Author: Zen, PANews

A partner at a16z fell asleep on the spot for over 30 minutes, while you could only finish presenting a $15 million Series A funding pitch to a person who was "unconscious"… This sounds like dark humor, but it is the true story of a VC roadshow experienced by Greg Isenberg, the founder of Late Checkout and LCA.

Last week, Greg Isenberg shared this experience on X, which quickly resonated within the Silicon Valley startup community.

"This is venture capital," Isenberg stated, noting that founders sometimes fly across the country just to “perform” for a group of people who may not even be awake. Fundraising is like a dance, sometimes the founder leads, sometimes they follow, and sometimes the dance partner has already fallen asleep.

He believes that nearly every founder has a similar story, but few openly discuss it because they might still need to raise funds in the future and do not want to offend VCs. In fact, Isenberg did not name specific firms, only saying it was a top three venture capital firm. In the end, it was that sleeping partner—Marc Andreessen of a16z—who acknowledged the embarrassing incident and joked that it wasn't his fault; it was due to founders in San Francisco constantly telling him to try "psychedelics."

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

Absurd Moments at Roadshows

Isenberg's complaints spread rapidly and prompted more entrepreneurs to share because 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 dignified business negotiations between elites, but in reality, it is not always like that.

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

During the frenzied period of SoftBank Vision Fund, Jack flew for over 30 hours from Melbourne to London while running a high fever of 39°C to pitch. However, the investors arrived late, showing up completely barefoot 90 minutes into the meeting.

When Jack officially began his project pitch, the opposite party opened a bag of peanuts, munching while listening. About 30 seconds later, the investor interrupted him and asked how much money he wanted to raise. Jack replied $100 million to $150 million, and the investor immediately said: "I'll give you $300 million; we can make you the industry leader." Just 20 minutes later, the entire meeting was over. Jack later joked that the time it took him to get from Heathrow Airport to the office was longer than this meeting that decided the company's future.

The story of this "barefoot master" immediately resonated with Y Combinator partner Tom Blomfield. He said he might have seen the same person because the individual had been picking their toes, grabbing food with their hands, smoking, and finally extinguishing the cigarette in their lunch, then pouring coffee over it to put it out.

However, Blomfield also left a profound impression on the presenting entrepreneur due to some "quirky" behavior. Philip Johnston, co-founder and CEO of Starcloud, mentioned that during a Zoom pitch, one partner spent the entire time throwing peanuts into the air, catching them with his mouth, and then crunching them. Blomfield candidly admitted that the partner was himself, humorously replying: "I thought we agreed not to talk about your interview at YC."

Besides these modern roadshow anecdotes, Uber co-founder and former CEO Travis Kalanick recalled a humorous incident from as far back as 2001. Before a scheduled meeting, Kalanick intercepted a partner attempting to escape at the VC's office door, and ended up completing the pitch sitting in the passenger seat of the partner's Lexus. Midway, the partner's big belly was pressing against the steering wheel, and he even grabbed Kalanick's laptop to quickly flip through the PPT. Kalanick ultimately left with one remark: "The fundraising in 2001 was indeed quite a feeling."

Some stories resemble dark comedies created by language and situational mismatches. Dirichlet, co-founder of Sphere Labs, was once asked during a dinner by existing investors to pitch to a high-net-worth individual managing a large fund with a net worth exceeding $10 billion.

The introducer reminded him: "His English is not very good, but you still have to do a good pitch." So, Dirichlet slowly and simplistically introduced the company for 30 to 45 minutes, with the individual nodding continuously and occasionally saying "Yes," while also ordering a dessert in reasonably good English. It wasn't until the dinner ended, complete with handshakes and hugs, that he realized the person actually understood not a single English word except for "Yes" and the Greek yogurt on the menu.

More Eye-Catching than Absurdity is the Power Dynamics

If going barefoot, eating peanuts, and pitching in a car carry a comedic undertone, then other stories vividly showcase the inequality in fundraising relationships.

Matthew Prince, co-founder and CEO of Cloudflare, mentioned that Cloudflare was once rejected by a Sequoia partner on the grounds that he did not believe a woman 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, only to find that Andreessen thought 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 because he had not prepared, and he eventually framed that rejection letter.

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

As the dinner was nearing its end, Michelle and Lee left to go to the restroom, and Khosla leaned over to Prince and said he was impressed with Prince, but was not optimistic about the other two co-founders. If Prince was willing to fire them, he could give their shares to Prince. Prince found that the most benign explanation could perhaps be that it was a character test, but he was still deeply offended and subsequently blocked Khosla.

