The Ledger

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why aren't all 32 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 3 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Assertion Open · timeframe Jun 2036
Stebbings: Menlo to make $10B carry on Anthropic, Founders Fund more on SpaceX
“Menlo will make ten billion dollars in carry Spot will too, plus Founders Fund will make more than that from SpaceX.”
Harry Stebbings Jun 4, 2026 ▶ 1:25:09 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
Opinion
Browder: Large VCs selling secondary shares creates fatal signaling risk
“If Menlo Ventures sell secondary in a company, the company is dead because the signaling risk is, is huge or any firm.”
Josh Browder May 18, 2026 ▶ 1:17:49 Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
Disclosure
Menlo Ventures' Anthropic position is worth over $10 billion
“No, our position is, is north of that, but that's not that you can do the math on what carry usually is.”
Matt Murphy Jul 27, 2026 ▶ 55:02 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Assertion Supported
Lovable scaled from zero to $300M ARR within one year
“Where you see a company go from zero to something like three hundred million in a year. I think we intercepted them around, well, we kind of got, tried to get in when they were around 30, 30 of error, but we around, we did was around one 50.”
Matt Murphy Jul 27, 2026 ▶ 19:18 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Assertion Partly supported
Lemkin: Anthropic publicly warned Menlo Ventures against SPVs last year
“Anthropic last year warned Menlo, one of its best investors and others, enough with the SPVs, they said publicly, enough with the damn SPVs.”
Jason Lemkin May 14, 2026 ▶ 5:48 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
Assertion Not checkable as stated
Anthropic matched ChatGPT performance pre-launch using 1/50th of the capital
“All the benchmarks you could see that they were kind of better or at the same level of performances as ChatGPT at the time. And they'd spent like, I don't know, A 50th of the capital.”
Matt Murphy Jul 27, 2026 ▶ 3:25 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Insight
Outlier venture investments do not require internal partnership dissent
“I don't really ascribe to this point of view where you need like a bunch of no's and there's one person who's a yes, and that leads to an outlier. I know there are examples of that, but that's not really been my experience in the firms I've been part of or wit…”
Matt Murphy Jul 27, 2026 ▶ 54:25 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Insight
VC funds should never sell early stakes in outlier winners
“Like I think if you're a believer, I think more than ever, we're in an environment where your outliers, your winners will compound and drive fund returns. So those are certainly not the ones you want to sell from.”
Matt Murphy Jul 27, 2026 ▶ 14:02 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Assertion Supported
AI startups are reaching $100M revenue in one year
“When we look around and see these companies doing zero to a hundred in a year, never seen anything like it. And there's more examples of that than I can probably count right now.”
Matt Murphy Jul 27, 2026 ▶ 52:15 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Disclosure
Menlo Ventures broke its standard investment criteria to back Anthropic
“And I'll, that's, I'll take you back to our investment in, in Anthropic. Like, same thing. It's like, This doesn't really fit. This isn't what we normally do, but wow, if this works, I mean, you got such a special founder in Dario and an amazing market.”
Matt Murphy Jul 27, 2026 ▶ 44:42 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Disclosure
Menlo Ventures raised its instant seed check limit to $8M
“We've got the specific seed strategy where three partners can, you know, right up to an eight million dollar check, like on the spot that used to, that number used to be three.”
Matt Murphy Jul 27, 2026 ▶ 36:16 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Assertion Contradicted
O'Driscoll: First venture rounds for OpenAI and Anthropic were $23B and $4B
“The first venture round at OpenAI was twenty-three billion pre with Thrive, and the first venture round at Entropic was four billion pre with Spark and Menlo, you know, right?”
Rory O'Driscoll Jan 15, 2026 ▶ 56:40 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Jason Lemkin: AI music startup Suno retains only 20% of customers annually
“They just said they have, they only retained 20% of their customers in a year”
Jason Lemkin Nov 27, 2025 ▶ 55:03 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Assertion Supported
Pishevar: Menlo's $26.5M Uber investment grew to nearly $6.7B
“For twenty million at the time, later I got another six and a half million through secondary for Menlo. So that investment at today's prices is worth almost seven billion dollars.”
Shervin Pishevar Jan 13, 2025 ▶ 12:01 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Disclosure
Pishevar: Menlo Ventures passed on Snapchat seed and Series A rounds
“I, so, I brought Snapchat to Menlo. Evan and I hit it off. I really believe that. I was on it in the first 30 days, because my kids were on it, and so they showed it to me, and I was chasing it, and Evan and I hit it off and unfortunately Menlo passed on the, …”
Shervin Pishevar Jan 13, 2025 ▶ 1:17:37 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Assertion Not checkable as stated
AI developer stack startups are rapidly taking off after early struggles
“So there's so much more there, and I think we started off investing in that area two, three years ago. Nothing really came out of it. Now these companies are really taking off.”
