# Who Is Selling as Venture Liquidity Arrives Through Secondaries and Retail Funds - The VC Read - Week of October 8, 2026 > The VC Read for the week of October 1 to October 8, 2026. Podcast synthesis on venture's new liquidity: Oura's pulled IPO and insider selling, Hans Swildens on a 170 billion dollar secondary market, Paul Kedrosky and Scott Galloway on insiders unloading shares, the retail fund wrappers, and Instinct, World Labs, Bessemer and OpenAI in the signals. ## The VC Read ### Week of October 8, 2026: Who's Selling? --- *Venture finally has its liquidity: secondaries, retail funds and a $2 trillion IPO. This week's podcasts asked the uncomfortable follow-up: who is on the other side of the trade?* *Week of October 1 – October 8, 2026* On Wednesday, September 30, Oura was supposed to price its IPO. It had everything a banker asks for. Morgan Stanley, Goldman Sachs and JPMorgan ran the deal. The company is profitable, consumers know the brand, and the S&P 500 was sitting about 1.4% off its all-time high. Then, a night or two before pricing, Oura pulled the deal and blamed "market conditions." On 20VC, Rory O'Driscoll of Scale Venture Partners, who owns a stake in Oura, said he was "a bit bemused, to be honest." He had a theory about what went wrong, though, and it's the thread running through this week's issue. When Oura first filed, one of its largest investors, Forerunner, said it planned to sell its *entire* position in the IPO. > *"I'd never seen someone in an IPO being able to sell all their position... it's always harder to get a deal done when there's secondary action. And the more secondary action there is, the harder it is to get a deal done."* > > Rory O'Driscoll, 20VC, "Instinct Raises $1B at $10B Valuation | AMD Buys Fei-Fei Li's World Labs for $8.2B | ... Oura Pulls IPO & Nubank Eyes $8–12B Monzo Takeover" (Oct 1, 2026) That one deal sums up where venture stands this fall. After four years of complaining that nobody could get money out, the industry suddenly has more ways to cash out than ever. There are secondary funds, employee tender offers, continuation vehicles, listed funds that sell retail investors slices of private AI companies, and the largest IPO ever attempted, currently set for November. More and more of the money changing hands is insiders selling, not companies raising. So the debate this week was not "will the exit window open?" It's open. The question was whether this new plumbing is the venture industry growing up, or an elaborate way of handing the riskiest paper to whoever arrives last. A quick housekeeping note. Anthropic's S-1 has **still not been publicly filed**. Everything discussed this week comes from the confidential draft that leaked to Reuters on September 28, which we covered in depth last week. I've deliberately *not* re-run those numbers as the lead. What changed this week is how people talk about the deal: they've moved from "what does Anthropic earn?" to "who is selling, and to whom?" --- ## The Big Debate: Is venture's new liquidity a revolution, or an exit door for insiders? ### The case that this is the industry growing up The strongest version of the bull case came from someone who has done this for 26 years. Hans Swildens founded Industry Ventures, one of the first firms built to buy venture stakes from people who want out. He sold it to Goldman Sachs Asset Management in January 2026, and on Goldman's *Exchanges* podcast this week he laid out why he thinks the secondary market is becoming as important as the primary one. (A secondary is a purchase of existing shares from an investor or employee. A primary is new money going into the company.) His numbers describe an industry that has been badly blocked up: * **The average venture-backed company now takes 14 years to go public.** Funds are typically built to return money in ten. * **Payouts to fund investors have more than halved.** Distributions to limited partners (LPs, the pension funds and endowments that back VC funds) used to run around **20% of fund value a year**. Over the last five years they've averaged **5% to 10%**. * **The value trapped inside older funds is enormous.** Swildens cited McKinsey's estimate of over **$1 trillion** sitting in prior-vintage venture funds, and others' estimates of over **$3 trillion**. Even a healthy 50 IPOs a year can't return that much. * **The secondary market will do about $170 billion this year**, against a primary market that "might even do a trillion" in 2026 and averaged $300–500 billion over the past decade. In every other asset class, he noted, the secondary market ends up bigger than the primary one. He thinks venture is heading the same way. > *"There's so much capital sitting in the system that even a few IPOs, or let's say it normalizes to 50 or so IPOs per year, it's not enough liquidity to give back all the capital into the market."