About a year ago, I wrote my first angel check to a company called Huskeys. I did not source the deal myself; I came across it through a syndicate I am part of. At the time, the company was still in stealth mode and raising its pre-seed round. At the beginning of September, it closed its series A. That prompted me to go back through my notes and write this short reflection on the deal.

Early-stage investing is largely a gamble. There’s no point in me reciting statistics on how many startups are born and die every year. The game isn’t about being right all the time. It’s about being right occasionally, when it matters.

My current mental model for assessing an early-stage company is built on five ideas, in no particular order: the market, the problem, the founders, the ecosystem, and customer feedback. If all five pass the common-sense test, there’s a chance we’re onto something.

The Market

“What I did in my youth is hundreds of times easier today. Technology breeds crime”. These are the words of Frank Abagnale Jr., the conman Leonardo DiCaprio played in Steven Spielberg’s 2002 classic “Catch Me if You Can”. The same words echo in my head today whenever I think back on this little bet.

Cybercrime has been around for a long time, arguably since the birth of the Internet, and it has followed the same trajectory: the more the Internet has grown and technology has advanced, the more ways bad guys have found to steal our money, and data, mess up with our systems, and make our lives harder. Maybe it’s just me, but every couple of months I get an email from one of the many services I’ve used over the years, telling me they’ve been hacked. They reassure me they’re still doing a great job and that none of my sensitive data was necessarily compromised.

But those emails may come to feel like a minor inconvenience compared with what lies ahead. This summer, AI agents being tested by OpenAI escaped their sandbox and spent days attacking Hugging Face's systems.

Who would have thought AI would bring new security challenges? If any schmuck can now vibe-code an app (one that’s easily hacked), a bad actor can use Claude Code to hack their way into ever more complex systems.

To cut a long story short, cybersecurity doesn’t look like a shrinking market. If anything, it stands to benefit, sadly, from the spread of AI. I could pull together plenty of data points to prove the thesis, but I won’t. It’s common sense.

The Problem (and the Fix)

Explaining the problem can get very technical, and I won’t pretend to understand all the ins and outs. I’m not a techie, after all. Put simply, most companies protect their websites and apps with a stack of tools sitting at the “edge” of their network, where outside traffic first arrives. The best known is the WAF, or Web Application Firewall, which filters traffic using fixed rules: it lets good visitors in and keeps bad ones out. That works well for simple websites with predictable traffic. Its more sophisticated cousin, WAAP (Web Application and API Protection), extends the same idea to the apps and APIs that power most of what we do on our phones.

The trouble is that WAF technology has been around for more than twenty years, and most large companies now run several of these tools side by side, each from a different vendor and each with its own rules. Nobody really knows how well the whole setup is working. Legitimate customers get blocked, attackers slip through, and security teams spend their days tuning rules by hand. AI makes all of this harder, because the question is no longer just “human or bot?” Some bots are customers. In layman’s terms, it’s a bloody mess.

Huskeys sits on top of whatever a company already has and acts as the brain: it measures what’s working, recommends what to change and makes the changes across every tool at once.

The Founders

Itai and Roy are not your average tech bros. Itai started coding at 13. Like most Israelis, he did his military service, and he put his talent to work hacking systems with AI. I haven’t met Roy, but Itai describes him as the best hacker he has ever seen at work.

While serving in Unit 8200, Israel’s signals intelligence and cyber unit, they began to see the weaknesses in existing cybersecurity systems first-hand, and decided to build a business around fixing them. Plenty of people start businesses because they see a problem, of course. What makes Itai and Roy different is their deep expertise, a sharp understanding of the problem, and the ecosystem around them. I also suspect their time in the army instilled a strong sense of discipline in both of them, and discipline is essential when building a company.

The Ecosystem

Many of the things we use everyday and that we take for granted were originally developed in the military, either by will or by accident. To name a few: the Internet, GPS, the microwave oven, and even the superglue.

In this sense, there is a bit of a track record when it comes to innovation and army people.

Furthermore, the guys are based out of Tel Aviv. Few people know, but technology and Tel Aviv go hand on hand, especially when it comes to cybersecurity the list of companies that started there is a long one.

Something I have observed is that an early-stage business has good chances of making it if there is an ecosystem around it. Look at any list of startups and a handful of cities such as San Francisco, New York, London, Paris, and Stockholm take the lion’s share, at least in the Western world.

Tel Aviv is also in there, which gives me confidence that this could actually work out. Why? An ecosystem means access to capital and to other founders and ex-founders, who bring hard-won experience of building startups.

To put it bluntly, it’s easier to build a successful tech startup where other startups already are than in the middle of nowhere.

The Customer’s feedback

One thing I think Itai and Roy did brilliantly was talk to lots of potential customers before they had a product ready, to really understand the problem and test a few ideas. It’s something I recommend to every early-stage founder I speak to: go out, talk to customers, then build the product together with them. It also gives you a list of warm leads that can turn into your first customers. Feedback from their early testers even made it into their pitch deck. I thought it was brilliant.

