2018: Review

This writing is a personal reflection of my work and perspectives in 2018. My experimentation this year explored music production, rap, filmmaking, software development, new startups, research, travel and sleep. Some of them were successes and some of them were failures. I usually learn more from my failures.

These reflections are broken into the following chapters:

  1. Experiments
  2. Geography (in progress)
  3. On Depression (incomplete)
  4. 2019 (incomplete)


Since late 2017, my experimentation has been surrounding a question that is essentially: "What is the extent of possibility with my talents, a MacBook Pro and an Internet connection?"

This is a set of reflections on each of my experiments in 2018.

  1. Everyday (completed, July 15 2018)
  2. 100 (in progress)
  3. Desk (completed, Nov 18 2018)
  4. Learning to code (in progress)
  5. Float (delayed, in progress)
  6. Futureland (on going)
  7. 4am (failed, recalibrating)


project everyday was an experiment I started near the end of 2017 to understand what could be learned through making some kind of music everyday.

Prior to this experiment I had not made any music in my life. As I continued on with this experiment it started to become a spiritual experience for me. This is difficult to put into words and to understand this you must go through the experience for yourself. I can only say that at some point the process of making something from start to finish irrelevant of my depression, how tired I was, the time, the situation and so on began to rewire my brain and transform how I saw the world around me. I became hyper aware that at any point I could make something that altered my reality. Some days it was as if anything I looked at instantly became art. This feeling still persists today and the more I create things, the stronger it gets.

This photo of my new born son and I was taken shortly after I started the project everyday in 2017. I was exhausted.

I completed the experiment on July 15, 2018 after outputting 365 tracks for 365 consecutive days with a total run time of 20 hours and 28 minutes. I summarized many of the things I learned from this experiment in a well received Twitter thread entitled, "What I learned making some kind of music for 365 consecutive days:"

In a lot of ways it is sad knowing that this project is over. But it is. It was a ride that captured my emotions from a transformative period in my life. I will never be able to go back to being the person I was before I started this project. I am changed forever.  

This is project everyday in its entirety. The album starts on the 365th track and is played in reverse. The recording you hear on the 365th track is a recording from a phone call with my dad. I called him one day this year when I was feeling down. He did not know I was recording.


project 100 is an experiment to observe what happens to a human who attempts to rap over 100 beats with no real prior experience.

This project is much more difficult than project everyday because it goes beyond just making music and is an experimentation with my actual voice and my identity. There is nothing to hide behind when you are rapping like this.

The way I structured the description of this experiment is revealing of my own personal limitations. The part about, "no real prior experience" is my way of protecting my ego and also a way of demonstrating that I am diving in without knowing how to swim. It is almost obvious what the findings of such an experiment would be. If you rap over 100 beats, you will probably get better. What makes this experiment interesting to me then is that I have always wanted to rap, but why am I just starting now?

I had a personal computer before I knew anything about hip-hop. My dad was a Software Developer and for reasons I do not understand I had access to the Internet before other kids had computers. My dad extended this access to the Internet to two of my childhood friends, Varun and his older brother Vam. Both of them were much more talented with computers than I was. One day when I was 11 years old, I got off the school bus with Varun and he was talking about someone named Busta Rhymes and an application called Winamp. He described a digital music player that allowed anyone to play something called an .mp3 file. I did not really understand what he was talking about, but I will never forget the excitement in his voice. Then he told me that you could change the way the music player looked, even making it wood grain. Everything he was saying sounded so futuristic.

Varun's older brother Vam was deeply connected to a community that was distributing Warez (illegally distributed software and other content through the Internet). At the time there was no Napster so you needed to know somebody to get the good stuff. Vam's alias was Wesson, short for the gun manufacturer Smith & Wesson. We went over to their house and Varun asked Vam if he could show me Winamp and all of this music he was listening to. Vam was more intelligent, creative and cultured than both Varun and I. I am still deeply inspired by him. He then went on to show me Rapper's Delight, Wu Tang Clan, Busta Rhymes, A Tribe Called Quest - I'll never forget that night. It was the first time I felt pure excitement about something.