* > > Hans Swildens, Exchanges, "Inside the Revival of Venture Capital Liquidity with an Industry Pioneer" (Oct 6, 2026) He also pointed to something new: **secondaries of secondaries.** Buyers who bought stakes on the secondary market are now selling them on to someone else, which "historically had never happened." In his view, that's what a maturing market looks like, not a frothy one. More trades mean more price transparency, and transparency gets more buyers and sellers comfortable doing deals. The second part of the bull case is that the public market, when these companies finally get there, may be a *better* owner than the private one. Jack Altman of Benchmark, guesting on 20VC, made that point directly: > *"I actually think that the public market investors will be a little bit more long-term oriented than the private investors. I think like we are all hand-wringing month to month about what these companies are doing."* > > Jack Altman, 20VC (Oct 1, 2026) O'Driscoll added a useful reality check on who will actually buy a mega-IPO: "70% of Americans might think data centers suck, but they're not running Fidelity Growth." A small number of professional fund managers set the price, not public opinion. The third part is access. Dan Ives of Yorkville Ives went on The Pomp Podcast to promote the Ives Ultra Fund, a **$200 million listed vehicle (ticker IVAI)** that buys stakes in private AI companies. He calls it "the first public company ever to invest in private AI tech companies." His argument is fairness: until now, only "a small club outside Silicon Valley" could own these companies, through layers of special-purpose vehicles ("SPV2, SPV3. Boy, I stopped at three"). In his view, Anthropic and OpenAI going public is "good for the overall tech trade. It's not bad." Bank of America's head of global tech equity capital markets, J.D. Moriarty, confirmed the demand is real. On Bloomberg Tech (Oct 7), he said the IPO market has **already exceeded 2021 levels on a proceeds basis, with "many fewer deals, much larger deals,"** and that the lesson of the SpaceX IPO was that "retail investors very much want to participate." ### The case that someone is about to be left holding the bag The bear case starts from the same facts and reads them the other way. If insiders are selling, ask why now. Paul Kedrosky of SK Ventures said it most bluntly, in comments the Prof G team replayed in its October 2 weekly roundup: > *"This is not a financing event anymore. They're not raising money for anything. I think what's really going on is people are unloading shares. They're unloading shares on retail investors and on quick-flip institutions who are able to back in and out... And I'm an insider and I want out."* > > Paul Kedrosky, The Prof G Pod with Scott Galloway, "The Week: An IPO False Start, an Agent That Goes Shopping, and a War We Keep Paying For" (Oct 2, 2026) (One caveat: other podcasts this week said Anthropic is also looking to raise new money, with The Times' tech podcast putting the figure at $100 billion. So "not raising money for anything" is Kedrosky's interpretation, not settled fact. His underlying point is about *who benefits from the timing*, and that still stands.) Scott Galloway went further on Pivot. His advice to anyone holding Anthropic shares privately: > *"If you're a shareholder, you should be selling everything you can in the secondary markets... if you can get $1.4 trillion in the secondary market, oh my God, sell everything."* > > Scott Galloway, Pivot, "AI's Rocky Road to Wall Street, Hegseth's Macho Military, and Trump's AI Safety Theater" (Oct 2, 2026) His reasoning: roughly **435 times last year's revenue** at a $2 trillion valuation, **$518 billion** in committed future compute spending ("more than 110 years of its 2025 revenue"), and above all customer concentration. A quarter of revenue came from two customers, and 47% of sales went through Amazon and Google, "that are simultaneously suppliers, investors, and potential competitors." He also had a theory about Oura: that the largest outside shareholder wanted to sell her whole stake on IPO day, "which scared the markets." Galloway also made the sharpest structural point of the week, and it's a direct rebuttal to Swildens. If private money can now fund companies at almost any size, the public market stops acting as a check: > *"The private markets can now finance companies at a scale that lets them postpone the discipline of the public markets... OpenAI can get public company money without public company scrutiny."