Episode Details

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.

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