Welcome to a new issue of Playing the Long Game.

Here is what I have to share with you this week.

Things I'm Thinking About.

Why Blindly Creating a SaaS May Not Be a Smart Move to Begin Your Entrepreneurial Career.

"Have you been trying to grow your SaaS-based startup but still find yourself at the starting point, but worse?

I know how that feels.

When I first jumped into the entrepreneurial journey, my focus was clear. I wanted to grow a SaaS business that led me, and my environment, to the moon and beyond. Technology was my thing, and I couldn't stop seeing startup successes everywhere around me. I had lived that firsthand as the first hire and CTO of Facephi —a brand-new startup in the AI space. It seemed obvious. Innovating in tech was my key to success.

But here's the (counterintuitive) thing: a SaaS is often the wrong type of product to begin your entrepreneurial career."

In this week's article, I dig into why starting with SaaS can be a costly mistake and show you other instruments that may suit you better in the beginning.

Want to have a look? You can read it here.

Gems I Found.

Wild Bill's and The Jobs of Premium Soda.

This week I stumbled upon this piece by Andrew Glaser.

I didn't know Andrew before, but, I just found out, he co-founded Laser Ventures, a hybrid consulting VC with Bob Moesta.

Bob has been one of the most influential people I discovered in recent years. He's one of the creators of JTBD. His work and teachings have profoundly shaped the way I approach creation nowadays.

For those who don't know it, JTBD is a tool for studying consumer behavior. It helps you uncover why people buy one product instead of others. And as such, it's a game-changing tool for shaping solutions people will be willing to buy and adopt.

They studied Wild Bill's Premium Soda and the jobs that people hire it for. What did they find out? Well, definitely not what they expected.

Want to see JTBD in practice and the revealing insights you can get with it? If so, you can read the whole article here.

Stop Going in Circles and Ship Work that Matters.

Ryan Singer and Chris Spiek have greatly influenced my understanding and approach to product and innovation in the last few years.

In this talk at Fintech Devcon 2022, they come with a new iteration of Shape Up, the approach that the folks at 37Signals (and many more companies and teams nowadays) employ for product growth.

From their work at Autobooks, they show how, as a startup now entering the scaling stage, they faced a whole new set of challenges that the original method was not well suited for. So they had to introduce new changes. A must-watch if you're interested in learning new ways to improve your product development efforts.

Want to know what the new version looks like? You can watch the talk here.

And if you've never heard of Shape Up, here is a short video introduction by Ryan.

Don't have enough yet? You can also take a look at the book where Ryan introduced the idea to the masses for the first time. Grab your free copy here.

Why We're Leaving the Cloud.

Basecamp’s leaving the cloud.

In this article, DHH, co-founder and CTO at Basecamp, gives the reasons behind their choice.

The first reason is cost. From his perspective, harnessing the cloud only makes sense when your load is highly unpredictable. According to him, it's not their case.

The second is its negative impact on society as a whole. From a broader systemic standpoint, the “everything running on the cloud” philosophy is leading to re-centralization and the end of the Internet as it was initially conceived. And that’s a dangerous thing with potentially dramatic consequences.

“It strikes me as downright tragic that this decentralized wonder of the world is now largely operating on computers owned by a handful of mega corporations. If one of the primary AWS regions go down, seemingly half the internet is offline along with it. This is not what DARPA designed!”

Definitely, a switch against the current that’s worthy of reflection.

Are they right? Are they wrong? Or, more precisely, are they making the right tradeoffs? We’ll follow them closely to see how this movement plays out.

Want to know more? Read the whole article here.

Brilliant Quotes.

"The problem is not people being uneducated. The problem is that people are educated just enough to believe what they have been taught, and not educated enough to question anything from what they have been taught." —Richard Feynman

Don't blindly follow what you've been told it's right.
Be skeptical. Question everything If you want to make more sustainable choices for yourself...and your environment.

Thanks for reading Playing the Long Game. Did you enjoy it? I hope you did.

Get on board. Was this newsletter forwarded to you? Still not subscribed? Sign up here if you want to receive more issues like this one right in your inbox and support my work.

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And that's all for now folks.

Have a creative time.

Welcome to a new issue of Playing the Long Game.

Last week, I got the newsletter back on after a long time on standby. And today, I come to you with a new issue to keep the flow going.

In the last episode, I told you I chose to rebrand this publication. I decided to leave Expedition Signals aside and give birth to Playing the Long Game as the new brand name. I also gave you the reasons behind this choice.

But today, I come with a new twist.

I've decided to recover the Expedition Signals brand.

"What?" Yeah, I know. I created a new brand just to throw it away one week later. But wait.

Don't rush too fast to conclusions.

Playing the Long Game isn't going anywhere. Far from it. It will still be the umbrella under which all the content in this publication will be shared.

No change around that.

But there is something I didn't get right. I understood Playing the Long Game as a direct replacement for the Expedition Signals brand. Yet, there is a different interpretation.

I'm starting to see Playing the Long Game as a broader publication where Expedition Signals can just be a section within a more ample range of content.

For now, Expedition Signals will be the only content within the publication.

But I think that configuration makes more sense and seems more flexible in the long term.

I want to be open with you about changes like this one.

People often convey the false image that they got everything right from the start. They like to appear as if they got the perfect plan on the first try —by the way, we'll also talk about this later. But evolution is an inseparable part of sustainable growth. And that's why I think this change was worth sharing with you. That helps me apply what I preach and lets you see how I do it. 

