Building AI for growth marketing teams @OptimizePilot | @Harvard CS | Exploring research → product | Coffee & corgis
Cambridge, MA
Joined March 2009
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Is it just me or is Claude Ultra sipping tokens this week? Kind of feels like the "it was never 20x" fallout might have resulted in it `actually` being 20x now...
This morning, I wake up 2,000 miles away from my home state of Texas, and I’m sad. Yesterday’s election results went in a way that I don’t think anyone could have predicted. And damn, how I wish I was there to celebrate Texas being this blue for the first time in my life.
All of the LinkedIn "thought leaders" posting about the Accenture AI "cap" have obviously never worked in consulting, worked with consultants, or spent 30 seconds (that's .1 hours) talking to one. The firms don't care about AI as long as it can be billed to a client.
So Katie Zacharia made it .5 Scaramuccis as press secretary. We can only hope that this is the first of many firings leading up to and following the midterms.
For me, the new HomeView's most disappointing design decision is the lack of third-party apps. I use an older iPad Mini as my cooking companion for the NYTimes recipe app and was hopeful the new device would replace that use case.
There's a lot of track between an AI following the directives of a website owner and issuing fines. The issue isn't that Claude follows rules very literally; it's that AI tools are being exploited by less scrupulous actors to game the systems that we've granted trust to over the last ~3 decades.
This is insane. A massive system of population control and subordination through compliance is coming with AI, and last night I felt it for the first time.
Claude refused to access a news article because the NY Post lists Claude’s bot as disallowed in its robots.txt file.
This will only get worse.
Claude will soon refuse to do any knowledge work related to link building for SEO because it’s “against Google’s policies.”
In the future, Claude will also issue automated fines for swearing in public or for overtaking a cyclist at 5 mph on a straight road with no oncoming traffic but a solid white line in the middle.
We are sleepwalking into a mechanistic, 100% compliant, 100% AI controlled world where the only people allowed to “break the rules” or think outside the box will be those controlling the AI companies.
Now that we’ve passed the two-year mark since @photomatt’s WordCamp attack on @wpengine, it’s worth reflecting on how much a forced pivot can change your life.
Through 2024, I had spent 12 years as a full-time WordPress services provider. I carved out a great niche delivering custom engineering, architecture, and unbiased advice for SMEs. I built a great life on my earnings from WordPress and volunteered with WordCamp and meetups in Austin to give back.
The downside of SMEs, especially in conservative verticals like commercial real estate, legal, accounting, and healthcare, is that they are risk-averse.
When WP.org access was cut, sites hosted on WP Engine started throwing server errors and I had to explain to clients why theirs sites were down and why I couldn’t do anything about it.
When your business depends on stability, vendor-driven fragility is scary. Many didn’t just leave WP Engine; they abandoned WordPress.
Six figures in recurring billing vanished within two weeks. Two projects were paused and ultimately cancelled.
Fortunately, I hadn’t spent 12 years just building websites, 75% of my work at the time was custom development.
Coincidentally, a friend had recently stepped away from a 30-year marketing agency career, and we teamed up.
Finding our footing took some time, but today we run a growing engineering and consulting business that surpassed my best-ever WordPress earnings in our very first year.
On top of that, stepping out of the WordPress maintenance treadmill gave me the bandwidth to build an AI-powered SaaS and pursue a computer science degree at Harvard.
I haven’t fully stopped touching WordPress and I think there are advantages to it for some limited use cases, but the work I do with it now looks much different and could be applied to any modern PHP stack. It will also account for less than 5% of my revenue in 2026, and likely closer to 1% in 2027.
Mullenweg proved that unchecked ego and vendor shakedowns can single-handedly torch decades of ecosystem trust and accelerate a massive developer brain drain. But personally? I’m grateful he did it. He forced me to outgrow a stagnant sandbox, and my enjoyment of life, work, and balance sheet have never looked better.
Drate Berry retweeted
President Trump’s decision to lift sanctions on Russian fuel amidst Putin’s ongoing and brutal attacks on civilian targets in Ukraine makes no sense and is a betrayal of the legacy and leadership of the late Senator Lindsey Graham.
While Ukraine fights for its survival, Putin’s war machine continues to prosecute his terrorist war on civilian populations and innocent Ukrainians are dying every day.
Now, Instead of implementing the tough sanctions Lindsey Graham fought to his last breath to enact, President Trump has announced the United States is lifting sanctions on Russian energy, fueling the Putin’s war machine.
As I saw firsthand in Ukraine last month, Putin is losing this war. Ukraine has fought the Russian military to a standstill and reinvented warfare with drones taking the fight into the heart of Russia.
