Beyond respect and trust in capital and valuation, this is the most enduring backdrop of Silicon Valley's entrepreneurial stories.

Written by: Zen, PANews

a16z's partner fell asleep for more than 30 minutes, and you can only talk through a $15 million Series A funding material at a "unconscious" person... This sounds like dark humor, but it is the personal experience of Greg Isenberg, founder of Late Checkout and LCA, during a VC pitch.

Last week, after Greg Isenberg shared this experience on X, it quickly resonated in the Silicon Valley entrepreneurial circle.

"This is venture capital," Isenberg said, founders sometimes fly across the country just to "perform" for a group of people who are not necessarily awake. Fundraising is like a dance; sometimes the founder leads, sometimes they follow, and sometimes the partner has already fallen asleep.

He thinks almost every founder has a similar story, but few openly discuss it because they may continue fundraising in the future and cannot offend the VCs. In fact, Isenberg did not name specific institutions, just mentioning it's a top-three venture capital firm. In the end, it was that sleeping partner — a16z's Marc Andreessen who took the initiative to admit this embarrassing moment and joked: it's not his fault, it's all because the founders in San Francisco have been telling him to try "psychedelics."

After Isenberg fired the "first shot," many founders and investors also stood up to share their personal experiences during the fundraising process.

Absurd Moments During the Roadshow

The reason Isenberg's complaints spread quickly and triggered more entrepreneurs to share is that he unveiled a side of the fundraising process that is rarely publicly described. In the imagination of ordinary people, project roadshows should be rational, efficient, and decent business negotiations between elites, but in reality, it is not always the case.

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

During the most fervent period of the SoftBank Vision Fund, Jack had a high fever of 39°C and flew for over 30 hours from Melbourne to London for a roadshow. However, the investors showed up late, arriving 90 minutes later, walking completely barefoot into the meeting room.

When Jack started the project presentation, the other side opened a bag of peanuts, chewing while listening. About 30 seconds later, the investor interrupted him and asked how much he wanted to raise. Jack replied $100 million to $150 million, and the other party directly said, "I’ll give you $300 million, we can make you the industry leader." Just 20 minutes later, the whole meeting was over. Jack later joked that the time he spent rushing from Heathrow Airport to the office was longer than this roadshow that decided the company's future.

This "barefoot master" story immediately resonated with Y Combinator partner Tom Blomfield. He said he might have seen the same person, as that person once picked their feet during a meeting, grabbed food with their hands, smoked, and finally extinguished the cigarette in the lunch, then poured coffee to put out the cigarette.

However, Blomfield also left a deep impression on startup founders due to some "quirky" behaviors during project pitches. Starcloud co-founder and CEO Philip Johnston mentioned that he once pitched on Zoom, during which a partner spent the entire time tossing peanuts into the air and catching them in their mouth, crunching away. Blomfield honestly admitted that this partner was himself and humorously replied, "I thought we agreed not to talk about your YC interview."

In addition to these recent new generation roadshows, Uber co-founder and former CEO Travis Kalanick also recalled his interesting story from 2001. Before a scheduled meeting, Kalanick intercepted a partner trying to escape at the VC office door, ultimately completing the roadshow from the front 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. Kalanick finally left with a sigh: "The fundraising in 2001 definitely had a special feeling."

Some stories are more like the dark comedy created by a mismatch of language and context. Sphere Labs co-founder Dirichlet was asked during a dinner by existing investors to pitch to an ultra-high-net-worth individual with a net worth of over $10 billion who manages a large fund.

The introducer reminded him, "His English is not good, but you still need to do a good pitch." So, Dirichlet slowly and simply introduced the company for 30 to 45 minutes, and the other party kept nodding, occasionally saying "Yes," even ordering a dessert in fairly decent English. It was only after the dinner concluded, with handshakes and hugs, that he realized the other party did not understand a single English word apart from "Yes" and that Greek yogurt on the menu.

More Eye-Popping Than Absurdity Is Power Dynamics

If bare feet, eating peanuts, and pitching in the car still carry a sense of comedy, then other stories fully showcase the inequities in fundraising relationships.

Cloudflare co-founder and CEO Matthew Prince mentioned that Cloudflare was once rejected by a Sequoia partner because he did not believe 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, but Andreessen assumed it was a formal roadshow and brought the entire a16z partner team. When someone pointed out that he "didn't seem prepared," Prince admitted this was true, as he hadn’t prepared and ultimately framed that rejection letter.

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

As dinner was nearing its end, Michelle and Lee left to use the restroom, and Khosla leaned over to Prince saying that he was impressed by Prince but not too optimistic about the other two co-founders, and if Prince was willing to fire them, he could give Prince their shares. Prince thought the most charitable explanation was that this might be a character test, but he still felt deeply offended and subsequently blacklisted Khosla.

