
Investing in fintech and AI @acrewcapital. Co-Founder @assembliai @Perplexity_AI Fellow. @Penn @Wharton @HotchkissSchool. Building? [email protected]
San Francisco / New York
Joined January 2025
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Everyone loves to hop on the retrospective founder DMs trend when an amazing company announcement happens. Almost all of them are the sad "missed that generational opportunity" type. Well, I'm happy to say this is the ecstatic "start of an amazing partnership" type! I first learned about @tankots and @WisprFlow in May '25 when I was at a dinner and the AI Grant whatsapp group chat was lighting up nonstop - the entire dinner - after @natfriedman asked if anyone had tried this new thing called wisprflow. There was so much excitement about it. So much so that one AI grant founder said their office had "become a zoo where we all talk to our computers." Fast forward two months, Tanay presented it to the Perplexity fellowship and it blew my mind how seamless the product experience was. It truly "just worked." Fast forward a year, and I'm stoked to say that @AcrewCapital is fortunate enough to partner with Tanay for his $280M Series B at $2B valuation, led by our friends at @MenloVentures ! We're avid Wisprflow users - especially Tom Porter who must hold some kind of spoken words world record at this point - and love how much better we communicate because of it. The product is magical and the business is absolutely crushing it. We can't wait to see how this funding unlocks their next phase of growth!
Andrew McKinzie retweeted
So basically, today PHP got two critical bugs that let anyone run code on your server without even logging in, which is bad, and then the details leaked before the patch was even out, which is worse, and it works on WordPress and MediaWiki and Magento and Joomla and Laravel, and Censys says like 1.5 million servers are running a version with no fix, so the NSA was like "take your system offline," and the FBI was like "take your system offline," and CISA and the UK and CERT-EU were all like "take your system offline," and then the Prime Minister of Japan, the actual Prime Minister, posted at 5:55 in the morning telling 48.8 million people to take their system offline, so everyone took their system offline, like the Dutch cybersecurity agency took its own website offline, and the Dutch parliament went offline, and the Port of Rotterdam went offline, and Finland and France and Denmark started pulling government sites, and Wikipedia went down, and Archive.org went down, and Asana and GOG and Something Awful went down, and the University of Vienna's webmail went down for some reason, and that's just PHP. Because GitLab also dropped a CVSS 10.0, which is the highest score they give out, for a bug that's been there since 2014, so that's every self-hosted GitLab for twelve years, and then LiteLLM 1.107.0 got hijacked and shipped a credential stealer and a remote access trojan in every single wheel and the Docker images, including latest, and you didn't even have to import it, just installing it was enough, and it's the second time this year, and then Railway paused every deployment on the entire platform because someone got into the environment variables, so now everyone has to rotate every secret they've ever stored there, and TiDB Cloud said someone was walking around inside with stolen credentials for basically a month and an extortion group says they took 10.6 terabytes, and Zeabur got breached for the second time in two months and is just shutting down, like the whole company, and Node.js patched remote code execution and a TLS bypass, and CISA says Plex is being actively exploited, and someone took over 300 Tor exit relays to steal SSH passwords, and SafePay ransomware has hit over 600 critical infrastructure orgs, and India's biggest bank filed a data loss incident, and Japan has been in an official state of emergency in cyberspace since October 9, which honestly explains the 5:55 AM post. Oh, and eMudhra, a certificate authority that's issued over 60 million certificates, whose entire job is proving websites are who they say they are, was supposed to be using private keys that are random numbers over a hundred digits long, and one of them was 4. Just 4. And the others were like 66 and 237. Anyway, it's Wednesday.
As serious as it gets.
Effective Immediately, all organizations using PHP for their systems are advised to be prepared for an update addressing two critical vulnerabilities. PHP is widely used for web applications. These vulnerabilities often provide a direct path to the server's file system or database. If an immediate update is not feasible, it is recommend that organizations take the system offline until it can be fully mitigated. NSA will follow up shortly with more specific guidance.
in just over a month, we've had
- flying cars
- AI solving a Millenium Math problem
- A new antibiotic discovered by AI lab
- 722 AI written Math papers released at once
- A solution to AI alignment
- Google reducing errors 40× in quantum computing, making it practical
- Opus 5 level AI running fully offline
- Opus 5.5 solving motion graphics and automations.
And that's just in the last 5 weeks. IYNYK.
Incredible time to be alive
Andrew McKinzie retweeted
BREAKING: White House is monitoring a suspected plague outbreak in Russia, per Axios
Andrew McKinzie retweeted
Stripe acquired OpenRouter. Ramp launched Router.
Both are leaning into stablecoins.
Cloud, mobile, and APIs are now table stakes, not an investable category.
The next era of finance is something else.
Absolutely incredible!
Chief Design Officer @jgebbia officially unveils America.gov, the new online home for the United States of America
Andrew McKinzie retweeted
We knew this tipping point would come but this is still a crazy moment for anybody who sweated over building 3-statement models in Excel from scratch
Today is the day that AI passed the "financial modeling Turing test" for me.