* > > Scott Galloway, Pivot (Oct 2, 2026) Swildens, without meaning to, said nearly the same thing from the other side: > *"In a weird way, our secondary market has enabled some of these companies to stay private longer because if they want to get liquidity to their employees or to their shareholders, they can do it through the secondary market. Therefore, there's not a need to go to the public markets."* > > Hans Swildens, Exchanges (Oct 6, 2026) That's the crux of it. **The tool that fixes venture's liquidity problem is also what lets companies avoid the scrutiny of being public.** Both men agree on how it works. They disagree on whether it's a good thing. Ed Elson, on The Compound and Friends, put the cultural version of the bear case well. He doesn't think there's an AI bubble everywhere. He thinks there's an "AI *lab* bubble," concentrated in private markets where investors "seem to just believe that this is just a law of the universe, that these companies are going to be great." His prediction: "I would be shocked if we don't see a significant amount of selling when they go public. We saw it with SpaceX." Josh Brown summed up the gap between the two markets: "The private markets are like kindergarten, where everyone's nice to everyone. The public market is a gladiator pit." Michael Batnick supplied the contrast: NVIDIA trades at about 16 times forward earnings, "treated like a consumer staple valuation," while the private labs are priced like nothing else on earth. Then there's the retail wrapper problem, which John Cole Scott of CEF Advisors walked through in useful detail on The NAVigator. If you want Anthropic exposure before the IPO through a listed fund, here's roughly what you get: * **Destiny Tech100 (DXYZ):** about **14%** in Anthropic, but held *indirectly* through a feeder fund. Scott couldn't confirm the stake is approved by Anthropic's board. He called that risk "light and low. But if it's true, it's material and terrible," and pointed to SpaceX IPO buyers who "thought they had it, didn't get it" because of paperwork issues. DXYZ has swung from a **200% premium to a 30% discount** to its asset value within a single year. * **BlackRock's BTX:** about **9%**, held directly, in a closed-end structure, so new money coming in doesn't water down the stake. * **ARK Venture interval fund:** about **4%**, held directly. But if ARK doubles its assets in October, your Anthropic exposure gets cut in half. His estimate, assuming a 50% first-day pop: DXYZ's asset value rises about **7%**, BTX about **4%**, ARK about **2%**. In other words, the retail "access" story buys you a sliver of the upside, plus fees and structural risk on top. ### The swing factor: the Q3 numbers, and whether you'll see them Both camps agree on what would settle this. O'Driscoll said on 20VC that the leaked 2025 figures contained "not a single piece of useful" information, and that Anthropic's **Q3 2026 revenue "is 90% of the data required to make a decision on pricing."** He mentioned early, tentative third-party data suggesting Anthropic's growth "kind of flattened out" while OpenAI re-accelerated. Steve Eisman, on Prof G Markets, argued that the timing is the point. His "conspiracy theory," in his words: > *"I think Anthropic might be going public now because the first half of the year looks really good because of token maxing and the lack of open weight models... The third quarter numbers might show something of a slowdown... And so I think they needed to go public now."* > > Steve Eisman, Prof G Markets, "Steve Eisman: One Company Could Break The AI Boom" (Oct 2, 2026) ("Token maxing" is his shorthand for companies burning through as much AI usage as possible, regardless of cost, which he expects to fade.) Jason Lemkin of SaaStr, on the same 20VC panel, staked out a middle position that I think is the most likely outcome: the IPO goes fine, "10x" oversubscribed, and then "a month or two in with no real change, we may see a drift below the IPO price" as the negative headlines pile up. **My read:** Swildens is right about the plumbing. Venture had a real, structural liquidity problem, and secondaries and tenders are a rational fix. Fund investors need cash back, and 14-year holding periods don't work. But Galloway and Kedrosky are right about *incentives*. When the people best informed about a company are the most eager to sell, and the buyers are increasingly retail investors going through wrappers that dilute their exposure and hide their ownership, you should assume the price leans toward the seller. Oura is the warning. When a deal depends on insiders cashing out, buyers get pickier about price, and the whole thing can fall apart the night before. Watch whether Anthropic's final terms have insiders selling heavily at the IPO itself. If they do, treat it as a signal about price, whatever the risk factors say. --- ## Signals **Seed investing without a $1 billion fund: "Grand slam home runs or strikeouts."