Flexport founder and CEO Ryan Petersen's story involves a somewhat inexplicable market misjudgment. During one roadshow, a well-known VC told them that the global logistics market size was only $6 billion (while it is actually in the trillions of dollars). This ridiculous number made his CFO ask on the spot, "So you mean this market is smaller than the USB data cable market?"

Figma AI lead Ted Benson also described his awkward experience. When he started his first venture and flew to Redmond, during a meeting, a VP suddenly interrupted him, asking, "Why am I talking to you? Who do you know that put this meeting on my calendar?" Then added: this won't have results, but you have 15 minutes; want to chat?

In more specific funding structures, Mercor CEO Brendan Foody pointed fingers at the so-called "Sequoia scam." He stated that in the past six months, he has seen several cases where Sequoia entered the same round of funding with two batches of funds and two valuations, but the market narrative only emphasized the higher valuation, which the founders then conveyed to employees and angel investors.

Sequoia partner Shaun Maguire later responded that similar situations had occurred about five times during his seven years with Sequoia, but he believed labeling it as a scam was unfair. His explanation was that for popular companies, especially AI companies, other investors are willing to pay far above Sequoia's valuation, so Sequoia tried to separate "company-building partners" and "capital price," ultimately leading to two investments with different valuations close in time. He emphasized that VCs play a long game, and intentional misdirection does not align with long-term interests.

The aforementioned power dynamics exist not only between VCs and founders but also between funders and VCs. Equal Ventures founder and managing partner Rick Zullo recalled that when he raised his first fund, one LP required to meet at 7 AM on Monday morning, while his daughter had just been born two days prior. The other party arrived 45 minutes late, eating a breakfast burrito while listening to the meeting, and ultimately said they did not intend to make an additional investment.

Some have commented that this is downward transmission of abuse: LPs devalue GPs, GPs devalue founders, and founders then devalue non-founders. Zullo responded that this cycle has no reason for existence. Just because others were jerks to him does not give him the right to be a jerk to others.

When Investors Truly Stand by Founders

However, this chain reaction triggered by Isenberg is not just a collective complaint against VCs. Many founders also mentioned that there are indeed investors in the fundraising world who genuinely want to help the company, respect founders, and even change the fate of the company at critical moments.

For example, the Vinod Khosla who was previously "sowing discord" appears in a completely different light in the words of other entrepreneurs.

Startup Grind and Bevy co-founder Derek Andersen recalled that in May 2017, he had only six weeks left before running out of cash. One morning, he told his wife while sitting on the couch that he was running out of money and might lose everything. His wife simply said, "You’ll figure it out." So he sent emails all night, prayed, and at 1:39 AM sent an email to Khosla, whom he had only interviewed a few times at Startup Grind and did not know very well.

At 7:34 AM, Khosla replied and requested a phone call, and then called him while driving to a meeting. Andersen said the advice and encouragement from that phone call helped him raise $1 million within six weeks, ultimately saving the company.

Linear co-founder and CEO Karri Saarinen provided another more complete counter-example. He said he hasn’t encountered many distressing matters regarding VCs; the worst situation usually involves being very polite but clearly uninterested.

After founding Linear, he deliberately kept the company in a "non-funding needed" state, only participating in pitches when both parties had genuine interest. When Sequoia initially asked to meet him, he clearly stated that he was not raising funds but still brought materials to meet more partners. After the project roadshow, the other party asked how much he intended to raise; he again indicated he wasn’t fundraising. 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 stories of the founders of Figma, Nansen, and Profound.

Figma co-founder and CEO Dylan Field recalled that in 2013, when Figma was raising its seed round, most people did not understand the product, but most of those he met were very friendly. Reddit co-founder Alexis Ohanian also came out to admit that missing Figma was his misjudgment. Because several similar products had failed previously, he mistakenly thought that no one could succeed in this direction.

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

Profound co-founder and CEO James Cadwallader remembered that before the roadshow for Series B at Sequoia Menlo Park last year, partner Alfred Lin asked him if he needed anything. He said he wanted coffee, and minutes later, Alfred Lin personally brought the coffee back, without calling an assistant or handing it to someone else. This was just a small gesture, but before a tense meeting that would determine whether funding could proceed, it was enough to make a founder remember for a long time.

The Silicon Valley-themed fundraising story relay ultimately presents not a simple conclusion of whether VCs are good or bad but more like a collective pressure release of the entrepreneurial funding ecology. Founders recount those absurd, rude, and even humiliating moments, demonstrating that fundraising is never just about matching capital and projects; it is a complex interaction revolving around information, status, trust, and control.

But these stories also indicate that the relationship between founders and investors does not have to be this way. Good investors may not always invest in every company and may not always give the highest valuation, but they will at least take the entrepreneurs sitting across from them seriously and understand the long-term commitment and preparation behind a roadshow.

Beyond respect and trust in capital and valuation, this is the most enduring backdrop of Silicon Valley's entrepreneurial stories.