I always wanted to make music. I always wanted to experiment with Rap, but none of it felt like it was part of my identity and that's why I didn't do it. I was always worried about what might happen to my future self. I was worried about some future where all of my career opportunities would disappear if I started experimenting with Rap.

At some point in our life we select an identity and this identity contains instructions to ourselves about the level of success we can achieve, what we are allowed to do and what is not allowed. I do not understand all of the details about how this happens but I am coming to believe that most of your creative potential is based on the identity you select for yourself. At any time, you can decide to open your mind to new experiences. You can try out new perspectives, adopt completely different views if you want, thereby selecting a new identity. When this happens your potential can dramatically expand.

It does not matter whether my music is good or not. Experimenting with Rap has widened my identity. It has increased the range of what I am willing to experiment with and that means the project has made me more creative. project 100 has humbled me and has given me an endless respect for the performing arts.

This experiment is still in progress and I will share more as I continue learning throughout 2019. This is track 20 / 100 from this project appropriately titled, "mediocre music":


project desk was an experiment to launch a startup called Desk in under 24 hours that allows anyone to find a new place to work, anywhere in the world.

I live streamed this process via Twitch on Nov 17 2018 and launched a beta version of Desk in just over 21 hours. A documentary of this experiment was made and shared in real time as I worked to realize the project.

A still from the real time documentary made about realizing Desk. The documentary was shot entirely on an iPhone X by filmmaker Howie Cheung

In late 2017, while I was in Los Angeles I found it very difficult to find a place to work. I needed a desk for a few hours on different days in various areas throughout the city. I had an idea for an app called Desk that functioned like some combination of AirBnB and Uber. It would allow anyone to quickly find a new place to work anywhere in the world.

I created a concept page where anyone could subscribe for updates on Desk and over 300 people signed up. This surprised me. I took a break from the concept primarily because I had no idea how to build it, but throughout 2018 people would always message me about it. Most of the messages were people saying they could really use something like Desk.  

I do not know how to code. But on November 17 2018, I decided to just throw myself into a situation that forced me to find a way to build this app. The idea was I would attempt to build Desk by any means possible in under 24 hours and share the entire process on live stream. Live streaming was a way of forcing myself to go through the process from beginning to end.

I ended up launching a version of Desk on a platform called Sharetribe, without having to learn how to code. Two days later I helped a restaurant near my apartment in Toronto called Thai Green Chili turn itself into a coworking space using Desk. Then later that day someone paid me to use a Desk there for a few hours.

There's something very cool about trying to build things that solve your own problems. I went from not having a desk to work at for extended periods to having access to a late night co-working space in front of my apartment just because I created something. It is a very powerful experience.

I quickly hit the limitations of my technical abilities because I could not code. There was valuable user feedback I could not act on. I felt this way at the end of 2017 and I still feel the same way now. Learning how to program seems to be the most effective way of realizing the types of ideas I am thinking about right now.

In order to do the types of projects I want to I need to dramatically increase my ability to realize projects via code in 2019. I'm not satisfied with how much progress I have made on learning how to program in 2018.

Learning to code

One of my goals for 2018 was to become proficient enough in programming to start building software I was excited about. I made progress but not as much as I would like. Still I built a few apps in Swift in an extremely guided way and completed term 1 of an iOS Developer Nanodegree from Udacity.

There is a seemingly infinite number of paths to learn programming right now but the initial steps seem universal.

  1. Select a programming language based on the types of things you want to create
  2. Select how you want to learn this programming language
  3. Go through a disciplined process of building things and studying with that programming language everyday until you are creating the things you want to

When I asked some talented developers what the best methods of learning programming were almost all of them said the best way to learn programming was to jump in and just start making things. They would actively tell me to avoid taking courses.

The idea here is that when you take a course you are learning things you may not need to know to build the things you want to. But when you jump in and start just making things you are forced to learn exactly what you need to know in order to build what you want. This makes sense to me, but as I started to try and build my own things I felt I needed a stronger understanding of some core programming concepts. Some times I found I did not have enough core knowledge to get around problems I was stuck on. I went against the advice I was given and signed up for the iOS Developer Nanodegree Program with Udacity to learn Apple's programming language Swift.

