Sid Probstein (@sidprobstein) header
Sid Probstein (@sidprobstein) profile picture

Application Development as a Software Company | Founder @ https://teapawt.org/t.co/ByOyJNYoii | Co-Founder @ Tokenome AI | Founder/CEO @ SWIRL

Boston, MA
Joined September 2008
Photo by Sid Probstein (@sidprobstein)Photo by Sid Probstein (@sidprobstein)Photo by Sid Probstein (@sidprobstein)Photo by Sid Probstein (@sidprobstein)Photo by Sid Probstein (@sidprobstein)Photo by Sid Probstein (@sidprobstein)Photo by Sid Probstein (@sidprobstein)Photo by Sid Probstein (@sidprobstein)Photo by Sid Probstein (@sidprobstein)Photo by Sid Probstein (@sidprobstein)
Sid Probstein retweeted
New in Claude for Legal: a gallery of ready-made artifacts for contract review, regulatory horizon scans, cite checks, and more. Start from the built-in example, add your own documents and connectors, and share it with anyone across the business.
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Sid Probstein retweeted
MikeOSS 2.0 is here: a free open-source AI harness for legal work which you can self-host, connect to any model, or run fully local. What’s new in 2.0: - Integrated Drafting Interface (IDE): a Cursor for legal UI with a file explorer, document viewer/editor & chat side by side - Word add-in + workflows in Word - Subagents for big reviews - Web search - Memory (account and project scoped) - Side chat - Slash commands - Orgs & audit logs - Wider model provider support: Azure, Bedrock, @grok, @vercel AI Gateway, @MistralAI, @OpenRouter, @opencode Go and more - Local AI with Ollama integration Website: mikeoss.com (link to github on main page) Thank you to all contributors, including @solirvine @Pabz @b1rdmania @Diya_555696 @BitGrateful @SadhakaDev @b1rdmania @antoinelouis_ @snowyukitty
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I highly recommend cloudflare's security audit skill: github.com/cloudflare/securi… Run it on all your software. Run it with the free models. Use it even if you used a model to audit something - it will find much more things. Works in all agent harnesses and is model independent.
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Sid Probstein retweeted
The biggest misread of anyone predicting the end of software engineering was imagining that the world only needed a certain amount of software, and bringing automation to the field would reduce the need for labor. Exactly the opposite is happening where essentially most things are actually turning into software. Because agents can use tools, work with computers, write software on the fly, and process data like humans (but far faster), we can now throw “software” at problems that never could reasonably be digitized before. What that leads to is the role of engineering taking on greater importance in the economy, because we can now engineer far more systems and processes than were possible before. If you’re a bank trying to do new forms of trading, engineers are often your first bet. If you are in life sciences, you expect more and more research and lab work to be engineering centric. If you’re in manufacturing, you’re trying to automate more of the supply chain, all that is engineering. More and more work is shaped like software problems. Yes we’re not going to be coding manually in the future. But almost everything will be code, which means those that understand it are in a fantastic position.
Some observations about the "total" automation of software engineering: 1. There are more software engineers now than in 2025, and demand is growing. 2. Software engineers have never worked harder than they do now. 3. They largely don't write code anymore, agents write ~100% of the code. 4. The bottom line of the companies that employs these engineers and agents (i.e. the terminal purpose of all this code) is typically not budging as a result of AI adoption. This is why you have to think in terms of systems. Automating one aspect of a system creates its own friction and moves the bottlenecks elsewhere.
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Sid Probstein retweeted
An IBM slide from 1979.
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Replying to @sidprobstein
Yes. Undo without the basis is just a mystery in the log. Keep the reason next to the change and an agent can learn from the reversal instead of guessing.
