Dakota Rainmaker Podcast

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. 

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 Angel Oak Capital, Cambiar Investors, and AIM/INVESCO. These experiences culminated in the co-founding of Sarmaya Partners, where Karl saw the opportunity to build a firm aligned with his vision and values.The conversation dives deep into Sarmaya’s unique investment strategy, which centers around a thematic belief in a new commodity super cycle. Rather than chase overcrowded markets, Karl and his partner Wasif identified a return to tangible assets like gold, silver, and copper as the next long-term trend. After initially structuring the firm as an LP, they pivoted to launching an actively managed ETF in January 2024 to better serve a broader investor base.Karl shares Sarmaya’s go-to-market strategy and how they’ve grown from two founders to a six-person team, carefully hiring seasoned professionals with deep industry relationships. He emphasizes the power of focus, targeting RIAs, family offices, and mid-sized broker-dealers—segments often overlooked by larger firms but open to differentiated strategies. A major theme throughout is the importance of relationships over transactions, and Karl’s approach is deeply rooted in decades of trust and credibility built across the industry.Sales process and infrastructure also play a key role in the discussion. Karl highlights the importance of having a clean, well-maintained CRM as the central nervous system of the firm’s sales efforts. Partnering with Dakota has helped Sarmaya stay agile and organized in an environment where client rosters and firm dynamics are constantly shifting.The episode also explores Karl’s leadership style, which blends high accountability with trust and autonomy. He believes in empowering experienced salespeople to execute without micromanagement, while maintaining clarity through communication and shared goals. His mantra—"take the bit out of the mouth and let them run"—underscores his belief in hiring the right people and giving them room to perform.As the episode closes, Karl speaks candidly about the biggest challenge facing Sarmaya: growing assets under management. Yet his energy is unwavering. With a strong product, clear strategy, and relentless optimism, Karl’s approach to sales and leadership provides an inspiring blueprint for anyone building a firm from the ground up. This episode is a masterclass in execution, resilience, and the long game of relationship-driven sales.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 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 approach enables the team to pursue every opportunity without the friction of internal handoffs. It also empowers salespeople to build relationships fluidly, regardless of territory or advisor type.Another highlight of the conversation is the team’s relentless focus on email strategy and personalization. Ryan explains how seemingly simple changes, like testing subject lines or inserting personal references, have driven a dramatic increase in meeting conversions. He emphasizes that, in an industry where performance can fluctuate, consistent access to meetings and thoughtful storytelling is what truly moves the needle.Ryan also offers insight into Swan’s open, feedback-driven communication culture. Weekly calls with firm leadership, including the Swan brothers, ensure alignment between what clients are saying and how the firm positions its strategy. This connection helps inform both marketing and product direction.The discussion dives into Swan’s use of HubSpot CRM, where Ryan stresses the importance of clean data and tracking pipeline with intention. From updates on advisor movements to segmented drip campaigns, the CRM is central to their disciplined sales process.Leadership-wise, Ryan balances autonomy with accessibility, encouraging his team to own their territories while remaining unafraid to ask for help. He stresses the importance of transparency, especially when setting expectations with advisors around Swan’s options strategy, a product that demands both clarity and consistency to be fully understood.For those new to the field, Ryan advises shadowing experienced professionals, actively networking, and approaching every interaction with authenticity. He closes by reflecting on the importance of standing out in a crowded investment space through honesty, conviction, and a commitment to delivering long-term value.This episode is packed with practical sales wisdom and strategic insight for professionals looking to elevate their fundraising and relationship management skills.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 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 identity is a fierce commitment to risk management—reflected in their trademarked tagline, Built to Conquer Risk—and a bold content strategy that sets them apart in a traditionally conservative industry.The episode explores how Potomac adopted the Entrepreneurial Operating System (EOS) to improve communication, accountability, and execution across all departments. Manish explains how EOS meetings, scorecards, and cross-functional transparency have fundamentally changed how the firm operates and drives growth. This operational discipline is mirrored in their use of CRM—specifically HubSpot—not just as a contact database, but as the central nervous system of their sales and marketing efforts. “If it’s not in the CRM, it doesn’t exist,” Manish says, underscoring the importance of tracking and acting on every client interaction.But what truly sets this conversation apart is the deep dive into Potomac’s content engine. From producing as many as seven pieces of content a week to launching creative projects like “Industry Gossip” and a Seinfeld-inspired series featuring advisors in classic cars, Manish and his team have taken an unconventional, personality-driven approach to branding. He’s unapologetic about avoiding product talk in content, emphasizing that building trust and brand recognition always comes before the sales pitch.Manish also reflects on leadership—how becoming a father shifted his perspective, and how he’s learning to blend hard-charging expectations with empathy and kindness. He opens up about the challenges of scaling people and culture alongside business growth and offers pointed advice for young professionals entering the industry: stay curious, stay visible, and never underestimate the power of showing up.Whether you’re a CEO, a sales leader, or a content creator in the investment space, this episode is a masterclass in modern firm building. Manish’s blend of operational rigor, creative risk-taking, and cultural intentionality offers a fresh, actionable blueprint for success in a rapidly changing 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. 