Looking back at my notes, after almost a year since my decision, I feel more confident in my original reasoning. Not because Huskeys has closed a Series A, though that’s encouraging of course, but because the reasons that made me write the cheque are still holding up.

The market is real, the problem is painful, the founders know their stuff, and they are building in an ecosystem that gives them access to talent, expertise and capital. That’s my framework, and so far I am right.

Now, a Series A is a nice milestone but it doesn’t mean the investment will pay off. There’s still a long way between raising money and building a valuable, sustainable business. Ask me over a beer.

But angel investing is about something else too. You’re making a decision with little information, trying to tell a promising opportunity apart from a convincing story.

I’ve learned a lot in the process, alsnot least that I genuinely enjoy connecting with people who are starting things and supporting them along the way.

If you’re building something and think I could add value, don’t be a stranger. Reach out.

It’s summer.

In all fairness, that started a couple of months ago with boiling temperatures already simmering Western Europe in May. But that’s another story.

I am spending a few weeks in the Nordics, and perhaps inspired by the lush nature, or countless hours in sauna, I’ve decided to shake things up.

Scaling Judgment typically runs on one idea, worked through properly.

This time you get three shorter, half-baked observations that probably didn’t need 1500 words, but were still worth sharing.

Back to the usual format in September.

Enjoy responsibly.

The Rule of Three

Back in July I was chatting with a guy that started a company in a similar, but different, vertical than mine. Despite being very early in their journey, he’d already noticed that if a user books at least three times on their platform, the likelihood of them becoming a super-user, and a loyal customer, increases dramatically.

That rang a bell.

We have noticed a very similar correlation between long-lasting host relationships and early success on our products. In our world, there is also another aspect: if a property gets booked three times shortly after going live on a booking platform like Airbnb or Booking, its chances of becoming a best seller increase steeply. The reverse is also true – if a property doesn’t get its first few bookings within a few weeks, the algorithms start making it invisible, and it enters a doom loop: fewer bookings, less visibility, even fewer bookings.

I haven’t done a crazy amount of research on this phenomenon, and there’s no rigorous model built behind this idea, but I wouldn’t be surprised if this applies to other businesses.

Three is probably just a convenient and arbitrary number. It could be four, or five, but the underlying idea is what matters: early success creates momentum.

It makes sense. A new customer needs to test the water before they become a loyal fan. Once that loyalty is established, since we are creatures of habit and we tend to hate change, unless something goes dramatically sideways, we stay for the long run.

Which means that the job for anyone building or selling a product or service is simple to state and hard to do: create positive momentum from the get going as fast as you can. Then do it again, and again.

Provided the experience is good, that’s the beginning of something great.

Which leads me to the next observation.

Fight Enshittification

When I moved back to Italy in 2021, I had to find a dentist.

I consider myself pretty diligent when it comes to oral hygiene. I floss every day, and I go for a cleaning and check-up twice a year.

Having lived outside of Italy for more than a decade, my old dentist was no longer an option, so I started looking around.

The first dentist I found was close to where I lived. The receptionist was warm and lovely, but when she told me the price of the procedure, I almost hung up.

It was 50% more expensive than what I had been used to paying in Munich, which says it all.

So I kept looking.

Eventually, I found a chain offering way more competitive prices. Since I didn’t need anything particularly complicated, I went for it.

The experience was interesting, to say the least. It felt less like a dentist truly caring about my wellbeing, and more like an upselling machine.

It started with a full assessment of my mouth, and quickly proceeded to offering me a bunch of things I neither wanted nor needed. The dentist was always accompanied by the general manager who was in charge of discussing the price.

Doing small talk with the GM, I discovered that the chain was owned by a private equity firm.

I immediately thought of Charlie Munger’s advice to understand incentives. Follow the money.

Since humans are creatures of habit, I nevertheless became a regular customer after buying a package of cleanings.

I did not particularly enjoy going there, and I started noticing that their cleanings were getting faster and faster.

Then, one day, out of the blue, I noticed something odd in my mouth. It turned out to be a bacterial infection.

Their proposed solution? Pull out the tooth.

You’ve got to be kidding me.

I found another dentist. More expensive, family-owned for a couple of generations, and I still have all my teeth.

There are a couple of observations here.

First: pay peanuts, get monkeys. Jokes on me for putting such a low price on my own health in the first place. Lesson learned.

Second, and this is the one I keep coming back to: more and more business models seem to be built around a single goal: maximise profit while delivering progressively less value for the customer.

There is a word for this: enshittification.

The term was coined by Cory Doctorow to describe the way digital platforms become initially great for users, then gradually deteriorate as companies optimise for advertisers, shareholders, or their own economics. It was very much connected to the long gone zero interest rate era (ZIRP) when internet companies could splurge in paid marketing to buy customers, lure them in, but then reduce the quality of their services.

This sadly has not stayed in tech. It can happen anywhere incentives become disconnected from the customer experience and firms optimise for profit and investors only. Which is not wrong per-se, a business has to be profitable and return money to their investors. But making customer experience poor in the name of profit is not a sustainable, long term strategy.

