Veteran venture capitalist Keith Rabois, a longtime figure in Silicon Valley’s investment ecosystem, recently shared some candid career guidance for young professionals eager to forge their path in the world of venture capital. Speaking during an episode of *The Rise* podcast, Rabois offered a perspective shaped by decades of firsthand experience in both startup operations and venture investing. He advised that, with very few exceptions, individuals—particularly those with strong technical skills—should either immerse themselves in the early stages of a startup or take the bold step of founding a company themselves. In his view, these experiences provide essential education that no classroom or theoretical training in finance or entrepreneurship can adequately replicate.
Rabois elaborated that many aspiring investors express an interest in “getting into venture” without truly grasping what the profession entails. According to him, when asked about their motivation for pursuing this career path, most answer with responses that are, at best, surface-level. They often conflate the popular media portrayal of venture capital—with its glamorized depictions of pitch meetings and overnight success stories—with the nuanced, often painstaking reality of the work. The venture industry, he emphasized, demands a sophisticated understanding of business building, product-market fit, and human psychology that can only develop through direct operational involvement.
To that end, Rabois argued that anyone hoping to succeed in venture capital must first internalize the mechanics of building a company from the ground up. This process, he suggested, not only helps an individual gain confidence in their career decisions but also forms a critical practical foundation for evaluating future investments. He outlined three key benefits derived from such experience: first, it reinforces conviction that venture is indeed the right professional path; second, it dramatically improves one’s ability to perform the job effectively; and third, it imbues the investor with a level of credibility that cannot be faked and which, in turn, enhances both reputation and performance. Confidence, competence, and credibility—these, he implied, are the indispensable cornerstones of success in an industry that prizes judgment above all.
Rabois’s advice carries significant weight, given his remarkable background in technology and investment. As a managing director at Khosla Ventures, he has guided and supported numerous groundbreaking companies. His portfolio includes board roles at major digital platforms such as Reddit and Yelp, alongside his position as cofounder and chairman of Opendoor Technologies, a company that revolutionized the real estate transaction process. His career exemplifies the lifecycle he advocates for: first building, then investing, with deep operational knowledge underpinning every decision.
During the interview, Rabois discouraged the increasingly common ambition of freshly minted graduates who aspire to leap directly into venture capital roles. He characterized this as a “bad idea,” explaining that without exposure to the day-to-day realities of startup life, young professionals lack the contextual understanding necessary to make sound investment judgments. He did, however, acknowledge one measured exception: joining a venture firm as an associate for a brief period—perhaps a couple of years—could serve as a useful training ground. Such a role allows newcomers to observe how the industry functions, interact with portfolio companies, and determine whether the field genuinely aligns with their passions and skills. Over time, this observational period provides a rare vantage point from which one can evaluate scores of startups and, eventually, identify an exceptional company to join.
Rabois’s advice follows a deliberate logic. The ideal sequence, he proposed, involves first learning by observation within a fund, then taking the plunge into an operating role at a fast-growing company, and only thereafter—after having contributed to building something substantial—returning to venture investing with a sharpened eye and mature perspective. By following this order, a professional dramatically increases their odds of long-term success. Enter the field too early, he warned, and one risks sacrificing the depth of experience that later distinguishes exceptional investors. As he put it, starting immediately after school can limit one’s exposure to the formative trials of entrepreneurship. By the time such a person reaches thirty, they may have had only a handful of chances—perhaps just one or two meaningful opportunities—to participate in a startup adventure.
When contacted for further comment, Rabois directed inquiries to a reflective blog post by Founders Fund partner Delian Asparouhov, who previously distilled several key lessons learned from working with Rabois, including practical guidance on building a path into venture capital. In his writing, Asparouhov outlines a progression that closely mirrors Rabois’s philosophy. He asserts that an aspiring investor’s success rests on four foundational elements: starting as a junior generalist to develop broad exposure, gaining hands-on experience within a rapidly scaling startup, learning how to allocate capital alongside seasoned venture partners, and continuously seeking mentorship from the most accomplished figures in the field.
Asparouhov further underscored a central truth often overlooked by novices: securing a position in venture capital requires convincing an existing VC that you possess the potential to excel in that same capacity. In other words, it’s not enough to express interest—the credibility must be earned through demonstrated expertise and sound judgment. Both traits, he noted, develop only over time, through deliberate effort, continuous learning, and a commitment to being intellectually rigorous. There are, as Asparouhov concluded, no shortcuts to acquiring the hard-won wisdom that defines the best investors.
Together, Rabois and Asparouhov’s perspectives form a coherent message: the route to a meaningful career in venture capital is neither linear nor instantaneous. True understanding arises from lived experience—building, failing, iterating, and ultimately learning what it takes to transform an idea into a sustainable enterprise. Only those who have experienced the challenges of creation firsthand can fully appreciate the qualities that make a startup succeed, and in turn, become the kind of investor capable of identifying and nurturing the next generation of innovators.
Sourse: https://www.businessinsider.com/keith-rabois-advice-how-to-break-into-venture-capital-vc-2025-10