Without tricks.

But newsletter changes aside, here is what I have to share with you this week.

Things I'm Thinking About.

How to Shape a Base Software Architecture for Your SaaS as a Beginner Founder to Adapt to Changes Fast (And Without Going Crazy).

"As an early-stage founder, your resources are scarce. And I'm not talking just about money. Your time and energy are even more critical.

But when you build on the wrong foundations, you're putting them at risk.

Like a building on top of muddy ground, your system doesn't hold up. You waste yourself into constant hesitation and technical battles that lead you nowhere. And in the meanwhile, you and your customers suffer."

In a previous article, we saw a high-level process for tackling complexity without prematurely taking on more than necessary.

We looked at three crucial complexity sources in any software project: the logical, the temporal, and the physical architectures. And we saw how different configurations along these dimensions formed a ladder to climb up.

In today's article, we'll dig into the first stage of the ladder. We'll see how to get to a neat logical architecture while keeping the temporal and physical distribution as simple as possible.

Want to grow a base architecture that grows with you without friction? If so, keep reading.

Gems I Found.

How to Learn Web3: Some Useful Steps to Understand the World of Blockchain Better.

I have encountered feelings regarding Web 3.

On the one side, I'm excited to see what it can offer. And on the other, I feel skeptical because of all the hype and blind faith I see around it. Often, what I stumble upon on the Internet almost sounds like a religion.

And that makes me cringe. I don't believe in magical solutions that promise to solve nearly all of humanity's problems.

It sounds like snake oil.

But staying up to date with emergent tech can be game-changing.

What you expose yourself to establishes the range of possible solutions you can think of. And I believe that, far from the extremes, there can be something handy there. We can't obviate it if we want to improve our efforts at enabling sustainable growth.

And that's what this publication is all about.

I've been trading crypto assets, but, technically speaking, I've just scratched the surface of Web 3 so far.

I know the high-level basics. But I still have lots of blind spots. I've got many things to learn about yet.

I want to dig deeper.

And here is where this comprehensive learning roadmap by Francesco Ciulla, online creator and Developer Advocate at daily.dev, comes in.

I'm in exploratory mode at this point.

I don't intend to go all-in but rather start learning on the topic at my own pace, to see what I find out and see if I discover something valuable with the potential to enable sustainable growth. For now, I'm more interested in the technological fundamentals and how it relates to the world where it is to operate. Not so much in the practical matters of Web 3 development —at least for now. My goal is to get a systemic perspective on its practical uses.

Not wishful thinking but realistic, pragmatic thinking.

Do you want to dig into Web 3? If so, take a look at Francesco's guide here.

And if you've already gotten deeper into Web 3, I'd love to hear your thoughts.

Do you believe it can help entrepreneurs, creators, and innovators grow more sustainably? Do you think it can help them bring sustainable progress to society and our world? If so, how?

Or do you think it's the opposite and believe it's all a bubble?

Whatever the case, I'd love to hear your thoughts.

Leave a comment

Taming Model Malpractice.

"Too many models ensure the models are doing specific jobs at the expense of broad understanding. Too few models ensure people use the same language at the expense of doing jobs well."

In this article, John Cutler, Product Evangelist at Amplitud, digs into two common problems in organizations: 1) having too few models or 2) having too many models. The former leads to usefulness problems. The latter leads to collaboration problems.

Want to know his advice on how to address this issue? You can read it here.

A Tale of Two Top-Downs.

Here is a two-part series by Joe Norman.

As with many concepts, the term "top-down" is highly conflated. It's not the first time I've felt confused when someone uses the term. It's not rare to see people conflating top-down and waterfall as the same thing.

But as Joe points out here, there are two types of top-down approaches to design and growth: the blueprint, waterfall top-down, and the coarse-to-fine top-down.

They have nothing to do with each other. The former tries to impose a blueprint onto the world. The latter, however, unfolds and adapts better to the environment's complexity.

This is not a new discovery but a resource I've found myself turning back to over and over. I love how Joe articulates the difference. So I thought you might find it helpful too.

Whether you’ve never heard about the concept, you feel confused about its meaning, or simply find it hard to explain it to others, this is a fantastic source to improve your understanding.

Do you feel intrigued? If so, keep reading here.

Brilliant Quotes.

"When the oak tree grows, there is no blueprint, no master plan, which tells the twigs and branches where to go.

We know in general that it will have the overall form of an oak, because its growth is guided by the pattern language of an oak tree (its genetic code). But it is unpredictable, in detail, because each small step is shaped by the interaction of this language with external forces and conditions – rain, wind, sunlight, the composition of the earth, position of other trees and bushes, the thickness of the leaves on its own branches.” —Christopher Alexander.

Thanks for reading Playing the Long Game. Did you enjoy it? I hope you did.

Get on board. Was this newsletter forwarded to you? Still not subscribed? Sign up here if you want to receive more issues like this one right in your inbox and support my work.

Suscríbete ahora

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And that's all for now folks.

Have a creative time.

It's been quite a while since the last issue, but we're here again with a new episode.

I'm still experimenting with the newsletter, trying to come up with something that feels right. And in that pursuit, today I come with some news to share with you:

The newsletter has gone through a rebranding.