A "push button" build from scratch Skill that one-shotted a model on $MU that is indistinguishable (to me) from a model that a junior analyst would build from scratch. With full, impeccable adherence to all aspects of who i like to format, design & build models (took a few turns to dial it in).
Opus 5.5 is unbelievable.
I keep hearing from fintech founders right now that it’s a very confusing time to be building, that the bar for venture funding keeps being raised, and that it feels like the world around them is moving at warp speed with AI companies scaling to $100M ARR in the blink of an eye. They all ask me some form of the same question: “given this market environment, what do you think we should do?”
My answer is typically very simple: study the hypergrowth winner playbooks. This advice comes after: 1) always build something people love and 2) always keep your customer your top priority.
So, given I keep fielding these questions, I thought it made sense to make a post laying out the hyper growth winner playbooks, or as Tolstoy would put it, the architectural traits of the "happy families in fintech." These traits might appear incredibly obvious. I think that’s actually the point.
Andrew McKinzie retweeted
Our latest research paper explores the growing connection between AI and digital assets and explains why broad AI adoption may drive new demand, utility and applications across the digital asset economy. blackrock.com/us/individual/…
Very well put by @venkyganesan @MenloVentures on the disorienting venture capital market right now. 🎯
A few thoughts on the current state of venture capital.
When the Music Is Playing
In July 2007, a few weeks before the credit markets seized up, Chuck Prince, then the CEO of Citigroup, gave an interview to the Financial Times. The line everyone remembers is this one: "As long as the music is playing, you've got to get up and dance." He was mocked for it for years afterward, and he lost his job a few months later. But I have come to think he was saying something honest. He wasn't claiming the music would play forever. He was admitting that he couldn't sit down while it was still going, and neither could anyone else in his seat.
I've been thinking about that quote a lot lately, because right now is the most disorienting period in venture capital I can remember, and I have been doing this for a while.
Here is what makes it disorienting. It's not that things are bad. Some things are spectacular. We have companies in our portfolio growing faster than anything I have seen in my career, and I don't say that lightly. At the same time, we have companies with no revenue, no product, and a founding team you could fit in a conference room raising billions of dollars at valuations of $10 to $50 billion. Both of these things are true at once, and if you try to reason about them with the same framework you will drive yourself crazy.
Two ideas have helped me make sense of it. Neither is mine.
The first is reflexivity, which George Soros has been writing about since the 1980s. In most of life, perception follows reality: the weather is what it is, and your opinion of it changes nothing. In markets, it runs the other way too. Prices change what participants believe, and what participants believe changes the prices. The feedback loop can run for a long time, and while it's running it looks exactly like progress.
Here is how reflexivity is playing out in AI. Full disclosure: Menlo is an investor in Anthropic, so read the following with that in mind. People watched a frontier lab go from a $4 billion valuation to $18 billion, then $60 billion, then $180 billion, then $380 billion, and now something close to a trillion. They drew the obvious conclusion: that is what a neo lab looks like. So the next neo lab gets priced off that path, not off anything it has built. Then it gets marked up in a subsequent round, and the markup itself becomes the proof. Look at Thinking Machines. Look at Reflection. At that point valuation has stopped being an output of the metrics and has become the metric. Nobody is discounting cash flows. They are discounting the last round.
Soros is very clear about one thing, and it's the part people skip: you cannot know when or how a reflexive process ends. You only know that it does. Every one of them has.
The second idea is Chuck Prince's, and it explains why smart people keep dancing even when they can see the loop for what it is. As far as I can tell, there are two groups on the dance floor.
The first group got in early. Firms like ours were in some of these AI companies before the numbers got silly, and the paper gains are enormous. When you are sitting on gains like that, you start to feel like you're playing with house money. I have been around long enough to know that house money is the most dangerous kind, because you don't respect it the way you respect money you had to earn.
The second group missed the early rounds and knows it. Their LPs know it too. So they are trying to make up for lost time by writing very large checks very late, which is the one strategy almost guaranteed to turn a missed opportunity into a real loss.
House money on one side, FOMO on the other, and reflexivity feeding both. That's the whole story. Everyone has a reason to keep dancing, and the reasons are different, which is why nobody can talk anyone else off the floor.
So what do you do? The instinct in our business is to answer with company identification: just pick the right neo lab and you'll be fine. I think that's the trap. When price has become the signal, being right about the company is not enough, because you can be right about the company and still be wrong about the price by a factor of ten. The public-market investors I admire figured this out a long time ago. They spend as much time on how much to own as on what to own.
The winners in venture over the next decade will be the firms that treat portfolio composition and position sizing as seriously as they treat sourcing. How much of the fund is in companies whose valuation rests on the last round rather than on revenue? What happens to the portfolio if the reflexive loop breaks next year instead of in five? Those are not exciting questions. They are the ones that will matter.
The music will stop. It always does. Dance if you must, but know where the chairs are.
Andrew McKinzie retweeted
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