André Oliveira

Super excited about our new initiative at @Pixelmatters_, positioned to help overseas enterprises open their Tech Hub in Portugal. 🇵🇹 ℹ️ +info here: pixelmatters.com/insights/open-… If you'd like to know more, just DM me here on X! 💪

Obrigado, André Villas Boas 💙🐉🏆

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The 1st @joinupsideclub Poker Night is in the books! 🃏 Another experiment, another one to repeat. It was so much fun. And I won, so that made it even better. 😂 More of these coming! 🔥

I spoke to five Fortune 2000 execs today about the state of AI. I asked each one “What’s the most challenging part about this moment in AI?” The CISO said: “There is an ocean-sized gap between hype and reality, which makes discerning what’s real exhausting.” The VP of AI engineering said: “Everyone acts like they’re an expert, yet the main reason so few AI use cases have reached production in enterprises is because true expertise requires experience in scaled systems, enterprise politics, AI fluency, governance and guardrails, and deep process knowledge. Almost no one is actually an expert.” The CTO said: “Our remit is to cut costs, but you can’t actually take AI transformation seriously without increasing AI/R&D budgets up front to ultimately drive bottom line once things are in production and performant. It’s an unrealistic expectation.” The Chief of Staff said: “My job is to drive AI upskilling across the organization, and after doing it for 2 years I’m exhausted. Yes there’s potential ROI from all of the agentic workflows we’re building, but soul and humanity are being sucked out of our processes.” The Finance leader said: “We acquired a multibillion dollar old school business. Getting that business to be AI-native is incredibly painful largely because people aren’t ready or willing to adopt it.” I’m having convos like this every day because I'm building an invite-only AI community for enterprise execs (and interviewing folks before I let them in), but if you find these notes helpful I’m happy to keep sharing them!

We're renaming @Pixelmatters_ conference. Just kidding. 😂 It's still Craftmatters. But honestly, if we'd called it AImatters, it would've sold out by now. The focus is craftsmanship. But there'll be plenty of AI! May 29 @ Hilton Porto Gaia. ~50 tickets left. 🎟️ luma.com/craftmatters-2…

@BancadaDragao Isto está maravilhoso. Nunca acabem 💙

Esta sequência de entrevistas é uma matrioska de benfiquismo. Um bem haja ao jornalista pela sua bravura e desfrutem destes 3 minutos de prosa lampiã.

This is obvious. We’ll soon look back and wonder how we took this long to build better UI for agentic workflows. We’re doing just that at @pixelmatters_.

Hiroki Asai spent 18 years as creative director at Apple under Steve Jobs. He was described as "a silent force who could channel Steve." He taught Brian two of the most important principles: "The first was simplicity. Startups are naturally simple because you have no money. Lack of abundance creates natural constraints. Once you raise money and hire a bunch of people, you go in a lot of directions and lose your sense of focus. You start to lose your muscle for simplicity. Hiroki taught me that simplicity is not removing things. Simplicity is distilling something so fundamentally that you understand its essence. The second was a sense of craft and details. How you do anything is how you do everything. Everything must be perfect. John Wooden, the winningest coach in college basketball history at UCLA. The first hour on his team, he spends an hour teaching you how to put your socks on. Bill Walsh said the way you tuck your jersey into your pants was one of 10,000 details that determined whether you won. Don't focus on winning. Focus on getting all the inputs perfect. We do focus on growth, but we kind of stopped focusing on growth. We started focusing on making everything perfect. If everything is perfect and you don't grow, then you focus on the wrong inputs. But if you have the right inputs and make them perfect, then you'll grow really fast."

Huge amount of value dropped right here by @bchesky under 2mins

@thealepalombo How many Lisboners have you heard saying they’re proud to be Lisboners? When you meet someone from Porto one of the things it’s almost guaranteed the person will say is that he/she loves the city and is proud of it.

@smackingg Ok, but I'd say also Lisbon has it :) No?

Many people seem to prefer Porto to Lisbon. Why?

@thealepalombo That, plus one of the biggest hidden-secrets for tech companies who want to open an engineering, product or AI hub abroad 🇵🇹 pixelmatters.com/tech-hubs-in-p…

I am in Porto these days, and it’s one of those rare places where the food is as good as in Rome. Have you ever been to Porto?

