Tuesday, October 27, 2026

Tiny Tentacle 🐙: A vibe-coding success story



Introducing Tiny Tentacle

My goodness is it fun to build something that actually solves a problem 🥳

Tiny Tentacle is a simple Mac menu bar utility that eliminates two steps when repeatedly sharing screenshots with a desktop LLM application:

  • Switching back to the LLM application
  • Using a keyboard shortcut to paste the screenshot

That might seem like nothing, but I frequently copy/paste dozens of screenshots a day into LLMs, and that little friction adds up and is suuuuper annoying.

Using Tiny Tentacle, I now hit ⌘⇧T, select the area to screenshot, and it automatically pastes the screenshot into the conversation I have open in my pre-selected destination (Claude or ChatGPT).

Capture happens locally, it doesn't allow annotations right now, and Tiny Tentacle itself doesn’t press Send.

That's it! And it's awesome.

Friday, October 16, 2026

Chess observations and thoughts

A running list in no particular order
  • I am objectively bad/a beginner 
  • Chess is a brutal game, losing hurts, rating doesn't lie 
  • Whenever I make a jump rating, I inevitably lose it all and more at some point and have to gain it all back again. This used to hurt, now I consider it a "burn down," expect it, and just ride the rollercoaster 
  • My #1 chess vices are moving to fast / losing concentration, it's a sure way for me to lose quickly 
  • Losing rating is easy/fast, gaining rating is challenging/slow 
  • Playing fewer games leads to more focus, shocker! 
  • Chess Youtube is a great / fun place 
  • I play 15:10 time control 

Saturday, September 26, 2026

AI Doomer, how has your behavior changed?

A lot of people in and around frontier AI say they assign a meaningful probability to AI causing human extinction. I find this quite hard to take seriously. 

To be crystal clear, I think there are plenty of reasons to take AI risk seriously without believing that humanity is about to be wiped out, i.e.

  • It is already creating serious cybersecurity problems
  • It could displace huge numbers of workers
  • It could concentrate power in very uncomfortable ways
  • It could destabilize industries, institutions, and politics

What I have much more trouble with are  extraordinary claims that there is a meaningful chance that everyone is dead in 10 or 20 years, or that we are building something fundamentally beyond human control.

Which leads me to a much simple question: what would we expect those beliefs to look like in practice?

I don't intend this to read as a gotcha.

Extraordinary beliefs should produce some extraordinary behavior.

And if there isn’t much extraordinary behavior, that’s meaningful information to have.

I genuinely wonder whether such folks are changing their behavior in clear ways. That would change how I think.


Question What it’s intended to reveal
What percentage of your net worth have you spent trying to reduce AI risk? Whether the belief is strong enough to materially change how you allocate your own money.
What political donations have you made to candidates who would slow frontier AI development or data-center expansion? Whether concern translates into concrete political spending when there are opportunities to impose real constraints.
What long-term financial or life plan have you changed because you think there may not be a long term? Whether AI risk actually changes your planning horizon.
Have you told your family or close friends to materially change their financial or life plans because of AI risk? What did you recommend? Whether you apply the belief consistently when advising people you care about.
What is the largest personal sacrifice you have made because of your belief about AI risk? Whether the belief has imposed any meaningful personal cost.
Have you donated your equity grant to efforts aimed at slowing AI development or reducing AI risk? Whether you are willing to give up direct financial upside from the activity you believe may be dangerous.
What power, money, or influence have you voluntarily given up because accumulating it conflicted with your safety principles? Whether safety beliefs ever place a limit on self-interested accumulation.
What action would be bad for your career but good for AI safety, and have you ever taken it? Whether AI safety actually wins when it comes into direct conflict with career incentives.


"What do you think people get wrong about you?"

"What do you think people get wrong about you?"

A recruiter asked me a few years ago, and what an incredible question!

  • It caught me off guard
  • It forced real introspection
  • I discovered something about myself
My answer 👉 People misunderstand my humor and energy. 

I can be pretty ridiculously excited and energetic at work 😅 it's a bit embarrassing actually.

It's easy to imagine someone reading that enthusiasm as a lack of seriousness. 

A sober demeanor is much better suited for signaling seriousness. Alas, I'm genuinely having fun.

Incredibly dorky and ridiculous, but true! 

At the same time, I'm quite serious about my work, career, and producing shareholder value 😜

Here's what that looks like.

In my free time:
  • Reading tech analysts like Ben Thompson and Benedict Evans to understand how they view what's changing
  • Reading earnings reports and transcripts to understand how public company moves are playing out and how they might affect the startup landscape
  • Tracking which startups are shipping, raising, growing, and actually finding traction vs. just riding a hype train 
  • Trying new software constantly, not because I love shiny objects, but because I view understanding what's new, possible, and actually useful as part of my job
  • Writing and thinking through what I'm learning so I actually develop a point of view

Seriousness is something I calibrate to the situation, it's not my default demeanor.

What I Gained from 5 Years in Crypto

I worked in the crypto industry from 2018-2023 and boy was it a funny thing.

At the time, I got into it because from my somewhat-naive perspective, it looked like the next big thing. 

New technology, all sorts of interesting promises and ideas were coming out of it, and I was drawn to the technical nature of blockchains. I still am, in fact, it's interesting technology.

Looking back, I do feel a bit of embarrassment about my time in an industry which produced a truly stunning amount of grift, gambling, and other bullshit.

And yet, I don't regret it. 

In no particular order, here's what I gained from my time:

  1. Leading at scale
  2. Learning venture capital
  3. Distinguishing hype from reality
  4. Learning just how adversarial financial markets are

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