Dakota Rainmaker Podcast

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 them under co-working brands, a strategy that was derailed by COVID-19. Rather than retreating, Paul pivoted and launched an investment bank focused on operationally complex, niche real estate strategies, including outdoor hospitality, sports infrastructure, and surf infrastructure. This work eventually merged with Thesis Driven, a real estate media company he co-founded with entrepreneur Brad Hargreaves, focused on innovation in the built world through a capital markets lens.A central theme of the conversation is the untapped opportunity for investment managers to build audiences through content marketing. Paul and Gui agree that the investment management industry represents the largest white space in content marketing today, most firms hide behind corporate brands and compliance concerns rather than humanizing their story. Both point to Jon Gray of Blackstone and Andreessen Horowitz as rare examples of founder-led brands that have embraced media to build trust at scale. Paul notes that the psychology behind this is rooted in parasocial relationships, when someone sees your face and hears your voice consistently, their brain begins to feel like it knows you, which creates a powerful foundation for trust in capital raising.Paul shares his own experience building a LinkedIn presence over the past year, emphasizing that the mental shift that got him started was reframing content creation from self-promotion to education. By sharing what he was seeing in the capital markets and emerging asset classes, he found an authentic voice that resonated with his audience. Gui echoes this, noting that the most engaging posts are never about funds or accolades, they're about real experiences, lessons learned, and genuine insight.The episode closes with a discussion on AI and its implications for business. Paul introduces the concept of agentic AI, specifically his experience setting up an AI-powered capital markets analyst named "Sarah" using an open-source local infrastructure tool. Sarah reasons through tasks, builds databases, drafts email campaigns, and conducts research autonomously. Paul describes the experience as the most mind-blowing development he's seen since first using ChatGPT, underscoring the idea that AI agents are beginning to function like real employees.When asked about his biggest challenge, Paul cites focus, the entrepreneurial temptation to chase every new AI-driven opportunity rather than staying disciplined on core priorities. It's a fitting note to end on: in a world of expanding possibility, clarity of purpose remains the competitive edge.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data. 

Morgan Holycross, co-author of Be Kind and interviewer, guides a candid talk on leadership, culture, and kindness in the workplace. He recounts leadership missteps and a turning point that reshaped his approach. Conversation covers transforming toxic locker-room culture into high-performance teams, balancing playfulness with standards, and the difference between being kind and being nice.

Michael Sidgmore, partner at Broadhaven Ventures and founder of Alt Goes Mainstream, builds bridges between private markets and wealth. He talks about market plumbing, why education drives allocation, the rise of owned media for distribution, and how content and brand humanize private investments. Short, practical takes on niche focus, sales amplification, and making private deals tangible for advisors and clients.

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 isolating, Spencer saw a clear gap in professional squash: the absence of teams, local identity, and a product that resonated with American sports fans. The NSL was designed to answer a simple but powerful question he was asked repeatedly as a pro: “What team do you play for?”BG Lemmon brings a complementary perspective, blending his background in competitive collegiate squash with his career in finance and private investing. As a co-owner of the Philadelphia Lightning, BG discusses how his involvement grew organically, from persistent interest as a fan to hands-on participation in league operations. His experience reinforces a central theme of the episode: early-stage organizations require everyone to wear multiple hats, regardless of title.A key focus of the discussion is how the NSL has intentionally broken from traditional squash formats. With six-player rosters, three-on-three matches, timed periods, substitutions, and power plays, the league prioritizes pace, strategy, and fan engagement. The power play, in particular, introduces a risk-reward dynamic that encourages aggressive, creative shot-making, something rarely seen in traditional professional squash.Looking ahead, Spencer outlines the league’s near-term and long-term vision: measured expansion into new U.S. markets, a more robust match calendar, and continued emphasis on high-quality live events. Both Spencer and BG stress the importance of disciplined growth, proving the product, building the right partnerships, and earning credibility before scaling too quickly.The episode closes with a discussion of the partnership between the NSL and Dakota, grounded in shared values around relationships, community, and bringing people together through sport. At its core, the conversation highlights how team culture, on the court and in business, can transform an individual pursuit into something much bigger.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data. 