The story from Ryan Petersen, founder and CEO of Flexport, illustrates some inexplicable market misjudgments. During a pitch, a well-known VC told them the global logistics market size was only $6 billion (in reality, it is worth trillions of dollars). This absurd figure prompted his CFO to ask 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 awkward experience. When he first started his business, he flew to Redmond, and during the meeting, a VP suddenly interrupted him, asking: "Why am I talking to you? Who do you know that got this meeting on my calendar?" Later, he added: there wouldn't be any outcome from this, but you still have 15 minutes; do you want to chat a bit?

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

Sequoia partner Shaun Maguire later responded that similar situations had occurred about five times since he joined Sequoia seven years ago, but he believes calling it a scam is unfair. His explanation is that for popular companies, especially AI companies, other investors are willing to pay significantly more than Sequoia's valuation, leading Sequoia to attempt to separate "company building partners" from "capital price," ultimately resulting in two investments with valuations close to each other over time. He emphasized that VCs are in for the long-term game, and intentional deception does not serve long-term interests.

The aforementioned power dynamics do not only exist between VCs and founders but also between funders and VCs. Rick Zullo, founder and managing partner of Equal Ventures, recalled when he was raising his first fund, one LP requested a meeting at 7 a.m. on Monday morning, just two days after his daughter was born. The person arrived 45 minutes late, listening to the meeting while eating a breakfast burrito, and ultimately said he did not intend to make a new investment.

Some commented that this is a downward transmission of abuse: LPs belittling GPs, GPs belittling founders, and founders belittling non-founders. Zullo responded that this cycle has no reason to exist. Just because others were rude to him does not mean he has the right to be rude to others.

When Investors Truly Stand by Founders

However, this relay initiated by Isenberg is not merely a collective accusation against VCs. Many founders also mentioned that within the fundraising world, there are those who genuinely want to help companies, respect founders, and even change the fate of companies at critical moments.

For example, Vinod Khosla, who was earlier portrayed as "stirring discord," presents a completely different image in the words of other entrepreneurs.

Derek Andersen, co-founder of Startup Grind and Bevy, recalled that in May 2017, he had only six weeks left before running out of cash. One early morning, he told his wife while on the couch that he was almost out of money and might lose everything. His wife just said, "You'll figure it out." So he spent the entire night sending emails and praying, finally sending an email at 1:39 a.m. to Khosla, whom he had only interviewed a few times at Startup Grind and did not know well.

At 7:34 a.m., Khosla replied to the email, asking for a phone call, and then called him while on his way to a meeting. Andersen said the advice and encouragement during that call helped him secure $1 million in funding within six weeks, ultimately saving the company.

Karri Saarinen, co-founder and CEO of Linear, provided another more comprehensive counterexample. He mentioned that he did not encounter many frustrating experiences regarding VCs; the worst case was usually just that they were very polite but clearly uninterested.

After founding Linear, he intentionally kept the company in a "no need for funding" state, avoiding pitches unless both parties had genuine interest. When Sequoia initially scheduled a meeting with him, he clearly stated that he was not fundraising but still brought materials to meet more partners. After the project pitch, they asked how much he planned to raise, and he reiterated that he was not fundraising. However, 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 appeared in the stories of the founders of Figma, Nansen, and Profound.

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

Alex Svanevik, co-founder and CEO of Nansen, also stated that over the years, he had encountered more than 100 VCs, with positive experiences far outweighing negative ones.

James Cadwallader, co-founder and CEO of Profound, remembered that before the B round roadshow at Sequoia's Menlo Park last year, partner Alfred Lin asked him if he needed anything. He said he wanted coffee, and a few minutes later, Alfred Lin personally returned with coffee, without asking an assistant or handing it to someone else. It was just a small gesture, but before a tense meeting that would determine the progress of funding, it was enough to leave a lasting impression on founders.

Ultimately, the relay of Silicon Valley funding stories presented is not a simple conclusion of good versus bad VCs; rather, it serves as a collective release valve for the entrepreneurial funding ecosystem. Founders recounting those absurd, disrespectful, or even humiliating moments reveal that fundraising is never just a matching of capital with a project, but a complex interaction surrounding information, status, trust, and control.

Yet 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 or provide the highest valuations, but they will at least take the entrepreneur sitting across from them seriously and understand the long-term investment and preparation behind a roadshow.

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

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