Startup Founders Share Stories About Venture Capitalists: From Sleep to Sexism

Venture capitalists are key players in the world of tech startups, but their behavior during meetings with founders often crosses professional boundaries. This week, a wave of posts on X* emerged, where entrepreneurs shared their "horror stories" about pitches. The most common theme involved partners at venture funds falling asleep during project presentations.

Greg Eisenberg, founder of Late Checkout studio, recounted how during a $15 million pitch at one of the top 3 funds, a general partner fell asleep for 30 minutes. No one present reacted, and the meeting continued as if nothing had happened. Similar stories were confirmed by other entrepreneurs, including Zynga co-founder Mark Pincus. Notably, some of these "sleepy" investors later offered deals despite their apparent lack of interest.

However, not all stories were amusing. Cloudflare co-founder Matthew Prince cited an example of sexism: a Sequoia partner refused to invest in the company because he didn’t believe a woman could lead an infrastructure project in the security sector. Today, Cloudflare is valued at $87 billion, and its co-founder Michelle Zatlyn serves as COO. Another shocking incident involved investor Vinod Khosla, who allegedly suggested Prince fire his co-founders and take their shares.

Despite the negative examples, some founders noted that most venture capitalists are professionals who genuinely help startups. However, as Pincus emphasized, entrepreneurs are no longer afraid to speak openly about investors' inappropriate behavior. These stories not only entertain but also expose industry issues: lack of transparency, power imbalances, and double standards.