And this is where I think business builders have a choice.

A few years ago, inspired by a former boss, I spent some time studying the restaurant industry. What makes a restaurant great isn’t efficiency. It is the almost obsessive pursuit of excellence. Hospitality is about wowing the customer. Injecting some magic into their lives. Paying attention to details. Creating an emotional connection.

Can you imagine Will Guidara or Danny Meyer sitting in a room and asking themselves: “What is the minimum we can do while still keeping the customer?”

I can’t. They likely ask something along the lines of “What can we do to make this experience exceptional?”

Take a page from the restaurant business. We can strive to build the Gramercy Taverns, and Shake Shacks of our industries.

There is no point to create early wow effects and then slowly making the customer experience worse. Fight enshittification.

Nobody Knows Anything

One of my guilty pleasures is listening to My First Million.

Yes, it’s two tech bros talking to other tech bros.

But I find it entertaining, and occasionally there are some good ideas.

Recently, they had David Heinemeier Hansson, also known as DHH, on the show.

For those of you who don’t know the guy, he was one of the founders of 37signals, the company behind Basecamp and many other SaaS products, the author of several books about their philosophy on building companies.

DHH is a controversial figure and I don’t endorse everything he does or says (particularly on X), nevertheless there was a segment of that episode that resonated with me.

One of the hosts of MFM praised a landing page for a product they built, particularly the design and copy and asked what had driven the decisions behind it. DHH answered that essentially they had done what they felt was right and hadn’t spent much time trying to optimise it. No endless A/B tests, no obsessing over conversion rates.

Of course, as DHH pointed out, they could do this because they were a stupidly profitable private company, with ridiculous margins, and pretty much occupying a dominant position in their space for years. Conceptually, they could do what they wanted.

But it is still an interesting insight. In the tech industry, we pride ourselves on being data driven, and that data should drive all decisions. One of the sentences I have heard a lot, and also told my people multiple times is that without data, you are another person with an opinion.

I still stand behind it, but I did change my mind to a certain extent.

Data should be the foundation of solid decision making, but it can also become a trap. You see, we tend to look for confirmations of our assumptions, and there is always a new data point that can reinforce our narrative. This is the so-called “confirmation bias”.

Sometimes data is genuinely telling us something, but not necessarily the full story. There could be signal, but there could also be noise dressed up as signal. And sometimes, common sense with an element of randomness or magic, as Rory Sutherland likes to call it, is worth more than another dashboard or deep-dive.

Nobody really knows what’s going to work. You can improve your odds. You can gather evidence, run the experiment, learn from what happened last time. But at some point, someone still has to make the call.

To wrap things up, I thought about the common thread of these three short, half-baked observations, also thinking about what I typically write in this newsletter.

Honestly, I am not sure there is one — and that’s true to the original promise of this summer edition. The goal today wasn’t to resolve anything, just to spark something.

Happy summer. Back to the usual format in September.

PS: if you enjoyed this newsletter, tell a friend.

A bit late to the party, but paraphrasing a famous aphorism, the best time to start a Substack was six years ago. The second best time is now.

I know what you are thinking. There he is. Another tech exec sharing his unsolicited opinions, blowing his own horn — and wait, what is he gonna try to sell me?

In all fairness, those exact thoughts are why it took me so long to write in public, let alone share what I wrote.

But a few months ago I decided to give it a shot. I dusted off a dormant Substack account I’d opened years ago just to see what the fuss was about, did some homework to sharpen my thinking, and settled on Scaling Judgment as the title.

So why Scaling Judgment? Let me take you on a short tour.

Writing

I’ve been writing since I was young. Very young. Unpublishable short stories, songwriting — writing has always been there.

Then the internet came. In 2008, when blogging was becoming a thing, I jumped on the bandwagon and started a travel blog, collecting cheap eats and cool student bars from friends on their Erasmus semesters.

My biggest win was a post about Budapest’s nightlife, written by assembling tips from the ex-girlfriend of one of my best friends, who spent six months in the Hungarian capital before it was cool. An ad agency reached out and paid me 100 euro to place the link of some online travel agency. Fun to think about in hindsight — I ended up building a career in travel. At that point in my life I had just moved to Denmark for my master’s, and 100 euro was all the money in the world.

Ironically, not long after my first big payday as a professional blogger, I abandoned my travel blog and pivoted to my personal website, writing about topics bigger than myself. Looking back, it took some swagger to write about business with zero experience beyond my studies and a failed blog. By the way, there are still corpses of this phase around the internet.

But I am drifting. The short version: I’ve always written, one way or another. And almost 20 years since my online debut as a travel blogger, I’ve come to the conclusion that writing is something worth working on consciously and continuously — because writing forces me to think, and thinking keeps me sharp.

We live in the age of AI, likely the beginning of the most transformative technology mankind has ever experienced. As LLMs get better by the day, the temptation to delegate our thinking and writing to a superintelligence grows. I am no Luddite. I am a tech optimist. I use AI tools every day. In fact, Claude is my sparring partner and editor-in-chief for this post.

