serial operator + investor in fintech, B2B SaaS, AI; @communitascap prev: @m12vc, @getvgs, @jobyinc; exited to @jpmorgan; head of @Visa Ventures; stats nerd

San Francisco
Joined July 2006
Founders, evergreen advice: - do — references on your VCs - don’t — give VCs rights you’ll regret or don’t want to honor
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Hardly Strictly Bluegrass is a love letter to the city of San Francisco from Warren Hellman (co-founder of Matrix Partners) and family. Free to the public and no sponsors. Every year since 2001. It should inspire us all to consider what we can contribute to the fabric of SF.
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I’ve been a founder, an LP in 30+ VC funds, and now a VC. Many of the founders who create the biggest outcomes are deeply technical, systems-oriented, and often introverted. They build exceptional products and teams, move incredibly fast, and endure years of uncertainty and grind. Many are not natural salespeople. The VC persona the market often rewards is different: finance-fluent, polished, exceptional at building relationships with capital allocators, and a marketer at heart. They have to communicate access, judgment, and conviction to LPs long before returns are visible. LPs want outlier returns, but are accountable for visible mistakes. Missing a great emerging manager is rarely scrutinized; backing a fund that performs badly is. So LPs naturally favour things they can diligence and explain: a known brand, a clear track record, strong references, respected co-investors, and a manager who inspires confidence. That is the tension in venture: the biggest returns come from backing unusual people early, while most capital naturally follows what already looks safe.
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Peter retweeted
Replying to @cyantist
We live our lives forward, but understand life backwards.
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Forbes 30 under 30 to fraud pipeline remains undefeated
The top editor of Forbes, Randall Lane, was fired last month after the company discovered that he had received a payment of about $6 million from the founder of a firm that does business with the magazine, according to people familiar with the decision. nyti.ms/4xXqVjB
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“we sandboxed the agent” meanwhile the agent:
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Peter retweeted
Travis is an apex predator put on ice in 2017 and only recently reactivated from cryogenic slumber. Standards for male behavior have moved so far that he's actively perplexed by it. Our current ecology was last home to performative frat bros nearly a decade ago. So when Travis tells TBPN he jet skis to work, and Jordi + John ask whether he does his best thinking on the jet ski, he pauses. You can visibly see him get confused, with an expression like "What the fuck are you guys talking about?" Then he quite literally voices his frustration: "No guys...it's a fucking notch on the belt. Who else do you know who jet skis to work? Nobody. I'm the guy." Even the literal technology brothers are incapable of fathoming a man who does things just for the bit. Travis in 2026 is like the T-rex from Jurassic Park 2 who finds himself in modern day San Diego being like, yo, what the FUCK is this place? And then just stomps everything in sight. xitter.cf/tbpn/status/2081039302…
.@travisk's commute takes 5 minutes on a jet ski going 70 mph on Lake Austin. "Who else do you know is jet skiing to work? Nobody. I'm the guy."
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I'm a second-generation bookseller. My family runs Houston's largest used & rare bookstore and I'm building an AI tool for used bookstores. We got hit by exactly these orders, including a single order for 70 obscure books that made us pause online sales entirely. So I dug in. I don't think this connects the way people want it to. Every ingredient of the viral story is true. ISBNdb really does advertise sourcing books for AI companies. Anthropic really did destructively scan millions of books though they were mostly acquired through things like library deaccessions, not bookstore inventory. And booksellers really are getting bizarre bulk orders. But "rare" here isn't what you're picturing. It's The Insider's Guide to Metro Denver (1995) and how-to-use-WordPerfect 1991 manuals. Obscure, but often not precious. When we combed through our orders, nearly every book bought from us was either unavailable on Amazon or listed there at 5, 10, 20x our price on the platform they were purchased on. And the shipments are going to FBA prep companies: which is what you do with a book you're about to resell, not one you're about to cut apart. There is more than circumstantial evidence that this is a well-funded company running algorithmic arbitrage, buying underpriced or out-of-stock books to relist on Amazon at markup. This evidence includes an official denial that they are selling to train AI but I don't want to mention them for several reasons. You can Google it. That's more mundane than the shredder story. The actual risk is worse, though, because it's quieter: books that don't sell via FBA eventually get liquidated. If we really hold the last copies of some of these (and comparing platforms, it looks like we might) we're feeding them into a portal they may not come back from. No AI company required. Everyone assumes the internet preserved everything. It didn't. Many of these books have almost no metadata anywhere, just a scattered listings across proprietary databases then nothing. That's what my project is for: building better bibliographic records for these books than exist anywhere else, so we at least have a map of what we stand to lose. So the Library of Alexandria is still burning, just more slowly, and kore from “who cares” than from some cinematic villain. (I am open to being corrected.) Full writeup: open.substack.com/pub/charli…