The prior brand name was not very clear to the outside world. It was too focused on me and my own journey. The show's title, Expedition Signals, reflected that fact. I could picture people's thought process when stumbling upon it for the first time: "So this is about an expedition...alright. For what? No idea. Should I care? Meh! Ok, let's move on."

It didn't convey much about what this publication is all about.

This newsletter's always been about sustainable life, business, and product growth. It's about helping people like you become more sustainable entrepreneurs, creators, and innovators in tech. So in response, I've decided to baptize it under a new name: Playing the Long Game.

I believe it better conveys the core idea and philosophy behind the publication.

But changes have not stopped there.

The newsletter also moved to a new home.

I decided to give it a chance to Substack. It's lately being praised far and wide for its growth-boosting features (namely, referrals, recommendations, Boost, and a long list of enablers and upcoming improvements in that area). You can have a look at this article if you want to learn more about the latest Substack's growth features.

And as it couldn't be otherwise, this publication now lives under a new, independent domain: playingthelongame.com.

Of course, I'd love to know your thoughts about these changes. 

If there is something you'd like to share, please let me know. Let's see how the experiment plays out.

That said, here's what I have to share with you this week.

Things I'm Thinking About.

How to Engineer Your SaaS Architecture as a Beginner Founder to Move Fast Today (Without Paying the Price in the Future).

"What if we cannot easily change the system later? What if it can't scale? What if it goes down? What if...?"

I've been building software for 15+ years, and I still remember those feelings when I started building my first SaaS. You want to account for every possible circumstance...but you drown in a sea of permanent hesitation and overwhelm.

However, there is a way out. In this article, I'll show you how to grow a sustainable architecture that can adapt more quickly to your evolving needs.

Want to take a look? Let's dive in.

Gems I Found.

How Big Tech Runs Tech Projects and the Curious Absence of Scrum.

Do companies actually use Scrum?

In this piece, Gergely Orosz, an ex-tech leader at companies like Uber, Microsoft, or Skyscanner, offers a detailed deep dive into how different organizations (big and small, tech and non-tech, consulting or product-oriented) approach project management.

A surprising insight for many might be the absence of Scrum at big tech companies.

But maybe that shouldn't be that surprising after all.

As we saw in a previous episode, overly prescriptive solutions are too rigid. They tend to sell better but suffer in highly-complex, evolutionary environments. And Scrum is no exception.

Want to take a look? You can read his article here.

As a side note, I recently joined Gergely's newsletter, The Pragmatic Engineer, as a paid subscriber. It's an incredible source to keep the pulse of the industry. Totally recommendable.

If you want to look at more of his insightful content, you can visit his site here.

Opportunity Blindness.

As entrepreneurs, or simply as human beings, our goals often make us blind to unique opportunities that show up in our way.

In this episode of his newsletter, Louie Bacaj explains the topic, grounded in historical discoveries and his own experiences as a newborn entrepreneur.

Interested? If so, keep reading.

Did Figma Actually Win Sketch?

This week I stumbled upon this Twitter thread by Justin Jackson.

The news about the recent $20 billion Figma acquisition by Adobe has been all around. And as usual, the reactions have not been long in coming. The popular conclusion is the one we often find in the media: Figma's won Sketch.

But that results from the typical, misleading, winner-takes-all mindset that is so harmful.

Justin makes a powerful argument on why Sketch has not necessarily lost.

Want to see what he had to say? You can read it here.

Brilliant Quotes.

"There is only one success: to be able to spend your life in your own way." —Christopher Morley.

Thanks for reading Playing the Long Game. Did you enjoy it? I hope you did.

Get on board. Was this newsletter forwarded to you? Still not subscribed? Sign up here if you want to receive more episodes like this one right in your inbox and support my work.

Suscríbete ahora

Say it out loud. Is there anything you disagree with? Anything missing that you'd like to add? I'd love to hear your thoughts, so please leave them in the comments. Or if you prefer more privacy, email me directly at hi@playingthelongame.com.

Leave a comment

Share it. Do you think someone you know may enjoy this episode too? If so, please forward it to them.

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And that's all for now.

Have a creative time.

Happy New Year! I hope you had a nice holiday break.

Here we are back again, beginning a new exciting year with a refreshed look at the future.

As you may already know, if you’ve followed this newsletter before, everything here is about growing more sustainable lives, businesses, and products. And in this episode, I have some new lessons and tools to share with you on this matter.

But first things first. Here is what I’ve been up to since the last episode.

First of all, I refined my creative system. This newsletter was initially intended to happen once or twice a week. Yet, it’s turned out more into a quarterly one. It’s been plenty of things happening around, lots of learning, and much stuff I’m having to get used to, so it got hard to keep up with all fronts.

But that’s no excuse so, to improve matters, I’ve been refining my creative system to become more prolific and get a better handle on things.

In this sense, I reviewed my workflow and refactored my second brain. It’s been a full review of the system from the ground up that I’m putting to the test right now.

I hope (and genuinely feel) this will help me enhance my output both in quality and quantity. I’ll tell you more in future episodes if everything goes as expected.

In another vein, since the last episode, I also built a prototype for an exciting SaaS project I am collaborating on.

Related to that, I wrote a short article where I go through the work I did and why prototyping before building the actual system might be a clever idea for you as well —but more on that below.