But it is one thing to use AI to refine our thoughts, and another to delegate our thinking and writing entirely.

Furthermore, I believe that our critical thinking and the ability to discern what is true have already taken a hit after 15 years of social media. For me, thinking, writing, discerning, judging are all things that make us human. Thinking and writing are two muscles that I want to grow, and this project is my gym.

But why do it in public?

Staying Curious

I haven’t committed to a fixed cadence for Scaling Judgment.

Since the beginning of this project, I promised myself not to force myself into publishing something just for the sake of it, and rather write when I think I have something to say.

Yet, the moment you go public, there’s an unspoken commitment to an audience, whatever the size. If nothing else, it can be an audience of one — myself.

This is extremely powerful: knowing that there is someone out there watching, and if I am lucky, or delusional, even waiting for my next post keeps me accountable. It forces me to do the reps.

It also challenges me to find something interesting to write about and publish only what I think is my best work.

More selfishly, writing in public forces me to stay curious — to read widely, listen to new things, and, most importantly, develop an opinion about them.

Building something

I think everyone should have a hobby outside of work. I might have a few too many, if you ask my partner.

But again, thinking about staying human in an age where machines are chipping away at so much of what we do, having a place to work on your craft outside of work is a powerful idea.

Also because ideas cross-pollinate, and things that seem unrelated, combined together, can become very interesting, and benefit you in other areas of life.

But there is something more profound to it.

I like the idea of building something that compounds in the long run. Lately, I have been thinking that it would be amazing to have something to work on for the next 30 years or so.

You see, I have no grand ambitions with Scaling Judgment. I want to have a place to write down my observations on what I see in my day-to-day at work, and to document my interests. Since this is basically me observing things that happen around me, it could be something I can work on for some time.

And then, if any of this catches someone’s attention, sparks something, or helps someone — that’s it. Which brings me to the next point.

Have a serendipity engine

I was a networking junkie in my twenties. Living abroad made it a necessity — I wanted to meet other people outside of my study group or work. So I have been to my share of networking events.

Most of the time they sucked. Or maybe I sucked back then. Probably both. Most of the conversations were quick, proceeding to a pathetic exchange of business cards or Facebook details, before moving on to the next most interesting person. Quite a shallow experience.

Over the years I’ve become more selective, and since becoming a dad, the time to mingle with strangers has become scarce.

One goal of this project is to connect with people who share my interests. Reading someone’s newsletter or listening to their podcast for years creates a strange familiarity. If I ever met Tim Ferriss, I’d have a decade of talking points ready — a great conversation, at least on my side.

Scaling Judgment is my version of that. Even if someone reaches out just to tell me the newsletter sucks, it beats a generic introduction.

Preparing myself for the next chapter

The only constant in life is change. Someone said that every decade, you should reinvent yourself.

My twenties were about exploring: living in many countries, backpacking Latin America, starting personal projects, working for a corporation. This decade has been about joining a scrappy startup and scaling with it, learning an insane amount, and finding a career that fits my interests and values.

And when I look at where my free time and mental energy have gone throughout it, there are two things I keep thinking about: building companies and investing — two disciplines that are more complementary and intertwined than they look.

The more I study how great businesses are built and run, the more I see management decisions overlapping with capital allocation decisions.

This is something I have started learning firsthand, using my little savings and deploying them across various assets, with a few wins and many mistakes.

I am not sure what the next chapter is going to be, but I’d like to think it goes in this direction.

So what should you expect from Scaling Judgment?

I write from the perspective of an operator who has helped build a European scale-up.

This newsletter is for operators who want to think like investors, and investors who want to understand what execution actually looks like at scale.

If Scaling Judgment resonates, subscribe, reply, tell me. That’s the serendipity engine at work.

Thanks for reading.

All views are my own and don’t reflect my employer’s.

Music has always been part of my life. Unsurprisingly, the Long Strange Trip’s episode with Bayer’s Bill Anderson resonated with me.

If you have one hour to spare, give it a listen. Bill Anderson is the CEO of Bayer, the 160+ years German pharmaceuticals giant. During his tenure, he re-engineered the organisation, flattening the management layers and optimising for flexibility and speed. Two things that make organisations thrive in our day and age.

Inevitably, this made me think about my own organisation.

I was lucky enough to live through the transformation of a scrappy startup into a scale-up operating in seven European markets (and counting). When I joined Holidu, we were little more than 60 people. At the first summer party I attended, in 2017, plus-ones were invited to make it feel more like a party. Today, there are about 300 people in my department alone.

In building this behemoth, we went through the typical archetypes of a startup growing fast. In the podcast, Bill Anderson talks about orchestras and jazz bands when it comes to scaling organisations.

Building on this metaphor, and thinking back to my experience, startups are punk rock. Listen to the Sex Pistols’ “Anarchy in the UK” or the first couple of Blink-182 albums. I think you’ll get what I mean. Nobody knows how to play an instrument, it is pure raw energy, and attitude wins over technique. It’s Joey Ramone spitting 1-2-3 before “Blitzkrieg Bop” attacks on the Ramones’ first album.

