This episode explores the multifaceted world of angel investing, contrasting the landscape of the early 2000s with the current environment. Against the backdrop of the post-dot-com crash, Keith Rabois recounts his early angel investing experiences, highlighting the scarcity of investors and the resulting ease of securing deals. More significantly, he emphasizes the importance of building credibility through early successes, achieved in his case by focusing on investments in former colleagues. As the discussion pivoted to investment strategy, Rabois reveals his "barbell" approach to personal wealth allocation, concentrating risk in high-growth ventures while maintaining conservative holdings elsewhere. For instance, he shares his initial lack of focus on financial returns in favor of gaining experience and building a track record. In contrast to his early, less price-sensitive approach, he now advocates for a more disciplined strategy, particularly for larger check sizes, leveraging his reputation to influence pricing. Ultimately, the conversation underscores the crucial role of effective filtering in angel investing, the challenges of maintaining a high hit rate, and the diverse motivations behind pursuing this investment path, concluding with insights into the evolving dynamics of the venture capital industry and the importance of clear company values.