On the other hand, continuing my last article on the topic, I published a new essay on software engineering. Titled “The Majestic Monolith Demystified“, here I dig further into how to engineer monolithic web applications in a more sustainable manner.

Apart from that, and to wrap up the chapter on writing, I also published “Sustainability is Your Unfair Advantage for Hiring,” a reflection on how to hire great folks when you’re still at an early stage.

And last but not least, I kept publishing and engaging on Twitter. As I told you in previous episodes, I’m highly focused on growing the community and audience around me. Investing in Twitter is one of my main bets in this respect.

What I’m Doing Next.

With the end of a year and the advent of a new one, it’s time to zoom out again to re-assess the current state of affairs and set the direction for my next steps.

Keeping up with my previous efforts, one of my main priorities will be growing my community and audience. To do so, I will invest further in engaging and helping people online to build meaningful relationships. That will happen on Twitter and other online communities.

Regarding content creation, I’m going to double down on shorter-form content. I have many things to share but, since the day only has 24 hours, long-form writing has become a bottleneck. I sincerely enjoy it, but it takes too much time to produce, so I will experiment more with shorter-form content.

That’s not to say I’m going to give up on long-form. I’ll keep posting articles, but I’ll combine them with other, more condensed pieces —like tweets or Twitter threads— for more quickly experimenting with ideas and shortening the feedback loop.

Finally, I want to build my first info product and start a new SaaS project. In the last episode, I told you I wanted to begin a new small software project. I couldn’t get my hands around it. Yet, my desire is still latent, so I’ll try harder this time.

I’m not sure yet what those two projects will be about, but I have some ideas. I’ll keep you posted as I make progress on this matter.

Things I’m Thinking About.

The Majestic Monolith Demystified.

A monolith becomes majestic when it makes life better for its users and makers alike. It becomes majestic when it remains easy to understand and work with. It gets majestic when it can quickly evolve smoothly and consistently with the business and the rest of its environment.

Building a monolith instead of microservices is usually a safe choice when starting a new business. But is that enough to grow sustainably? How can we shape our monolithic app to move fast today without paying the price in the future?

Keeping up with the last article I published on the topic, here goes my final essay for 2021.

Want to have a look? Here it goes.

Prototype Before Building the Real Thing.

Consumer research and design over paper can only bring you forward up to some point. Once there, you need to see the solution. You need to touch it. And you need to test it in the real world to fill in gaps in your understanding.

When creating a new product, we usually do research, write specs, draw sketches and diagrams, and a long etcetera of activities for finding the right shape.

However, there is a cap on how far we can go with these tools. There is a moment when we feel stuck and need to move into the concrete.

So what should we do then? Should we go all-in to build the actual product?

In this short article, I try to provide some answers. You can check it out here.

Sustainability is Your Unfair Advantage for Hiring.

Getting people on board when you’re still not ready, when you stand on weak foundations and a wrong direction, will only get you off track sooner. And what’s even worse, it can trigger harmful side-effects further down the road you can’t anticipate beforehand…

I’ve been there multiple times.

You excitedly begin your new startup adventure only to soon crash into the cruel reality: hiring is tough. You compete with perks, security, salary, and a whole bunch of things that other bigger, more established companies can offer.

Apparently, you start from a position of inferiority. But is that all we can offer?

Or is there anything we can do to get over other, more established businesses?

In this article, I try to throw some light on those questions. Want to find some answers?

Prescriptive Solutions Sell (And Break) More Easily.

The more prescriptive a solution, the easier it is to sell.

Thinking is exhausting, so simpler, pre-cooked solutions are usually easier to digest. The problem often comes when you discover they have essential flaws and do not fit your context well.

So…is there a way to design flexibility in a prescriptive (more sellable) solution to get the best of both worlds, or are these mutually exclusive by nature?

This was the core of a discussion I held with Edo Van Royen on Twitter a few weeks ago.

Our conclusion?

They are opposite ends over the same scale. We can say that the more prescriptive a solution, the less flexible it is, but also the more marketable it is —and vice-versa.

Prescriptive solutions tend to sell better, but they also break more easily upon changes in the environment they operate in.

Want to take a look at our discussion? Here is my answer to his first tweet. And here is my reply to his second one.

Gems I Found.

Magic Sidebar.

Here is a brand new tool I’ve been trying out lately. Built by Tony Dinh, it radically dopes your Twitter experience.

Especially powerful for me to set reminders, schedule retweets, and replies, or see the history of interactions I’ve had with specific people. Very much needed features that have been missing on Twitter for too long.

And to top it off, everything stands as a browser extension that magically blends within the same Twitter UI. It’s like having an integrated CRM to get in control of your community, a renewed Twitter, on steroids.

Want to level up your game on Twitter? You can learn more here.

David Perell’s Three Principles of Writing.

If you want to grow a sustainable business these days, writing is one of the most valuable skills you can cultivate without a doubt.

In this short piece, David Perell outlines his three principles of writing: write from abundance, write from conversations, and write in public.

The three are interconnected and propel a virtuous cycle. More abundance of ideas drives better conversations which in turn leads to more (and better) ideas.

Writing in public is an amplifier. It propels conversations one step further, broadening the exposure of your ideas to new, more diverse contexts and perspectives, again leading to more (and better) ideas.

Want to read the whole piece? Here it goes.

On Liberty, Constraint, and Coercion.