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 recruiting platform that worked with major global brands. Despite making early mistakes, Adam credits cold email as the single most important driver behind acquiring customers, raising capital, and ultimately exiting the business—experience that later became the foundation for his current company.A major theme of the episode is how dramatically the cold email landscape has changed since the mid-2010s. Adam explains that tactics that once worked, such as sending high volumes of emails from a primary domain, are now actively harmful. Today, success starts with infrastructure: properly set up sending domains, inbox warming, and protecting domain reputation. Without that foundation, even strong copy and targeting won’t matter because emails won’t reach the inbox.The discussion then shifts to measurement and optimization. Adam cautions against tracking open rates in cold email, noting both deliverability risks and unreliable data. Instead, he emphasizes reply rates as the most meaningful signal of success, since a reply confirms both inbox placement and message resonance. Sudden drops in reply rates, he explains, are often an early warning sign of deliverability issues.Beyond tactics, the episode dives into the psychology of cold outreach. Adam and Gui agree that the biggest barrier to success isn’t technology, it’s mindset. Cold email doesn’t feed the ego and requires resilience in the face of rejection. Adam frames email as nothing more than a tool to connect party A with party B, arguing that professionals who can stomach direct feedback and rejection will consistently outperform those who avoid it.The episode closes with actionable guidance on email construction, from concise, relevant subject lines to short, direct body copy that clearly states purpose, value, proof, and a call to action. The takeaway is clear: when paired with the right infrastructure and mindset, cold email remains one of the most scalable and reliable ways to build pipelines.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data. 

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 think linearly, diagnose problems, and stay disciplined when things didn’t work the first time. Those habits—problem-solving, persistence, and accountability, became foundational as he transitioned into product specialist and sales roles within Mellon.A pivotal chapter followed at SEI Investments, where Pokora gained broad exposure to how asset managers, consultants, and investment teams operate. His time at SEI provided a full view of the institutional ecosystem, from OCIO mandates to consulting dynamics, while reinforcing the importance of preparation and repetition in winning mandates. Despite success, Pokora recognized a gap in his experience: he wanted to work closer to firms actually managing capital.That realization led him to Brandywine Asset Management and later to what he describes as a career-defining move, joining Paulson & Company in 2006, just ahead of the Global Financial Crisis. Fundraising during this period required more than performance figures; it demanded the ability to clearly explain complex strategies to consultants and allocators navigating fear, skepticism, and unfamiliar instruments. Pokora emphasizes that sales at this level is ultimately about education and translation, not persuasion.Throughout the conversation, Pokora outlines a clear fundraising philosophy. First, knowledge is non-negotiable, knowing your product, understanding portfolio fit, and being fluent in competitors’ strategies. Second, there are no shortcuts. Even decades into his career, Pokora still prioritizes volume, preparation, and follow-through. Third, disciplined CRM usage is a competitive advantage, enabling better client engagement, internal reporting, and accountability.Beyond tactics, Pokora highlights the less discussed but equally important role of energy and leadership. Investor relations professionals set the tone within an organization, particularly during challenging periods. Showing up prepared, optimistic, and transparent builds trust internally and externally.The episode closes with practical advice on internal communication, executive interaction, and final presentations, reinforcing a recurring theme: success in fundraising is built through consistency, clarity, and doing the work, day after day, cycle after cycle.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data. 