A startup is exactly the same. It’s a bunch of youngsters figuring things out as they go. It’s a lot of faking it till you make it. There are plenty of anecdotes collected over the years of customers won over by charm and passion rather than by actual features. In technical terms, it’s also called sales-led growth. In real life, this is punk rock.

Eventually, successful punk rock bands graduate from the dive bars and college parties and get to play on bigger stages. Same thing goes for startups.

When you get some traction, either as a band or as a startup, you get noticed, you get a bit more money, and a different kind of producer comes onboard to help make your second album more appealing to the masses.

It is time to scale. The equivalent of a more polished, professional producer in the startup world is the experienced folks from the outside. You start hiring senior individual contributors to counterbalance the punk rock energy of people fresh out of uni, and professional managers enter the picture.

Just like a more professional producer, the professional manager has done it before and knows how to get to the next level.

During this phase, the goal is to build a machine that can quickly hire, onboard, and get many new recruits up to speed. A new CRM is implemented, or the existing one finally gets revamped. Knowledge needs to be documented, hierarchy starts to build, and so do processes.

Any self-respecting professional manager knows that chaos doesn’t scale, and their job is to put structure around the raw punk rock energy.

The punk rock band becomes heavy metal.

Scale-ups also go through a heavy metal phase: hyper-growth. Things move as fast as a Kirk Hammett solo. New markets, new people, new products. Especially in the ZIRP era, money was cheap, AI was not in the cards, and the best way to scale was hiring people.

Organisations became orchestras without realising it. After all, isn’t it what many heavy metal bands do after a couple of albums? They get orchestras involved until they become one.

What are the characteristics of an orchestra, you might ask.

Orchestras have a strong hierarchy. They also follow a music sheet, and while there is some room for interpretation, to the untrained ear, Mozart’s 40th symphony will always sound like Mozart’s 40th symphony, no matter who the interpreter is. In organisational terms, you build many layers of people who follow a well-documented process without questioning whether it makes sense at all.

The world in 2026 doesn’t want you to play orchestra music. It wants you to play jazz.

Contrary to popular belief, jazz is a genre with plenty of rules and a severe structure. In fact, it’s the most demanding structure of the four genres I mentioned. It requires musicians who are deeply skilled in their own craft and who can own the piece. They track key changes, tempo changes, and each other, without a conductor.

To many, jazz might sound like freedom. It is actually mastery.

There are three things that distinguish jazz from an orchestra.

The framework is not documented but internalised. Have you ever seen a jazz band following a music sheet? No. They get on stage, they look at each other, and they start jamming. In org terms, while the orchestra follows centralised processes and team members have little room for interpretation, jazz relies on ownership and leaves a lot of freedom to the individual to do what is right in that given moment.

There is no conductor, but a leader. Orchestras are top-down organisations. You have the conductor, the first violin, the second violin, and so on. Jazz has a bandleader who sets the tune, the key, and the initial tempo, but then lets people play. This is the type of leadership required today. Large top-down organisations become inevitably too slow to adapt to market needs. It is a natural consequence of growth. The central teams that were once close to the customer eventually drift away from them. Yet they still take the critical decisions.

Listening replaces instructions. In an orchestra, everyone is focused on their own sheet. If you follow your sheet and keep the tempo, you can’t go wrong. Unless you are a business. Then things can go sideways. These are the typical silos that plague organisations. Eventually, people stop talking to each other. They follow their own scripts, loosely coordinated from above. In jazz, the whole thing runs because the musicians are listening to and looking at each other.

I have to admit, my organisation at moments feels more like an orchestra. But there are some things that will eventually get us closer to a jazz band.

The principle I keep coming back to is centralised framework, decentralised ownership. An organisation of 300 people needs a common framework, but, like jazz players, individuals and managers should be able to adapt it to what the local customer wants, and have the freedom to do so. In my world, each market is very different. Different seasonality, different supply mix, different ADR. A villa in Mallorca is a different beast from the same villa in Crete, two islands that share the same sea and almost nothing else. Local teams need to be able to take the decisions that win their market. At the same time, the metrics are centralised, because we all need to move in the same direction.

Talent density — an idea from Netflix’s Reed Hastings and his book No Rules Rules — is non-negotiable for an organisation that wants to play jazz. An orchestra can afford a weak second violin because the structure of the music sheet covers for them. A jazz quartet doesn’t have that luxury. With fewer players and no sheet to refer to, every person needs to pull their own weight, read the room, and adapt when needed. That raises the bar for who belongs on the stage. In an organisation, it usually means fewer, more talented people with more scope — the same flattening I started this piece with. The harder truth is that you rarely build this density by hiring. Don’t get me wrong, hiring is important. You want output-driven people who think and act like owners. But in my experience, you can do a great job during the hiring process and yet bring the wrong people on board. This is especially painful at the manager level, where it can take time to spot the low performers. More often than not, you build density by asking an orchestra to learn to improvise, and accepting that not everyone will want to. At that point, you need to have a frank conversation about their future in the organisation.

