Managing Partner @rainsllp. AI-Enabled Corporate Lawyer, Head of Policy @bitcoinpolicy, ex-@DavisPolk, @YaleLawSch, @WilliamsCollege

Brooklyn, NY
You shouldn't use an AI as your lawyer. But if I had to have a current AI model as my lawyer, I'd want it to be ChatGPT Astra.
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One of the best things that AI unlocks for law is new ways to ingest context from clients. It’s easy for your client to write a long rambling email (or markdown file) with all of the stuff your AI needs to do a good first cut at the contract or memo.
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If only they got rid of Vincent, this would be a life-changingly good product for me.
We’ve just launched Clio for Codex – an MCP plugin that gives lawyers a new way to access Vincent’s capabilities directly from Codex. Fantastic article by @goclio's VP Eng @angelfaus on how we designed it: clio.com/enterprise/blog/cli…
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Do not let the light cone become a utility monster.
>be me >discover effective altruism >apparently normal charity is inefficient >why donate to random sad thing when spreadsheet can tell you optimal sad thing >fair enough >buy mosquito nets >save lives >numbers look good >feel powerful >couple years later >someone asks an innocent question >why only count people alive today >huh >future people matter too >obviously >my grandchildren shouldn't matter less just because they haven't spawned yet >reasonable.jpg >keep following logic >what about their grandchildren >also yes >what about people in 500 years >sure >5000 years >why not >500 million years >starting to get weird but morality is morality >open calculator >humanity could survive for an astronomically long time >could colonize galaxy >could have trillions upon trillions of descendants >maybe digital people too >maybe simulated civilizations >maybe dyson spheres full of happy uploaded minds >calculator starts smoking >realize currently living humans are rounding error >8 billion people suddenly looking extremely beta >future contains potentially 10^something people >can't even fit beneficiaries in google sheets >new moral priority unlocked >protect the long-term future >stop thinking in units of "people helped" >start thinking in "fraction of cosmic endowment preserved" >malaria? >terrible >but only kills existing humans >AI extinction could delete the entire light cone >nuclear war could permanently derail civilization >bad institutions could lock in terrible values for ten million years >someone invents wrong constitution in 2140 >quadrillions suffer >better fund governance workshop now >friend says maybe we should improve hospitals >explain opportunity cost >friend says hospitals are full of actual sick people >explain scope sensitivity >friend stops inviting me to dinner >need to decide what to fund >easy >expected value >suppose project has one in a million chance of preventing extinction >sounds tiny >but extinction destroys 10^50 future lives >multiply >mother of god >$10 million project has expected value of several galaxies >charity evaluation complete >someone asks where the one-in-a-million number came from >expert judgement >which expert >us >how calibrated >extremely thoughtfully >reduce estimate to one in ten million to be conservative >still beats curing cancer by 38 orders of magnitude >epistemic robustness achieved >someone says maybe project doesn't work >assign 20% chance >still astronomical >maybe project makes problem worse >assign 5% chance >still astronomical >why 5 >because 30 felt pessimistic >publish 46-page report >contains seventeen sensitivity analyses >every sensitivity analysis begins after assuming intervention has positive sign >critic says you're multiplying enormous hypothetical stakes by extremely uncertain probabilities >yes >that's literally why it's important >critic says the uncertainty might be structural rather than numerical >make probability smaller >critic says no, I mean maybe your model is wrong >make probability smaller again >critic begins rubbing temples >discover AI safety >perfect longtermist cause >AI might kill everyone >or create utopia >or seize galaxy >or tile universe with paperclips >or create billions of conscious software minds >finally a problem with numbers big enough for me >start AI safety nonprofit >mission: prevent dangerous AI >hire smartest people available >smartest people immediately start building better AI to understand dangerous AI >interesting >we must understand capabilities to understand safety >we must scale models to study alignment >we must race ahead so less responsible actors don't get there first >we must deploy systems to learn how deployment can go wrong >we must build the thing quickly because building the thing quickly is dangerous >outsider asks why the people most worried about AI apocalypse all work at AI companies >complicated field >company releases stronger model >very concerned >company begins training even stronger model >extremely concerned >company raises $14 billion >concern reaches unprecedented levels >need to influence government >future is at stake >normal democratic process too slow >politicians don't understand exponential curves >public doesn't understand x-risk >experts must guide them >who counts as expert >people who understand x-risk >who understands x-risk >our friends >someone objects that this seems politically convenient >explain we're representing future generations >future generations unavailable for comment >develop concept of value lock-in >terrifying possibility that one ideology controls civilization forever >therefore extremely important that civilization adopts correct values before lock-in >whose values >let's circle back >begin with impartial morality >end with small group of people deciding what quadrillions of hypothetical beings would want >beautiful arc >meanwhile actual humans keep doing annoying things >voting wrong >having parochial attachments >loving family more than strangers >caring about local community >getting upset when told their suffering is cosmically negligible >evolutionary biases everywhere >explain that moral intuition cannot be trusted >except intuition that future digital people count >and intuition that extinction is uniquely bad >and intuition that our probability estimates are sane >and intuition that our institutional choices improve the future >those intuitions survived peer review >someone donates $5k to local homeless shelter >inefficient >could have funded 0.0000000000003% of an AI governance researcher >think of all the simulated people you just killed >okay maybe don't phrase it that way publicly >PR team says "future generations deserve a voice" >much better >journalist asks what longtermism means >say "future people matter" >everyone agrees >great >journalist asks what follows from that >well technically we should redirect enormous resources toward low-probability interventions affecting astronomical futures >journalist raises eyebrow >return to "future people matter" >motte has entered the chat >critic: of course future people matter >me: glad we agree >critic: I don't agree that your institute knows how to help them >me: why do you hate our grandchildren >eventually notice uncomfortable implication >if future value dominates everything >then helping people today mostly matters through effects on future >education matters because future institutions >health matters because future productivity >democracy matters because future trajectory >human beings slowly become instrumental variables in their own moral philosophy >see starving child >feel compassion >check spreadsheet >child's direct welfare contribution negligible >but perhaps childhood nutrition improves national institutional quality >compassion restored >tell myself this is impartial altruism >one day assistant asks obvious question >"how do you know your intervention actually improves the far future?" >silence >open spreadsheet >increase column width >add confidence interval >assistant asks again >"no, I mean how do you know the sign is positive?" >stare into cosmic light cone >10^50 people staring back >none of them exist >none of them can tell me >none of them can falsify my assumptions >realize I have invented the perfect constituency >infinitely important >completely silent >and always represented by me
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Use AI for the difficult tasks (like going public), not just the easy ones.
