Author: Zen, PANews

A partner at a16z fell asleep for over 30 minutes on the spot, and you had to grit your teeth and finish presenting the $15 million Series A funding materials to a "conscious" person... This sounds like dark humor, but it's a VC pitch story personally experienced by Greg Isenberg, the founder of Late Checkout and LCA.

Last week, after Greg Isenberg shared this experience on X, it quickly resonated with the Silicon Valley startup community.

“That’s venture capital,” Isenberg said. Founders sometimes fly across the country just to “perform” for a group of people who aren’t necessarily thinking straight. Fundraising is like a dance; sometimes the founder leads, sometimes they follow, and sometimes their partner is already asleep.

He believes almost every founder has a similar story, but they rarely talk about it publicly because they might still need to raise funds in the future and don't want to offend VCs. In fact, Isenberg didn't name any specific firm, only saying it was a top-three venture capital firm. Finally, it was the sleeping partner—Marc Andreessen of a16z—who admitted to the embarrassing incident, jokingly saying: "It's not my fault; it's all the fault of the San Francisco founder who kept telling me I should try 'psychedelic drugs'."

After Isenberg fired the "first shot," many founders and investors also came forward to share their personal experiences in the fundraising process.

Absurd moments at the roadshow

Isenberg's rant spread rapidly and inspired more entrepreneurs to share it because he revealed a rarely discussed aspect of the fundraising process. In the public's imagination, project pitches should be rational, efficient, and dignified business negotiations among elites, but in reality, it's not always like that.

The story of Jack Zhang, co-founder and CEO of Airwallex, is one of the most vivid.

At the height of the SoftBank Vision Fund's frenzy, Jack flew over 30 hours from Melbourne to London for a roadshow while running a 39°C fever. However, the investors arrived late, 90 minutes late, and walked into the meeting room completely barefoot.

When Jack began his formal project presentation, the other party opened a bag of peanuts and listened while munching. About 30 seconds later, the investor interrupted him, asking how much money he wanted to raise. Jack replied $100 million to $150 million, to which the investor immediately said, "I'll give you $300 million, and we can make you the industry leader." The meeting ended just 20 minutes later. Jack later joked that the time he spent getting from Heathrow Airport to his office was longer than the roadshow that would determine the company's future.

The story of this "barefoot master" immediately made Y Combinator partner Tom Blomfield identify with the person. He said he might have seen the same person before, because the person had picked his toes, eaten with his hands, and smoked during meetings, eventually putting out his cigarette in his lunch and then pouring coffee on top to extinguish it.

However, Blomfield has also left a deep impression on entrepreneurs pitching their projects due to some "eccentric" behaviors. Philip Johnston, co-founder and CEO of Starcloud, said that during a Zoom pitch, one of his partners kept tossing peanuts into the air, catching them in his mouth, and then crunching them. Blomfield frankly admitted that the partner was himself and humorously replied, "I thought we agreed not to talk about your YC interview."

Besides these recent generational roadshows, Uber co-founder and former CEO Travis Kalanick also reminisced about an amusing incident from 2001. Before a scheduled meeting, Kalanick intercepted a partner trying to escape outside a VC office and ended up sitting in the passenger seat of the partner's parked Lexus to complete the roadshow. Midway through, the partner, with his large belly, pushed against the steering wheel and grabbed Kalanick's laptop, quickly flipping through the PowerPoint slides. Kalanick concluded with a remark: "The fundraising in 2001 definitely had a special feel to it."

Some stories are more like dark comedies arising from a mismatch between language and context. Dirichlet, co-founder of Sphere Labs, was once asked by existing investors at a dinner to pitch to an ultra-high-net-worth individual with a net worth of over $10 billion who also managed large funds.

The introducer reminded him, "His English isn't very good, but you still need to give him a good presentation." So Dirichlet gave a slow, simplified introduction to the company over 30 to 45 minutes. The other person nodded repeatedly, occasionally saying "Yes," and even ordered a dessert in fairly good English. It wasn't until after dinner, after the handshake and hug, that he realized the other person didn't actually understand a single word of English, except for "Yes" and the Greek yogurt on the menu.

What's more glaring than the absurdity is the power relations.

If going barefoot, eating peanuts, and roadshows in cars have a certain comedic element, then other stories fully demonstrate the inequalities in financing relationships.

Matthew Prince, co-founder and CEO of Cloudflare, mentioned that Cloudflare was initially rejected by a Sequoia partner because the partner did not believe that women could lead a security infrastructure company.

On another occasion, he was introduced to a16z co-founder Marc Andreessen, thinking it was just a casual meeting. Andreessen, however, mistook it for a formal pitch and brought the entire a16z partner team. When someone pointed out that he "didn't look ready," Prince admitted it was true, because he really wasn't prepared, and eventually framed the rejection letter.

Prince also added a story about Vinod Khosla, the founder of Khosla Ventures. When Cloudflare was preparing for its Series C funding round, Khosla submitted a letter of intent to invest and invited Prince, along with co-founders Michelle Zatlyn and Lee Holloway, to dinner.

As dinner drew to a close, Michelle and Lee left to use the restroom. Khosla approached Prince and said he was impressed with him but less optimistic about the other two co-founders. He offered to give Prince all their shares if he were willing to fire them. Prince thought the best-case scenario was a test of character, but he was still deeply offended and subsequently blocked Khosla.

