Founders Reveal Startling Venture Capital Experiences
Securing venture capital is a pivotal milestone for tech entrepreneurs, yet many founders recount unsettling experiences during this process. A recent surge of discussions on social media platform X has unveiled a series of such narratives, ranging from humorous to deeply concerning.
Greg Isenberg, a prominent startup podcaster and founder of Late Checkout Studio, initiated the conversation by sharing an incident where a general partner at a leading VC firm fell asleep during his $15 million Series A pitch. Despite the partner being out cold for 30+ minutes, the meeting proceeded without acknowledgment of the situation.
This phenomenon of VCs dozing off during pitches appears to be more common than one might expect. Mark Pincus, founder of Zynga, recounted a similar experience where a VC fell asleep mid-presentation. He humorously likened the scenario to a blend of Weekend at Bernie’s and Silicon Valley.
Surprisingly, such inattentiveness doesn’t necessarily preclude investment. Liz Wessel, co-founder of WayUp and now a partner at First Round Capital, shared that after a 2015 pitch where one partner slept and another scowled, her team received a term sheet just two hours post-meeting. They declined the offer, much to the VC’s astonishment.
The prevalence of these stories prompted former a16z partner Arianna Simpson to question, Are VCs ok?? Narcolepsy appears to be running rampant.
Beyond inattentiveness, founders have faced more egregious behaviors. Instances of VCs signing term sheets only to withdraw at the last moment, or ghosting founders entirely, have been reported. Adding insult to injury, some of these VCs later acted as if they had invested, requesting company updates or references. One founder even noted a VC’s attempt to claim a share of post-acquisition proceeds.
Travis Kalanick, co-founder of Uber, shared a particularly audacious story. Upon realizing a VC was attempting to leave a meeting prematurely, Kalanick followed him to his car and continued the pitch from the passenger seat.
While many founders have faced such challenges, others report positive interactions with VCs. Some have never encountered issues, and a few even shared commendations for specific investors. Nonetheless, the frequency of negative experiences led Pincus to remark, I fcking love this moment, when founders no longer have to be afraid to call out VCs for dumb behavior.
Among the most striking accounts is that of Matthew Prince, founder of Cloudflare. He revealed that a Sequoia partner declined to invest in Cloudflare, doubting a woman’s capability to lead a security infrastructure company—a reference to co-founder and COO Michelle Zatlyn. Given Cloudflare’s current valuation of $87 billion and projected annual revenue of $2.8 billion in 2026, this judgment has aged poorly.
Prince also recounted an interaction with investor Vinod Khosla, who offered to invest but suggested Prince fire his co-founders and take their stock. Offended, Prince ceased communication and even blocked Khosla’s number. He later reflected that while Khosla is extremely smart/clever and has an impressive track record, he wasn’t the type of personality Prince wished to collaborate with.
Not all of Prince’s stories cast VCs in a negative light. He recalled a meeting with Marc Andreessen, co-founder of venture firm a16z, expecting a casual meet-and-greet. Instead, Andreessen arrived with his entire investment team, ready for a formal pitch. Unprepared, Prince did not secure the investment and humorously mentioned framing the rejection letter he received.
Another anecdote comes from Julie Fredrickson, a founder-turned-investor. Before a meeting at a VC firm’s office, she received a call from an associate warning her about a rock formation visible from the window that resembled male genitalia. This led her to humorously nickname the firm Dickrock Ventures.
While Silicon Valley’s VCs were the primary focus of these stories, founders also shared experiences involving international investors. Some VCs even recounted their own challenges when pitching to limited partners.
These narratives highlight the opaque nature of the fundraising process and the real power dynamics at play. The experiences founders often discuss privately are more widespread than the industry publicly acknowledges.
As Isenberg aptly summarized, If you’re raising right now, just know: every founder has a story like this. The process is weird. The power dynamic is weird.
A secondary takeaway might be: If Andreessen agrees to meet with you, be prepared—he means business.
