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