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Episodes from Dakota Rainmaker Podcast
Paul Stanton on How Founder-Led Brands, Content Marketing, and Agentic AI Are Reshaping Capital Raising
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 University of Richmond, where he started in brokerage at Newmark before moving to the investment and development side. He later pursued a forward-thinking thesis around flexible office space, acquiring boutique Class B office buildings and operating...
Be Kind and Win: Gui Costin, Dakota
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 avoidance. The episode reinforces a core leadership principle: words, tone, and daily behavior from the top ultimately define culture and performance.Tired of chasing...
Michael Sidgmore on Winning the Wealth Channel
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 one of the world’s largest student-run hedge fund and private equity conferences. That early immersion led to ro...
The National Squash League: Reinventing Pro Squash
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 to co-founding the NSL alongside his partners. After years of playing an individual sport that often felt is...
How Cold Email Really Works Today with Adam Rosen
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 sport management in college to discovering entrepreneurship late in his academic career. That pivot led to his first startup, a college...
Why Discipline Matters in Fundraising With Larry Pokora of Tilden Park Capital
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 starting point: working as a programmer analyst at Mellon Financial Services after attending the Community College of Allegheny County. That early technical role, he explains, trained him to...
From Operator to Investor: How Nate DaPore Built Roo Capital Around Talent and Execution
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 and earning enough to fund his education. That formative experience reinforced two core themes that would define his career: accountability and...
Andrew Fentress on Building a Risk-First Private Credit Platform
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 competition, entrepreneurship, and professional athletics. Exposure to business builders and elite performers at a young age instilled an appreciation for discipline, preparation...
Building Trust at Scale: Brian Willer on Leading High-Performing Institutional Sales Teams
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 rather than formal guidance, eventually leading him to Bryant University, where a trading simulation room cemented his desire to enter the industry. He launched his career...
Mark Tower on Consistency, Connection, and Leading with Purpose in Institutional Sales
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 career.Tower shares his background growing up as the youngest of eight children in New Jersey, an experience that helped him develop strong interpersonal communication skills. After initially exploring a career...
Karl Engelmann on Building Sarmaya, Selling with Conviction, and Leading Through Relationships
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, from aspiring journalist to accomplished sales leader. His communication skills and passion for storytelling laid the foundation for a career that spanned roles at...
Ryan Williams on Mastering Sales with a Lean Team and a Personal Touch at Swan Global Investments
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 strategic decision to operate without channel segmentation. With just four wholesalers covering the entire country and all advisor channels, this appr...