Finding time for unplanned time

This weekend we held Founders annual offsite. When planning for it, different people made me realise that we had probably underplanned it. "Sounds great", they said as they were telling me about offsites that turn out to be a little more than a long long meeting in a location far from the office. But I started to have my doubts. 

In our busy business life there is a clear bias for efficiency. We want everything to run smoothly, we want to be doers and we want to use every single minute in the most optimised way. Going the opposite direction feels sloppy and it is difficult to kick away that guilty feeling. Then, as the first day unfolds,  you start to see the magic happening. People that would normally barely have time for a quick "good morning" getting together and engaging in deep conversations, lots of side discussions getting to the bottom of past situations not properly closed, plans being made, ambitions being shared. 

I think now that feeling comfortable with unplanned time takes courage and experience. Falling back to filling every moment with an agenda item is the easy thing. Controlling for efficiency can guarantee a safe outcome, but it will never be like optimising for serendipity. It's like engaging in a long dialogue and feeling comfortable with keeping silent. Try it. 

Starting is irrational, continuing is delusional, succeeding is obvious

I came across an old post from Sam Gerstenzang which summarises pretty well what I have learnt in four years of starting companies through Founders. 

"Silicon Valley loves the mission-based startup and retroactively constructs a founder mythology. But big companies get started because someone takes the leap, she listens to encouragement, and ignores the haters until the company reaches product-market fit. That part is always the same."

It reminded me of a chapter in "Thinking, fast and slow", dedicated to entrepreneurs' innate, and illogical, optimism. It also reminded me of Indiana Jones and the last Crusade, when Indi is facing the second trial and has to take the "leap of faith" to reach the Graal. Imagine if he had simply fallen down, ending his quest, and the movie, in the most unglamorous way. Celebrating faith is easy when it turned out to be the right choice, yet any rational person should not have attempted that in the first place. 

There are a couple of ways to overcome rationality and take the leap. The first one is to be blind to the challenge, either because we believe so much in ourselves or because we are naive and wholly unprepared. The other one is to trick our mind and push any true probability assessment to a later moment. This is Paul Graham's "questions", and it still the best trick I know to get started. 

Each startup is a journey against sound thinking and probability. It begins with the irrational decision to attempt something that is doomed to fail and it continues through the delusion of persevering when any sane person would quit and do something better with their life. Until one day you make it, and it all becomes obvious.

False consciousness in the freelancer age

Every time I walk into a WeWork I can't help thinking about Marx. What do a modern, hipster, co-working space and Das Kapital have in common? After all, WeWork is a symbol of today's entrepreneurial renaissance: scruffy startups and hustling freelancers breaking the yoke of salaried labour to realise their dream. All true. But there is more under the surface. Behind the cosy vintage-looking furniture, the coloured coffee-table books and the free beer, I see an army of hard-working people struggling to make ends meet while happily handing over a large chunk of their income to a multi-billion dollar real estate company in exchange for what is basically a Dilbert-style cubicle. Don't get me wrong here: everybody is just doing their job, no scam, no forcing of anybody to take up the deal. It reminds me, tough, of the discussion around positive externalities and consumer surplus which we are receiving from our ads-driven internet giant. True, we get a lot of stuff for free, but at what real cost? Let's call a spade a spade, free beer and cosy furniture have a price. A certain German philosopher would have a name for that: false consciousness.  

My vision or yours

I have opinions on most topics. At time quite strong, often - at least I hope - weekly held. Given that what I do consists in large part in thinking about product ideas, I also have a lot of opinions about what would work, and wouldn't, in a wide range of markets. 

It's both a blessing and a sin. Every time I meet an entrepreneur working on a new product, I fall inevitably in the confirmation trap. Is she working on the angle I think would work? It's a terrible way of judging other people's ideas, and yet a very human one. I understand much better now the difference between a good investor and a rookie: the rookie will pretend - consciously or not - to know more than the entrepreneurs and seek teams that fit in his or her frame, the good one instead will remain objective, and open-minded, and let the entrepreneur show the way. Entrepreneurs are the ones creating the future. 

There is a consequence to this. A good investor will inevitably tend to be sceptical and will try to underpin her judgment by looking for facts. The team's track record, usage metrics, growth, etc. Investors are patient and often prefer to wait precisely because they understand that their judgment - everyone's judgement - is easily biased. 

But what to do when you can't wait? If you are a founder, or a co-founder, or an investor that wants to get in before any solid fact reaches the table, the only thing you have left is vision. Conscious of my bias, I will be happy taking a risk if it means following my vision. Right or wrong, it is at least mine. The only alternative is to buy into someone else's - and thus make it mine. 

So this is my decision criteria in these situations: it's either my vision or yours, in all other cases I'd rather wait. 


