The Ledger
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Pishevar spent millions investigating Fusion GPS smear campaign
“It was worth it to me to, you know, spend millions of dollars on a, legal fees and doing the, we filed seven, four, the latest one is against Fusion GPS, and the judge found with us last year, and is gonna force Fusion GPS to say who hired them”
Dan Gill would pass on investing in OpenAI, Anthropic, and xAI
“I wouldn't invest in any of them. I think that the foundational models are trending towards commoditization and it's gonna be difficult to capture all of the gains relative to what, you know, Google, Google can capture and Microsoft can capture and others.”
Benioff: Salesforce Shifted Help.Salesforce.com to 100% AI Agents
“This week, I think I already told you, we turned on help.salesforce.com. I stripped out my previous support infrastructure. I've plugged in a new support infrastructure and it's all 100% agent base.”
Arison disclosed conservative Republican views to Grindr board before becoming CEO
“You know, when I was taking this job, I actually told the big shareholders. At this point, Grant was still private, so they're kind of the owners, like, look, I'm a conservative guy. I'm Republican. I'm also gay. I'm very social like, on on these social issues…”
Jason Citron explains why Discord rejected Microsoft's acquisition offer
“Microsoft has been a really fantastic partner for us. And there certainly are things that we could have done together with them that we can't do independently, but ultimately it was about You know, controlling your own destiny, I suppose, and really seizing th…”
Altman: Product strategy is a personal weakness and current area of uncertainty
“The thing I'm struggling with most this week is I feel more uncertain than I have in the past about what our, like the details of what our product strategy should be. I think that product is a weakness of mine in general and it's something that right now the c…”
Hamid: Invested in Slack at a $250M valuation on $500k ARR
“It was 500 K of ARR at the time... Two hundred fifty million post.”
Wang: SCGE goes long Nvidia and shorts moatless server hardware stocks
“We can go long NVIDIA and then we can short a bunch of the companies that I think don't have the depth of modes that NVIDIA has.”
Wang: Chinese companies have become less transparent over time
“It is, it has been more difficult for us to say invest in Chinese companies. And it's not just the macro, right? It's. It's these companies have been become less transparent with us over time.”
Tinder's executive team threatened to quit unless Sean Rad returned as CEO
“There was one point where the entire executive team, unbeknownst to me, went to the board and basically said, if Sean doesn't come back in the CEO role, we're all quitting.”
Chirls: Asylum Ventures Blacklists Untrustworthy VCs Permanently
“Now there's many folks that I will never work with again. And maybe that doesn't matter to them, but like I think it will. There will be a company, there will be an opportunity where someone wants to work with a company that we work with we'll never work with …”
Maguire received dozens of death threats following October 7
“You know, I've had dozens of death threats, some of which were pretty credible after October seven.”
HubSpot rejected a $3M Facebook deal at $3M ARR to maintain focus
“I mean, I think we're at two, three million in revenue at HubSpot and one rep brought Facebook to the table as a customer. It was like a three million dollar contract. It would have doubled our revenue. And he said, no, we were being pulled, said no.”
Grady: Sequoia rejected a $5B buyout for a now-struggling portfolio company
“There's one in our portfolio now that I'm not going to name, but we had an offer from somebody to buy the company for almost five billion dollars. We own just north of 20%. That would have been a huge home run. Now the company looks like it is, ah, kind of not…”
Vasavada: Vise Leadership Meetings Were Consumed by DEI and Infrastructure
“When we went into our leadership meetings, we weren't talking about we weren't talking about that. We were talking about making infrastructure decisions that will matter in 2026 and rewriting our code to better position ourselves four or five years down the li…”
Hoffman Offered to Cover OpenAI Salaries When Elon Musk Departed
“When Elon had announced to the company that he was leaving and not financing it anymore, and, you know, blah, blah, blah. And, you know, Sam called me, and I said, look, I'll cover the salaries, and on, and he asked me if he joined the board, and I said, yes, …”
Siroker: Limitless rejected 22 $1B offers to accept a $350M Series A
“We had offers, actually, we had 22 offers at a billion dollars. We turned them down and took 350.”
Benioff: Salesforce threatened to pull Dreamforce until San Francisco leaders delivered
“I mean, I had to kind of lay down the gauntlet. You probably saw that. I had to threaten the city and all the leaders and say, if you guys don't get your act together, we're not coming back, and They delivered.”
Lemkin: Multi-Billion Fund Refused 28 Board Meeting Requests for Top Startup
“I have one of my top investments right now, like, I mean, there's a few asterisks and downgrades, but there's nothing not to love, ok? Double digits in ARR, growing triple digits, A very multi-billion dollar fund led the pre-seed, right? Owns 15% of the compan…”
Emad Mostaque: Why I Signed the Open Letter for an AI Pause
“The reason I signed that letter, because I think there's a six month pause to get all of our shit together before things go completely insane, and next year this is everywhere, and everyone's investing in everything, and it's just absolute chaos.”
Socher: Google deranked You.com across all sites, causing immediate traffic drop
“We just got deranked in all our sites from Google and saw like a drop right away.”
Lessin: Slow Ventures avoids Y Combinator deals because they lack signal
“As an investor, you know, we've stayed away from it for a long time, partially because there's no signal in it because everything comes off the factory line looking exactly the same, packaged properly.”
Lemkin rejected a 10-figure secondary offer for his SaaStr fund holdings
“I recently had a conversation with one of my LPs last week about a secondary offer. You know, that was 10 figures, a 10 figure secondary offer, ok? And we both agreed no was the answer.”