@tiagopita O melhor post recente a ilustrar o que referes é este x.com/mattshumer_/st…

@ManuAlzuru @EspressioAI That’s an @joinupsideclub tshirt right there 🔥🔥🔥

Yesterday I went to @EspressioAI’s coworking space in Lisbon and something clicked. It felt like 2017 again. But this time… it’s AI agents. 1/10

@Clara_Gold We need to bring honesty to SF @cisco_raio @joinupsideclub

6 months ago, I moved to San Francisco. It’s the best place in the world to build, and one of the worst places to stay human. My unfiltered take: 1. SF is both overhyped and underrated The overhyped part: there are a lot of people with incredible resumes who are deeply unimpressive in real life. They were at the right company, at the right time, in the right market, and got carried by the wave. They made money, got comfortable, and now spend their time “exploring opportunities” over coffee, wasting your time. The underrated part: the top 1% here is insane. But almost impossible to get. Hiring in SF feels like being a guy on a dating app: everyone you want is out of your league, and everyone in your league wants someone out of theirs. The best people have unmatchable packages, endless options, and are optimizing for maximum impact: labs, frontier companies, or startups raising $100M pre-seed rounds. If you raised $10M from Tier 1 investors, you’re not hot shit here. You’re a B-player. It’s humbling. 2. There are fewer mission-driven people than I expected Especially on the application layer. A lot of people are in “secure the bag before it’s too late” mode. And honestly, it gives me the ick. The real religious builders I’ve met are often in labs, hardware, biotech, deeptech, defense — places where the work is hard enough that you can’t fake obsession. 3. The status game favors builders This is what SF does better than anywhere else. It rewards obsession. It rewards weirdness. It rewards people who make building their entire personality. Europe punishes that. SF gives it status. If you’ve felt like an outsider your whole life because you care too much, work too much, think too radically, or refuse to be chill about things that matter, this city will make you feel less insane. 4. The market liquidity is absurd Even if you don’t build a billion-dollar company, if you manage to build a strong product with a great team, someone smart might still acquire you for $ 100M. Yeah I know, it’s not your dream outcome as a founder, but on the days you feel desperate, it helps to keep going. 5. SF does not care about the meaning crisis that’s coming Anyone paying attention here can feel that something massive is happening with AI. But I’m shocked by how little people talk about the meaning crisis coming next. Everyone wants to talk about AI liberating humanity. Almost no one wants to talk about what happens when work — the thing that gives most people identity, structure, dignity, status, and purpose — starts disappearing. The vacuum will not be peaceful. People are underestimating the chaos that comes from humans suddenly having no idea why they matter. And I really feel like no one cares. 6. Personally, I’ve never been more unhappy I moved to SF and entered the matrix. I’ve always been intense. I’ve always worked crazy hours. But here, I lost the last parts of myself that were not about building. I don’t go to events. Most networking events feel like theater for people pretending to be important. The only events worth going to are small, curated dinners with people who are actually alive. I’ve made 0 real friends. I don’t do well with transactionality. I don’t do well with people constantly performing greatness. I don’t do well with rooms where everyone is optimizing and no one is being honest. So yes, SF is lonely, transactional, delusional, addictive, inspiring, boring, extraordinary, and completely insane. But it is still the only place to be right now if you’re a founder trying to build the next wave of humanity. And for now, that’s enough.

Last week, @Apple announced that @tim_cook is transitioning to Executive Chairman while John Ternus is becoming the new CEO by September 1st. Reading through the blog post, I found some patterns to the CEO transition plan we also did at @Pixelmatters_ → Announcement made before the effective transition takes place → An explicit mention to the period of time between now and Sep 1st, during which John will basically shadow Tim and they'll do everything together → John was already at the company for several years, as @bmfteixeira was Obviously, there's no possible comparison between @Pixelmatters_ and @Apple except for how passionate both company cultures' are for doing great work. But observing these similarities felt like a good validation of the approach we took. 💪 Happy to advise anyone going through - or planning! - a similar transition.

@fcportomaradona @FCPorto Deve ter havido um acordo verbal com o Thiago Silva para ele jogar e tentar a ida ao mundial. Com a eliminação da LE e da Taça, sobram agora estes 4 jogos. Penso que será isso…

É para mim incompreensível a insistência em Kiwior como LE. O @FCPorto perde o seu melhor central e fica com um lateral absolutamente banal. Quanto ao resto é 11 expectável e espero que seja o 11 que conquiste 3 pontos absolutamente fulcrais para a conquista da @ligaportugal!💙💪🐉

@cisco_raio We need this to become your new avatar

How to nail your Sunday before noon 💪🏻

The awesome @mchgli flew from Italy 🇮🇹 to interview me! And the interview is now out 📽️ go watch it! youtu.be/qaTm-alikhk

Bullish on the @joinupsideclub