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Founders share VC horror stories, and some are naming names

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Asking venture capitalists for investment is a rite of passage for tech founders. This has led to another universal experience: the VC pitching horror story. A massive conversation sharing such stories has taken place all week on X with the comments both funny and infuriating. We read through them all to find the most interesting ones so you don’t have to.

Greg Isenberg, a startup podcaster, newsletter writer, and founder of Late Checkout Studio — a holding company whose previous ventures include a company acquired by WeWork — got the conversation started with a story about a VC falling asleep during a pitch meeting. Isenberg has a large following on X, and his post clearly struck a nerve.

“I was once pitching in a board room at a top 3 VC firm for a $15M Series A. 12 people in the meeting. One of the GPs fully fell asleep. Out cold for 30+ minutes. Nobody acknowledged it. Everyone just kept going,” he shared on X.

VCs sleeping through pitch meetings was far and away the most common horror story shared. Not just drowsing, but full on zonked.

Zynga founder Mark Pincus told his VC-asleep story. “I looked at my friend who set up the meeting and asked if i should keep presenting and she said yes. It was ‘weekend at bernies’ meets Silicon Valley,” he wrote.

Interestingly, falling asleep didn’t mean the VC wouldn’t invest. Multiple founders reported receiving term sheets from partners who’d dozed off during the pitch.

“I once pitched a partnership in 2015 for our Series A where one partner (famous Midas lister) fell asleep & another couldn’t stop scowling. Got a call 2 hrs after the IC that they were sending a term sheet over,” wrote Liz Wessel. Wessel, who co-founded and sold HR startup WayUp and is now a partner at First Round Capital, said her team didn’t take the money — and that the VC was shocked.

There were so many stories about VCs sleeping that former a16z partner Arianna Simpson wrote, “Are VCs ok?? Narcolepsy appears to be running rampant.”

There were, of course, more than a few stories about VCs signing term sheets then pulling out last minute, or ghosting, never wiring the money. The even more galling part? Some of these VCs apparently went on to treat the founders like portfolio companies anyway, asking for company updates or to serve as a reference. One founder said the VC even wanted a share of the post-acquisition proceeds.

Travis Kalanick, the Uber co-founder renowned for his determination, told a story about discovering that a VC was attempting to ghost the meeting and leave the building. Kalanick said he followed the VC to his car and pitched from the passenger’s seat.

Not everyone had bad experiences to report. Some founders said they’ve never had anything but great experiences with VCs, with a few even sharing love stories about specific investors. Yes, most VCs are hardworking, genuinely try to be helpful, and don’t take naps during meetings. But poor experiences are so common that Pincus exclaimed, “I f*cking love this moment, when founders no longer have to be afraid to call out VCs for dumb behavior.”

The most stunning stories

Still, the stories that truly stunned were the ones posted by Cloudflare founder Matthew Prince. “A Sequoia partner passed on Cloudflare because he didn’t think a woman could lead a security infrastructure company,” Prince wrote. The woman in question is Cloudflare’s co-founder and COO Michelle Zatlyn. Given that Cloudflare is now an $87 billion market cap company, with expected annual revenue of $2.8 billion in 2026, the judgment hasn’t aged well.

Sequoia partner, Shaun Maguire, no stranger to controversy over his remarks himself, replied that he’s always admired Zatlyn, and asked Prince to spill the name of the partner who said that. Prince punted, “Maybe over a drink one day. But I bet you have a good guess already.”

But wait, Prince dished more!

He told a story about prominent investor Vinod Khosla, who offered to invest and then, according to Prince’s recollection, suggested that the founder “fire” his co-founders and take their stock. “I think the charitable read was it was a test of my character. But I was so offended that we never spoke again. Literally blocked his number.”

Prince was quick to add nuance about Khosla: “He’s extremely smart/clever. Has been an incredible investor — can’t argue with his track record. Just not the personality I’d choose to work with.”

