my avatar

2023 yearly review

January 07, 2024

Happy 2024! This year, I am continuing the tradition, which has been going strong for 5 years, of summarizing my year. I truly enjoy doing this as it allows me to reflect and realign. It's a fun exercise that I believe everyone should engage in.

I feel pretty good about 2023 because I managed to achieve what I wanted to do with the year. 2022 was marked by the seismic shift of moving to a new city (Lisbon) and starting to live with my girlfriend, whereas 2023 was all about settling down, building new habits, and creating a new life here.

So, here are the highlights of 2023, both personal and professional:

  • Successfully set up a nice home and daily routine that I enjoy
  • Spent quality time with my family and reconnected with my brother.
  • Bonded with new friends who really make me look forward to getting back to Lisbon every time I am away.
  • Got in great shape, despite experiencing my first injury (knee tendinitis).
  • Explored a few hobbies more seriously, like Padel and Surf (I want more of this in 2024!)
  • Explored Portugal a bit with some weekend getaways
  • Spent some amazing moments with old friends too, thanks to many weddings.
  • Typefully hit $1M ARR. This is the culmination of 10 years of collaboration with my good friend Fabrizio and an amazing example of compounding of knowledge, expertise and trust.
  • Survived the Twitter take over by Elon Musk.
  • Witnessed the acceleration of the AI revolution and integrated AI in my daily life with tools such as ChatGPT, GitHub Copilot and much more.

Life in Lisbon: One Year and a Half Later

So, how is life in Lisbon?

Mostly sunny, lots of work, lots of uphill walks, lots of lunches at the park, lots of nice cortados1, and working from coffee shops. Lots of walks everywhere, lots of gym sessions with lovely serendipitous meetups with friends because we basically all live in the same neighborhood, and the occasional 20-minute drive to get a good surf.

I would say life in Lisbon has been pretty good, so much so that every time I get away, I miss the city, the vibe, the quality of life, and the people.

It took a while to get into this mood. I definitely didn't feel this way at the beginning of 2023. But around halfway through the year, something flipped. Maybe I just relaxed and exited the hyper-planning mode that was needed to set everything up when I first moved there.

In hindsight, I can now say that moving to Lisbon definitely feels like an amazing decision, both in terms of quality of life, networking, and, of course, financially, thanks to NHR2.

However, I still have some doubts regarding the long-term implications on my life trajectory of moving here. Should I go back to Italy? When? What about having kids and buying a house? I am thinking about these subjects without stressing too much, taking it one step at a time, and enjoying the journey.

The only real downside of being in Lisbon has been the distance from my family in Italy. It now takes two flights and a full day of travel to get here, so I have been visiting them less frequently3. However, I have managed to reduce this a bit by having them fly to me or organizing small family trips4.

What I Worked On

2023 has been the crazies year of my professional career. We almost doubled Typefully's MRR year over year, going from $50,000 MRR in 2022 to $95,000 MRR in 2023.

Those are some huge numbers, and if you told me years ago that we would have reached the bootstrapper dream of $1M ARR this year, I would have had a really hard time believing you!

More than the financial gains, these numbers are an indication of how far Typefully has come! I believe we have now become an established name when it comes to publishing on Twitter, with over 100k sign-ups and a growing subscriber base.

Now for the bad part: about half of that MRR is devoted to paying $42k/mo for the Twitter API Enterprise tier, required to run Typefully.

This change dramatically altered our trajectory and made me acutely aware of platform risk. Instead of expanding the team and accelerating growth, we found ourselves at breakeven and spent half of the year adjusting to this new reality. We experienced downtimes, performed API migrations, and worked on implementing and adapting to new features like Long Form posts. As of now, we are still waiting for API support for Long Form.

So, yeah, Typefully has been my exclusive work focus this year too. I felt the need to start working on a new project, but the opportunity cost felt too big to ignore Typefully, even for a month. It is being used by so many people and growing at such a fast pace. I am curious to see if the team and I will manage to carve out some time in 2024 to explore new ideas. I would surely like that!

So, what did we ship in 2023?

Apart from this, there has also been a huge focus on taming tech debt and rewriting core parts of Typefully to be more future-proof and easier to expand. This is a requirement now, as the product is becoming more complex with the increasing number of platforms it needs to support.

I am especially proud of the work we did refactoring our rich text editors, our sync layer5, and the work we are doing these days to level up our commenting capabilities.

As is now tradition, here is a screenshot comparing Typefully in 2022 and 2023. I think this speaks for itself and makes me really excited about where we are going.

Recognizing When Things Aren't Working and Taking Action

I feel like this has been a theme for the year as well, from technical things that we had to rework, to ditching my old coworking space6 because I wasn't really getting much out of it, to having to part ways with employees because it wasn't working out.