The story of Ryan Petersen, founder and CEO of Flexport, is a somewhat inexplicable misjudgment of the market. During a roadshow, a well-known VC told them that the global logistics market was only $6 billion (actually trillions of dollars). This absurd figure prompted his CFO to retort on the spot: "So you mean this market is smaller than the USB data cable market?"

Ted Benson, head of Figma AI, also recounted his embarrassing experience. When he was starting his first business, he flew to Redmond, and in the middle of a meeting, a VP suddenly interrupted him, asking, "Why am I talking to you? Who do you know that put this meeting on my schedule?" He then added, "This won't be resolved, but you have 15 minutes left. Would you like to chat casually?"

On a more specific financing structure, Mercer CEO Brendan Foody pointed the finger at the so-called "Sequoia scam." He stated that in the past six months, he has seen several cases where Sequoia entered the same financing round with two rounds of funding and two valuations, but the market narrative only emphasized the higher valuation, and the founders then passed this narrative on to employees and angel investors.

Sequoia partner Shaun Maguire later responded that similar situations had occurred about five times in his seven years at Sequoia, but he believed it was unfair to call it a scam. His explanation was that for hot companies, especially AI companies, other investors were willing to pay far more than Sequoia judged. Therefore, Sequoia attempted to separate the "company building partnership" from the "capital price," ultimately resulting in two investments with different valuations at similar timeframes. He emphasized that VC is a long-term game, and deliberately misleading investors is not in the long-term interest.

The aforementioned power dynamics exist not only between VCs and entrepreneurs, but also between investors and VCs. Rick Zullo, founder and managing partner of Equal Ventures, recalled that when he was raising his first fund, an LP requested a meeting at 7 a.m. on a Monday, even though his daughter had been born just two days earlier. He arrived 45 minutes late, ate a breakfast burrito while listening to the meeting, and ultimately said he didn't intend to make any further investments.

Some commentators have described this as a downward cycle of abuse: LPs belittle GPs, GPs belittle founders, and founders then belittle non-founders. Zullo responded that this cycle has no reason to exist. Just because someone treated you badly doesn't give you the right to treat others badly.

When investors truly stand on the founder's side

However, this chain of events sparked by Isenberg is not just a collective indictment of VCs. Many founders also mentioned that the world of fundraising also has investors who are genuinely willing to help their companies, respect their founders, and even change the fate of their companies at crucial moments.

For example, Vinod Khosla, who was accused of "sowing discord" in the previous article, is portrayed in a completely different light by other entrepreneurs.

Derek Andersen, co-founder of Startup Grind and Bevy, recalled that in May 2017, he was only six weeks away from running out of cash. One early morning, he told his wife on the sofa that he was almost out of money and might lose everything. His wife simply said, "You'll figure something out." So he spent the whole night sending emails and praying, and at 1:39 a.m., he emailed Khosla, whom he had only interviewed a few times at Startup Grind and didn't know well.

At 7:34 a.m., Khosla replied to the email and asked for his phone number, then called him from his car on the way to a meeting. Andersen said that the advice and encouragement in that call helped him raise $1 million in six weeks, ultimately saving the company.

Linear co-founder and CEO Karri Saarinen provides another, more complete negative example. He says he hasn't encountered too many unpleasant experiences with VCs; the worst-case scenario is usually that the other party is very polite but clearly uninterested.

After founding Linear, he deliberately kept the company in a "no-funding-needed" state, avoiding pitches and only moving forward when both parties had genuine interest. When Sequoia initially met with him, he clearly stated that he wasn't raising funds, but still brought materials to meet with more partners. After the project pitch, when asked how much he planned to raise, he again stated that he wasn't raising funds. However, a few weeks later, when Linear finally decided to raise funds, Sequoia competed with other interested VCs and ultimately led the seed round.

Similar positive memories also appear in the founder stories of 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 admitted that missing out on Figma was a misjudgment. Because of the failures of several similar products before, he mistakenly believed that no one could succeed in this direction.

Nansen co-founder and CEO Alex Svanevik also said that he has met with more than 100 VCs over the years, and the positive experiences far outweigh the negative ones.

James Cadwallader, co-founder and CEO of Profound, recalls that before their Series B roadshow at Sequoia Capital's Menlo Park last year, his partner Alfred Lin asked him if he needed anything. He said he wanted coffee, and a few minutes later Alfred Lin returned with the coffee himself, without calling an assistant or handing it to anyone else. It was a small gesture, but it was enough to make the founder remember it for a long time before a tense meeting that would determine whether the funding round could proceed.

This Silicon Valley-style fundraising story relay ultimately didn't present a simple conclusion about whether VCs were good or bad; it was more like a collective release of pressure within the startup fundraising ecosystem. Founders recounted absurd, rude, and even humiliating moments, demonstrating that fundraising is never just about matching capital with projects, but also a complex interaction revolving around information, status, trust, and control.

But these stories also illustrate that the relationship between founders and investors isn't limited to this. Good investors may not always be able to invest in every company, nor may they always be able to offer the highest valuation, but they will at least take the entrepreneurs sitting across from them seriously and understand the long-term investment and preparation behind a pitch.

Respect and trust that transcend capital and valuation are the most enduring foundation of Silicon Valley's entrepreneurial stories.

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