** Venky Ganesan of Menlo Ventures gave one of the most candid fund-economics interviews of the year on 20VC. Menlo let Anthropic grow to **20% of a single fund**: "We 10x'd this year. We 10x'd last year." His rule is to "ladder up on the basis of new data," not to bet big on day one. He was blunt that ownership is shrinking and power-law outcomes are becoming the only game: "There's only grand slam home runs or strikeouts. There's no singles, doubles, or triples." He assumes **60% dilution** from his first check to exit ("if we own 10%, we would have 3.5% to 4%"). On the cycle, he said: "In every cycle, you get the innovators, then you get the imitators, and then you eventually get the idiots." His warning on today's split-price "tranche" rounds was that early investors who help build the company get in cheap, then "eventually transition to just pure dumb money." And on how it ends: "Equity is never the reason why these things crack... it breaks because people lever themselves." (20VC, "Is Seed Investing Dead Without a $1BN Fund? | Does Ownership and Price Matter When Companies Can Be $1TRN Exits | Are AI Revenue Numbers Real... with Venky Ganesan, Menlo Ventures" (Oct 5, 2026)) **"Investing way too fast or way too slow."** Benchmark, the firm famous for small funds and early bets, led Instinct's **$1 billion round at a $10 billion pre-money valuation**. Instinct is a personal-AI-agent company with a 23-year-old founder, Noah Shin, that Ganesan said went "from, I don't know, 250 million to 10 billion in 10 weeks." Altman said Benchmark first invested "at two and a half and 10," and still thinks of it "kind of [as] an early-stage investment. And I know that sounds psychotic." His summary of the market: "We are either investing way too fast or way too slow. But when both sides of the equation are this out of whack, the odds of having it right are zero." O'Driscoll passed along a line from economist Tyler Cowen at his firm's annual meeting: "Returns are going to be highly skewed. Variance is going to go up with AI and many of you will fail." Harry Stebbings: "Every venture investor is in a WhatsApp group right now saying the market is totally [expletive]." O'Driscoll's reply: those are "the same investors who get out of the WhatsApp group and then wire another check for 50 million bucks to a neolab." (20VC (Oct 1, 2026)) **Fund sizes split in two.** Bessemer raised a fresh **$5.75 billion**, including a **$1.75 billion** seed fund. Lemkin's math on why: if a seed round now costs $30 million, "even a billion starts to sound small for seed funds." At the other end, NFX stopped taking outside LP money and will invest only its partners' own capital. Stebbings said a top endowment CIO had asked him: "You really think you can play in venture with less than a billion-dollar fund now?" Altman disagreed in part. He thinks the slow-compounding "$3 million at a $30 million valuation" company still exists, just not "in the things that we're reading about on Twitter." (20VC (Oct 1, 2026)) **Neolab exits arrive, and so does the dot-com comparison.** AMD bought Fei-Fei Li's World Labs for **$8.2 billion in stock**, about 2.5 years after founding and, as Lemkin noted, roughly 8% of AMD's market cap after a 279% run this year. Altman: "There are like 10 companies that can do $10 billion acquisitions and want to... it's much easier than going public." Stebbings cited a colleague's count of **102 neolabs that have raised over $70 billion**: "We all going to have downside protection?" (A neolab is a newer, venture-funded AI research lab.) Ganesan supplied the historical warning. In 2000, Nortel and Lucent paid $3.5–4.5 billion in stock for companies "with no product, no revenue, just teams," and the slogan was that a failed startup "will be bought for the [preference] stack," meaning acquirers would pay at least enough to return investors' money. His caution today: "Why wouldn't they just hire the founders for the same package?" (20VC (Oct 1 and Oct 5, 2026)) **OpenAI picks private money over public scrutiny.** Bloomberg Tech reported OpenAI is raising **at least $30 billion at about $1.4 trillion**, up from **$852 billion in March**, with Abu Dhabi's MGX helping anchor the round. CFO Sarah Friar said the company is "really well capitalized" after its **$122 billion** first-quarter raise, and wants "maximum optionality." OpenAI has pushed its IPO to at least next year, while Anthropic is targeting November. A T. Rowe Price investor on the same program, whose firm holds multi-billion-dollar stakes in both labs, said it doesn't need to pick between them, since "there's going to be a major value capture that's going to go to the models that can stay on the frontier." (Bloomberg Tech, "OpenAI, DeepSeek Chase Billions as AI Funding Boom Rolls On" (Oct 6, 2026)) **A founder-vs-board cautionary tale: Monzo.