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 relationship-driven selling.Following college, DaPore co-founded Benefitfocus, a healthcare software company that digitized employee benefits enrollment at a time when paper processes dominated. Starting as the firm’s first salesperson and eventually leading a 200-person sales organization, he helped scale the business from zero to $200 million in recurring revenue and through an IPO. The experience gave him firsthand exposure to scaling teams, building go-to-market engines, and operating through rapid growth.DaPore later founded and served as CEO of PeopleMatter, a venture-backed SaaS company focused on talent management for hourly workers. While the company was ultimately successful, raising over $60 million in venture capital and exiting to a strategic buyer, the experience revealed critical shortcomings in traditional venture models. As a founder, DaPore observed that many investors were capital providers first and operational partners second, often lacking the infrastructure or incentives to meaningfully support execution.Those lessons became the foundation for Roo Capital. DaPore built the firm around a three-part model—capital, talent, and growth, designed to actively support founders beyond the check. Roo integrates an in-house executive search business and a dedicated growth team that works directly with portfolio companies on hiring, go-to-market strategy, pricing, and systems. This structure allows Roo to participate deeply in value creation rather than relying on passive oversight.A recurring theme in the conversation is DaPore’s emphasis on transparency and relationship-building, particularly with LPs. Roo replaces traditional static quarterly reports with interactive video-based portfolio updates, featuring founders directly and allowing real-time Q&A. This approach not only strengthens trust but also gives LPs a clearer understanding of how value is being created between annual meetings.On the investment side, DaPore outlines Roo’s disciplined early-stage framework, centered on the “6 Ps”: People, Passion, Pain, Possibility, Priorities, and Product. The firm prioritizes founder quality and problem relevance, investing primarily at the pre-seed, seed, and early Series A stages across cybersecurity, healthcare, and vertical SaaS.The episode closes with practical insights on fundraising as a sales process. DaPore emphasizes repetition, iteration, and feedback, using early LP meetings as pressure tests to refine messaging and sharpen differentiation. By treating fundraising like enterprise sales, Roo was able to exceed its first fund target and build momentum for future growth.Overall, the conversation highlights how operator empathy, disciplined sales execution, and hands-on engagement can translate into a differentiated and durable investment platform.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data. 

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, and accountability, themes that recur throughout his career. That competitive mindset was reinforced at Boston College, where he spent four years on the varsity sailing team, learning how consistent effort and teamwork translate into performance under pressure.After college, Fentress entered the workforce through a direct sales role outside of financial services, gaining early, hands-on experience with prospecting, persistence, and client engagement. Recognizing the need for stronger technical and financial grounding, he later pursued an MBA at UNC’s Kenan-Flagler School of Business. Graduate school proved to be a critical inflection point, equipping him with the analytical tools and language necessary to operate effectively in institutional markets.His entry into Wall Street came through opportunistic networking rather than a traditional recruiting path. A last-minute opening in Morgan Stanley’s summer analyst program provided the gateway into institutional finance, where he went on to build foundational skills in communication, risk-taking, and navigating complex organizations. Fentress describes the trading environment as a daily test of judgment and accountability, where feedback is immediate and credibility matters.In the mid-2000s, Fentress transitioned into private credit, helping to build a platform at a time when the strategy was still relatively nascent. That experience, combined with living through the Global Financial Crisis, shaped his long-term perspective on risk. He emphasizes that credit investing is ultimately defined by losses avoided, not just returns generated, a lesson that continues to inform his approach todayThose lessons became central when Fentress co-founded ACRES Capital. He explains that the firm was built with a risk-first mindset, emphasizing discipline, downside analysis, and alignment across the platform. Rather than optimizing for short-term market conditions, ACRES was designed to endure volatility and perform across cycles.Throughout the episode, Fentress also highlights the importance of staying close to clients and assets. Being on the road, meeting investors, and seeing markets firsthand is not just relationship-building, it’s a critical learning tool. For him, real insight comes from continuous exposure to people, properties, and conditions on the ground.The conversation ultimately underscores a consistent message: durable success in investing and sales comes from preparation, humility, and respect for risk. Cycles change, markets evolve, but discipline and curiosity remain enduring advantages.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data. 