Here is a new challenge. I normally write in the morning, before waking up the kids. I never have more than thirty, maybe forty, minutes. Sit down, look at some notes I have typed the day before, anything new on my mind after the night? The clock races. If I am not done by 6:50 we'll be late again. Writing more than 500 words is a painful process, I published something yesterday I wasn't happy about. I should be better at throwing out an entire draft and start from scratch when it just doesn't work. Writing short is different. Open the editor, even the phone is just good enough. The cursor is blinking, what time is it already? Today I wanted to write about visions and narratives. I had this conversation the other night and I realised something about how I tend to make decisions, it would make for a good short post. Not today though. As I am typing these words, my laptop tells me I running out of battery, the charger at work - thank you apple. I will push "save and publish" now, it's 6:42, I am on time, for once. 

Netflix and the intermediate step

We see a lot of attempts these days to take us through a new technological leap. Voice computing and AR are two noticeable examples. In these moments, it is easy to follow a linear path: first, something doesn't exist, then you get a crappy version of it, then a better one and then it works. 

From a pure technology point of view this makes sense, nothing is born in its perfect version. Things, however, gets more complicated from a user - or usage - point of view. We are sold dreams that don't exist, and that annoys us. A good example is a few attempts I have seen recently to capture meeting notes by listening to conversations. We are too far today from a sufficiently good version of this, and I am also asking myself whether this is something I would ever want. 

But this is not the point. If we imagine the perfect experience as being one where: you meet with your colleagues, you start talking through the agenda, you agree on next steps, you stand up and leave the room and, magic, all notes are perfectly there - what is then the intermediate step? 

To find the answer, we need to look at Netflix. In its early days they already had a clear idea that streaming would be the future, but where did they start? The didn't offer a crappy streaming product, the sent DVD's to people. Here is what Reed Hastings says about that: 

"We always viewed the DVD by mail as a digital distribution network, and then we knew eventually... that's why we called the company Netflix and not 'DVD by mail'" 

This is the perfect intermediate step. 

Digital is getting physical

I look forward to a future where digital and physical mix and where we go back to have a mostly physical life, but digitally enhanced. 

There are a lot of good reasons to worry about that, and I have listed some in a previous post. Leaving this aside for a moment, there are also many reasons why we should be happy that our inescapable digital future that has so far sucked us into two-dimensional glassware will finally spit us back to the three-dimensional world where we belong. The future that awaits us is one where we freely utilise data generated by living in a world of bits to make choices in a world of atoms. 

An interesting example comes, not surprisingly, from Amazon whose CEO is on record saying that there is nothing "new" about opening physical stores and that the focus of the company will always be delighting customers and if customers want - also - physical stores then this is what Amazon will do. 

This recent tweet with photos taken from one of the first Amazon bookstores shows where the potential lies.

Data tracked from our digital interaction with amazon and kindle is used to create innovative classifications and smart in-store signage. Just judging from these photos it seems already a better way than "history", "politics", "fiction" or simple alphabetical sorting. It is worth noticing that Amazon can do this because we have now been buying books on its website for a long time and that, since introducing kindle, it has been also able to track what we read, what we highlight, what we finish and what we don't (and where we stop in those cases). 

Again, forget about how creepy this all sounds when we really think about that - this part will have to be solved, at least I hope [1] - and think about a future where the same level of tracking can be embedded in our physical world. The optimistic view is to see that as the time where digital loses its advantage against physical. I want to be optimistic. 

[1] Every time I think about this I see no alternative to a system where we have private ownership of data combined with the ability to give third parties access to it. 

A cultural history of...

There is a type of book or study that I often look for but seldom find. In my imagination it's called "a cultural history of.." and it's a kind of travel guide to the mentality of a place. 

Countries, large regions and even cities, have a distinct mentality. It is more than "traditions" or "cultural events" and it goes beyond a collection of ethnicities, religions and sub-cultures. A place's mentality is a persistent yet invisible fabric that guides the people living there toward a certain type of recognisable macro-behaviour. It transcends individual beliefs and political views, and it applies to the newly settled just as much as to those who have been inhabiting a place for generations. 

When I wrote about California as the "land of dreams" in my previous post, I meant the distinctive DNA that ties together Hollywood with Silicon Valley, going back to the Gold Rush and passing through surfing culture of the South and counterculture of the North. A mentality is the product of a place's history and the history of the people who lived there. However, a traditional history book will only give you the input to understand a mentality. These books are normally a sequence of events and don't spend too much time trying to understand how each event is related to the next (beyond a strict causality) and how they stratify and ossify to produce a place's mentality. 

If you move to Rome today, you will see Roman ruins next to baroque fountains next to churches dating to the beginning of Christianity next to the balcony where Mussolini declared war next to a monument erected for a Piedmontese king which is also the tomb of the "unknown soldier" from the first world war. The innate sensibility of its people, their invincible cynicism, their allergy towards authority, and the sense of tragedy mixed with comedy that pervades every conversation, cannot be grasped without understanding this past. 

I wish there were more books and travel guides that could help the foreign visitor and the occasional expat to a better understanding of this "mentality". You cannot understand a place without grasping how its people think, even when they don't know they think like this. 

Land of dreams

Last weekend I watched Empire of Dreams, the 2004 documentary on Star Wars (you can find it on youtube). I was never one of those huge fans of the series - of the two Harrison Fords I loved Indiana Jones [1] more than Han Solo. The documentary though is really great, the epic of Star Wars being even better than the Star Wars epic. 