If we must coerce our sisters and brothers, it should be done with the utmost respect and reservation. Anything less is an insult to liberty.

These days, society is extremely polarized. From the naive libertarian views to the coercive, authoritarian stances, most people seem to be leaning towards the extremes.

What both sides have in common: they all usually speak in the name of freedom. Obviously, something is quite not right here.

As usually happens, in reality, things tend to be fuzzier than what many try to make them seem.

In this article, Joe Norman brings up a much-needed perspective that I deeply believe we should be trying to recover as a society. We are still on time.

Want to take a look? You can check it out here.

Brilliant Quotes.

“Everything we hear is an opinion, not a fact. Everything we see is a perspective, not the truth.” —Marcus Aurelius

Thanks for reading Playing the Long Game. Did you enjoy it? I hope you did.

Get on board. Was this newsletter forwarded to you? Still not subscribed? Sign up here if you want to receive more episodes like this one right in your inbox and support my work.

Suscríbete ahora

Say it out loud. Is there anything you disagree with? Anything missing that you'd like to add? I'd love to hear your thoughts, so please leave them in the comments. Or if you prefer more privacy, email me directly at hi@playingthelongame.com.

Leave a comment

Share it. Do you think someone you know may enjoy this episode too? If so, please forward it to them.

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And that's all for now.

Have a creative time.

Greetings from Alicante.

Welcome to the second episode of Expedition Signals.

A few years ago, I learned a precious lesson from Benjamin Hardy. Our energy and cognitive capacity are limited, so periods of high intensity at work demand periods of deep recovery. That’s an essential part of creative work. Without rest, you cannot perform your best.

That’s a lesson I’ve been trying to stick to for a long time. I must recognize it’s tough for me to do. Somehow, I’ve always had some kind of addiction to work. I enjoy what I do, so, “If I could only push a bit farther…”.

But I know that’s a terrible mistake.

So, counterintuitive to what my mind usually tells me, I decided to take a vacation. I took a couple of weeks off. After several months of hard work, that’s something I very much needed. I needed to disconnect, reflect, and take a fresh look at things from 10000-feet high.

But, since the last report, not everything has been rest and relax.

I also started to refactor my note-taking system. As I said in the last episode, it’s a vital part of my creative work. Inspired by the Zettelkasten system, lately, it’s gotten a bit chaotic. So, to improve matters and take my second brain to the next level, I started reading “How to Take Smart Notes” by Sönke Ahrens, a really promising book on the topic. I’m really eager to finish it and tell you more about it.

Beyond that, I published a new article on software engineering and a few other posts —but more on that below.

And last but not least, I dove a bit further into crypto trading. That’s a terrain I started learning about at the beginning of the year, and I believe it can be a fantastic tool for tech creators like me.

You can learn precious lessons from it that you can directly apply to your life, businesses, and products. And you can get an excellent source of income without compromising your time too much.

It’s a risky thing if you’re not cautious enough but, if tackled carefully, I’m sure it can be an incredible tool toward financial independence.

I abandoned it in the last three months as I focused all my attention on deep creative work —like starting this newsletter, publishing new articles, and engaging on Twitter, among other things. But after that nice creative spike, it was time to resume it.

As a side outcome, I built a small tool on Google Spreadsheets for tracking my trades, seeing how I’m doing, and increasingly improving my odds of success. If you want to use it, you can find it here.

What I’m doing next.

Now, looking at the near future, next I’ll be moving the needle further with crypto trading. I’ll lower the time I dedicate to it, however, so I can focus on other things. My goal is to shape a sustainable, repeatable, and predictable system for generating consistent income on a regular basis while leaving room for other stuff.

Apart from that, I’ll also be publishing a new article on software engineering, promoting the last one, sharing and engaging on Twitter, and optimizing my content creation and publishing process, including my note-taking system.

And last, I want to start a new small software project. I’ve been some time away from coding, and my geek self is eagerly demanding to go back to it. I want to use it as an excuse to try some new tech. I still don’t know what I’ll build, so I’ll keep you posted as I approach a more precise roadmap.

Things I’m Thinking About.

Escaping the Microservices Wormhole.

Should I build a monolith? Or should I go with microservices instead?

Answering these questions when you’re starting a new software product is not an easy challenge. Or is it?

In this article, I dig into what I believe is a familiar struggling moment for many software creators.

Here is an excerpt:

Avoid microservices when you’re starting a business.

You’ll have more food on the table to handle, and that can trigger a vicious cycle. With more to handle, you’ll need to grow your team to address the increasing complexity. And when your team grows bigger, the organization will become harder, so again there will be even more to handle.

Like fast food, it is a great way to make your company fat.

Want to know more about why a distributed app can quietly break your business when you’re starting up? If so, you can read the whole article here.

Core Principles for Trading.

In any problem domain, there are essential, invariant properties common to every successful solution that succeeds in solving the problem. And trading is no different. There are core rules that every successful trader adheres to. Indeed, following them is not a guarantee of success. But not doing it is certainly a ticket for failure.

Throughout the past year diving into the trading space, there is a problem I’ve been recurrently experiencing: derailing from those original rules I told myself I’d never break.

I know I shouldn’t do it, but yet I do it. It’s pretty frustrating.

I believe this is a pretty common problem for other people as well, so, in this post, I try to consolidate and share the core set of principles that, up to now, I deem as essential for success.

