Sergio Maldonado
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sergiomaldo.bsky.social
Sergio Maldonado
@sergiomaldo.bsky.social
Lawyer and Entrepreneur (PrivacyCloud, Sweetspot, Divisadero). Marketing + Privacy + Data + Tech. Yet another podcaster (Masters of Privacy). Pondsman in the making. NC & London.
Absolutely brilliant - it is not about how much #AI can do but about how limited we always were. www.newyorker.com/magazine/202... #AI #thought #language by James Somers
The Case That A.I. Is Thinking
ChatGPT does not have an inner life. Yet it seems to know what it’s talking about.
www.newyorker.com
November 16, 2025 at 2:42 PM
A few thoughts on the future of legal services. Buying pre-packaged #AI solutions may be the wrong way to go. Also, I would avoid #OpenAI et al open.substack.com/pub/privacyc...
How about law firms becoming software providers (instead of being replaced by them)? (Part I)
An investment in external tools could hamper a firm's ability to compete
open.substack.com
September 28, 2025 at 5:55 PM
Tony Fish, always inspiring. Fantastic conversation. On #AfterTheMagic

open.substack.com/pub/atmagic/...
Tony Fish: Navigating a constant state of transition
What vehicle do we need to enable us to start working with AI?
open.substack.com
September 28, 2025 at 5:52 PM
How will #AI Agents affect #Ecommerce? Have LLMs reshaped keyword-based product search? How can leading retailers ensure proper governance of their AI stack while maintaining their competitive advantage? We have asked my brother Angel: www.youtube.com/watch?v=2BJ0... #afterthemagic (limited series)
Angel Maldonado: How Agentic AI reshapes Ecommerce
YouTube video by After The Magic
www.youtube.com
August 6, 2025 at 10:34 AM
Reposted by Sergio Maldonado
[EN] Can we move beyond “dark patterns” to define Manipulative Design or Interface Interference? How could we expand website and mobile app monitoring to a company’s ad stack? We asked Christine Desrosiers (Boltive) in the 5th installment of our #PrivacyTech series.
www.youtube.com/@MastersofPr...
Masters of Privacy
Hoping to better understand a human-centric, demand-led future, we have spent a few months interviewing entrepreneurs and pioneers at the intersection of Marketing, Data, Privacy, and Technology. This...
www.youtube.com
July 28, 2025 at 11:46 AM
[EN] Here goes another ToS change to make room for #AI training (user content/files), followed by the predictable backlash. This time it is #WeTransfer ’s turn - Solicitor Neil Brown argues in favor of an “implied copyright license” in the UK. In TheRegister www.theregister.com/2025/07/18/l...
WeTransfer ToS adding 'machine learning' caused freakout
Analysis: WeTransfer added the magic words 'machine learning' to its ToS and users reacted predictably
www.theregister.com
July 21, 2025 at 10:00 AM
This gets really interesting. A particular kind of query would incorporate “intent” and beat the opposite flow (a conversation/search that starts on Shopify), and whoever owns the query can commoditize everyone else. “OpenAI to take cut of ChatGPT shopping sales in hunt for revenues” - on FT #retail
OpenAI to take cut of ChatGPT shopping sales in hunt for revenues
Artificial intelligence start-up has shown brands a prototype of its new checkout feature
www.ft.com
July 16, 2025 at 3:18 PM
In 2021 I interviewed the great Julian Wilson, who sadly has just passed away. We covered the interplay between Self-Sovereign Data and Open Banking. His ideas remain as relevant as ever mastersofprivacy.com/julian-wilso... May he rest in peace.
Julian Wilson: Self-Sovereign Data meets Open Banking - Masters Of Privacy
Julian Wilson began his career at Apple in the late 80s. Here he worked on projects such as the world’s first set top box, hybrid CD / internet games console and as part of the...
mastersofprivacy.com
July 9, 2025 at 11:28 AM
Yet again. Expecting a probabilistic system to produce an accurate output #AI
May 28, 2025 at 7:22 PM
Depth of reasoning can now be determined on the fly, rather than responding to an on-off switch. #AIAgents
May 28, 2025 at 6:54 PM
Reposted by Sergio Maldonado
Researchers have wildly variable views about what the future of A.I. will bring. “Which is it: business as usual or the end of the world?” Joshua Rothman writes.
Two Paths for A.I.
The technology is complicated, but our choices are simple: we can remain passive, or assert control.
www.newyorker.com
May 27, 2025 at 10:01 PM
Possible #DSA fine over TikTok’s missing “ad library”. It really will get interesting once people start getting their hands on these repositories (creative+target audience)… and how does it work with black boxes? “EU takes action against TikTok over online content rules” www.ft.com/content/6fee...
EU takes action against TikTok over online content rules
Ad transparency investigation is one of several ongoing European cases against social media platform
www.ft.com
May 15, 2025 at 12:32 PM
Reposted by Sergio Maldonado
Kenya’s high court recently ruled that Worldcoin, the biometric startup co-founded by Sam Altman, has to delete the personal data of over 300,000 Kenyans.