It’s worth noting that recollections of conversations tend to vary, and we don’t know what Khosla actually said, meant, or remembers. But eyes popped at such open talk about one of the Valley’s most successful, powerful VCs. Many people called Prince’s candor an example of having “FU” money. Prince, of course, is a billionaire these days.

Not all of Prince’s stories cast VCs as the villains. Specifically, he thought he had lined up a simple meet-and-greet on a Monday with Marc Andreessen, the cofounder of venture firm a16z. Instead, Andreessen showed up with his whole investment team, ready to be wowed. The ill-prepared Prince did not impress. “I framed the rejection letter they sent,” he said of the result. Others told similar stories of meetings with Andreessen and his firm.

Perhaps the funniest story came from Julie Fredrickson, a founder-turned-investor, who received a call from a VC associate before arriving at a firm’s office — warning her about a rock formation visible outside the window that, apparently unbeknownst to the investors inside, was shaped like male genitalia. “The firm will forever in my mind be Dickrock Ventures,” she wrote.

While the Valley’s VCs got roasted most heavily, founders shared incidents involving international VCs, too. Some VCs also dished about pitching to limited partner investors.

The threads are worth reading not just for the laughs, but for what they reveal: the fundraising process is opaque, the power dynamic is real, and the experiences that founders whisper about privately are a lot more common than the industry tends to acknowledge publicly.

Perhaps Isenberg explained the moral behind all of these stories best. “If you’re raising right now, just know: every founder has a story like this. The process is weird. The power dynamic is weird,” he wrote.

A second lesson may be: if Andreessen agrees to meet with you, he means business.

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Folarin Balogun Tipped To Join Dominic Solanke At Tottenham Hotspur Later This Month

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AS Monaco of France’s Nigerian-born striker, Folarin Balogun, could be on his way back to London, England, later this month, with the possibility of linking forces with another attacker of the same descent, Dominic Solanke, at Tottenham Hotspur.

Sports247 gathered that Monaco are eager to cash in on the 25-year-old star’s spotlight outing with Team USA at the recent FIFA World Cup, where a bolt of controversy trailed him after his red card against Bosnia was suspended by FIFA’s egg heads.

READ ALSO: Folarin Balogun’s Suspended Red Card Faces Fresh Criticism, As Norway Complain About 2026 World Cup Controversy

Balogun found himself in a storm after he was expelled in the USMNT’s 2-0 win over Bosnia-Herzegovina, only to have it ‘suspended’ by FIFA after US president Donald Trump interfered with a phone call to the world football governing body’s boss, Gianni Infantino.
However, aside from the controversy that painted him and FIFA in a bad light, the former Arsenal youth team player ended up as USA’s top scorer with three goals before their eventual elimination by Belgium, and Monaco are now thinking about making a huge sale with the hitman’s exit.

UK’s Sun Sports disclosed, “Balogun looks likely to leave Monaco this summer. It’s understood that Roberto De Zerbi is looking to add more depth up top to challenge Dominic Solanke, and should the price be right for the former Arsenal youngster, a deal could be on the table.”

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Nigerian airlines may go extinct within 30 days

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The Vice Chairman of the Airline Operators of Nigeria (AON) and Chairman of Air Peace, Allen Onyema, has warned that several domestic airlines could cease operations within the next 30 days unless the Federal Government urgently intervenes in the challenges confronting the aviation industry.

Mr Onyema said the industry is facing an existential crisis driven by high operating costs and multiple financial obligations.

He spoke on Wednesday in Lagos at the launch of Pathways, Pilgrimage & Destiny: The Biography of Alhaji Muneer Bankole, the biography of the founder of Med-View Airline.

“Going into aviation is not a piece of cake. It is an industry that is not very rewarding. It is capital-intensive, yet less rewarding. Today, we are facing a phase that poses existential threats. Except something drastic is done very quickly within the next 30 days, a lot of airlines might go extinct,” Mr Onyema said.

