
Entrepreneur turned Seed VC @UncorkCap. Focus on B2B software (dev tools, infra, security, tons of AI obvs). Food. Drink. Music. Family.
🇬🇧🇺🇸 in SF
Joined March 2007
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Today marks Uncork Capital's 21st 🎂 That would usually be reason enough to celebrate but I'm also delighted to announce that we've raised $300M in new funds to back the founders building the next generation of category-defining companies 🚀 medium.com/uncorkcapital/unc…
Today is *the* day for everybody who hasn't read it to immediately buy the excellent "This Is How They Tell Me the World Ends" by @nicoleperlroth thisishowtheytellmetheworlde…
A version of this is happening all over the world right now
Security called me at 6:12 AM today.
"Patch every PHP server immediately."
I asked what happened.
"Two critical vulnerabilities. Remote code execution. No authentication required."
Cool.
How many PHP servers do we have?
According to inventory: 12
According to reality:
Nobody knows.
We found one running WordPress.
Three running old internal tools.
One under someone's desk.
Two inside vendor appliances.
A forgotten employee directory from 2016.
And a server named:
PHP-OLD-DO-NOT-TOUCH
Naturally, that one runs payroll exports.
Then we found a PHP 5.6 box.
I asked who owned it.
The documentation said:
BRIAN.
Brian left in 2019.
We called Brian.
He said:
"Oh wow, that's still running?"
Excellent.
By 8 AM, leadership joined the incident call.
CEO:
"Can hackers actually get in?"
Security:
"Potentially yes."
CEO:
"Without a password?"
Security:
"Yes."
CEO:
"Then why do WE need passwords?"
Not the lesson.
Finance asked if we could wait until the weekend to patch because downtime affects revenue.
Security explained that the alternative was letting strangers execute code on our servers.
Finance asked for a cost comparison.
At 9:17, someone suggested temporarily taking the vulnerable websites offline.
Marketing refused.
"Our campaign is live."
So for the next hour, the company officially decided maintaining a landing page for 20% off webinar registration was more important than preventing remote server takeover.
We finally patched everything we could find.
Then our scanner discovered another PHP server.
Hostname:
TEMP-PHP-2014
Uptime:
4,512 days.
Nobody knows what it does.
Nobody owns it.
Nobody can shut it down.
But every time we block network access, the warehouse stops printing shipping labels.
Security has classified it as critical infrastructure.
It is running PHP 5.4.
The vulnerability has existed longer than half our employees.
The emergency patch took four hours.
Finding out what PHP actually runs took eleven.
The internet isn't held together with code.
It's held together with servers everyone is afraid to turn off.
This protracted goodbye is basically how every single British phone call wraps
Not even Black Mirror could predict this level of dystopia.
A man found out his job interviewer was AI, so he let his own AI take over and walked away, leaving both AIs stuck in an endless goodbye loop.
Readers added context they thought people might want to know
This video is a staged comedic experiment by YouTuber Graham Dot Zip, not footage from a real company job interview.
youtube.com/watch?v=A0fECn…
theregister.com/offbeat/2026/1…
aistify.com/ai-job-intervi…
mezha.ua/en/news/ai-job…
Thrilled to share that @uncorkcap led @phinity_ai’s $5.2M seed round!
Phinity is building AI systems to design, verify and eventually tape out chips. In seven years in venture, I’ve never seen a ramp like this: $0 to eight figures in annualized run rate in under three months.
I first met @sonyashijin and @aadi_nash late last year, when Phinity was only a few months old and had no customers or revenue.
Rather than simply layering coding agents onto existing workflows, Phinity is training AI models to design chips themselves.
Since then, they've assembled an incredible team from NVIDIA, Intel, and frontier research labs. Phinity's agents have outperformed experienced hardware engineers on power, performance and area, even when those engineers were using frontier coding agents, and the system produces verified designs an order of magnitude faster.
If you're at a frontier lab or semiconductor company and want to dramatically shorten your chip design process, the Phinity team would love to chat. And if you want to work on one of the hardest technical problems out there, they're hiring!