I completed Term 1 of this program by late 2018 and it included the creation of two iOS applications in a supported learning environment. The first was an app that allows you to record and modulate your voice using effects like reverb and echo. The second was an app that you can use to create simple memes by allowing you to add text on top of any image you select. The course guided you through the creation of these apps and I learned a lot.  Term 2 of this program starts on January 8 2019.

Overall I am not satisfied with how much progress I made with programming in 2018. I felt that learning how to code was an important priority for me this year and I do not think I ran enough experiments with Software. In 2019, I will complete my iOS Developer Nanodegree with Udacity and force myself through a high volume of software output.


project float is an experiment to understand the value of a space designed for hyper focused creative work by combining innovative design and float tank technology.

The concept for this project came out of my own frustrations and experiences with trying to find places to work that would make it easier to achieve deeper states of focus. When working on my own or at cutting edge technology companies, I found it difficult to find a physical space that would allow for long periods of uninterrupted concentration. This is because most of technology companies and coworking spaces use an open office design. I would often book a "phone room" for a few hours just to have a quiet place to work. This focused work was always a secondary use for these rooms, the primary one was of course a phone call. These open office designs always confused me. I always felt like it was a drain on the value a knowledge worker could produce.

While I was living in Mexico City in early 2018, I read Cal Newport's Deep Work and it crystalized many of my perspectives. Deep Work is an excellent book that unpacks the value of designing your creative process and live in a way that allows for long periods of uninterrupted concentration. Cal Newport presents a very compelling perspective on why this way of working allows you to produce work that is orders of magnitude greater than the work you can produce through methods rooted in contemporary tools and designs which lean towards multitasking, connectedness and ultimately more distractions. I found Cal Newport's book to be very inspiring and it captured so many of my own frustrations.  

There is an architectural concept in the book called the Eudaimonia Machine created by an architect and professor named David Dewane. He says the goal of the machine, "is to create a setting where the users can get into a state of deep human flourishing - creating work that is at the absolute extent of their personal abilities." David goes on to outline the various area of the space, things like a gallery for inspiration and a focused work enviornment and how they could work together on a psychological level to produce the ideal working environment. This concept captured my attention and I was shocked to learn that it had never been realized.

Sketch of Eudamonia Machine office layout by Alan Ruby

I started to wonder what it could look like if it we realized today. I am an avid user of float tanks and I started to wonder how they could be used in an environment designed for deep work. My wife Sachi was very interested in working on this project, so we talked about it a lot in Mexico City and she helped me put a business plan together. A few months later we had secured a loan from the bank to launch this project in Toronto. The whole process was super exciting.

When we got back to Toronto in the summer, we started meeting architectural studios that we felt could help us realize this project in a compelling way. It was through this experience that I met one of my new and good friends, the architect Reza Niik. He was immediately into the concept of the project float and he would me sketches of his thoughts via iMessage. This high speed, early sharing way of working was a dominant theme of my collaborations in 2018 and it is becoming my preferred way of working on projects.

Early sketches of project float architectural idea by Reza Niik
Early sketches of project float architectural idea by Reza Niik
Early sketches of project float deep work space by Reza Niik
iMessages between architect Reza Niik and I evaluating the creative potential of a location

I would visit locations with Reza and other team members to understand each location's feasibility relative to the vision of the project. We found a few locations that were very compelling in excellent areas of Toronto but the price point was consistently very high. The availability of commercial property in Toronto is at an all time low, at around 2% and our location has very specific requirements. There were a few leases that we almost signed, but it never felt right. We were about to commit millions of dollars to this project without having a lot of data. We started looking for cheaper locations in other parts of Toronto that are less trafficked, but I felt we were just moving our costs from one part of the project to another. We were saving on rent, but then would have to spend more on marketing and promotion to attract users to this new area. All of this felt off to me. I felt it was important for the project to be in a prime location.

My wife and collaborator Sachi and I scout a potential lower cost location

I started to wonder if there was a low cost way to create this space digitally before investing millions into a physical space. I decided to put project float on hold for a few months to test out a concept for a multidimensional creative community called Futureland. Perhaps I could build project float and many other projects in collaboration with this community.