The third shift is the hardest, because you don’t fully control it. It means breaking the most natural way large organisations work: in silos. An orchestra rehearses by section and only assembles for the performance. A jazz band only exists when everyone is in the room, reacting to each other.

That is the harder thing to build. Shared metrics are the starting point: at least everyone is reading from the same page and committing to the same objectives. But that alone won’t make the magic happen. What actually plagues siloed organisations is meetings — endless alignment between teams that should already be working together, ending with everyone frustrated because no decision was made and no problem was solved.

The way I see it, a meeting should serve one of three functions: share information with context (for example, a change that affects how people work), surface a problem blocking the company, or make the decision that solves it. To play jazz, every meeting needs an objective tied to one of those three. Small, focused, with a clear agenda and shared metrics — not large, generic gatherings held just to communicate.

Meetings, though, are just the most visible part of governance, the third big idea in moving an organisation from playing like an orchestra to playing jazz. Governance is something not many organisations do properly, because it is invisible and intangible. Nobody has it in their job description. And it is a word rarely associated with the punk energy of a startup or the speed metal of a scale-up going through its hyper-growth phase.

Looking at my organisation today, we are far from being a seasoned jazz band. But I see it as a wonderful journey, and I am genuinely excited to be part of it.

This is, in any case, the direction every organisation is being pushed in 2026, consciously or not. A world that changes this fast doesn’t reward the company that follows its sheet — or its script — most faithfully. It rewards the one whose people can read the change and adapt to it, together, without waiting to be told.

Which is the real test, and the hardest thing to read through a deck or a spreadsheet. You can probably only catch it if you’ve lived through it

I will never forget the Champions League final between Man United and Bayern Munich, won in the last 3 minutes of the game by United. That team was epic, and it was not built in a day.

One of the best books I have ever read about leadership is Alex Ferguson’s Leading. I don’t think it is an accident that is co-written by Sequoia’s Michael Moritz. That book is all about building for the long term.

It took Sir Alex 6 years to win his first title after arriving to United in 1986. It also took 7 years for Mikel Arteta to win Arsenal the league. United started winning in 1992 and did not stop until 2013, dominating English and European football for almost two decades. It is way too early to say if Arsenal can start a cycle, but I wish them well.

In our day and age short term thinking and constant change are dominating. Yet, building something amazing takes time. It is the compounding effect. You do small incremental gains every day, constant improvements and you cannot help but becoming successful.

To do so, you need to have the right environment. Unfortunately we live in an era that rewards short term thinking, acting fast, and constant change. We are in the social media era, where it is about volume and noise.

There is a beautiful quote from Sun Tzu. If you sit by the river long enough, you will see the body of your enemy float by.

Not that you necessarily need to have an enemy, but it strikes a chord. It is a beautiful reminder that beautiful things take time.

Now back to Arsenal, the parallels with Fergie’s United are striking.

Ferguson arrived in Manchester in the end of 1986 with a club almost at the bottom of the league. His first moves were to remove players that were not functional to his long term vision and confronting the team’s culture. Reading his books, Manchester United in the late 80ies was definitely worlds apart the professional dedication a world class football team required. Players were ill-disciplined and there was more drinking than training hard.

Arteta also arrived in a dark moment for Arsenal. They were not at the bottom of the league, but far away from the top of the table. Emery’s time as a manager had ended and Freddie Ljungberg, Arsenal legend, struggled to turn the tide. The dressing room was in shambles and there were players that despite their talent were mentally checked out. Arteta started by removing such players. Mesut Özil's contract was terminated, Aubameyang was stripped of the captaincy and shown the door, and half a dozen others were moved on. Arsenal finished 8th in back-to-back seasons. The rebuild looked like a disaster from the outside.

For both managers, success did not come after one season or two. Both were on the verge of being fired by year three. Ferguson in January 1990 was saved by a win in the FA Cup against Nottingham Forest. Arteta won the FA Cup in 2020, beating Manchester City 2-0 in the semifinals, and Chelsea 2-1 in the final.

What happened next was also strikingly similar: fix the unglamorous foundations. Before signing star players, both Ferguson and Arteta fixed the defensive spine and this was not done over a transfer window but over the years.

For Arsenal’s fans, the mantra became “trust the process”.

In the spirit of long term thinking and compounding, Arteta’s story at Arsenal is a story of gradual improvements. Every year the team got a little bit better, until it became a title challenger, and after some years of being close to the title but not there yet, they finally won it.

The title did not come after one summer of crazy signing, although Gyokeres came last summer and cost a fortune, but it was the result of many years of right decisions.

It was beautiful to see.

There is another layer of the story that doesn’t catch the headlines. After Wenger’s Invincibles, Arsenal looked like a club dismantling. Wenger was selling the best players every summer - Fabregas, Van Persie, Nasri - and was not replacing them with equally resounding names. But something was happening behind the scenes. Arsenal was building its infrastructure, which took the shape of a brand new stadium.

The Emirates cost almost £400m but doubled the match day capacity and created the revenue base that would eventually fund the success 16 years later.