Mohnot: VCs who opposed Saudi money are now hypocritically seeking it
“We haven't, but I think it is very hypocritical that all these folks who were anti-Saudi money are now over there just praising everything.”
Stebbings: None of my employees feel or act like owners
“I wish everyone felt like an owner of my businesses, but the truth is, Jen, none of them do. None of them. Only I act like an owner, and that may be unhealthy in many respects, but like, how do you hire this ownership mentality?”
Khosrowshahi: Uber's investment in self-driving division ATG was a mistake
“Where we got it wrong was when we went outside of our core. So for example, we had a very large self-driving business, ATG, trying to develop autonomous tech, and that wasn't what we were passionate about every day, and it was outside of the core, and ultimate…”
Cohen: Navan is seeking Slack alternatives due to declining product quality
“The team right now is looking for alternatives. Not because you know, we love Slack. But you can see that over time, the search works a little bit, you know, worse. The buttons are moving to the wrong places. I care a lot about product and design. And I think …”
Stebbings: Hot seed rounds raised by executive founders consistently underperformed
“I looked at the seeds, and I looked at those that haven't really worked, and all of those that haven't really worked have often been head of product at Twitter, head of product at Twitch, head of product at amazing company, the hottest of hot seed rounds with …”
Meta's Oculus Go failed due to atrocious user retention
“That product was called Oculus Go. It was a 200 dollar VR headset that was built to be kind of your everyday, you know, VR device, and it sold really well, but had absolutely atrocious retention, which means it obviously failed. And, you know, it was basically…”
Armstrong: Internal political activism was a major distraction at Coinbase
“We weren't aligned internally about being apolitical. And we had a small vocal percentage of the company just kind of who thought we should be engaging in all these social issues. So it was a major distraction internally.”
Singerman: Founders Fund never plans or calculates capital reserves for follow-ons
“I don't think about reserves ever. Period. Like, I literally never think, I never think a second about reserves.”
Gerstner: Altimeter invested over 30% of its debut fund into Snowflake
“Our first fund VC won hell. I couldn't even raise it. I was 20 or 25% of the fund. And I put, we put over 30% of that fund in Snowflake at a point in time that the world thought we were crazy.”
Samani: In crypto venture deals, equity will be worth nothing
“Mechanically speaking, with a lot of the private round market deals that get done these days they're legally structured as SAFs, excuse me, as SAFs with token warrants or equity rounds with token warrants, but the primary asset that we believe will have value …”
Shah: Primary angel investing goal is minimizing time, not maximizing returns
“Number one principle of my angel investing is solve for minimizing time, not maximizing return.”
Shah: Zero founder meetings or calls held for angel investments
“No founder calls or founder meetings at all. Even pre-investment, even during the decision process.”
Grinda Auto-Signed All Angel Investment Legal Documents Without Reading Them
“Every document that was ever sent to me, legal document that was sent to me, SPA, anything like company selling, et cetera, I auto-signed, or actually my virtual assistant in the Philippines who had my signature would auto-sign for me all the docs that I never…”
Mac Conwell raised RareBreed Ventures with zero GP capital commitment
“So I have no GP commit. I didn't have the money for it.”
Basecamp does not beta test products or survey users before launch
“This is the thing I think that's so important, and this is why, like, when we build products, we don't beta test them, really, and we, sometimes we get a few people in, but we're not, like, asking people what they think.”
Reber: Selling Wunderlist to Microsoft felt like selling to the enemy
“When I sold Wanderlust, it felt like I'm selling my child to the enemy. I didn't want to get bought by Microsoft. I viewed Microsoft as the enemy, and it was just stupid.”
Jurvetson Has Never Sold a Single Share of Any VC Investment
“In fact, I've never sold a single share of anything I've invested in as a venture capitalist.”
Zeev Ventures keeps little to no follow-on reserves in its funds
“I pretty much do not keep reserves, or keep very, very little, and the reason is, because I do cross-fund, I don't feel that I need to keep reserves, because I can invest from the next fund, if I want to”
Esipov: Top Silicon Valley executive search firm sent 95% male candidate slate
“For example, I am working on several executive searches right now, and the first slate that one of the top tier executive search firms here in the Valley brought me was like, 95% male, and the five percent that was not male were candidates that I had put forwa…”
Khosla: I Avoid Board Meetings Because Most Are a Waste of Time
“I don't go to a lot of board meetings now. I focus on this because I find most Most boards don't operate this way, and a waste of time for the founders.”
Stanton turned down Juul CMO role, calling the company ridiculous
“So Jewel is a ridiculous company. They had approached me while I was working at Color, and Color, as you know, is a health tech company trying to help people stay healthy by understanding their genetics and predispositions to things like cancer, and a recruite…”
Eddy Lu: GOAT faked early seller listings using different Home Depot tiles
“In the beginning, we were the only seller since no seller would wanted to list on code because we were unknown. So what we did is that we went to Home Depot and bought a bunch of different tiles. So you see, you have like the wood tile, those one foot by one f…”
Minted avoids diversity quotas in favor of a meritocratic hiring process
“We're not a company that says we must have this level of diversity at all levels. We are a company that says we must have a bias free and meritocratic process to evaluating sourcing talent and evaluating it.”
Founder Collective avoids pro rata rights due to founder misalignment
“We don't do a lot of Parada for a bunch of reasons, including we don't think In most cases, in many cases, Parada's aligned to the founder, because the problem with Parada is you're always a net buyer of the founder's company, and they're always a net seller.”