Futureland is an experiment to see what happens when you bring talented creative minds from all over the world into the same digital place.
Futureland logo by designer and art director Ryan Davis

Like many of my projects recently, Futureland comes out of my own frustrations and experiences. It has always been very difficult for me to connect with other creative minds who might be interested in the same things I am. I have heard many of these same frustrations from my friends and collaborators. I personally do not know where to start when it comes to meeting other creative minds. I have heard that it helps to go to parties and events, but this is not how I like to connect and it takes too much time away from my focused work. I thought it could be interesting and valuable to see what happens if I ran a series of experiments to connect creative minds in interesting digital locations.

The first experiment was to create a community on Slack which you can join at: www.futureland.tv

I started this experiment about two weeks ago and 80 people have joined so far. The conversations have been very stimulating and the quality of work being shared is super compelling. It's still early in this experimentation, but it has already been a motivating and inspiring experience for me.  I have made many new friends who are super talented. Each day something new and interesting happens. I am excited to see how this evolves in 2019.

I have also been working with Ryan Davis on a visual identity for Futureland. Ryan has created a visual system that includes logos and type hierarchies and is currently working on some experiments with apparel. I am hoping to work with him a lot in 2019.

I am hoping that Futureland will become the identity of many experiments and collaborations that aspire to yield transformative value for creative minds all over the world.


project 4am was an experiment to see what would happen if I started waking up everyday at 4am and livestreamed to the public as proof that I was up and as a way of keeping me disciplined.
A still from my first day streaming live to the Internet for project 4am

I wanted to do this experiment because I have always struggled with waking up early. Every morning I struggle to get out of bed, I work a lot and am always sleep deprived. So I thought I could use some of my methods to increase discipline and apply it to waking up earlier. It worked. Overnight, I went from someone struggled to wake up in the morning to to someone who was regularly getting up at 3:50am. I would tweet when I was up, get a glass of water, brush my teeth and then begin a live stream on Twitch as proof that I was up. This method of pursuing your goals in public is still the most effective path I have found of immediately increasing your discipline.

However, I would consider this a failed experiment because I stopped it after 17 days.

The reason I stopped is because I was waking up everyday between 3:50am - 4am irrelevant of when I went to sleep. So if I went to bed at midnight or 1am, I would still wake up at 4am. If I was sick or if I could not sleep, I would still wake up at 4am. After two weeks this started started to take wear me down. On the days when I was able to go to bed at 8 or 9pm (which were rare) I woke up in the morning feeling tremendous energy. On some days it was as if my body would automatically wake up and have energy. The challenge was that my life rarely enabled me to go bed at 8pm. It meant sacrificing time with my friends and my wife because everyone else operates on a schedule where they hang out and party at night.

On one of the days of the experiment, it was my sister's 30th birthday party and I left almost immediately after arriving so I could get home and get enough sleep to wake up at 4am. I ended up sleeping at around 11:30pm, so I only slept for 4.5 hours. For a few days, I tried to sync my exposure to screens with my exposure to the sun. So as the sunset, I would stop using my iPhone or MacBook. I would turn off all the lights in my apartment. I would read physical books and make notes on paper instead of using my iPhone. This had a huge positive effect on my sleep quality but I felt it wasn't sustainable - especially in winter when it gets dark so early. I get a lot of stuff done in the evenings and a lot of that output is centered around my iPhone and MacBook. And yes I have used the feature that takes the blue light out of both screens, it is nowhere near as effective as cutting our screen use entirely in the evenings.

On days where I was getting enough sleep, the biggest benefit was the additional hours of productivity in the morning. By noon, I had already completed an 8 hour work day. This is what makes me want to pursue experiment again, but sleeping at 8pm or 9pm requires some fundamental changes to my lifestyle. I also need more data on whether this kind of routine has an overall positive impact on output. There is something about the night that really seems to spark my creativity.