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 a multicultural family, studying operations research at Cornell, and entering finance through roles at GE and HSBC. She later joined Kimmeridge in its early stages, where she initially handled everything from accounting to IT. Over time, she found her niche in investor relations, eventually becoming a strategic leader within the firm. Her early exposure to both technical and financial disciplines laid the foundation for her ability to engage deeply with complex investments and communicate them effectively to investors.Neda discusses the philosophy behind Kimmeridge’s investment strategy, which emphasizes a technical, data-driven approach to energy investing. With $6 billion in assets under management, the firm is diversified across upstream energy, public activism, and energy transition strategies—including Chestnut Carbon, a nature-based carbon removal business that Neda helped incubate. Her involvement in underwriting and scaling portfolio companies gives her credibility and fluency in investor discussions, enabling her to build trust through substance and insight.A recurring theme in the episode is the importance of communication—both internal and external. Neda shares how she structured Kimmeridge’s investor relations team by client type, tailoring outreach to the specific needs of pensions, sovereign wealth funds, family offices, and other investor categories. She emphasizes the value of storytelling in simplifying complex investment theses without losing nuance, noting that connecting authentically with investors is more effective than giving polished lectures.Internally, she highlights the importance of clear, consistent communication across teams, especially in a scaling organization. Tools like Salesforce and Tableau have been game-changers, helping the firm track engagement, manage investor relationships, and build institutional memory. Neda candidly acknowledges that implementing CRM systems is a “new muscle” for many teams but argues it's essential for scaling with discipline and visibility.On leadership, Neda speaks about transitioning from an individual contributor to a team leader, emphasizing authenticity, resilience, and high standards. She believes great fundraisers and investors need to understand each other’s roles deeply, and encourages more real-time exposure for investment professionals to investor feedback.The episode closes with reflections on company culture, growth challenges, and advice for young professionals entering the industry. Neda encourages newcomers to be curious, take risks, and build relationships across their organizations. Her parting wisdom—“don’t hide at your desk”—captures the spirit of her approach: proactive, relational, and grounded in continuous learning.Overall, the episode is a rich look at what it takes to build and lead a high-performing investor relations function, with practical insights on scaling, communication, leadership, and strategy.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, 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 collaboration, culture, and putting people in positions to succeed.Chase outlines Harbor’s investment philosophy, focusing on sourcing and partnering with specialized boutique/institutional managers to deliver compelling strategies through vehicles like ETFs and CITs. With a strong belief in the future of active ETFs, he discusses Harbor’s growth in this space, noting the firm's ETF assets have doubled in just nine months, signaling a major shift in investor preferences.The discussion also dives into Harbor’s sales team structure, which includes 40 team members split between senior external professionals and internal staff. Chase highlights Harbor’s team-based, non-commission compensation model that fosters collaboration and shared success, as well as the firm’s commitment to constant communication and alignment through weekly meetings and bi-annual in-person strategy sessions.Chase also talks about the importance of CRM systems, particularly Salesforce, as a critical tool in capturing and leveraging client interactions for sales intelligence. He advocates for simplifying the CRM experience to increase adoption and maximize value.On leadership, Chase shares how he brings authenticity to his role, drawing inspiration from his brother’s military leadership experience. He sees his primary role as providing resources, eliminating obstacles, and supporting his team’s success rather than directing their every move. His advice to young sales professionals emphasizes continuous learning, passion, authenticity, and leveraging team strengths.The episode wraps with a discussion on prioritization and the importance of focusing on what truly matters. Chase uses the Eisenhower Matrix to manage tasks effectively and encourages leaders to carve out time for important but not urgent initiatives that drive long-term impact. Throughout the episode, Chase offers a practical, thoughtful, and team-oriented perspective on sales leadership in today’s evolving financial landscape.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data. 

Mark Levy, a differentiation strategist and founder of Levy Innovation, shares insights on how to make investment strategies stand out. He emphasizes the importance of being 'different' rather than just 'better,' suggesting techniques like flipping industry assumptions to discover unique approaches. Levy illustrates this with the Schlitz Beer story, showing how ordinary can be extraordinary. The conversation also delves into leveraging surprising narratives and passion to clarify every investment strategy's unique story.