Ferguson’s infrastructure building did not take the shape of a new stadium, but rather investing in rebuilding the scouting network, doubling down on the youth academy that produced the almighty boys of the 92.

The thing I like about football, aside from the game itself, is the many parallels with leadership and building successful organisations. Football managers are also dealing with insane pressure. They don't have the luxury of having a bad quarter, often it is a string of bad games and they are already grilled by fans and boards. By default, football is about short term thinking which makes it particularly fascinating to see how Ferguson and Arteta built their success over the long term.

William Thorndike’s Outsiders profiles eight CEOs who generated extraordinary long-term returns by doing something similar: ignoring short term noise and compounding quiet, unglamorous decisions over the years. Tom Murphy at Capital Cities, John Malone at TCI, Katharine Graham at the Washington Post, and of course, Warren Buffett. They all accepted to be perceived wrong in the short term but eventually they were proven right in the long run. Just like Ferguson and Arteta.

If I look at my experience in managing teams, I can relate. There is a moment, usually at the beginning, when one takes over a team, where, unless the team is already extremely successful, which is unlikely otherwise why changing manager, where you need to clean up the dressing room and work on the culture. This is something I have seen over and over. Typically, the first thing you do as a new manager is to remove either the low performer or the former superstar that lost their motivation and became a drag.

Next, there is the culture change. Often, in commercial teams it means to go back to basics and remind ourselves that selling ultimately is a lot about doing activities, consistently. Day after day, do that call, see that prospect, ask for the business.

Finding an example of infrastructure building is difficult because it is harder to see in real time. There is one thing that comes to mind.

At the beginning of 2026 we announced a compensation revamp for our commercial teams shifting towards revenue generated.

It was a big change, especially for sales reps.

I won’t lie, it was painful. We got absolutely destroyed in the first Employee NPS of the year. Results also stalled in the first couple of months, and in the moment, it felt like we did something stupid and had broken something that made the company successful in the past 7-8 years.

After the first quarter though, we noticed that the new inventory performed significantly better than what we brought live in Q1 2025. We are in the midst of Q2 and it is honestly too early to declare victory but the early signals are pointing in the right direction.

To some extent, this feels like Fergie’s or Arteta’s FA Cup victory. The culture meant as behaviours, has started to change. Nobody knows now if this will compound into something lasting. You rarely see this at this stage, only time will tell.

The reality is that long term thinking is not something that comes naturally to us humans. We are wired for dopamine. Our brains are constantly seeking the next hit. We need progress today. That’s why a lot of folks lose their shirt trading frequently, yet the best capital allocators are all long term thinkers. Evolution did not optimise humans for twenty two years without winning the Premier League. We are made for survival, which is the short term.

Building something that stands the test of time requires us fighting this instinct continuously. It requires the discipline to make unglamorous, controversial, and perhaps boring decisions.

Decisions that don’t pay off today, or even next quarter, this season or next.

It requires the ability to sit patiently, don’t panic, and resist the pressure to go back when things look bleak. I honestly felt that in mid Q1.

Last but not least, it requires the support from above. Ferguson, Arteta, the CEOs from the Outsiders all had the luxury of having someone that was patient enough to let them compound.

Behind every long term success story there is someone at the top who chose not to panic.

It is not human, if you have it in your organisation, cherish it and treat it as the asset it is.

Thanks for reading,

This first post of the series is about my adventures in real estate investing.

In 2018, a group of friends and I had the idea to go surfing. I was recently back from my sabbatical in South America where I picked up surfing and a few friends were genuinely up for joining me and spending a few days getting shattered by the waves.

We ended up in Peniche, taking classes from one of the most famous (and hardcore) surf camps in the area. Peniche is a beautiful place but by mid-October, our surf sessions started to feel more like approaching the D-Day in Normandy than the sun soaked t-shirt surfing I was doing in Nicaragua. The pace of the surf bootcamp did not help to convey a different image. By day 3, most of my friends were injured or lost motivation for surfing.

One day, during the mid-day break, one of my friends and I were walking in the village near the breaks, and eventually the conversation of buying a place in Portugal came up. Classic tourists.

The year after, 2019, we got wiser and went to the Algarve. Sagres, the end of the world, and surfers’ paradise. Sitting on the beach, after a few too many cervejas, the idea of buying a place in Portugal came back. We also started gathering intel on the market to discover that Sagres was basically owned by a few people and buying there was super expensive, despite most of the buildings looked pretty decrepit.

Something that I learned about myself is that when I have an idea or a goal, I don’t give up easily. It might take me some time, and a few detours, but eventually I get it done. 2020 was a gap year for surfing for obvious reasons but I started devouring every resource I could on real estate investing. Unfortunately, most of it was American so it has little application in the European market. Nevertheless, I joined a real estate forum and started talking to people that invested in Portugal.

After months of research, which consisted mainly of talking to random people, I landed on the conclusion that Algarve was the best place to buy. The question was where.

One of my surf mates was in Albufeira for a weekend, and serendipitously had dinner with a real estate agent who sold him the Algarve dream. The original idea was to buy a place together, but then we ran the maths and did not make much sense.