America should not be throwing a lifeline to Putin’s war machine. Now is the time to stand strong against Russian aggression as we did during the first Trump administration.
Putin doesn’t want peace. Putin wants Ukraine. I have no doubt that if Putin overruns Ukraine, it will only be a matter of time until Russia’s military crosses a border that our troops will have to deal with him.
America is the Leader of the Free World. For our National Security, for the security of our Allies in Europe including Ukraine, President Trump should rescind this deal immediately and return to the strong policies of our four years in the White House; impose harsh sanctions on any nation purchasing Russian energy and work with our allies to ensure Ukraine has the military support it needs to repel and defeat this Russian invasion once and for all. Slava Ukraini🇺🇸🇺🇦
Not a good sign for your company's future when one of your very well known investors uses his platform to say you're a second tier competitor.
You are a struggling second tier competitor that is more unethical and lying just because you have no decency or sense of proper behavior and shows your desperation. Straight out lying about if Chris being fired I thought would be below even you.
Readers added context they thought people might want to know
Khosla is an investor in both Cognition and Factory. khoslaventures.com/category/enter…
Is it just me or is iCloud Drive causing more issues because of weird syncing race conditions than it has previously? I'm working in a file now and keep getting the modified/choose one dialogue but both versions show as edited on my laptop ~4 minutes apart.
Just a reminder to look at your credit card statements, not just say, "Oh, the amount looks about right," and pay it. After spending $100/mo on AWS for an EC2 instance I haven't used for a personal project since April, I finally terminated the instance and the RDS.
While I’m seeing a lot of posts about @claudeai weekly limit reduction, my personal experience is that Fable 5.1 is much more efficient. I ran a 2 hour session building a review tool and used <50% of my 5-hour limit and <5% of my weekly Fable usage. With frontier models, I believe we’re back to prompting mattering a lot. It’s not that the models aren’t “smarter” it’s that they’ve been trained not to ask questions or say they don’t know/understand something.
How did I spend the last hour? Trying to get an ACH trace number from @Chime for a payment the receiving bank claims they haven’t received yet. 4 different transfers and no resolution. @thebancorp provides 0 support for their fintech partners (fair) but that’s who I had to file an OCC complaint against. The experiment with neobanks has been fun, but I think it’s safe to say that I’ve been wise to maintain my relationship with a traditional bank.
This sounds like the actions of a sane and reasonable majority shareholder that definitely shouldn’t be on leave…
Automattic’s board is out, days after its members voted to put chief executive Matt Mullenweg on leave, sources tell TechCrunch.
spr.ly/6018BGudLs
For anyone looking at a furnished relocation and renting via @theblueground I cannot advise you more strongly to NOT. Dealing with their “local” customer service agents that have never set foot in Boston has been abysmal. Since day 1, they’ve done nothing but shift blame over non-disclosed unfinished building construction, and are now “interpreting” a section of my agreement that says no fee is payable for a relocation to mean that a fee is payable. Absolute dogshit of a company. Looks like I may have to call in some favors with real estate and contract attorneys.
Drate Berry retweeted
I’m actually pretty upset Apple allowed this. While the feature is cool, the technical functionality that enables it is not cool.
If I was Tim Apple, OAI would be temporarily banned from the App Store until this is reversed, and here’s why:
I use iMessage because it’s quantum encrypted, with server keys I can own. Local caches are on devices that are encrypted with my passwords, not apples keys.
This makes it and computationally and legally impossible for anyone else to access chat history but the people I trust and directly communicated with.
But *now* the copies of my messages from years ago on *anyones* laptop in what is *supposed* to be an encrypted-at-rest local cache only can now be fetched directly by chatgpt without my permission or even knowledge and stored and processed in plain text forever on openai / Microsoft servers unencrypted and requested by any government entity at a moments notice without my knowledge and openai/Microsoft legally have to provide that, in federally enforced total secrecy. And they’re never legally allowed to admit they do it.
AND because of default chatgpt settings most people haven’t bothered to turn off, all those private texts can now be used for training and will end up in the weights of future models, so all future AI models will permanently know all of our private lives as a part of the weights, immortalized forever as training checkpoints.
Total architecture abandonment and user trust betrayal on Apples part. This should be the most viral story of 2026 by 100x. The permanent end of private communication in the US.
Do any of my Austin friends have any contacts at @BonterraTech? Working on a project and want to talk to someone technical about the API capabilities
This was a fun project to work on over the last couple of weeks. Training an imagine classifier to distinguish between two nearly identical breeds of dogs “sheds” a lot of light on what’s happening under the hood. Full blog post soon.
github.com/drateberry/not-co…
