Anyone who collects money in Silicon Valley today could publicly settle accounts with their investors tomorrow. At least that’s exactly what several American tech founders are currently doing – and are causing unrest in the startup scene.
The debate was sparked by Greg Isenberg, host of ‘The Startup Ideas Podcast’. Last week on
“12 people in the meeting. One of the GPs was completely asleep. Sound asleep for 30 minutes. No one noticed. Everyone just carried on,” Isenberg wrote, referring to an unnamed general partner.
Isenberg continued his presentation and showed the slides to an investor, whom he described as an “unconscious man in a Herman Miller chair.” “This is risk capital,” he wrote on X.
Different times, different customs
From Travis Kalanick’s perspective, the world of venture capital has changed fundamentally in recent years – pitch discussions used to be much more informal, the Uber founder replied to Isenberg’s post.
Kalanick remembers a fundraising meeting in 2001 that took place not in a conference room but in a parked Lexus. While the founder sat in the passenger seat, the investor took over his laptop.
The investor “grabbed” the computer, placed it “on his big belly,” pressed it against the steering wheel and began clicking through the presentation himself, says Kalanick. “In 2001, fundraising was completely different.”
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“What if you fired them all?”
This exchange spread like wildfire among the niche community of already successful millionaire and billionaire founders who are constantly online. And other founders and CEOs got involved.
Cloudflare CEO Matthew Prince recalls that a Sequoia partner turned down Cloudflare because “he didn’t believe a woman could run a security infrastructure company.”
Prince also reveals that he also once met with Khosla Ventures to discuss investing in Cloudflare’s Series C funding round. Vinod Khosla, the legendary tech investor and namesake of the company, invited Prince and his co-founders to dinner, Prince said.
Towards the end of the conversation, Khosla leaned forward and said: “I’m impressed with you, but not so much with the others. What if you fire her and I give you all her shares?”
Prince said he was so shocked that he never spoke to Khosla again.
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VCs defend themselves in X contributions
Other founders responded to Prince’s post and shared their own experiences with investor Vinod Khosla. The discussion quickly gained momentum – so much so that Khosla spent much of his Saturday making public statements. He responded to the allegations in more than a dozen posts on X.
In some cases he rejected the incidents described and demanded evidence. In most posts, however, he repeated one message above all else: honesty is the best strategy.
“I’m often wrong, but I always give honest opinions. Some find it harsh, but hypocritical politeness hurts founders,” he wrote in a post. “Brutal honesty gives the chance to evaluate and accept or reject the opinion. Great founders choose honesty. Offering brutal honesty is no fun.”
Khosla did not respond to our request for comment.
Other industry representatives rallied behind Vinod Khosla. Early-stage investor and founder Blake Byers referred to Khosla’s extraordinary career. Before he became one of Silicon Valley’s most influential venture capitalists, Khosla co-founded Sun Microsystems, one of the defining technology companies of the early computer industry. “He is one of the most sincere venture capitalists there ever was,” Byers wrote.
“Aha! Your father was a failure!”
Angel investor and robotics expert Mark Cummins also joins the series of unusual investor discussions. During a pitch conversation with a partner at a French venture capital firm, the initial discussion was not about his company, but about his parents’ careers. “‘What did your father do?’ the partner asked me in a strong French accent,” Cummins wrote on X.
When he explained that his father trained as a theoretical physicist before moving into business, the investor replied: “Aha! Your father was a failure!” When Cummins then said that his mother was a biochemist and later became a teacher, the next comment he said was: “A failure too!”
Cummins then tried to steer the conversation back to his company. “I have a hundred employees and we need funding. ‘Would you like to know about my company?'”
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Children and successful start-ups? According to a VC, a no go
Claire Vo also shared an experience that she particularly remembers from conversations with investors. The founder of ChatPRD reports that she was once interrupted by an investor during a pitch. He told her he was glad she wasn’t trying to have children and start a business at the same time.
“I love telling a nightmarish VC story!” wrote Vo.
Later, she also responded to the Vinod Khosla debate. According to her own statements, she turned one of his posts in which he defended himself against the allegations into a “pop-punk hit”.
