By: Zen, PANews
An a16z partner fell asleep on the spot for over 30 minutes, and you have to grit your teeth and finish presenting your Series A materials, worth $15 million, to a person who is "unconscious"... This sounds like dark humor, but it's a real VC pitch story experienced by Greg Isenberg, founder of Late Checkout and LCA.
Last week, after Greg Isenberg shared this experience on X, it quickly resonated within the Silicon Valley startup community.
"This is venture capital," Isenberg said, noting that founders sometimes fly across the entire country just to "perform" for a group of people who aren't necessarily alert. Fundraising is like a dance; sometimes the founder leads, sometimes follows, and sometimes the dance partner is already asleep.
He believes almost every founder has a similar story, but people rarely talk about them publicly because they might need to raise funds again in the future and can't afford to offend VCs. In fact, Isenberg did not name the specific firm, only saying it was a top-three venture capital firm. In the end, it was the sleeping partner himself—Marc Andreessen of a16z—who proactively admitted to the embarrassing incident, jokingly blaming it on founders in San Francisco who kept telling him he should try "psychedelics."
After Isenberg fired the "first shot," many other founders and investors have come forward to share their own personal experiences during the fundraising process.
Absurd Moments in the Pitch Room
The reason Isenberg's rant spread quickly and prompted more entrepreneurs to share is that he revealed a side of the fundraising process that is rarely described publicly. In the common imagination, a project pitch should be a rational, efficient, and respectable business negotiation among elites, but in reality, it's not always the case.
The story of Airwallex Co-founder and CEO Jack Zhang is one of the most vivid scenes.
During the most feverish period of the SoftBank Vision Fund, Jack once flew over 30 hours from Melbourne to London to pitch while running a 39°C fever. However, the investor arrived late, walking into the conference room completely barefoot after being 90 minutes behind schedule.
As Jack began his formal presentation, the other party opened a bag of peanuts, chewing while listening. About 30 seconds later, the investor interrupted him to ask how much he wanted to raise. Jack answered $100 to $150 million. The investor directly said, "I'll give you $300 million. We can make you the industry leader." The entire meeting ended just 20 minutes later. Jack later joked that the time it took him to get from Heathrow Airport to the office was longer than this pitch that determined his company's future.
This story of the "Barefoot Sage" immediately made Y Combinator partner Tom Blomfield feel addressed. He said he might have met the same person, as the individual had picked his feet, eaten with his hands, smoked during a meeting, and finally stubbed out the cigarette in his lunch, then poured coffee on it to put it out.
However, Blomfield himself has also left a deep impression on pitching entrepreneurs with some "quirky" behavior. Starcloud Co-founder and CEO Philip Johnston claimed that during a Zoom pitch, one partner spent the entire time tossing peanuts into the air, catching them in his mouth, and then crunching on them. Blomfield frankly admitted that partner was himself and humorously replied, "I thought we agreed we wouldn't talk about your YC interview."
Besides these more recent next-gen pitches, Uber Co-founder and former CEO Travis Kalanick also came out to reminisce about his own anecdote from as early as 2001. Before a scheduled meeting was about to start, Kalanick intercepted a partner who was trying to escape outside the VC's office, and ultimately completed the pitch in the passenger seat of the partner's parked Lexus. Midway, the partner's large belly pressed against the steering wheel, and he grabbed Kalanick's laptop to quickly flip through the PPT himself. Kalanick left only one sigh: "Fundraising in 2001, it really had a special feel."
Other stories are more like black comedies born from misaligned language and situations. Sphere Labs Co-founder Dirichlet was once asked by an existing investor to pitch to an ultra-high-net-worth individual with a fortune exceeding $10 billion, who also managed a large fund, during a dinner.
The introducer reminded him: "His English isn't great, but you still need to give him a good pitch." So Dirichlet spent 30 to 45 minutes introducing the company slowly and in simplified terms. The other party kept nodding, occasionally saying "Yes," and even ordered a dessert in fairly decent English. It wasn't until after the dinner ended, with handshakes and hugs, that he learned the other person didn't actually understand a single English word except for "Yes" and the Greek yogurt on the menu.
More Glaring than the Absurdity is the Power Dynamic
If bare feet, eating peanuts, and car pitches still carry a certain comic flair, other stories fully expose the inequality in the fundraising relationship.
Cloudflare Co-founder and CEO Matthew Prince mentioned that Cloudflare was once rejected early on by a Sequoia partner because the other party didn't believe women could lead a security infrastructure company.
Another time, he was introduced to a16z Co-founder Marc Andreessen, thinking it was just a casual meeting, but Andreessen thought it was a formal pitch and brought the entire a16z partnership team. When someone pointed out he "didn't seem prepared," Prince admitted it was true because he genuinely hadn't prepared, and he ultimately framed that rejection letter.
Prince also added a story about Khosla Ventures founder Vinod Khosla. When Cloudflare was preparing its Series C round, Khosla had given a term sheet and invited Prince, along with the other two co-founders, Michelle Zatlyn and Lee Holloway, to dinner.
Near the end of the dinner, as Michelle and Lee left for the restroom, Khosla leaned over and told Prince that he was impressed with Prince but wasn't as optimistic about the other two co-founders. If Prince was willing to fire them, he could give their equity to Prince. Prince believed the kindest interpretation was that it might have been a character test, but he was still deeply offended and subsequently blocked Khosla.