It’s still a work in progress. I’ll update it as my comprehension of the topic evolves.

Want to have a look?

Shortcuts do not work.

If you’re learning a new discipline and trying to grow on top of it, there is something that barely ever works: taking shortcuts.

You can try to skip steps and apply your ingenious “growth hacks.” Yet, experience tells me that it doesn’t take long for reality to slap you in your face.

If I had to attribute my most catastrophic mistakes to just one factor, I believe that would be the pursuit of hyper-growth. This isn’t the first time I talk about that. I’ve been speaking for a long time about it in the context of creating businesses and products, yet it’s easy to fall for its appeal.

In fact, beyond businesses and products, I’d say most of the critical mistakes I committed in my life in general, or things like trading in particular, are greatly influenced by it.

As in everything else, hyper-growth won’t get you to your destination sooner. Often, counter-intuitively to what you might think, more is less, and faster is slower.

So instead, study the system and walk the terrain first to get started. Then improve to come up with a system that fits you. And only when you have an approach that works for you, scale to optimize for more money, more time, or both, depending on your particular needs and goals.

1. Get started.  Understand how it works, get familiar with what it takes, and identify your blind spots.
   Aim to understand the system first. Study materials like books, webinars, courses, and the like to learn the concepts and theory. Start with the classics, look for the fundamentals, and grow from there.
   Mix the theory with practice. Walk the terrain at the same time. Practice and get familiar with what it takes to do the work.
   Here is extremely important you make minimal bets. Assume you’ll fail by default. You’re learning and still don’t know what you don’t know, so keep your risk at a minimum.

2. Improve. Shape a system that fits you.
   We are not all equal. Everyone has distinct circumstances and pursues different ends. Assuming a system can work for everyone in all situations is a naive perspective. You need an approach that matches your particular context and goals. Once you’ve learned the foundations, this is what you should aim to achieve.

3. Scale.
   Optimize your system to earn more money and/or free up more of your time to do more of what you intrinsically value or other things that help you get there.

Remember, the right steps, in the right sequence, are essential to succeed.

Don’t Let Your Results Fool You.

We tend to judge our decisions based on the results we get. But is that the right thing to do?

When we start learning to code, it’s usual to follow guided exercises, tutorials, and the like. The boundaries are clear, and we have instant feedback on whether we solved the initial problem or not: either the program works according to spec, or it doesn’t. The factors out of our control are relatively small, and outcomes tightly correlate with our decisions.

So judging our choices based on the results is…we could say…fair enough.

However, things get wicker as we move into the real world and start growing real businesses and products.

We might make the right choices along the way and still don’t find a problem worth solving. We might discover a worthy problem and still not find a suitable solution for it. And even if we do, we can build a whole system that works…and still fails.

Complexity becomes massive, and there are infinitely more elements out of our control than under it.

On the one hand, there is a longer delay to see the results.

It’s one thing to build and launch a product, but it can take a long time to see long-term results like customer adoption or consistent, sustainable revenue. So did we make the wrong choices?

Or simply haven’t we seen the effects of those choices yet?

On the other hand, the driving factors for those results may not be apparent.

They hide far behind a complex causal chain of mechanisms, most of which may not be under our control. Did we fail because we chose the wrong problem? Was it because we shaped the wrong solution? Was it because the messaging we conveyed did not resonate with people? Was it because of the pricing we set out?

Or was it due to other external factors, like a new, unexpected competitor jumping into the scene, a disruptive external event (like COVID), or maybe someone in your team getting off track?

It’s hard to know. 

Maybe it was even none of the above. Or, more likely, it was a combination of several factors that led to that result.

Yet, one thing is clear: creating and growing businesses and products is more about failing than about succeeding. Luck and randomness play a critical role.

You can make the right choices and still get bad outcomes. And you can make the wrong choices and still get good results. And, still, it’s frequent to emit a judgment exclusively based on the results.

So how should we judge if we are doing right or wrong then?

Well, we’ll have to save that for another time. But for now, don’t let the results of your past decisions fool you. Judging your choices just by their outcome will lead you to the wrong conclusions.

When that happens, success gets still more random and elusive.

Gems I Found.

Thinking in Bets.

We are often fooled by randomness. Luck plays too big of a role. So how can we make better decisions?

Based on Annie Duke’s book, Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts, in this article, Ana Lorena Fabrega brings out some lessons to help us do just that.

She puts it in the context of childhood education, but it’s equally applicable to every person crafting a business, a product…or simply living a life.

Want to take a look? You can check it out here.

Small Tools for Shaping.

Design work is messy work.

There is no clear route. It’s more like a maze with many dead ends. And as a result, it’s easy to get stuck, lost in the weeds, and without a clear way out. But why? Why can’t we move forward? And what can we do about it?

After many years in the trenches shaping and building software myself, I’ve faced this struggle so many times. Although I’ve come to internalize different ways to overcome those roadblocks when they arise, there are many struggling moments where I don’t know where to go and get myself down into wormholes.

In this article, Ryan Singer does a great job establishing a common language and making some of those challenges explicit as a set of patterns.

It’s not a process with a clear sequence but rather a set of tools to use, just in time, upon what the situation demands. Each tool tackles a common struggling circumstance that every creator repeatedly faces in any given project.

If you want to get unstuck, start by recognizing those situations and what to do about them.

Want to learn more? You can have a look at the article here.