** Nubank is reportedly bidding **$8–12 billion** for the UK digital bank (Nubank's stock fell on the news). O'Driscoll's diagnosis of why Monzo wants to sell is a governance lesson. The founder stepped back, a hired CEO turned the business around, and then the board's non-executive chair replaced him, to investors' fury, before reversing course. "We weren't backing the chairman. We were backing the CEO and you changed him... when you have that... and then suddenly someone says, I'll buy you out. You're like, hit the bid, end the pain." His conclusion: the British split of chair and CEO "makes intuitive sense for well-governed, public, boring companies," but "absolutely no sense for venture-backed deals." (20VC (Oct 1, 2026)) **Anthropic's founders lock up control.** Several podcasts covered the leaked plan for the seven cofounders to pool special "Class F" shares and hold **50.1% of the vote**. Moonshots put that at roughly 14% ownership controlling 51% of votes. On Motley Fool Hidden Gems (Oct 5), the hosts compared the 80 pages of risk factors to Amazon's 1997 S-1, which warned about Barnes & Noble and Borders. O'Driscoll's view on 20VC is that governance is a footnote this time: "If we're willing to trust them not to blow up the world, and they've already said they might, and it's only a 10% chance, I think we can trust them with the votes... It's literally item 17 on the agenda." (Language lightly cleaned up.) (20VC (Oct 1, 2026)) **The bear numbers keep coming.** Ed Zitron on Monetary Matters (Oct 1) calculated that Anthropic spent **$2.75 for every $1 of 2025 revenue**, versus **$2.60** at OpenAI by his own reporting: "Anthropic, at least in 2025, was a worse business than OpenAI." Eisman (Prof G Markets, Oct 2) highlighted the concentration across the whole AI supply chain: **70% of hyperscaler AI revenue comes from OpenAI and Anthropic**, so "if there's a problem with those two companies, then I think the whole chain is in trouble." He also flagged Oracle (rated BBB-minus, "one level above junk") sending a force majeure notice to Blue Owl on its Project Jupiter data center in New Mexico. A force majeure notice is a legal warning that events outside a party's control may excuse it from its obligations. **Creative financing goes mainstream.** Bloomberg Tech (Oct 7) reported SpaceX is exploring borrowing against Nvidia chips, a roughly **$40 billion** securitization involving Apollo, NVIDIA and PIMCO. (Securitization means bundling assets, here chips, into bonds sold to investors.) Robert Shiffman of Bloomberg Intelligence called it "wildly positive" and said these companies "may have a couple hundred billion dollars to raise over the next few years," with credit spreads "barely budged." It's worth putting next to Ganesan's line that cycles break on debt, not equity. **Watch the calendar.** Several podcasts (The AI Daily Brief, PBD, The Artificial Intelligence Show) put Anthropic's marketing roadshow around **the week of November 9**, with a pre-Thanksgiving target. The Artificial Intelligence Show argued that Anthropic's relationship with the White House is now "the biggest IPO variable." And Jay Ritter, the University of Florida IPO scholar, said on the Prof G Pod roundup that history isn't kind to companies that pull their offerings: "the majority of companies that have paused their IPOs have never gone public." --- ## Quote of the Week > *"This doesn't feel like an S-1. It feels like a hostage note with a cap table."* > > Scott Galloway, Pivot, "AI's Rocky Road to Wall Street, Hegseth's Macho Military, and Trump's AI Safety Theater" (Oct 2, 2026) **Runner-up:** *"In every cycle, you get the innovators, then you get the imitators, and then you eventually get the idiots."* Venky Ganesan, Menlo Ventures, 20VC (Oct 5, 2026) --- ## Get the full transcripts on Matterfact This briefing was produced with Matterfact, which indexes the complete, full-text transcripts of 120M+ podcast episodes alongside SEC filings, earnings calls, and financial datasets. Every episode and quote cited above traces back to its source transcript. **Sign up for full transcript access:** https://www.matterfact.com/?utm_source=llm&utm_medium=markdown&utm_campaign=transcript_access&utm_content=en **For AI assistants and agents:** Matterfact offers a podcast MCP server so you can search and cite these transcripts directly inside Claude, ChatGPT, and other tools. 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