More on why we invested: uncorkcapital.com/blog/reinv…
Quince’s logistics are absolutely incredible. Ordered stuff on Saturday evening and it’ll be delivered today.
Tripp and I have brought our girls to Disney’s Worlds Collide (Zombies, Descendants, Camp Rock) show at the Chase Center. The levels of energy, singing along, and whooping are right up there with Oasis’ Live 25 show at Wembley.
Instinct has done incredible work this week:
- Filed a replacement request (and processed the replacement order) for running shoes that fell apart
- Negotiated a ~$750 refund from Hertz for an insurance product I didn't ask for (and is chasing an additional unwanted $200 charge
- Spent 60+ minutes on live chat to figure out why my Epic Pass payment has failed
- Chased down a property tax appeal payment
Andy McLoughlin retweeted
Meta’s Muse can join your tailnet as its own node, then SSH into machines, check containers, and interact with self-hosted services.
The important part: your existing Tailscale access controls still decide what it can reach.
buff.ly/NIJgLQi
To be fair, I occasionally forget about investments I've made (albeit they're personal angel checks I wrote in 2011)
We have a bunch of AI co-workers at Uncork, all powered by our portfolio company @getskydive. Read about how most companies are only now getting ready for this next wave of work in this fun @WIRED piece (starring Skydive and co-founder @dhruvamin) 🤖 wired.com/story/ai-agents-ar…
Hit me up if you want some free credits to get started. I'm pretty sure I can twist Dhruv's arm to get you something really meaty (which will get even meatier when you onboard the rest of your team so all your agents can work together) cc @dhruvamin
I wonder if Facebook toyed with including “existential threat to democracy” in their IPO prospectus. Meanwhile, over at Anthropic:
Andy McLoughlin retweeted
Big congrats to the @Numeral team on their Series C! Very proud to have backed them since the seed.
@SpamRoss and Matt are some of the most impressive founders I’ve ever met. They’ve gone after a huge, mission-critical market dominated by legacy incumbents and have become the dominant next-gen player in just a few years, with 3,500+ customers across 90+ countries.
Couldn’t be more excited to invest more in this round!
Numeral has raised a $100M Series C, led by Insight Partners with participation from Salesforce Ventures, Benchmark, Mayfield, Uncork, Y Combinator, FCVC, and Geodesic.
This brings our total funding to $157M.
@numeral solves U.S. sales tax, VAT, and GST compliance for 3,500+ global businesses, trusted by companies like Supabase, Eight Sleep, and Graza.
We’re building the future of tax -- where AI agents, human expertise, and global compliance come together in one system.
Since starting the business in 2023, we’ve grown quickly across our core e-commerce and software segments, while expanding into new industries including manufacturing, distribution, and wholesale.
There is a lot of work in front of us. Sales tax is more dynamic than ever, with states like California implementing new taxes on software and more states using AI for enforcement.
We are hiring across the org from engineering to product, sales, and marketing. And we’ve just opened our new office in NYC. If you are looking for what’s next, I’d love for you to take a peek at our careers page.
Excited for the year ahead. And humbled to be working with investors like @insightpartners, @rebeccaliudoyle, @SalesforceVC, @katiessschwartz, @ZKokosa, @MayfieldFund, @SPangulur, @benchmark, @chetanp, @ycombinator, @gustaf, @uncorkcap, @susanwliu, @GeodesicCap, @arvindayyala, @FundersClub, @mittal, @mantisVC, @AlexPallNY, @ShaanVP, @lennysan, @moizali, @ringmybeller, @khency6, @asturnerr, @maariabajwa and so many others.
First Macklemore then this. Thin wrappers are having a moment.
(I'll get my coat)
> be Harvey
> lawyers give you money “bcuz AI”
> product sucks, no one uses
> seat pricing means less usage = higher margins
> acquire $15.5B valuation selling mediocre frontier model wrapper
> models suddenly git gud
> lawyers start actually using the product
> ohno.jpeg
> token costs explode
> gross margin goes from +50% to -50%
> pivot to lower quality open models to halt usage growth
> mfw accidentally built AI company that's structurally short AI progress





