Vaccine Mandates Are a Systemic Risk.

Vaccine or no vaccine? We’re being forced into believing, almost as a religious act, there is no dilemma at all about it.

Vaccines are the ultimate answer to our problems, and everyone, almost without exception, should unquestionably get them.

Those who doubt it are against the collective. Hence, the vaccine should be compulsory. Vaccine mandates are more than justified. For our safety. All in the name of science.

But is that “the truth”?

This is something I’ve been trying to get my head around for a long time.

Here, in this post, Joe Norman very well articulates many of my concerns and thoughts around it —and, as always, massively enriches them.

Want to have a look? You can do it here.

And if you want to dig further into the topic, here is another conversation he held with Harry Crane in “The Academy,” a Youtube channel they started not so long ago where you can learn about interesting, current affairs from a complexity-based optic.

These days it is relieving to hear an honest chat between people genuinely looking to get closer to the truth, out of the official dogmas and the weakly grounded conspiracy theories that flood us every day.

Brilliant Quotes.

“The problem with the world is that the intelligent people are full of doubts, while the stupid ones are full of confidence.” —Charles Bukowski

Thanks for reading Playing the Long Game. Did you enjoy it? I hope you did.

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Have a creative time.

Greetings from Alicante.

This is our first report from the expedition, and I’m psyched to get on with you in this new and exciting adventure.

Last week I finally started working in public. This is something I have been struggling with for a long time.

I’ve been too focused on working inwards, learning, reflecting, and building stuff…but hardly ever sharing. I think it’s high time to turn my attention to the outer side of the equation.

In this vein, I managed to consistently publish on Twitter every day.

Also, I submitted an article to “Start it Up,” the Medium publication. Titled “Escaping the Microservices Wormhole – Why a Distributed App Can Quietly Break Your Business When You’re Starting Up,” it was an essay I wrote by the end of last year but never published. I got stuck into other stuff and never managed to do it. Hopefully, now will be the time for it —better late than never, right?

And to top it all, today I’m launching this newsletter!

Public-facing matters apart, I also re-adjusted the scope for my email course on product engineering for indie tech-creators. Now, with a narrowed-down scope, I’m considering whether to keep pushing this project further or apply the circuit breaker for now and shift my attention to something else.

Definitely, the last week’s been a giant leap to be proud of.

Now, turning our sight towards the future, this week I’ll be keeping up with sharing and engaging in communities. My main goal is to stay consistent to get used to it and what it takes. As I keep learning, I’ll also try to optimize and free up as much time as possible for other stuff.

If nothing happens, I’ll publish the article I submitted, either in “Start it Up“ —if it gets accepted— or in any other place.

And finally, I’ll refine my note-taking system. It’s an essential part of my system for doing creative work, but lately, it’s gotten a bit chaotic.

Coolest things I learned.

Public retrospective.

As I told you above, working in public has been burdening me for a long time.

If you’re like the old me, you’re always trying to craft a masterpiece before publishing. You want to sound smart, so you feel you need to make your creation the last word. Otherwise, you feel like an impostor.

It’s overwhelming but also a common situation to be in. As are its results: you publish nothing, ever —or if you do, it happens very sporadically.

But you don’t need as much to start sharing your work.

There is no last word. Share your journey as it happens. When you see what you publish as a work in progress and make everything about sharing what you’re doing, learning, finding, and thinking at the moment, the road gets easier and more joyful —that’s what I’m actually feeling as I’m writing this newsletter.

It’s like doing a retrospective but in public.

I was practicing retrospectives as part of my journaling process before. And I was practicing them in development teams even before that. But I never saw them this way.

When done in private, definitely a fantastic tool for accountability and reflection that brings clarity to your mind.

But when done in public, it’s a bomb. Now, I can make the most out of my time simply by sharing what I’m already doing. I’m just picking the low-hanging fruit, so it makes it a great return on investment. And logically, it demands a bit more effort than working in private, but the benefits are outstanding.

I’m not working in the shadows anymore, and you neither have to.

I learned this from David Perell in his revealing appearance in Nathan Barry’s Show. This is what he calls “burnt-ends content.” You can have a look at the shortened clip where he talks about that here.

Or if you want to watch the full episode, you can also do that here.

Small pieces.

You don’t have to craft an extensive and profound essay to start sharing. You look for consistency first. Quality comes second.

Start by sharing just small pieces —like this one. That will help you stay visible to the outside world and begin making crucial relationships while building and connecting your thoughts into broader, more whole concepts.

Just one channel.

When you start working in public, there are many things you don’t know and many moving pieces to fit in.

You have to learn and practice skills like writing or speaking—depending on your chosen medium.

You’ve got to get into the dynamics, culture, language, and peculiarities of all the communities you’re trying to get into.

If you’re trying to syndicate content, you’ll have to understand their contribution policies and learn their submission processes.

You’ve got to learn the right tools, strategies, and tactics, often specific to each platform…

The list is daunting.

And if that wasn’t enough, you also have to keep up with the rest of your life and work.

It’s a very ambitious move. But also a hazardous one. Trying to reach so many channels, communities, and formats can be over-killing.

Instead, simplify. You’re trying to build a habit and learn what’s needed. When you’re starting, pick just one channel and master it. Once you’re comfortable, expand.

This is what I’m doing right now by focusing on Twitter alone.

Things I’m thinking about.