Changes in how we work at Typefully

Re-reading my 2022 review, I cringe a bit on my praise of async work and Basecamp. And also at the 2 weekly team syncs.

Don't get me wrong, we still work mostly async, but we made some big changes this year:

  • We no longer have two weekly team sync meetings because we didn't have enough things to say to each other, and it was too disruptive for deep work. We now have just one meeting every Wednesday afternoon, where we update each other on progress and discuss topics from an agenda.
  • We no longer use Basecamp. The concept was cool, but the implementation was so slow and clunky that it hindered our willingness to communicate. It took too much effort to navigate, send messages, and the mobile experience was terrible. We switched to Slack, which can be chaotic for big teams, but worked amazingly well for us. In general, this year I had a change of heart regarding communication. I went from the belief that we should communicate as little as possible and focus on our work, to the belief that we should over-communicate and share our progress and energy every day. This has been more and more important as a small remote team.
  • We started using Sunsama, which helps with planning your day and sharing progress with your team. At the start of the day, we share what we plan to do. At the end of the day, we share what we have actually done. All of this happens in a Slack's #progress channel, aided by Sunsama, which makes this process really frictionless.
  • We abandoned Shape Up, and nowadays it feels obvious what we should work on. Previously, we would have 2-3 projects running simultaneously, but now the entire team is dedicated to a single project and striving to complete it. We maintain a sense of urgency and avoid prolonging projects, but we no longer make hasty technical decisions that could cause problems in the future. It's really enjoyable to have the entire team working on the same thing. This approach works well for the three of us.

How much I worked and on what

I am still doing time tracking for every hour worked and in 2023, I worked a total of 1507 hours.

That's an average of 6 hours per day, Mon-Fri, excluding 3 weeks of holidays/vacation. The daily number looks more like 7-8h, so vacations were likely more than 3 weeks.

I really like this pace and think it's sustainable. I could work more, but it would probably burn me out. So, I think I will continue at this pace in 2024.

I don't have detailed analytics on where my time went (there's too much friction to track that too), but overall, I would say:

  • Coding new features
  • Maintenance (fixing bugs and infrastructure)
  • Code review
  • Pairing with team mates on features
  • Meetings

Notably missing from this list is time spent thinking about where to take the business, strategizing, or doing any kind of marketing. I feel like I didn't have the opportunity for this in 2023, but I want to make sure to allocate time for it in 2024, especially if we are able to hire more engineers. Don't get me wrong, I love coding and working on the product, but I'm not sure if it's the most effective use of my time at this point.

Media

And finally some recommendations on stuff I watched, read, and listened to in 2023 that I really enjoyed.

Books

This year, I finally reintroduced some fiction books in the mix and learned to enjoy them again. I kinda of dismissed that genre, but it's really nice to get to sleep by reading a good story before going.

Podcasts

This year, I fully switched to Spotify for my podcasts. I don't particularly like having music and podcasts in the same app because I don't use the two interchangeably and hate losing context when switching between them. However, what really impressed me is the quality of the recommendations and how easy it is to discover new podcasts or even episodes from the past that I might enjoy. In fact, this might be the year when I listened to the most new podcasts ever. It's a tough compromise because I really believed in RSS and open podcast apps (Spotify is not), but convenience ultimately always wins.

Articles

This year, I read quite a lot, aided by the amazing Matter. I especially love their text-to-speech feature that turns articles into podcasts. They also recently introduced the reverse. You can turn a podcast or YouTube video into a highlightable podcast.

Videos

Just a snapshot from my YouTube history of 6 months: some personal finance and investing, some geopolitics, some Italian news, some cooking, and some about working out. It's a good snapshot of my interests.

History & Geopolitics:

Investing & Personal Finance:

Health & Fitness:

Software engineering:

Other:

Footnotes

  1. Imagine a mini cappuccino with a 1:1 espresso-milk ratio and less foam https://www.google.com/search&q=cortado&tbm=isch ↩

  2. Which is ending in 2024. ↩

  3. For my standards at least! I used to come here every 2 months, now it's more like every 4. ↩

  4. I want to explore this idea more in 2024, it's a great way to also reconnect with friends and spend quality time together ↩

  5. It's the component responsible for synchronizing the changes to the backend when you edit a draft by typing or modifying its metadata. We have centralized the logic and made it incredibly easy to commit edits that are subsequently synchronized in batches to the backend, abstracting the network requests. ↩

  6. Am I the only one, or do coworking spaces never work? Usually, I am initially excited about them, but after a few months, I grow tired and hate going to the place. I am starting to think they are a poor substitute for the office life and colleague interaction that attracts many remote workers to them in the first place. Working from home and engaging in daily social activities has been working better for me for the past 6 months. ↩