All Things Fundraising

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 Episode 39 of The Emerging Manager Growth Show, Gui Costin breaks down how banks and broker-dealers fit into an emerging manager’s fundraising strategy—and how to engage them effectively.

Gui explains why execution matters more than market conditions, emphasizing early-year planning, disciplined outreach, and consistent activity as the true drivers of momentum. He debunks common myths around needing $500M+ in AUM or a large wholesaling team, and outlines how early engagement with home offices can shorten future sales cycles. The episode also covers city scheduling, cold outreach as a long-term brand builder, and why combining top-down and bottom-up coverage is essential when fundraising through bank and broker-dealer platforms.

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 today

Those 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 Dakota's Fundraising News Podcast, we cover newly launched RIAs like Valorem and acquisitions by Wealth Enhancement. Hear updates on commitments coming from The Sacramento County Employees Retirement System (SCERS), The Illinois Municipal Retirement Fund, and The School Employees Retirement System (SERS). Hear updates on searches coming from The North Attleboro Contributory Retirement System, New York City Comptroller's Office, and The Chicago Teachers’ Pension Fund. We also share the latest fundraising efforts from the newly launched National Startup Investment Guidance Fund, Goldman Sachs Group, and Clear Investment Group — plus a reminder to register for our next Dakota Cocktails event.

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 Mastering Salesforce for Investment Firms, Gui Costin and Tim Dolan discuss how Salesforce can be used as a true leverage tool for investment sales teams when configured and adopted correctly. They highlight best practices such as consistent activity logging, disciplined pipeline management, and the use of past activity reports to drive follow-ups and prioritize opportunities, with a focus on Dakota’s “Golden Field” as a simple way to track sales stages and account momentum. The episode also addresses common CRM adoption challenges and explains how simplifying workflows and aligning usage with incentives helps teams turn Salesforce data into actionable sales insight

Master sales with four game-changing principles: Focus on what matters, target the right people, craft the perfect pitch, and follow up like a pro. Packed with actionable tips, this guide helps you turn meetings into deals—fast! 💼🔥

In today's episode of the Dakota Fundraising News Podcast, we cover RIA activity including acquisitions by Constellation Wealth Capital and Wealthcarte Capital Management as well as newly launched RIAs like Willow Creek Capital Management. Hear updates on commitments coming from LSERS, Ohio Police and Fire Pension Fund and Montana Board of Investments. Hear updates on searches coming from Firefighters' Retirement System of Louisiana, Dallas Police and Fire Pension Fund, and the Pension Benefit Guaranty Corporation. We also share the latest fundraising efforts from January Capital, Goldman Sachs Asset Management, and ArrowMark Partners — plus a reminder to register for our next Dakota Cocktails event.

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 Episode 38 of The Emerging Manager Growth Show, Gui Costin shares why RIAs are the top fundraising channel for emerging managers—and how to break in effectively.

He debunks myths about needing large AUM, long track records, or fee flexibility, and explains why cold outreach is essential to success. Gui walks through city scheduling, crafting strong email invites, and using quarterly webinars to drive awareness. He also outlines how to leverage CRM for pipeline tracking and why asking two key questions in every meeting helps qualify real opportunities.

A must-watch for fundraisers looking to scale smartly.

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.