Dakota Rainmaker Podcast

In this episode of The Rainmaker Podcast, Gui Costin talks with Mark Allen, President and Chief Development Officer of Royal Oak Realty Trust, about building a fundraising operation from the ground up in an industrial REIT. Mark covers how Royal Oak grew its distribution team from three to eight by hiring geographically rather than by channel, why shared account ownership beats ring-fencing relati...

In this episode of The Rainmaker Podcast, Gui Costin sits down with Dan Amir, Managing Director of Investor Coverage at Crow Holdings, for a wide-ranging conversation on building a wealth distribution team, applying institutional rigor to the wealth channel, and leading a sales organization through a difficult fundraising environment. Dan grew up in New Jersey, spent the first 13 years of his care...

In this episode of The Rainmaker Podcast, Gui Costin sits down with Dominica Ribeiro, Chief Marketing and Distribution Officer at Breckinridge Capital Advisors, the legendary asset manager based in Boston. The conversation covers Dominica's non-traditional career path, the structure and discipline of Breckinridge's distribution team, and the leadership philosophy that has shaped how she...

In this episode of The Rainmaker Podcast, Gui Costin sits down with Keith VanOrden, Head of Retail Distribution for North America at TCW. Keith brings nearly 30 years of experience building and leading sales teams, including more than 13 years at BlackRock, most recently as the national sales manager for iShares, and earlier roles at Delaware Investments, Fidelity, and Putnam, where he started his...

In this episode of The Rainmaker Podcast, Gui Costin sits down with Stephen Tiller, who joined Sterling Global Financial roughly 13 years ago after a 35-year career across some of the most respected names in real estate finance and investment banking. Sterling, founded by David Kosoy more than 50 years ago, manages roughly $7–8 billion in assets across six countries and runs a platform that includ...

In this episode of The Rainmaker Podcast, Gui Costin sits down with Jeff Collins, Managing Partner of Cloverlay, for a deep conversation on what it takes to raise institutional capital for one of the most differentiated strategies in private markets. Cloverlay, now on its fourth fund, invests exclusively in uncorrelated, non-operating assets — wireless spectrum, intellectual property on the conten...

In this episode of the Rainmaker Podcast, Gui Costin sits down with Mike Castino, President of Sound Capital Solutions, for a deep dive into the mechanics of ETF creation, distribution, and the accelerating structural shift reshaping investment management. Mike's career began on the floor of the Chicago Mercantile Exchange, where he spent 12 years as an independent futures trader before trans...

In this episode of the Rainmaker Podcast, Gui Costin sits down with Paul Stanton, a partner at Thesis Driven and PTB, a real estate investment banking boutique. The conversation spans Paul's career journey, the power of content marketing in the investment world, and the transformative potential of AI for business builders. Paul's path into real estate began after college at the Universit...

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 dist...

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...

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 f...

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 execut...

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...

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...

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 beg...

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...

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...

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...

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 r...

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 col...

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 f...

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 fi...

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 communi...

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...

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 Ameritrad...