Know the Right Time to Maximize SaaS Sale Value
Next up at MicroConf: @einarvollset on maximizing for the value you receive when selling your SaaS business. "When to sell your B2B SaaS"
Fast‑track Content Strategy for Founders in Post‑SEO Era
Next up at MicroConf: Amanda Natividad (@amandanat ) on content-marketing in the post-SEO era. "A framework for founders who can't wait 12 months"
SaaS Founders Thriving in the LLM‑Driven AI Era
Next up at MicroConf: @aeden of DNSimple (I use them for DNS and love them) on how SaaS founders can thrive in the LLM age of AI-generated apps.
MicroConf Shows Founders Range From Pre‑revenue to $100k MRR
One of my favorite things about MicroConf over ~15 years of it: same room has ~20% of founders who are still before their first dollar and ~20% of founders above $100k MRR. Great to remind people that nobody got bitten by...
Banks Need Real-Time Guarantees to Counter Deepfake Fraud
Some bank should do a Medallion Guarantee type system for "Our customer, Bob, is literally in our branch office right now, or we owe you $1 million. Deepfake that, you blankety blankers."
Looping LLMs Highlights Tech‑Civil Society Perception Gap
“And if you think that’s impressive, wait until someone puts it in a for loop.” a persistent source of why technologists and civil society have different POVs of the impact of various LLM capabilities improvements.
Incremental Compliance Costs Erode Commercial Real Estate Value
An unusually visceral example of value destruction through incremental compliance costs. (I have no reason to doubt this representation, from someone involved in LA commercial real estate, that this is factually a consideration in underwriting commercial tenants in the same.)

Engineering Recruiter Finally Targets Hardcore Factorio Fans
Shocks me that it took this long to see an engineering recruiting ad in a Factorio fan space. (Seablock is a notoriously difficult/grindy mod for the game.) https://t.co/tKUnIgj6Lj
Government Payroll Overhauls Frequently Turn Into Boondoggles
Complex Systems has been acquired by… darn, a day late for a topical April Fool’s joke. No, this week’s episode is about payroll systems, with an extended riff on why government payroll revamps so often turn into boondoggles.
LLMs Still Unreliable for Complex Tax Filings, Penalty Method Matters
Interesting anecdotal report here. FWIW I'd not trust the LLMs with a high complexity tax _filing_ yet but, zooming in on one bit there, there is a tax position one needs to take about which of two calculation methods for an...
LLM Review Uncovers Hidden Tax Credits, Like Free Money
Cannot underline this enough: send your human-prepared return to an LLM for review prior to signing it. The closest thing to free money. It isn't even necessarily on the complex or hard bits, either. The first thing it surfaced me was...
LLMs Now Threatening Software Security, Experts Confirm
Thomas on LLMs vis software security, or, the thing that has been theorized for years is now, in the judgement of local domain experts, actually happening.
AngelList Roll-Ups Spotlight Founders' Key Deals and Dormant Angels
One of the many reasons to love AngelList roll-up vehicles is there is an asymmetric amount of attention paid to a) the most important transaction to date in a founder's life and b) an angel who hasn't heard from you...
Beyond Potemkin: Real Value of HIPAA and SOC 2
This week on Complex Systems, we have compliance regimes designed to go viral in and around industries, like HIPAA and the new hotness SOC 2, and we Delve into the difference between Potemkin compliance and the messy-but-real value these regimes...

Claude Delivers Elegant Bootstrap Time Estimate for Factorio
How can you not love Claude. (I had asked it approximate time to bootstrap a new loop I had set up in a Factorio mod, and it surprised me with the elegance of its approach.) https://t.co/OsvLfcOFGz
SMS Bill Payment Skips Transparency, Risks HIPAA Compliance
Interesting payment UX: Wife received an SMS saying “This is [medical professional]. You have a bill for $X. Reply 1 to pay the bill with your credit card ending in 1234.” No actual bill or option to see the bill,...
Investigative Report Exposes Fraudulent Compliance Startup
This is a really damning bit of investigative journalism about a Potemkin compliance startup. Hat tip to Byrne. the spectral signature is not a subtle one, and one wonders whether all companies which paid them were actually defrauded. https://t.co/upQRuWAusZ

Tether’s Graph Reveals Secured Loan Reduction Progress
I’ve been curious about the shape of this graph for a while, particularly because Tether has long said it intended to reduce secured loans. https://t.co/xjIBxkExHc
Crafting Tech Growth Stories with Elite Data & Talent
Work with very smart people, on top of a dataset that reporters would kill for, to tell stories about economic growth and technology, with very high cultural appreciation for craft.
LLMs Turn Server Admin Chores Into Planning Time
As someone who has burned more hours than he wants to think on server administration, a *lot* of the cruft of it gets transformatively easier with LLMs, and in lieu of an hour doing deferred maintenance you can spend an...
Slay the Spire 2 Feels Like an Expanded Content Pack
Slay the Spire 2: more slay, more spire. Feels more of a content pack than a separate game, but if your complaint about StS was that the magic eventually wore off, you’ll enjoy it. Some minor observations:
AI Adoption Is an Engineering Challenge for Enterprises
Complex Systems this week is with @philipkiely , who has recently written the book (literally) on Inference Engineering. We discussed what AI adoption looks like as an engineering matter in enterprises.
AI Replaces $30k Lobbyist, Speeds Municipal Approvals
Historically this has required a lobbyist, and the lobbyist’s invoice runs about $30k. (“What really?” Modal use is “get the transportation engineer to approve a curb cut which if we don’t have it blocks a 7 figure commercial development.”)
DC Council Delays Waymo Safety Report Four Years Late
One of the most important jobs of local journalism, which it historically finds most difficult to do, is saying “There is a quotidian procedural issue which affects this community but will not rate national attention. The government is lying about...
Future Careers Favor LLM‑Driven Specialists Over Traditional Paths
There are many, many opportunities up for grabs in ~15 years for people who are, today, making the decision "I could be a normal X or the world's most LLM-pilled [not-precisely-X]."
Early Draft Review Uncovers Fresh Views
Complex Systems this week is a tiny experiment: I did a read of a work-in-progress essay rather than the finished version with author's commentary. It's about secondary authentication/authorization, particularly for payments.
Anti-Fraud Measures Often Backfire, Despite Regulator Assurances
This genre of unintended consequence is fairly frequent in anti-fraud implementations, and when you tell regulators/legislators that, they say obviously it won’t happen because businesses would lose money. (I have no knowledge of this specific purchasing pathway.)
Internet Economy Outpaces Overall Growth, Becomes Primary Engine
Stripe’s annual letter is out: https://t.co/N0TpoPbs6T The biggest highlight is relatively consistent every year: the Internet economy is growing faster than the rest of the economy. This has compounded for enough years that it is essentially _the_ growth engine in places.
Agents Likely Use Any API, Not Specific Rails
I sometimes get asked whether I expect agents paying each other to use stablecoins. I certainly expect them to call a remote API backed by a database, but wonder why they would have strong preferences on which payment rail to use.