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Sid Probstein retweeted
Every week someone tells me they vibe-coded their app over the weekend and don't need developers anymore. Before it touches a paying customer, make sure it includes: > a schema someone designed, instead of one the AI improvised table by table > login that still works when someone puts a plus sign in their email > password reset links that expire and work once > MFA, plus a recovery path for the user who lost their phone > sessions that time out, and a way to kill every session for one user > SSO for the enterprise customer who won't sign without it > SAML, because that customer's IT team doesn't do magic links > SCIM, so a fired employee loses access the moment IT offboards them > roles and permissions deeper than "admin" and "everyone else" > checks that stop user A from reading user B's data by changing one number in the URL > tenant isolation, so one customer's bug never shows another customer's records > an admin "log in as this user" button for support, with an audit trail on every use > rate limits on login, so nobody can guess passwords at scale > lockouts that stop attackers without locking out your CFO the night before the board meeting > database migrations that run forward and roll back > migrations that don't lock the main table at 2pm on a Tuesday > indexes, because the query that was instant on 50 test rows times out on 5 million real ones > connection pooling, so a traffic spike doesn't exhaust the database > backups every night > a restore from those backups, tested, because a backup you've never restored is a hope > point-in-time recovery for the day someone runs a delete without a where clause > soft deletes, so "I deleted it by accident" is a support ticket and not an incident > validation on the server, not just in the form > timezones stored right, so the 9am reminder doesn't fire at 4am > the customer with an apostrophe in their last name > emoji, accents and right-to-left text in every field > money stored as integers, because 0.1 + 0.2 doesn't equal 0.3 in floating point > currency, rounding and tax rules for every country you sell into > a data model that survives your second customer asking for "one small change" > idempotency keys, so a retried payment doesn't charge the card twice > deduplication for the user who clicks submit four times > pagination that still works on page 400 > exports, because sooner or later every customer wants their data in a spreadsheet > imports that survive the CSV someone saved in 2009 > retention rules, and code that deletes what your contract says you'll delete > secrets out of the code, out of the repo and out of the AI chat history > rotating every key the AI pasted into a config file last month > confirming every package the AI installed exists and is the one you meant > dependency scanning, because the AI pulled in libraries nobody reviewed > input sanitization everywhere a user can type > protection against SQL injection, XSS, CSRF and the rest of the OWASP list > file uploads that get scanned, size-limited and stored where they can't execute > CORS rules that aren't "allow everything" > security headers on every response > encryption at rest and in transit > least-privilege access for everyone, including the AI agent holding production credentials > logs that record who did what, without recording passwords, tokens or card numbers > a penetration test before your enterprise customer's security team runs their own > answers to the security questionnaire every enterprise buyer sends, with evidence behind each one > a disclosure process for the day a stranger emails you a vulnerability > a plan for the day a laptop with production access gets stolen > SOC 2, which means policies, evidence and an auditor, not a checkbox > HIPAA, the moment a single patient record touches your system > a BAA with every vendor that touches that data, including your AI model provider > audit trails that show who viewed a record, not just who changed it > PCI scope, and card numbers kept out of your database > GDPR deletion requests that reach every table, backup and log > data residency for the customer whose contract says EU only > quarterly access reviews someone signs off on > dev, staging and production environments that match each other > infrastructure written as code, so the setup lives somewhere other than one person's memory > a deploy pipeline that runs the tests before anything reaches customers > one-click rollbacks, because Friday deploys happen > zero-downtime deploys, because your customers don't have maintenance windows > feature flags, so you can ship the code without shipping the feature > autoscaling for the Monday morning spike > a CDN, so the app loads fast in Singapore too > DNS, SSL certificates, and renewals that don't expire on a Sunday > background job queues, so slow work doesn't freeze the page > retries with backoff, so one flaky API call doesn't become a lost order > a dead-letter queue for the jobs that fail every retry > cron jobs that don't run twice the day you add a second server > caching, and clearing that cache when the data changes > SPF, DKIM and DMARC, so your password resets don't land in spam > bounce and complaint handling on every transactional email > storage rules, so you stop paying to keep 2021's temp files > cost alerts, so a runaway agent loop shows up the same day and not on the invoice (we learned this one for $1,382.59) > a disaster recovery plan, written down and tested once a year > a second region, if your contract promises uptime one region can't deliver > structured logs you can search at 3am > error tracking that groups the same bug instead of sending you 4,000 emails > uptime checks from outside your own network > alerts that page a human, tuned until they stop paging for nothing > dashboards for latency, error rate and throughput > tracing for one slow request across every service it touches > an on-call rotation, and a person who picks up > runbooks, so the engineer on call knows what "queue depth critical" means > postmortems that change something > a status page customers check before they email you > unit tests written by someone who knows what the logic should do > integration tests for every third-party API you depend on > end-to-end tests for signup, checkout and the other flows that make you money > load testing before the launch email goes out > test data that looks like production without being production data > regression tests, so fixing bug 41 doesn't bring back bug 12 > testing on the five-year-old laptop your biggest customer's ops team still uses > accessibility compliance, because