Problems need to be concrete.

As Ryan Singer commented on Twitter the other day, “What sounds like a problem often isn’t concrete enough.”

That’s a common trap with evil results.

You think you understand the problem, which often makes you underestimate what it takes, which in turn leads you to commit prematurely to it, and waste your precious resources on the way.

The devil is in the details.

When will it be ready?

How many times have I heard this question? When I worked for others and started working on a new product, they couldn’t stop asking: “When will it be ready?” They wanted a close estimate.

But when I founded my own business, nothing changed. Now it was my partners and myself asking.

I get it. It’s natural. As human beings, we all want to be in control of the future. We don’t like uncertainty, so we have to come up with an answer. How not?

If you are creating a new tech product, perhaps you think you can predict the future.

Or maybe, despite your reluctance to be so daring, you adopt a commitment that deep inside, not even you trust. You do it to get rid of the external pressure or satisfy your ego —or maybe even both.

In the end, experts do estimates so, getting people to trust you as an expert requires you to give an estimate, right?

Please, don’t do that.

Not all stages in product development are equal. Working on a consolidated product in the market at the Scale stage is not the same as starting something new.

Kickstarting a product from scratch have plenty of unknowns. Trying to predict the unknown will only serve you to set unrealistic expectations and unreachable deadlines.

You can try to convince yourself you can finish in three months, six months, one year…whatever, but in a highly uncertain context, nothing will save you. It’s a ticket for frustration and pain.

Like an apple released from a tree, the world does not care if we want the apple to rise to the sky. It will fall to the ground. The reality is that stubborn.

Your work is to reduce risk, not increase it, so embrace reality and act accordingly.

When you’re starting, you’re doing exploration work.

You still don’t know what you don’t know, so be honest:

• Work iteratively to walk the terrain.

• Bet your time and resources at each iteration but don’t commit to delivering anything at the end.

• Let yourself withdraw from the bet when the pieces in your puzzle no longer fit.

Remember, you need flexibility, not a rigid plan.

Gems I found.

The Embedded Entrepreneur.

Founders often build businesses and solutions looking for a problem. That leads to risky products that ultimately serve no one. That’s like going all-in when playing poker. Once your product fails, you are out of the game with nothing left.

However, in this book, Arvid Kahl exposes an approach that aligns pretty well with my view on entrepreneurship in the last few years.

If you want to create a business, do it sustainably. Do it with people from the start. Start embedding yourself in their community. Build “with” people and not “for” people.

That’s what he calls the “Audience-Driven approach.”

If you want to find your future customers, discover how you can help them, and build an audience while growing your business, this might be an invaluable reading.

A very actionable piece that will help you build a sustainable, people-grounded business.

You can check it out here.

Reading better.

Reading speed is a vanity metric. No one cares how fast you read or how many books you read last year. In the real world, what matters is what you absorb. Skim broadly to find something worth reading. Then dive in slowly and deeply.

We often brag about how many books we read last year. But that’s bullshit.

The act of creation is also a fight for attention.

Reading is one of the inputs we take for producing valuable work. But what happens when we are overwhelmed by a tsunami of information on every front? 

Those are the times we live in today. As creators, having all the information we want on our screens is a blessing, but it can also become a curse if we can’t process it effectively and efficiently. 

Shane Parrish and his content at Farnam Street do not usually disappoint, and in this excellent article, he gives us some keys on how to get the most out of our reading so we can get smarter at it and absorb the most powerful insights.

Function and Scale

A great explanation by Joe Norman in his April 2021 Applied Complexity Science newsletter on the relationship between systems scale and their revealed function.

The problem of scale, especially when reached too fast, is what, in the context of creation and entrepreneurship, we at Freegrowth have been trying to articulate for a long time:

Hyper-growth in businesses and products can lead them to realize the opposite function than the one initially intended and cause harmful effects on the environment they operate in, including their creators and everyone around.

If you’re dreaming of growing a lot and doing it fast, think about that first. Maybe that’s the perfect recipe to end up in a place you don’t want to be.

Here is an article we wrote in 2020 where we already talked about that.

And if you want to keep learning about complex systems, check out and subscribe to Joe Norman’s newsletter. You’ll get plenty of wisdom bites like this one.

Brilliant quotes.

“Knowledge without reflection is useless. Reflection without knowledge is dangerous.” —Confucius

If you study something but don’t reflect on it, your effort will be for nothing. But if you reflect without the proper foundational knowledge, things can get worse.

You’ll likely get drawn to wrong, dangerous conclusions, take them as facts, and get on a path that can ultimately make things worse for yourself and your environment.

To make positive progress, you need both. Always be studying, and always be reflecting.

And, of course, don’t take your conclusions as facts before you can possibly know. No matter our knowledge level, when we reflect, we tend to think we know enough to form an opinion —you can call it arrogance. Instead, be constantly aware of your own ignorance.

Thanks for reading Playing the Long Game. Did you enjoy it? I hope you did.

Get on board. Was this newsletter forwarded to you? Still not subscribed? Sign up here if you want to receive more episodes like this one right in your inbox and support my work.

Suscríbete ahora

Say it out loud. Is there anything you disagree with? Anything missing that you'd like to add? I'd love to hear your thoughts, so please leave them in the comments. Or if you prefer more privacy, email me directly at hi@playingthelongame.com.

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And that's all for now.

Have a creative time.