🦔AI companies are bulk-buying rare books, scanning them through high-speed machines that cut the spines off, and shredding the originals. A service called ISBNdb facilitates orders of up to a million books and keeps buyers anonymous. Pre-2022 books are premium because they're free of AI-generated text. A federal judge ruled the practice is fair use because eliminating the original means only one copy exists at a time. Anthropic hired the former head of Google Books partnerships to obtain "all the books in the world." My Take This got to me. A bookseller told 404 Media that rare books with almost no surviving copies are being fed into this pipeline. Books that survived wars, fires, and centuries of handling are being shredded so an AI can learn to write a better marketing email. ISBNdb's website literally says "'AI company destroys two million books' is not a headline that generates sympathy," and they still built an entire business around making it happen quietly. They offer NDAs as a feature. They coach clients to call it "digital preservation." I've covered AI companies scraping the internet, torrenting libraries, and stealing music. This is worse because it's irreversible. You can re-upload a website. You can reprint a bestseller. You can't replace the last three copies of an 18th-century botanical text once someone shreds them for training data. And the judge said it's legal. So it's going to accelerate. "We shred rare books and offer NDAs so nobody finds out" is a legitimate business model in 2026. What a timeline. Hedgie🤗
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This amazing website, called "Worse on Purpose," is cataloguing all the ways companies are deliberately and secretively degrading their own products As usual, in most cases the culprit is private equity extracting enormous sums while everyone else is left worse off.
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Easily a new episode of Silicon Valley…. Lawyers for Gavin Belson’s Hooli accidentally email “Yang Jian” instead of “Jian Yang” because they don’t understand the family name first convention. Richard is still bumbling. Gilfoyle still playfully racist. Hijinks ensue.
NEW: Emails show Apple's lawyer mixed up two Asian OpenAI employees' names in its initial outreach over trade secret concerns, setting off a tense exchange between OpenAI's and Apple's attorneys months before Friday's lawsuit. nbcnews.com/tech/apple/apple…
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Peter retweeted
Sorting which financial docs are worth an analyst's time is surprisingly hard for frontier LLMs. With an expert-labeled dataset and on-policy distillation, Bridgewater fine-tuned a model to do it reliably and cheaply. thinkingmachines.ai/news/lea…
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— Charles Bukowski, 1992
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I've now seen 50 screenshots of the Cursor founder in people's DMs and I'm convinced the real product was the outbound. man ran a one-man SDR team against the entire tech industry and closed it at $60B
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Peter retweeted
Replying to @b6nbrown
My favorite “what could have been” for SF are the original 1960-61 BART route plans that went from SF to Marin(!), the South Bay, and deep into the East Bay. If only! (second map shows estimate transit times from SF at rush hour! 🤯)
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Peter retweeted
Likely an even better podcast transcription tool, with Q&A and search xitter.cf/kaz/status/20618798756…
Replying to @peter
nice! had just come across podscript.xyz/ yesterday...I like the ability to "ask about this transcript" instead of only being able to do a keyword search.
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Peter retweeted
Left, Ferrari Luce $645k Right, Nissan Leaf $35k
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Peter retweeted
the real AI water threat is Almond Irrigation
Insane stat of the day: California almonds use roughly 3–5.5 million acre-feet of water per year, depending on methodology. That's ~4-7x more water than all data centers in North America used combined in 2025.
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Peter retweeted
adulthood is saying “after this week things will slow down a bit” over and over until you die.
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Personal update: I've joined Anthropic. I think the next few years at the frontier of LLMs will be especially formative. I am very excited to join the team here and get back to R&D. I remain deeply passionate about education and plan to resume my work on it in time.
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Peter retweeted
Anthropic with Software engineers:
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