Learn more about how Worldcoin operated in Kenya and other developing countries in this story from 2022.

⬇️⬇️⬇️
Deception, exploited workers, and cash handouts: How Worldcoin recruited its first half a million test users
The startup promises a fairly-distributed, cryptocurrency-based universal basic income. So far all it's done is build a biometric database from the bodies of the poor.
www.technologyreview.com
May 8, 2025 at 8:27 PM
Reposted by Sergio Maldonado
As a German I will forever be grateful to all who fought for the liberation of Europe.

But as a historian I am looking at front pages today and must wonder: What is the point of remembering #VEDay 80 years on, what is the point of our thanks, when we are failing to protect the sacrifices made? 🧵
May 8, 2025 at 8:59 AM
I had published this article in the UK's Privacy Laws & Business back in February. In essence, pondering server-side solutions, Conversion APIs, Data Clean Rooms and synthetic data as an alternative to the #ePrivacy trap after the EDPB's latest guidelines... www.privacylaws.com/reports-gate...
Avoiding the scope of the ePrivacy Directive in advertising
Sergio Maldonado of Privacycloud discusses AI-driven anonymisation, server-side solutions, and the recently adopted EDPB ePrivacy Directive Guidelines in the context of tracking
www.privacylaws.com
April 28, 2025 at 9:58 PM
Bertrand du Marais (CNIL), Stephen Almond (ICO), Des Hogan (DPC) discuss “Consent or Pay” models at #GPS25. Given the clear overlap with competition concerns (pricing!), yesterday’s DMA enforcement actions against Apple and Meta provide the ideal backdrop. @iapp.bsky.social #privacy #dataprotection
April 23, 2025 at 6:00 PM
Brilliant. This: “The internet is now optimised for metrics that have nothing to do with human enjoyment, or convenience, or the profits of anyone except the platform overseers.” by @jacobsilverman.com on @financialtimes.com www.ft.com/content/5d06...
April 20, 2025 at 8:24 PM
A powerful reality check delivered by @garymarcus.bsky.social - Generative AI will never evolve into AGI and people have wildly overestimated productivity gains from LLMs. We possibly need to integrate symbolic AI (to reach neuro-symbolic AI) and world models #nextai #ai
March 20, 2025 at 6:11 PM
@tarekbesold.bsky.social on the Unthinkable panel at #nextai : there seems to be a generational disconnect in terms of attribution (for public works online) and #explainability. Not necessarily due to a new utilitarianism (or lack of respect) but perhaps assuming collective ownership (and trust) #ai
March 20, 2025 at 2:40 PM
Brilliant Martina Larkin on the Humanity Paradox in the context of #AI: The cold pursuit of labour efficiency has a social cost, as does chasing engagement metrics in digital media.

We should instead enhance what makes us human. Human agency is a must. #nextai
March 20, 2025 at 11:18 AM
Reposted by Sergio Maldonado
The Pebble smartwatch team shares all of the ways Apple limits non-Apple smartwatches on the iPhone.

Your smartwatch can’t send texts, respond to notifications or talk to iOS apps unless it’s an Apple Watch. No one is allowed to build a device that connects to an iPhone as well as an Apple device.
Apple restricts Pebble from being awesome with iPhones
I’m surprised that you’re surprised
ericmigi.com
March 19, 2025 at 1:23 AM