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.

The article explores the intersection of angel investing and design, offering insights specifically tailored for designers looking to attract investment for their projects. It discusses key strategies, potential pitfalls, and the importance of aligning design principles with investment goals to create compelling pitches.

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.