Founders share VC horror stories, and some are naming names

Navigating the venture capital landscape is a rite of passage for many tech founders, often filled with unique challenges and unexpected encounters. Recently, a lively discussion erupted on X, where entrepreneurs shared their most unforgettable VC pitching horror stories, ranging from humorous to downright frustrating. It all began with Greg Isenberg, a startup podcaster and founder of Late Checkout Studio, who recounted a particularly bizarre incident during a pitch for a $15 million Series A at a prominent VC firm. He revealed that one of the general partners fell asleep in the middle of the presentation, remaining oblivious for over 30 minutes while the meeting continued around him. This sparked a wave of similar anecdotes, with numerous founders echoing experiences of VCs dozing off during critical pitches. Zynga's founder, Mark Pincus, shared a similar tale, humorously comparing his experience to a scene from 'Weekend at Bernie's.' Despite the lack of attention, several founders noted that falling asleep did not prevent VCs from eventually investing, highlighting a perplexing dynamic in the industry. Liz Wessel, a former co-founder of HR startup WayUp, detailed her own experience pitching to a well-known investor who dozed off, only to later receive a term sheet. However, her team chose to decline the offer, leaving the VC astonished. The conversation took an interesting turn when former a16z partner Arianna Simpson humorously questioned the sleep patterns of VCs, noting the alarming frequency of stories involving napping investors. Alongside these tales, some founders shared their frustrations about VCs who signed term sheets only to back out at the last moment or ghost them entirely. One particularly audacious founder, Travis Kalanick, co-founder of Uber, recounted how he chased a VC to their car to continue pitching after sensing they were trying to escape the meeting. Not all experiences were negative, however. Some founders praised their VC interactions, recounting positive relationships and productive meetings. Yet, the overwhelming number of horror stories led Pincus to celebrate the moment when founders felt empowered to speak out against unprofessional VC behavior. Matthew Prince, the founder of Cloudflare, delivered a shocking revelation about a Sequoia partner who passed on investing due to a belief that a woman could not lead a security infrastructure company, referring to Cloudflare’s co-founder, Michelle Zatlyn. With Cloudflare’s current valuation soaring to $87 billion, it’s clear that the judgment was misguided. In another anecdote, Prince shared an uncomfortable encounter with prominent investor Vinod Khosla, who suggested he fire his co-founders. Although Prince acknowledged Khosla's intelligence and successful track record, he expressed his discontent with Khosla's approach, ultimately blocking his number. Among the lighter moments, one founder humorously recounted how a VC warned her about a rock formation outside their office that resembled male anatomy, dubbing the firm 'Dickrock Ventures.' The discussions revealed that the fundraising process is often opaque, with many founders facing similar challenges in their pursuit of capital. As Isenberg aptly summarized, every founder has a story to tell in this unusual and often awkward journey through the world of venture capital.