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 at Fidelity Investments on the inside sales desk, gaining foundational training during the Global Financial Crisis. This period proved formative, teaching him how to navigate difficult market environments, client uncertainty, and the importance of preparation and resilience.After several years at Fidelity, Willer sought a path that allowed him to move into the field without leaving New England. Following a stint in recordkeeping sales, he joined Federated Hermes in 2013, entering the institutional business during a period of growth. Over time, he progressed into a leadership role overseeing an eight-person institutional sales team across North America, while working closely with the firm’s liquidity, treasury, and consulting relations groups.A central theme of the conversation is culture and communication. Willer emphasizes that Federated Hermes’ culture is built on trust, transparency, and long-term tenure, supported by a relatively flat organizational structure. He believes leaders must stay deeply connected to their teams, noting that sales leadership cannot be effective from a distance. His communication model blends structure and consistency—biweekly team meetings, monthly one-on-ones, and formal quarterly reviews—with constant daily interaction to stay close to opportunities, challenges, and client conversations.Willer also highlights the importance of tapping into collective intelligence. He encourages open sharing across the team, allowing reps to learn from one another’s positioning strategies, client objections, and successful approaches. By deliberately creating forums where ideas and insights are exchanged, he helps eliminate silos and raise the performance of the entire group. This philosophy extends beyond sales to cross-functional collaboration with product, marketing, and RFP teams.The discussion also covers the role of CRM systems, particularly Salesforce, as a core business tool rather than an administrative burden. Willer stresses the importance of data quality, capturing meetings early, and documenting detailed notes to support long institutional sales cycles. A well-maintained CRM enables better internal coordination, more relevant client outreach, and improved prioritization across teams.When asked about leadership philosophy, Willer describes his approach as trust-based and intentional. He prioritizes kindness, thoughtful communication, and honest feedback delivered in the right setting. For young professionals entering the industry, his advice centers on building relationships early and focusing on controllable factors such as preparation, process, and continuous learning. He concludes by noting that time management is his greatest challenge as a leader, and that prioritizing what best serves clients and the team is the framework he uses to stay focused and effective.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data. 

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 in radio while studying at Boston College, he pivoted to finance after a pivotal career fair encounter led to an internship at Orbitex. This early exposure to asset management sales shaped his view of the business as deeply relational rather than purely transactional.Throughout his career, from retail wholesaling to institutional alternatives, Tower has maintained a wholesaler’s mentality, centered on volume, persistence, and regular in-person meetings. He stresses that while the sales process has evolved, particularly in the post-COVID world, the fundamentals remain the same: show up, follow through, and build trust over time. Tower describes structuring his travel plans like a “milk route,” ensuring consistent visibility with clients, which builds credibility even when meetings aren’t immediately productive.At Asset Management One, Tower leads a small business development team but operates within a global firm backed by Mizuho Bank and Dai-Ichi Life. He explains how even with a lean U.S. team, global coordination is key, and everyone, from operations to compliance, is considered part of the broader sales function. Internal communication is facilitated through Microsoft Teams, allowing seamless collaboration across time zones and remote work environments.Tower emphasizes the critical role of technology, particularly CRMs, in organizing and scaling a salesperson’s efforts. He’s a strong advocate for Salesforce, especially when integrated with tools like Dakota Marketplace, which he credits for increasing efficiency and effectiveness in prospecting and follow-ups. He believes that proper CRM usage not only supports personal productivity but also improves firm-wide communication and accountability.Leadership-wise, Tower positions himself as a “player-coach,” actively supporting his team without micromanaging. He highlights the importance of empathy, advocacy, and leading by example, whether through hands-on involvement in RFPs or making time for late-night coordination with global colleagues.For aspiring sales professionals, Tower’s advice is simple but powerful: be present, be authentic, and be helpful. He encourages young professionals to prioritize face-to-face engagement, attend conferences, and resist the temptation to overly rely on digital outreach. In an era where emails and automation dominate, Tower argues that true relationship-building still requires showing up and offering genuine value.Overall, this episode delivers valuable insights into what it takes to build and maintain a successful institutional sales career in asset management. Tower’s experience-driven wisdom and grounded leadership philosophy offer lessons not just for sales professionals, but for anyone navigating a relationship-intensive industry.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.