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.
Some wild ideas on the future of legal services, from legacy firms supercharging Microsoft Word with Legoras and Harveys to Legal Quants building #Claude Skills and deploying local models. www.linkedin.com/pulse/legal-... #law
Legal AI vs. AI-native law firms
(You are reading a GenAI-free article, solely relying on auto-correct for some expressions and typos - and for a more readable version of my original 2x2 sketch. I published a first iteration of these...
www.linkedin.com
January 29, 2026 at 4:05 PM
Some wild ideas on the future of legal services, from legacy firms supercharging Microsoft Word with Legoras and Harveys to Legal Quants building #Claude Skills and deploying local models. www.linkedin.com/pulse/legal-... #law
Dreaming of a world in which opt-out signals and user-defined terms rule over consent banners… open.substack.com/pub/masterso... #ePrivacy
Browser-Supported Signals as a replacement for Consent Management Platforms
Can you even remember the days when the internet was clutter-free?
open.substack.com
January 21, 2026 at 6:38 PM
Dreaming of a world in which opt-out signals and user-defined terms rule over consent banners… open.substack.com/pub/masterso... #ePrivacy
In NYC on January 14? Join us for dinner and a live recording session on the impact of GPC and other opt-out signals across various jurisdictions www.mastersofprivacy.com/p/masters-of... #ePrivacy #AdTech #MarTech
Masters of Privacy LIVE NYC 2026
Privacy meets MarTech & AdTech (January 14, 2026).
www.mastersofprivacy.com
January 3, 2026 at 11:58 AM
In NYC on January 14? Join us for dinner and a live recording session on the impact of GPC and other opt-out signals across various jurisdictions www.mastersofprivacy.com/p/masters-of... #ePrivacy #AdTech #MarTech
I had a lot of fun recording this one with Gam Dias for #AfterTheMagic, and hopefully some of you will enjoy listening to it. We covered a lot of ground, from the pace of #AI (and agentic building blocks) to automating litigation and Empowerment Tech.
www.afterthemagic.com/p/just-wait
www.afterthemagic.com/p/just-wait
Just wait
Coping with the pace of agentic tools, bias, AI judges, Empowerment Tech, MyTerms, AI Ethics and the environment.
www.afterthemagic.com
December 12, 2025 at 4:17 PM
I had a lot of fun recording this one with Gam Dias for #AfterTheMagic, and hopefully some of you will enjoy listening to it. We covered a lot of ground, from the pace of #AI (and agentic building blocks) to automating litigation and Empowerment Tech.
www.afterthemagic.com/p/just-wait
www.afterthemagic.com/p/just-wait
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
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
More ideas on third party audits open.substack.com/pub/privacyc...
Accountability and third-party vetting in the age of wild automation
Cutting through the noise of third-party vendor credentials
open.substack.com
October 23, 2025 at 11:01 PM
More ideas on third party audits open.substack.com/pub/privacyc...
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
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...
Tony Fish, always inspiring. Fantastic conversation. On #AfterTheMagic
open.substack.com/pub/atmagic/...
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
Tony Fish, always inspiring. Fantastic conversation. On #AfterTheMagic
open.substack.com/pub/atmagic/...
open.substack.com/pub/atmagic/...
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
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)
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...
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] 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...
www.youtube.com/@MastersofPr...
[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
[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...
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
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
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
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.
Yet again. Expecting a probabilistic system to produce an accurate output #AI
Le gouvernement retire une vidéo générée par IA sur la Résistance, à la suite d’une erreur historique
Le gouvernement retire une vidéo générée par IA sur la Résistance, à la suite d’une erreur historique
La vidéo, diffusée sur les comptes TikTok et Instagram du gouvernement, représentait une résistante célébrant la libération de Paris. La présence à ses côtés d’un homme ressemblant à un soldat allemand a conduit à sa suppression.
www.lemonde.fr
May 28, 2025 at 7:22 PM
Yet again. Expecting a probabilistic system to produce an accurate output #AI
Depth of reasoning can now be determined on the fly, rather than responding to an on-off switch. #AIAgents
The company claims its ability to tackle complex, multistep problems paves the way for much more proficient AI agents.
Anthropic’s new hybrid AI model can work on tasks autonomously for hours at a time
The company claims its ability to tackle complex, multistep problems paves the way for much more proficient AI agents.
www.technologyreview.com
May 28, 2025 at 6:54 PM
Depth of reasoning can now be determined on the fly, rather than responding to an on-off switch. #AIAgents
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
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.
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
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...
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.
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Learn more about how Worldcoin operated in Kenya and other developing countries in this story from 2022.
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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
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.
⬇️⬇️⬇️
Learn more about how Worldcoin operated in Kenya and other developing countries in this story from 2022.
⬇️⬇️⬇️
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? 🧵
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
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? 🧵
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? 🧵
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
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...
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
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
Reposted by Sergio Maldonado
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
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...