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.
10
Stephen Tiller on Leadership, AI, and Picking Up the Phone
<p>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 Kossoy more than 50 years ago, manages roughly $7–8 billion in assets across six countries and runs a platform that includes private credit lending funds, development and construction businesses, trust companies, and banks. Stephen describes it as a microscopic-scale version of the Brookfield or Blackstone model, with real estate as its DNA.</p><p>The conversation opens wi...
Jeff Collins: Selling What Doesn't Fit in a Bucket
<p>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 content side, Broadway theatrical rights, litigation finance, pharmaceutical royalties, and other esoteric assets that don't sit neatly inside traditional buyout, credit, or real asset buckets. The result is a firm with a sales challenge that's fundamentally different from its peers: Cloverlay is...
Mike Castino on Market Makers, Platform Fees, and Building a Boutique ETF Firm
<p>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.</p><p>Mike's career began on the floor of the Chicago Mercantile Exchange, where he spent 12 years as an independent futures trader before transitioning into the investment management industry. His first sales role came at Claymore ETFs — one of the original ETF families, eventually acquired by Guggenheim and later Invesco — where his trading floor instincts translated directly into his commercial style. From...
Paul Stanton on How Founder-Led Brands, Content Marketing, and Agentic AI Are Reshaping Capital Raising
<p>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.</p><p>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
<p>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.</p><p>Tired of chasing...
Michael Sidgmore on Winning the Wealth Channel
<p>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.</p><p>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
<p>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.</p><p>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
<p>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.</p><p>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
<p>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.</p><p>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
<p>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.</p><p>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...