George Lucas is a Californian entrepreneur, and this is no coincidence. As I was watching pieces of the documentary with my daughter and discussing a future trip to Los Angeles, I couldn't avoid talking about dreams. Everybody has them. We have stories in Italy that are in no way less heroic and dramatic and grand as the story of Star Wars, Apple, Pixar and many other Californian dreams. But our stories follow typically a different trajectory: a young person starts working on the factory floor and goes through a series of hardships, he emerges as a smart fellow with ambitions bigger than working for others, over time he accumulates enough savings to break out and start his own firm, the firm develops from tiny workshop to global giant[2]. 

George Lucas dreamt about making a space movie. He wanted the ability and independence to produce his own story but needed the money to do so. He gets a budget from Fox, gathers a group of unproven, and mostly unknown, actors and special effects makers, bets on innovation that doesn't exist yet. It is a story of vision, near-death failures, last minute sprints and fixes and ultimate overwhelming, unexpected success. A great Californian story. 


[1] Riders of the Lost Ark is still one of my favourite movies. Nothing can beat archaeology mixed with history mixed with religion mixed with magic. And that soundtrack... 

[2] With few differences, this is the story of Ferrari and Luxottica, among others.

Love, shame and The New Yorker

I have never bought a copy of The New Yorker. I have read a number of articles over the years, and mostly liked them, and I have often thought about subscribing, without ever finding the courage to do it. The other day I saw an old issue on the table of a café. For I moment I decided to grab it, put it in my bag and read it on the flight home. Then I thought of what my father would think. 

My father runs a construction company. He has done that for his whole life after taking over from my grandfather who took over from his father in law. When my grandfather died my father was 32, he took over a company with more than 100 workers and a complicated financial situation. Back in those days, employing people was a pride and a responsibility[1]. Construction, like manufacturing, needs people of all kinds. The entrepreneur - in the Italian North-East trained on the shop floor more often than in school - a few engineers and architects, middle managers - if you are big enough, which is rare - and workers[2].

Visiting the construction sites is a daily ritual. Owner and workers know perfectly well about their different roles, and what that means. There is no illusion of equality and yet no tangible feeling of the opposite. As you arrive, the most visible symbol of status is left in the parking lot. Once in, differences fade. Your shoes carry the same mud, your hands are dirty with the same dust. You drink the same coffee - in the old days often mixed with red wine - and the fanciest place you can retreat to is a container turned office, where cigarette butts rest sadly in small plastic cups. 

It is partly the job and party, I guess, the town. I come from a small provincial town in the north of the country where everybody goes to public school and we don't really have an intellectual class. There are lawyers and doctors and other people with a degree. In my family, it is me and my mum - an English teacher. My father started but never finished. Education is not measured in habits or social circles - that's more of a big city thing. It is rather a matter of taste: the books you read, the place you visits, what you know of history and art. 

Contemporary art is where I often draw the line between education and intellectualism[3]. "Education" is the ability to appreciate the beautiful. Intellectualism requires a jump in sophistication, the one required to appreciate most contemporary art. You go to a museum or a gallery - by itself a deliberate act - and walk through art pieces whose meaning is rarely confined to what the eye can see. Classical art is more democratic and more popular, religious art in particular. It is exhibited or directly painted in churches that you can simply visit. Churches themselves are pieces of art meant to be seen and visited by everyone. Even today when most visitors are there more for the frescos than for the mass, churches attract the blue-collar tourists, the one arriving by bus with their home made sandwiches, the ones that don't really care about staying at an Airbnb so that they can experience local cafes at brunch time. 

My love-and-shame relationship with The New Yorker is all here. It is the struggle between what I like and what I fear becoming. I have moved abroad, I live in a city, I have recently been to the cinema to watch a documentary about some Japanese female divers from a remote fishing village. What do I have left in common with the workers in my father's construction company?   

Where the gap between my father and them was more about wealth mine is more about taste. Food and restaurant tastes, wine choices, books, the nearly complete elimination of tv from my life. Maybe all of this is normal and that's just the way it works when you decide to leave your hometown and do something else with your life. 

Maybe. I remember a story I used to listen to when I was a child. It was the story of this boy who is too good and then one day he wakes up with a pair of wings growing out of his back. He is becoming an angel. He then starts doing all kind of bad things, but he overcompensates and he becomes a devil instead, with tail and all. Finally, he manages to get back to normal. From that day he will again be a good boy, but when it is time to go to bed, just once in a while, he will skip brushing his teeth. That subscription can wait.  


[1] Since we are in 2017, the company doesn't employ that many people anymore. A couple of full-time staff in then office and contractors for the actual work. Since we are in Italy, the company is always on the brink of death. Everything related to the old days is coloured by nostalgia. 

[2]An under-explored topic in the transition from a manufacturing economy to a service and information one is the erosion of social diversity at the company level. In tech companies most people have similar status and education, there is little difference between them. When that exist, like in the case of uber drivers, it's pushed out of the company. 

[3] Not meant in a derogatory way.