Introducing GO Public – Cooley’s new AI-enabled offering for companies preparing to go public. Built for use with ChatGPT Enterprise, it helps teams move faster through IPO preparation and focus sooner on the strategic questions that matter most. cooley.com/news/coverage/202…
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This looks awesome! I’ve been really impressed so far with Astra’s performance on legal tasks.
Astra for Law: Frontier intelligence built for your practice. A new offering powered by GPT-6 Astra with tools, settings, and context to support the expertise and judgment of lawyers and legal technology firms.
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Zack Shapiro retweeted
Bitcoin Policy Institute's Zach Shapiro on where AI takes Bitcoin next: "We are going to rapidly move from an internet that is mostly used by humans to one that is mostly used by non-human agents." "Those agents may well use Bitcoin directly." 🦾
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Zack Shapiro retweeted
We were recording right when the Senate killed the Clarity Act. @zackbshapiro on the legal fight over whether writing Bitcoin code is a crime now headed to judges who don’t understand the tech. AI Risk. Regulatory capture. Superintelligence. Watch Now: piped.video/iZ7e0hY0WL8
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Zack Shapiro retweeted
I want to give a huge public thanks to @SenLummis and her staff for all their work. There were multiple, repeated attempts at “compromise” throughout this process that would have thrown Bitcoin and open source developers under the bus. At every turn she stood strong for what she believed was the right policy. We are very lucky to have her voice in Congress and she will be sorely missed next year.
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Whatever happens to CLARITY, I’m grateful for the extraordinary amount of work that went into protecting software developers along the way. Developer liability was never the biggest-dollar issue in this bill. Market structure, securities law, commodities law—those questions understandably consumed most of the oxygen. But developer protections implicated something more fundamental: whether the law can distinguish between the person who builds a tool and the person who uses it to commit a crime. I’m especially grateful to @SenLummis and her staff. They stood up for that principle under enormous pressure and kept fighting for it through every iteration of the bill. Senator Lummis will be sorely missed when she leaves the Senate. And I’m grateful to my colleagues at @bitcoinpolicy, @fund_defi, @coincenter, and especially @valkenburgh, who kept this issue from becoming an afterthought and consistently defended the rights of people who write and publish open-source software. The legislative fight may be ending for now. The legal one is not. That matters well beyond crypto. As software becomes more autonomous, and agentic commerce increasingly blurs the line between tools and traditional intermediaries, one of the defining legal questions of this century will be whether peer-to-peer systems can exist without making the people who build the software responsible for every bad act committed through it. The answer has to be yes. The work continues.
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And many more people deserve thanks for putting real time and energy into defending open-source developers through this process — @TheBlueMatt, @dbarabander, @jchervinsky, @KyleOlney, @MicheleKorver, @BitcoinConner, @neerajka, @intangiblecoins, @RitchieTorres, @RonWyden, @amandatums, @RebeccaRettig1, @m_mosier_, and others I’m inevitably forgetting. Grateful to have been in this fight with all of you.
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Agree with this. Exciting times!
If it isn’t clear enough by now, that these announcements are going to keep coming like the Harvey / Legora announcements in 2025. Pitching that you use Harvey and Legora basically sounds like you are pitching you have teams or copilot in your tech stack to clients. Every one has them, the clients have them too so they know they are not as impressive as the marketing suggests. So the cat is out of the bag.
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"The revised BRCA would still represent meaningful progress. Congress would, for the first time, put into statute the principle that developers who do not control user funds should not be regulated as money transmitters simply because they build the tools that allow people to transact."
The proposed BRCA changes are a tough pill to swallow coincenter.org/the-proposed-…
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No, the new BRCA does not strip protections under Section 1960. It just omits explicit reference to Section 1960. However, the text makes clear that 1960 (b)(1)(A) and (b)(1)(B) prosecutions of non-custodial developers and providers are foreclosed by inapplicability of licensing requirements. And it is silent on (b)(1)(C), although IMO suggests that “transmission,” under all applicable statutes, requires custody/control of assets. So treating this as a “rug pull” is incorrect and unhelpful.
🚨BRCA Changes in the New Clarity Act New BRCA strips out the proposed §1960 protections, leaving developers with regulatory exemptions but substantially less certainty against criminal prosecution. TLDR: Rug pull. Redlines vs last BRCA below. Goodnight, and good luck.
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I agree with this and with the policy implications that @DavidZell_ is getting at. But importantly this is an indictment of simplistic (and sometimes cynical) EA/consequentialist ethics. It does not mean, however, that we shouldn’t take X risk seriously.
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Top 3 things that won me business over the past five years (in descending order of importance): (1) Being commercially oriented. (2) Fast turnaround times for work. (3) Being cheaper than Biglaw.
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