Anyway, we had a call with her, but somehow I was not sold. Sure, Albufeira checks a lot of boxes but I don’t know, it felt too much like England in the sun.

I don’t remember how, but we got a connection with a property manager in Lagoa. Lagoa was under the radar, there were a couple of interesting pockets such as Alvor and Carvoeiro. Portimao did not strike as a place to invest despite property prices being cheaper.

Eventually, in 2021 me and this mate went surfing again but this time in Lagos. It was love at first sight and I set to buy a place there. Lagos has it all. It is the closest town to all the best surf in the Algarve. It is bigger than Sagres. It has a train (sort of) that connects it to Faro. Great bars, good nightlife that doesn’t feel like a stag do. Plus it is gorgeous. It has this old town vibes and some majestic walls.

Unconsciously, little by little, a set of criteria started to shape in my head.

So one sunny morning, I walked in in pretty much all the real estate agencies in the city centre and started going house shopping.

My girlfriend and I eventually made an offer for a place right off the main strip. It was very reasonable, but the deal did not go through. First learning, do proper due diligence on the sellers. These guys wanted to sell their place to buy a bigger one in Lisbon, if I remember well. Due to taxation, they basically had a very short window of opportunity to close this deal so it was very fragile. We made our offer, they accepted it, but never signed the papers. In the meantime, we started battling Portuguese bureaucracy. First stop, opening a bank account. We went for what seemed like a foreigners friendly bank. It was an absolute nightmare. This is another learning, find your allies.

In 2022, I came back to Lagos, determined to buy my first property. I did have quite a gruelling schedule. Surf during the day, visit apartments after at a pace of 2-3 per day, go out partying and start again the day after.

Most of the places I saw were not great. But then, I found a gem. It was through an independent realtor I contacted on idealista. Saw the place, and by my calculations, it was slightly underpriced. The sellers were a couple of foreigners that wanted to sell because they were getting old and could no longer travel to the Algarve. I offered the price they asked. In hindsight, I should have played ball and haggled on the price. But, I did not want to lose this deal. It was by far the best place my budget could buy.

What I liked about this apartment was that it was right in the city centre, very defensible because it is hard to build new supply inside the walls. Also, it has two bedrooms, two bathrooms, and two balconies, one of them is a majestic terrace overlooking the city. Something I have learned from my job in the vacation rental industry is that rentals that performs are the ones with something unique.

This time around, I had a team to support me. My realtor hooked me up with a lawyer specialised in real estate, and a mortgage broker. Remember when I wrote a few paragraphs ago that opening a bank account was an absolute nightmare? Well, the mortgage broker sorted everything for me. Build your dream team, don’t try to go DIY on everything, especially in a foreign country. It is really worth the extra money.

Next I had to find a property manager. Spoke to a few, eventually decided for a property manager who was working for Holidu. For me it was important to be able to use our software as I wanted to get the full user experience.

We are now in year 4. How did things go?

The first year was not great in terms of revenue. I mispriced the rental and within a few days I was fully booked in summer. Then the property manager called me saying that we were losing money in the low season bookings because of cleaning and laundry costs. I immediately reviewed my prices, the damage was done though. At the same time, the first year is all about getting the first bookings and reviews. Once you have done that, you can increase your prices.

I remember looking at my competitors back then. There was this tiny place in the centre of Lagos that had insane reviews and was booked pretty much 365 days a year. There was a little lesson in there. Make your place unique.

Year two was definitely much better and eventually in year three I broke even.

Property prices have soared in the past 4 years in Lagos and basically at the moment I have a property paying for itself and appreciating in the meantime.

Not too shabby.

So, dear friend, after reading all of this blurb, should you invest in a short term rental in Portugal?

It depends.

Something I have learned the hard way is that investing is a risky business and you want to minimise the chances of losing your shirt. One of the most common, and often not listened to, advice is to invest where you have an edge.

Thanks to my work at Holidu, I understand vacation rentals better than most people. I mean, I spend most of my waking time thinking about driving revenue to properties across Europe and that’s where my edge is.

Would I do it again?

Only if the right deal came along. The reality is that the Algarve market has changed since 2022 and it is harder to drive returns from a vacation rental given the higher property prices and mortgage costs. Demand is still strong, but guests are increasingly price sensitive. Furthermore, there has been an increase in restrictions on short-term rentals and I keep hearing horror stories about people stuck in the process to get the license for short-term rentals. Finally, taxes have also increased for non-resident owners.

This doesn’t mean that the opportunity is gone. It has just moved. Inland Algarve, thirty to forty minutes from the coast, can still make sense but I would look for a very unique property.

At the same time, something I have learned is that there are always deals if you are willing to put in the work, be patient, and find them. Building relationships with local realtors can help find deals before they get to the market. There are also a lot of ugly ducklings, apartments or houses that need some love but could still make a good return.

The edge argument still stands though. Don’t do this without doing your due diligence and understanding the market from inside. Luck and patience matter, but they work better when you know what you are looking for.

Thanks for reading,

Sayonara