the enterprise contract requires it > subscriptions, upgrades, downgrades and proration > failed-payment retries and dunning emails > invoices with the customer's PO number on them, because procurement won't pay without it > sales tax and VAT > refunds, credits and partial refunds > usage metering that matches what you bill, to the cent > annual contracts with custom terms your billing logic never planned for > revenue reports your finance team can reconcile > webhooks that verify signatures > webhooks that retry, with a log of every failed delivery > a versioned API, so you can change it without breaking your customers' integrations > API keys customers can create and revoke > API rate limits that protect you without blocking real integrations > a plan for the day a third-party API changes its response format without telling you > OAuth token refresh, because tokens expire at the worst possible moment > a sandbox where customers can test their integration > protection against prompt injection in every field that reaches the model > customer and patient data kept out of prompts that leave your network > a model spend cap per customer, so one heavy user can't run up your bill > evals, so you find out when a model update makes your answers worse > a fallback for the afternoon your model provider goes down > a migration plan for the day your model gets deprecated > prompt and output logs for debugging, minus whatever you're not allowed to keep > a human approval step for anything the AI does that can't be undone > pages that load on hotel wifi > empty states, loading states and error states on every screen > error messages a customer can act on, instead of "something went wrong" > forms that keep what people typed when one field fails validation > emails that render in every mail client your customers use > notifications people can turn off > undo > keyboard navigation and screen reader support > translations, with dates and numbers formatted for each locale > a back button that does what people expect > code a human can read > code review on every change > a branching strategy, so two people can work without overwriting each other > monthly dependency upgrades, so you're never two major versions behind > framework upgrades before the old version stops getting security patches > deleting the dead code the AI left behind from its first three attempts > splitting up the 2,000-line file the AI kept appending to > architecture decisions written down, with the reasons > a README that gets a new engineer running locally in under an hour > documentation for whoever inherits this > an admin panel for your ops team > support tooling, so customer success can answer questions without pinging engineering > a changelog customers can read > terms and a privacy policy that match what the code does > every account, domain and repo in the company's name, not the name of whoever built the prototype > a bus factor higher than one Oh, and besides keeping all of this working every day, forever… your vibe-coded app will still need people who know what they're doing: > reading every line the AI wrote before it ships (a senior engineer) > designing the data model before your second customer breaks it (a backend engineer) > explaining why the AI's fix for one bug created two new ones (a senior engineer, again) > deploys, rollbacks, servers and the cloud bill (a DevOps engineer) > answering the page at 3am when payments stop (whoever's on call) > patching the framework the week a vulnerability goes public (security) > walking an auditor through how patient data moves (security and compliance) > testing what the AI says it tested (QA) > running a migration on a live database without losing a row (a backend engineer) > saying no to the feature that breaks three others (a tech lead) > turning "works on my laptop" into "works for every customer at once" (an architect) > debugging the code when the AI that wrote it can't (a senior engineer) > remembering why it's built this way, a year from now (someone who was there) …wishing them the best 🫡
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Sid Probstein retweeted
There is unlimited demand for people who make complex things simple.
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Sid Probstein retweeted
Founders should take more chances on themselves. You're probably more capable than you think.
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Sid Probstein retweeted
Today we're open-sourcing pg_vectorsearch, a new vector search extension for PostgreSQL. The performance improvements over HNSW are pretty remarkable. At 100 million vectors: ◆︎ Faster queries, 4× less RAM: 6 ms vs. 8 ms at 95% recall, using 128 GB vs. 512 GB RAM. HNSW couldn't even build on 128 GB. ◆︎ 7× smaller indexes: 25 GB vs. 180 GB at 100M vectors. ◆︎ 50× faster index builds: 49 minutes vs. 42 hours on identical hardware. And at 1 million vectors, PRISM delivers 15 ms queries at 99% recall on just 2 GB RAM, versus HNSW's 392 ms on 4 GB. What leads to these improvements? Rather than traversing an HNSW graph with random memory accesses, our new PRISM index partitions vectors based on distance, compresses them using RaBitQ, and scans them efficiently using SIMD vectorization techniques. This takes better advantage of modern CPUs and memory locality. This is actually our second open-source vector index. We learned a lot from building DiskANN-based pgvectorscale, including some important limitations of graph-based approaches. Those lessons convinced us there was a better architectural foundation, so we started over. pg_vectorsearch is still in alpha, with more engineering ahead. But we believe fast, scalable vector search should live alongside your relational data, without requiring a separate vector database. Released under the permissive PostgreSQL License, just like our pg_textsearch extension for BM25 keyword search. Together, they provide the building blocks for hybrid vector + keyword search in PostgreSQL. Feedback and contributions welcome! Code and blog post below. ⚡️⚡️⚡️
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Sid Probstein retweeted
.@RollingStone magazine has posted a new, bonus video interview from their recent @RushTheBand cover feature story, with all 3 members of Rush sitting down together with senior writer @BrianHiatt to talk about the band's Fifty Something tour ... rushisaband.com/blog/2026/10…
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Replying to @sidprobstein
What fixed it for me was making the agent keep a short decisions file and update it before each compaction. The code shows what changed, but the why never survives a summary.
