Katelin Holloway – Human Side of Venture Investing at 776 (EP.490)

What It Covers

Katelin Holloway, founding partner at 776, explains how a decade as an HR executive at Pixar, Klout, and Reddit directly maps onto early-stage venture investing. She breaks down sourcing, selecting, and servicing founders through an operational lens, and details how 776 built proprietary software (Cerebro) to scale human-centered portfolio support.

Key Questions Answered

• •HR-to-VC Framework: Early-stage investing maps precisely onto three HR functions: sourcing (recruiting), selecting (behavioral interviewing), and servicing (enabling performance). Holloway argues operators with deep people-systems experience are systematically underrepresented in venture despite possessing the exact skill set required. Founders seeking investors should evaluate whether their cap table includes someone who can handle 2AM calls about personnel crises, not just financial modeling.
• •Cerebro Operating System: 776 built proprietary software called Cerebro to scale network access across their portfolio. Founders self-service introductions by setting parameters targeting specific roles (e.g., CMOs in a given sector), generating outreach drafts, and accessing the firm's full network without waiting for a partner to manually search their rolodex. All firm activity—calls, support interactions, deal notes—logs into Cerebro and is visible on 776's public homepage.
• •Hiring Timing: "Hire When It Hurts": Founders should perform a role themselves for several months before hiring for it. This builds genuine understanding of the job requirements, creates empathy for the incoming hire, and produces more accurate interview criteria. Holloway reports that every time she or portfolio founders compromised on this principle and hired prematurely, meaningful failures followed. The brain space freed after a well-timed hire directly enables innovation.
• •Termination Speed as Risk Management: The single most common founder mistake is delaying terminations. Across two decades of hiring and firing, no founder has ever told Holloway they regret letting someone go—every founder says they should have acted sooner. Holloway frames human capital work as risk management disguised as empathy: prolonging a misfit hire compounds failure for both parties and the business, while a clear, fast exit lets the departing employee invest in a role where they can succeed.
• •Founder Interviewing: Behavioral Over Credential: 776 indexes heavily on founder over product at early stage, using behavioral and values-based questions rather than credential or technical qualification checks. Holloway's investment in StarCloud (data centers in space) originated from a dinner conversation about wormholes and personal milestones—never a formal pitch. The goal is understanding how a founder's mind works and what their value system is, because the product will change many times before any liquidity event.
• •Restoring Social Contract Before Adding Process: At Reddit, Holloway's initial board mandate was to add process and mature the organization. Her actual diagnosis was a broken social contract, not missing systems. She spent her first weeks conducting multi-hour one-on-one sessions with all 75 employees, identified their shared identity as Redditors, and translated the community governance norms they already practiced online into an internal cultural framework. Revenue began recovering only after that social foundation was rebuilt.