His warning comes amid renewed concerns among Nigerian airline operators over the cost of aviation fuel, multiple regulatory charges, access to financing and the financial obligations imposed on carriers.

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Mr Onyema also criticised the planned picketing of airlines by aviation unions over the non-remittance of the five per cent Ticket Sales Charge (TSC), warning that such action could trigger a wider disruption in domestic air travel.

He said airlines would support one another if any carrier were picketed.

“If they picket any airline, others will go because there’s no need for that. There is nowhere in the world that government agencies use unions to talk about issues of debt.”

The five per cent TSC is a statutory charge collected by the Nigerian Civil Aviation Authority (NCAA) on tickets originating from Nigeria. The authority says the charge is collected under the Civil Aviation Act and shared with other aviation agencies, including the Nigerian Airspace Management Agency, the Nigerian Meteorological Agency, the Nigerian College of Aviation Technology and the Nigerian Safety Investigation Bureau.

The NCAA has also acknowledged challenges surrounding the timely remittance of the charge.

In February, the authority met with AON regarding its requirement that airlines provide advance payment guarantees to ensure the timely remittance of the statutory charge.

The NCAA said the measure was intended to safeguard funds collected from passengers and improve the predictability of funding for aviation agencies. It subsequently deferred implementation of the requirement for 90 days to allow operators to regularise outstanding remittances.

Mr Onyema, however, argued that the financial burden on airlines needed to be addressed through a broader review of government charges and the industry’s operating environment.

“The airlines are not against helping the government generate revenue. But no airline in the world is taxed directly for revenue. The airlines indirectly provide revenue for the government,” he said.

Rising cost pressures

Mr Onyema explained that the industry’s difficulties were not limited to the TSC, citing the capital-intensive nature of airline operations and the high costs of aircraft maintenance and daily operations.

He said the survival of airlines required urgent government action rather than measures that could further increase their financial burden.

“Everybody pities Nigerian airlines, yet nobody wants to do anything about their situation,” he said.

He added that the industry’s history showed how difficult it had been for domestic carriers to remain in business over the long term, noting that more than 50 airlines had exited the Nigerian market over the years.

AON has previously cited the collapse of more than 50 Nigerian airlines over a three-decade period as evidence of the industry’s long-standing financial difficulties.

The sector has continued to face pressure from rising aviation fuel costs, foreign exchange challenges, aircraft maintenance expenses and financing costs.

In June, Mr Onyema warned that airlines were borrowing from banks to purchase aviation fuel and reducing flight frequencies to limit losses. He also called for a review of aviation taxes and charges, particularly the five per cent TSC.

More recently, he said many operators had been forced to scale back operations due to the rising cost of keeping aircraft in service. He also warned that the financial pressure could lead to further airline failures.

Calls for government intervention

Mr Onyema’s latest warning adds to growing calls by airline operators for the government to review the financial and regulatory environment in which domestic carriers operate.

READ ALSO: Nigerian airlines now depend on bank loans as fuel costs soar — Onyema

The AON has previously sought direct engagement with President Bola Tinubu over aviation taxes and charges, arguing that the cumulative burden was undermining the viability of domestic airlines.

Mr Onyema called for an aviation taxes and charges review committee in June to examine the various levies imposed on airlines and recommend measures to improve the industry’s sustainability.

The debate comes as the government continues to defend aviation-sector reforms and the need for airlines to meet their statutory obligations.

The NCAA has said that the five per cent TSC is not an arbitrary levy but a statutory charge collected from passengers and remitted through airlines to fund key aviation agencies.

For airlines, however, the issue is part of a wider concern about the cost of doing business in an industry where aircraft acquisition, maintenance, fuel and financing are largely dollar-denominated.

Mr Onyema said that unless urgent measures were taken to address the pressures facing operators, more airlines could be forced out of business.


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