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Sid Probstein retweeted
Replying to @sidprobstein
the compaction thing gets me every time... the code is still there but the why behind it is just gone
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Sid Probstein retweeted
The longer you’re a founder, the more you realize speed covers up a lot of mistakes.
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Sid Probstein retweeted
Cloudflare ha liberado su propia skill para hacer auditorías de seguridad con IA. Es la que utilizan internamente en la empresa para detectar vulnerabilidades y ahora cualquiera puede utilizarla con su agente. Se llama Security Audit Skill y organiza cada auditoría en 6 fases: ✓ Reconocimiento de la arquitectura y superficies de ataque ✓ Búsqueda de vulnerabilidades por cobertura ✓ Validación independiente de cada hallazgo ✓ Generación de resultados estructurados ✓ Verificación final con agentes distintos ✓ Creación automática del informe de seguridad Lo más interesante es que el agente que valida una vulnerabilidad nunca es el mismo que la encontró, reduciendo bastante los falsos positivos. Es completamente gratuita, open-source y tiene licencia MIT. Repo 👇
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Sid Probstein retweeted
‘[Anika] brought a lot to the table, but more than her chops, more than her guts and her willingness to sit in that hot seat, she brought an intelligence and a story. I love her story.’ Geddy Lee #RushFamily
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Sid Probstein retweeted
.@RushTheBand plays the first of a pair of shows at Boston's TD Garden on their "Fifty Something" tour tonight at 7:30PM. Follow along for updates, the setlist, reviews, photos/videos and more ... rushisaband.com/blog/2026/09…
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Sid Probstein retweeted
For all the legaltech startups out there who are not Harvey and Legora - you are probably feeling bad that no law firm will pay attention to you. Law firms have a limited bandwith to look at products. This is not just an excuse they give. From the inside perspective, they are getting bombarded by literally hundreds of AI legaltech startups. The Harvey/Legora brands have been remarkably successful in rising up above this tide and monopolizing the attention of law firm decision makers. This is very unique for this cycle. In the previous 10 years of legal tech, firms were much more varied in what products they were looking at at any given time. If you spoke to a firm and they weren't in the market for your product, there was a reasonable chance the next firm you spoke to was. Another way to put it, is that firms have shopping lists of products that internal folks are agitating for. If your product is on the list, life is good. We are in a weird world where every firm has the exact same list with the exact same products on it (note that they can only check the item off the list after the long tail of fully rolling out and supporting the product is complete). Now some harsh real talk - if your product has merit you should be able to find at least one person at one firm to pay attention to you. If that person is not materializing, you might need to take a harsh look at what you are building. Conversely, if a stranger at big law firms with many other important things to do continues to take calls with you - that might indicate you are onto something. Unfortunately, it might just take a long time to materialize into something - because you have to wait for the current cycle of Harvey/Legora fixation to pass. And because it just takes a long time even in normal times. At Closing Folders it took about 2 years to get our first big Canadian law firm as a customer. We got 2 more in six months. I think it was around year 6 or 7 that we finally had every single major Canadian firm as a customer (there's only 20). All of these firms had seen demos of CF years prior but it just wasn't on their shopping list yet.
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Sid Probstein retweeted
More firms to follow suit. Big bets and big $ in legal AI have been made under this assumption.
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Sid Probstein retweeted
Will is one of the most prolific voices in legal tech today - and a voice that often dovetails with General Legal's fundamental worldview: you don't need to raise $500M to build great software for legal professionals. Relatedly, selling billions of dollars of software to overpaid lawyers doesn't necessarily mean you will change anything about the delivery of legal services or the client's experience. You need to actually be incentivized to do that. Thrilled and honored to be collaborating, @willchen500! More to come soon ;)
Replying to @MikeOSSTeam
@MikeOSSTeam has been sponsored by @gen_legal_inc, a leading AI-native law firm backed by investors such as YC, Audacious Ventures and SV Angel, to develop a new open source project (Mike[???]) that will shake up the legal industry. Currently in stealth. More details to come. Thanks @jaypmo @rwalk_xyz
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