The story of Flexport Founder and CEO Ryan Petersen involves some inexplicable market misjudgment. During one pitch, a well-known VC told them the global logistics market was only $6 billion (in reality, it's trillions). This absurd number prompted his CFO to retort on the spot: "So you're saying this market is smaller than the USB cable market?"
Figma AI lead Ted Benson also recounted his awkward experience. During his first startup, he flew to Redmond. Mid-meeting, a VP suddenly interrupted him, asking, "Why am I talking to you? Who do you know that got this meeting on my calendar?" Then added: This isn't going anywhere, but you have 15 minutes left, want to just chat?
On more specific funding structures, Mercor CEO Brendan Foody pointed the finger at the so-called "Sequoia scam." He claimed that in the past 6 months, he had seen several cases where Sequoia entered the same funding round with two tranches of capital at two different valuations, but the market narrative only emphasized the higher valuation, which founders then passed on to employees and angel investors.
Sequoia partner Shaun Maguire later responded, saying similar situations had happened about 5 times in the 7 years since he joined Sequoia, but he believed calling it a scam was unfair. His explanation was that for hot companies, especially AI companies, other investors were willing to pay prices far above Sequoia's judgment. Therefore, Sequoia tried to separate "company-building partnership" from "capital price," ultimately resulting in two investments with different valuations close in time. He emphasized that VC is a long-term game, and intentionally misleading doesn't align with long-term interests.
This power dynamic doesn't only exist between VCs and entrepreneurs but also between LPs and VCs. Equal Ventures Founder and Managing Partner Rick Zullo recalled that when raising his first fund, an LP demanded a meeting at 7 a.m. on a Monday, just two days after his daughter was born. The LP was 45 minutes late, listened to the meeting while eating a breakfast burrito, and finally said he wasn't planning to make any new investments.
Someone commented that this is the downward transmission of abuse: LPs belittle GPs, GPs belittle founders, and founders then belittle non-founders. Zullo responded that there's no reason for this cycle to exist. Just because someone was once an asshole to you doesn't mean you have the right to be an asshole to others.
When Investors Truly Side with the Founder
However, this chain reaction sparked by Isenberg wasn't just a collective indictment of VCs. Many founders also mentioned that in the world of fundraising, there are also investors who are genuinely willing to help the company, respect the founders, and even change the company's fate at critical moments.
For example, the Vinod Khosla who tried to "drive a wedge" in the story above presents a completely different image in other entrepreneurs' accounts.
Startup Grind and Bevy Co-founder Derek Andersen recalled that in May 2017, he was just 6 weeks away from running out of cash. One early morning, he told his wife on the couch that he was almost out of money and might lose everything. His wife simply said, "You'll figure it out." So he spent the whole night sending emails, praying, and at 1:39 a.m., sent an email to Khosla, whom he had only interviewed a few times at Startup Grind and wasn't close with.
At 7:34 a.m., Khosla replied to the email, asked for a phone number, and called him later while on his way to a meeting. Andersen said the advice and encouragement from that call helped him raise $1 million within those 6 weeks, ultimately saving the company.
Linear Co-founder and CEO Karri Saarinen provided another, more complete positive example. He said he hadn't encountered too many bad things about VCs; the worst usually was just the other party being very polite but clearly uninterested.
After founding Linear, he deliberately kept the company in a state of "not needing to raise funds," not casually accepting pitches, and only proceeding when both sides had genuine interest. When Sequoia first asked to meet him, he clearly stated he wasn't fundraising but still brought materials to meet more partners. After the pitch, they asked how much he planned to raise, and he again stated he wasn't fundraising. A few weeks later, when Linear truly decided to raise, Sequoia competed with other interested VCs and ultimately led the seed round.
Similar positive memories also appear in the stories of founders from Figma, Nansen, and Profound.
Figma Co-founder and CEO Dylan Field recalled that when Figma raised its seed round in 2013, most people didn't understand the product, but most of the people he met were very friendly. Reddit Co-founder Alexis Ohanian also came forward to admit that missing Figma was his own misjudgment. Because several similar products had failed before, he mistakenly thought no one could succeed in this direction.
Nansen Co-founder and CEO Alex Svanevik also said that over the years, he had met over 100 VCs, and positive experiences far outweighed negative ones.
Profound Co-founder and CEO James Cadwallader remembered that last year before his Series B pitch at Sequoia's Menlo Park office, partner Alfred Lin asked him if he needed anything. He said he wanted coffee, and a few minutes later, Alfred Lin personally brought back the coffee, without calling an assistant or handing it to someone else. It was just a very small gesture, but before a tense meeting that determined whether funding would proceed, it was enough for a founder to remember for a long time.
In the end, this Silicon Valley-style chain of fundraising stories doesn't present a simple conclusion of whether VCs are good or bad. It's more like a collective pressure release for the startup fundraising ecosystem. Founders recount those absurd, rude, and even humiliating moments, revealing that fundraising is never just about matching capital with projects; it's also a complex interaction revolving around information, status, trust, and control.
But these stories also show that the relationship between founders and investors doesn't have to be this way. Good investors may not always back every company or offer the highest valuation, but they at least treat the entrepreneur sitting across from them seriously, understanding the long-term effort and preparation behind a pitch.
Respect and trust that go beyond capital and valuation are the most enduring undertones in Silicon Valley's startup stories.
