When pitching to venture capitalists, it's crucial to directly ask them about the likelihood of their investment. This approach not only opens a dialogue but also helps entrepreneurs gauge the interest and concerns of the investors. Establishing this transparency can lead to a more productive conversation about potential investment opportunities.

Understanding the differences between venture capital strategies is crucial for founders seeking investment. The article outlines various VC approaches, from hyper-selective funds aiming for high returns through concentrated investments to volume-based players focusing on deploying large amounts of capital. It emphasizes the importance of knowing the type of VC being engaged to ensure alignment with business goals and expectations.

Gil Dibner responds to Sam Lessin’s 2025 update on the venture capital landscape, highlighting the shift from a factory model to a regatta model where startups navigate funding with varying time and capital. He agrees with Lessin's observations on the fragmentation of the VC market and the emergence of new investment strategies, while also critiquing some of Lessin's more provocative statements about software and the SaaS model's viability. Ultimately, Dibner suggests that venture capital is returning to its uncertain roots, where the most promising investments are often those that break the mold.

Collaborative Fund's bold investment of $5 million into a single startup in 2015 exemplifies the high-risk, high-reward nature of venture capital. The article explores the complexities of portfolio construction, emphasizing the balance between concentration and diversification while highlighting the significance of conviction in investment decisions. Ultimately, it argues that effective venture capital requires both strategic thinking and an understanding of the unpredictable landscape of startup success.