Part 2: Insights from looking at a growing market.

This is the second half of part 4 of 4 of a series of musings on the topic of online privacy. I don’t pretend to resolve the problem, simply exploring facets of the space and pulling at strings that may make the web a more wholesome place to explore and help builders think about the moral valence of their technical decisions. View the first half.

TL;DR — It’s a uniquely exciting time to work on Internet Privacy. Will privacy be defined by compliance to regulation, or new software abstractions? Should the default be transparent data-usage, or privacy-by-default? …


Part 1: A Topography of Privacy Tech.

Photo by Tobias Tullius on Unsplash

This is the first half of part 4 of 4 of a series of musings on the topic of online privacy. I don’t pretend to resolve the problem, simply exploring facets of the space and pulling at strings that may make the web a more wholesome place to explore and help builders think about the moral valence of their technical decisions. View part 3, second half of 4.

TL;DR — Changes in regulation, user sentiment and the tools available to developers has led to the creation of new data privacy tooling. From decentralized systems, to data loss prevention, as well…


An open payments standard for software distribution.

Navigating software ecosystems can be trying at times.

“Flectere si nequeo superos, Acheronta movebo” — Virgil on tech monopolies and decentralization.

I have recently been playing around with a few ideas and one of them caught my eye as being particularly interesting. Simply put the idea is to offer a single decentralized payment system built specifically for software distribution. This system would lower the bar for a curator to build an app store, and so would allow developers to choose from a wider range of distribution platforms, countering the negative impact software distribution monopolies (like the App Store or Play Store) have had over developer and user experience.


And can we salvage web 2.0?

This is part 3 of 4 of a series of musings on the topic of online privacy. I don’t pretend to resolve the problem, simply exploring facets of the space and pulling at strings that may make the web a more wholesome place to explore and help builders think about the moral valence of their technical decisions. View part 2, part 4.

TL;DR — Web 3.0 will unbundle online services by making data storage independent from app logic and ensuring users maintain control over their data. However running such systems is not a silver bullet and the likely outcome is…


A (hi)story of bad incentives.

This is part 2 of 4 of a series of musings on the topic of online privacy. I don’t pretend to resolve the problem, simply exploring facets of the space and pulling at strings that may make the web a more wholesome place to explore and help builders think about the moral valence of their technical decisions. View part 1, part 3.

TL;DR — Creator’s incentives on the web today are not aligned with their users’. Being transparent is hard, and being accountable is often undersirable. At best, it gets in the way of good UX; at worst, it directly…


And why you should care.

This is part 1 of 4 of a series of musings on the topic of online privacy. I don’t pretend to resolve the problem, simply exploring facets of the space and pulling at strings that may make the web a more wholesome place to explore and help builders think about the moral valence of their technical decisions. View part 2.

TL;DR — Privacy is about the consumer’s intent. Does a product do what you think it will with your data? Consumption choices are deeply personal, but informed consent requires knowing what you’re signing up for. Forthright stewards of data (i.e…


Disclaimer: I wrote the following for my own use and while in all things startup I have a mild allergy to the heavy pontification, self-aggrandizement and disingenuous emulation out there, I thought I’d publish this in case it’s of use to someone else.

Like doing the YC application early on in a project to see whether you can articulate your plans such as they live in your head (and keep an honest account of your thinking over time), writing down assumptions about your partnership can help uncover important topics: I propose an amended questionnaire.

Many have already written about founder…


So I was trying to walk my Mom through why crypto may well be a valuable asset class, and why certain elements make it so hard to tell thoughtfulness from rashness in the space. I started typing up what I thought would be a page, and ended up with a bit more. To amortize wrist-strain, I thought your Mom might enjoy reading it too (mine will say she did regardless :b).

Disclaimer: I freely editorialize and will make corrections as people point out my (many, I’m sure) mistakes here. Read at your own risk (like everything else online).

Much of…

Henri Stern

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