Manish, a self-described quant and lifelong Potomac team member, shares his journey from programming mechanical trading systems straight out of college to now leading a fast-growing, multi-siloed investment business. At the heart of Potomac’s i...

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42:48

Neda Jafar on Building Trust, Teams, and $6B at...

Dakota Rainmaker Podcast ·

2025/11/04

In this episode of The Rainmaker Podcast, Gui Costin interviews Neda Jafar, a partner at Kimmeridge, to discuss her journey, leadership philosophy, and the evolution of investor relations within a growing private equity firm. Neda offers a unique perspective shaped by her technical background in engineering and her experience building Kimmeridge’s fundraising and investor communications platform from the ground up. The conversation begins with Neda’s origin story—growing up in Connecticut in ...

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34:59

Chase Bower on Building Team-Driven Sales Success at...

Dakota Rainmaker Podcast ·

2025/10/21

In this episode of the Rainmaker Podcast, host Gui Costin speaks with Chase Bower, Senior Vice President and Head of Sales at Harbor Capital Advisors. The conversation explores Chase’s journey from his early days growing up in Philadelphia and playing college football at Dartmouth to his current leadership role in the financial services industry. Chase shares how his experiences on the football field shaped his approach to team building and leadership, emphasizing the importance of collaborat...

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39:59

Unlocking Differentiation: How to Make Your...

Dakota Rainmaker Podcast ·

2025/10/14

In this episode of the Rainmaker Podcast, host Gui Costin speaks with Mark Levy, a differentiation expert and founder of Levy Innovation, known for helping individuals and organizations stand out through what he calls “big sexy ideas.” Levy has worked with major companies and thought leaders, including Simon Sinek, and emphasizes the power of clarity, surprise, and storytelling in business communication. The episode centers around the critical importance of differentiation in the investment b...

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37:59

Afzal M. Tarar: Combining AI Expertise and...

Dakota Rainmaker Podcast ·

2025/10/07

In this episode of the Rainmaker Podcast, Gui Costin sits down with Afzal M. Tarar, Founder and Managing Partner at Quartus Capital Partners LLC, to discuss his journey in AI and technology, management consulting, venture capital, strategies for capital raising, and building a high-performance investment platform. Afzal shares his insights on the evolving landscape of alternative investments, the importance of disciplined investment processes, and the techniques that have allowed Quartus to d...

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33:49

Building Trust and Value in Private Equity with Alisa...

Dakota Rainmaker Podcast ·

2025/09/30

In this episode of the Rainmaker Podcast, host Gui Costin interviews Alisa Kolodizner, Co-Owner and Managing Partner at Prairie Hill Holdings, an alternative investment firm focused on triple-net lease commercial real estate. Alisa shares her compelling journey from immigrant roots to high-impact financial professional and entrepreneur. Alisa began her career in financial services at TD Ameritrade, eventually becoming one of the top five financial advisors company-wide within two quarters—des...

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32:12

Daniel Duncan on Building a Resilient Investor Base...

Dakota Rainmaker Podcast ·

2025/09/23

In this episode of the Rainmaker Podcast, Gui Costin sits down with Daniel Duncan, Managing Director of Business Development and Client Services for Seafarer Capital Partners, for an in-depth conversation about building a differentiated emerging markets manager distribution plan, navigating the U.S. investment professional landscape, and scaling relationships with institutional investors. Daniel, with decades of experience in global emerging markets, shares how his background managing complex...

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34:09

Streamlining Due Diligence and Deal Sourcing with...

Dakota Rainmaker Podcast ·

2025/09/16

In this episode of the Rainmaker Podcast, Gui Costin speaks with Michael Ashmore, Founder of Rondeivu, an end-to-end InvesTech platform transforming how institutional investors source diligence, transact, and monitor investments across private markets. Michael, with over 20 years of experience in finance, private equity, and venture capital, shares his journey from a background in law and economics to founding Rondeivu after recognizing the inefficiencies in private markets and deal processes...

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23:53

Dean Kantor on Creating Value in Mid-Market...

Dakota Rainmaker Podcast ·

2025/09/09

In this episode of the Rainmaker Podcast, host Gui Costin welcomes Dean Kantor, the founder and CEO of CoreGro, a private equity real estate firm focused on generating long-term value through strategic acquisitions and structured investments. Dean, who has over 20 years of experience in finance, private equity, and real estate, shares his journey from starting in wealth management to creating CoreGro, a platform focused on mid-market investments in U.S.Healthcare real estate. Dean reflects on...

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161 results

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