I have experienced the same challenges with my lifestyle while pursuing other projects, project everyday is a good example. It was a project that was beyond my current abilities and I just forced myself to do it. This has been a consistent pattern in my career. I find something that is difficult for me to do and then just use brute force to try and find a way to get it done. No matter the implications to my body or mind, I finished a track everyday for a year. Even if I was sleep deprived, drunk, depressed or bed ridden. But if I want to pursue even more difficult projects, I need to radically change how I am living.

In early March of 2018 I became obsessed with studying Kobe Bryant's daily routine and work ethic. I read tons of articles and watched interviews to try and piece together how he would spend each day. He would use an "all day process", where everything in his life was structured around putting more time into basketball. Kobe believed that the number of focused hours you put into your craft is directly related to the level of greatness you can achieve. In a salon during TEDxShanghai, Kobe reveals how he thinks about his schedule:

"Imagine you wake up at 3am and train at 4am. 4-6. You come home. Breakfast. Relax. Now you're back at it again. 9-11. Relax. Now you're back at it again 2pm-4pm. Now you're back at it again 7pm -9pm. Look how much more training I have done by simply starting at 4am...and as the years go on the separation that you have with your competitors and your peers just grows larger and larger... by year 5 or 6 it doesn't matter what kind of work they do in the summer they are never going to catch up."

Kobe was fine sacrificing sleep as well. In his book, "The Mamba Mentality", he says:

"I wasn't willing to sacrifice my game, but I also wasn't willing to sacrifice my family time. So I decided to sacrifice sleep and that was that."

This type of dedication to craft completely captured my fascination. I have been obsessed with this concept of an all day process and it is something I want to explore a lot more. In many ways both Everyday and 4am are experiments with that way of thinking.

One of the ways project 4am could have been improved is through a more focused use of my time when I was waking up early. Kobe Bryan and other great athletes are very precise with how they use their training time. They have an excellent sense of what they need to practice to become great at the game. I feel like this precision is missing in my training as a multidisciplinary creative person. I need to not only put more time into my craft but I also need to form a better understanding of the types of things I need to practice in order to realize my maximum creative potential. It seems as if it is harder to figure how to practice as a multidisciplinary, but I think being in a state of continuous output like I did with project everyday is a step in the right direction.

I want to run many more experiments with lifestyle changes as a means to improve creative output in 2019.


In our world, where you can work from anywhere and build world changing things with just a MacBook and an Internet connection - what is the value of a city?

In the early days of the film industry many American filmmakers moved out west to Los Angeles as a way of evading Thomas Edison's motion picture patents. In the east filmmakers were often being sued to stop their productions by Edison's company. So they started to leave. Another benefit of moving out to Los Angeles was the amount of natural light available for these film productions. It was a superior environment to create movies. This move to Los Angeles allowed for the rapid development of the film industry - making it one of America's largest industries and the global leader in this kind of creative output.

I think of cities like Operating Systems. Each one of them has strengths and weaknesses. A particular city can be better suited for certain kinds of creative output than others. In late 2017, I started experimenting with living in different cities with my family to understand how each one affected my work. What advantages could be gained from operating in one city over another? We started with Los Angeles and in 2018 expanded this experiment into Mexico City and then Tokyo.I'm still wrapping my head around all of this and I need more years of this kind of experimentation to form a better understanding.

Mexico City

I lived in Mexico City with my family from January 22nd to March 6th. I loved it there. Mexico City was cool because it provided a way for us to bring down our overall costs from Toronto and tap into Mexico City's thriving culture and art scene. The only negative is the earth quakes. We experienced a 7 point something earthquake that started in Oaxaca and rippled out from there to Mexico City. That was fucked up and scary. I don't have much else to say about that.

So far, I haven't been anywhere in the world that I found as inspiring as Mexico City. The museums, the galleries, the food, the music, the vibes - it's on another level for me. It has this raw quality to all of it that makes me feel very experimental and ok with trying new things. There's this seemingly strong appreciation for art and creativity everywhere. As a creative person, there's no better feeling.