Matt Murphy Jul 27, 2026 ▶ 1:03:37 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Disclosure
Menlo Ventures invested $10M in Anthropic before raising $500M+ SPV
“The first check was a little over 10 and then, you know, the, so that was kind of the starter check because the average, like I said, you try to kind of, you know, venture fund kind of have this kind of narrow window of what you invest, but then the next round…”
Matt Murphy Jul 27, 2026 ▶ 5:16 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Prediction Open · timeframe Jul 2031
Menlo Ventures does not aspire to raise a $10B+ fund
“We don't have a 10 or twenty billion dollar fund, nor do we aspire to have that.”
Matt Murphy Jul 27, 2026 ▶ 8:33 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Disclosure
Menlo's $500M+ Anthropic SPV was the firm's first ever
“Menlo had never done an SPV before. It just happened to be over five hundred million.”
Matt Murphy Jul 27, 2026 ▶ 15:42 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Disclosure
Menlo Anthology fund backed 50+ startups including OpenRouter and Whisper
“Like that's over 50 companies, somewhere between a hundred K and one million where you kind of get in a seed round and the companies that have graduated out of that have been open router, whisper, axiom math.”
Matt Murphy Jul 27, 2026 ▶ 50:14 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Insight
VCs rarely lose deals on valuation alone for top companies
“It's rarely just, like, straight up, you know, valuation, stuff like that. Yes, valuation can be painful. But for the right companies, you know, you do what it takes to be in.”
Matt Murphy Jul 27, 2026 ▶ 49:07 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Insight
Lacking a prior relationship is the main reason VCs lose deals
“The thing that's most often is that you were late to the party, right? Like, you know, you were not intentional enough that this was a company that you wanted to be tracking and building a relationship, so you're coming in, you know, a couple weeks or a month …”
Matt Murphy Jul 27, 2026 ▶ 47:49 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Disclosure
Menlo Ventures signed Anthropic term sheet two weeks after LP meeting
“So we literally came out of that meeting and said, all right, we've got to do this. We've got to figure out a way to lead the round. And two weeks later, We signed a term sheet. We, you know, aggregated all the kind of demand from RLPs and folks we knew and, y…”
Matt Murphy Jul 27, 2026 ▶ 12:07 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Assertion Supported
Lemkin: Menlo Ventures raised a $3B fund following its Anthropic bet
“Menlo just raised a three billion dollar fund after 50 years on the back of a crazy bed in Anthropik that, that, that went very well, right? When the margins were crazy”
Jason Lemkin Jun 25, 2026 ▶ 51:07 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Prediction Partly held up
Lemkin: Menlo Ventures will 10x to 15x its investment in Chime
“They said they did the Series B, right? So they did the Series B at 203 hundred. Maybe we can figure it out on the fly. They're going to, this will be a nine. There'll be some dilution. They'll 10 or 15 X their money, right? That'll be a fun returner or more t…”
Jason Lemkin Jun 5, 2025 ▶ 23:36 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Assertion Open
Pishevar: Closed Uber, Warby Parker, Tumblr, and Machine Zone in 90 days
“In my first 90 days, I closed Uber, Warby Parker Tumblr, and Machine Zone.”
Shervin Pishevar Jan 13, 2025 ▶ 6:26 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
What-if
Pishevar: Deal-by-deal carry yielded higher returns than Menlo's fund carry
“I got more carry than I would have gotten in the fund by agreeing to do deal by deal carry.”
Shervin Pishevar Jan 13, 2025 ▶ 13:08 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Disclosure
Menlo Ventures has invested in approximately seven AI labs
“We have very specific strategy around Neo labs too. We're in about seven of them.”
Matt Murphy Jul 27, 2026 ▶ 37:19 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Disclosure
Menlo Ventures wrote a sub-$50M check for legal AI startup Legora
“The round that just happened, you know, about six months ago. It was like it was kind of sub-fifty, but in that range.”
Matt Murphy Jul 27, 2026 ▶ 31:06 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Disclosure
Menlo Ventures pivoted its investment strategy to focus entirely on AI
“We've pivoted the firm to be all in AI.”
Matt Murphy Jul 27, 2026 ▶ 4:53 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Disclosure
Menlo Ventures has backed about eight drug discovery AI models
“We have about eight of these models. I mentioned Chai, but we have a company I can go down the list of companies building specific models to do drug discovery.”
Matt Murphy Jul 27, 2026 ▶ 1:04:20 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Assertion Supported
RealtyShares surpasses $200 million in funded deals with top VC backing
“RealtyShares recently announced an incredible two hundred million funded deals through the platform, so a huge congratulations to them. For that, and they've also raised funding from some of the world's best investors, including the one and only Union Square V…”
Harry Stebbings Oct 21, 2016 ▶ 0:22 20VC: Why Adaptability Is Key To Fundraising, Why Supply Is Always The First Priority In Marketplaces & Why Sometimes You Have To Hire Fast & Fire Fast with Nav Athwal, Founder & CEO @ RealtyShares
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