Then there is Panoram Studios. One of my favourite places in the world. I do not know all of the details of how this place came to be, but it's essentially a huge old house in Hippodromo, Mexico City that has been converted into a multi-level recording studio. Musicians and artists are walking throughout the place. Sometimes someone is taking a break with a cigarette and their guitar thinking about a new melody. The house is filled with little interesting objects and art pieces. As you walk through the house, sometimes there is a ceiling and sometimes there isn't. This is common in Mexican architecture. As soon as you step into the house, you are completely absorbed. The environment consumes you.

While I was there I made some good friends named Mario, Edgar and Andrea. Mario was a resident engineer there and in general just a really cool dude. We got along well. I started experimenting with rap while I was there and he was super supportive about the whole thing. He never judged me and encouraged me to keep going on days when I wanted to give up or thought something was lame. Edgar was the studio manager there and runs the place very well. He always made sure I was comfortable. I was introduced to Andrea (a singer and artist) by Mario. She started giving me singing and vocal lessons in her apartment while I was there. She's got good energy, a lot of fun to be around.

This experience at Panoram Studios taught me a lot about the benefits of immersing yourself in creative environments. Recording studios are a really useful for doing this because they are creative environments where everyone is working on things and if you're open there's always the possibility to collaborate with others. It immediately taps you into the creative culture of a place and it's a great way to meet new people. I've been thinking a lot about what other kinds of spaces in a city serve this purpose outside of great recording studios. Maybe a coworking space or some kind of residency. I'm not sure. But I think there is a lot of value in producing these types of creative environments. Ones that immediately cause immersion and expose you to a new way of thinking. Where talented people from all over the world are always coming in and out.


I lived in Tokyo with my family from March 27th to May 15th. Tokyo is one of those places I often find myself coming back to. There's so much to learn from their culture and their creative output. The inspiration is seemingly endless. There's something about the fashion there that immediately rewires how I think about the potential of my appearance. The range of clothing you see there and how people express themselves through it gives me the confidence to be more experimental in my own fashion choices. There's an endless set of references to pull from. I wish I took more photos of the characters there.

I hate talking about the negatives of a place, but it is what it is. Tokyo is futuristic in many ways and not so much in other ways. There were two times when I was stopped by police officers while walking home from the recording studio at night by myself, completely sober. In both cases I was surrounded by 5-8 police officers as they patted me down and searched my brief case. The experiences lasted between 40minutes and 1.5 hours and in one case they escorted me from the subway station to the apartment where I was staying to prove that what I was saying was true. In both cases I did not have my passport on me, just ID, which caused things to escalate. So if you are in Tokyo always carry your passport. Especially if you are a brown dude who has dyed his hair blonde. In order for a police officer in Tokyo to ask you for your passport (which they can do) they must believe that you are the suspect of a particular crime, which I obviously was not in both cases I was stopped and searched. This part of being in Tokyo sucked, but I did my best to forget it. I was super pissed off when it all happened, but my friends calmed me down with their iMessages.

21_21 Design Sight in Roppongi, Tokyo is my favourite place in Tokyo. The museum was created by the architect Tadao Ando and Issey Miyake. Ando describes the purpose of the museum as, "a place for researching the potentiality of design as an element that enriches our daily life, a place that fosters the public's interest in design by arousing in them different sights and perspectives on how we can view the world and objects around us." It is impossible to read something like that and internalize it in a meaningful way. You need to go to this place and experience it for yourself. I was living in Roppongi and I would go there multiple times each week to run, to think or to see an exhibit.

Tokyo in general is very expensive to live in. It's not a place I would go to if I was working on a particular project for an extended period of time and wanted to bring down my overall costs. But an unexpected benefit was the low cost of getting access to a recording studio. Noah Studios is a 24 hour low cost recording studio that can be found all over Tokyo. They are multi level buildings with many rooms that are available to make music. I was going here very often and it was super affordable. It's shocking that this concept does not exist in cities all over North America. It would be great for anyone who wants to make music or wants to record a podcast.

There is so much to Tokyo. It's a place that always blows me away and truly understanding it would take many more trips. I found it difficult to connect with the creative community there. I did not know where to start. I wish I spent more time understanding the technology scene there. I wish there was an easier way to immediately immerse myself in their creative ecosystem.