2020 yearly review

December 29, 2020

2020 has been the toughest year of my life.

The pandemic played a big role in this, amplifying all the negatives, but was not the main reason for my struggles.

At some point, everything was on the line, and I was hours away from making some terrible decisions that I would deeply regret.

I stand here, at the end of the year, still on my feet and in a better place physically, mentally, financially, and I am deeply grateful.

This is the story of all the shit that went on in 2020.

Recap 🕰

Let's start with some context.

I spent 2019 bootstrapping my company and enjoying the freedom of self-employment by nomading for a combined 3 months to Bali and Portugal with my co-founder and best friend, Fabrizio.

All of this travel stressed my relationships, some of them already strained, and led to a traumatic beginning of 2020.

Breakup + lockdowns = 💥

2020 started with the end of my 9-years-old romantic relationship. After that much time with someone, I didn't even remember what life was like by myself. I lived this breakup with a level of pain and intensity that I didn't think possible.

The end of this relationship had ripple effects on my whole life.

With huge efforts, I managed to use the pain as fuel to improve my situation: work, meet new people, strengthen existing relationships, work out, try new experiences, fight shyness, and become an all-around better person.

All of this came to a halt with the COVID lockdowns that soon followed. I went back to my parents' home in Sicily and was stuck there for a few months.

Away from my friends, hobbies, office, and everything that brought me joy, I spiraled into an existential crisis. It was incredibly tough.

After this emotional rollercoaster, I started taking everything more seriously and putting my full weight behind everything I do. It was like a near-death experience that awakened me in a way that's hard to describe.

Fuck it, no more half measures, no more hiding, bring it on.

Brewing something new ☕️

We spent the last 3 months of 2019 working on a cool new project called Mailbrew.

At the beginning of 2020, we were still in private alpha and had one paying customer. We were betting on this new project but still did not really went all-in on it. Boxy Suite was still paying the bills.

We had to make a decision and stop fucking around. I gave ourselves an ultimatum: let's make this work in 6 months, or reevaluate our life choices, possibly going back to a 9-to-5 job. Ramen-profitability was no longer enough for me, not with all the other shit that was going on in my life.

We used the alpha group's feedback to iterate on the product and worked our way up to a great launch. This fueled our confidence, as we quickly reached $2k MRR just one month after launching Mailbrew. The product was resonating with people.

Getting funded 💰

The great launch and customer validation gave us confidence in the idea and got us to talk with some interesting people.

One of them, currently working on a cool calendar app, suggested applying to YC.

We were initially skeptical. We have always wanted total ownership and no external influences in our decision. Least of all, someone to answer to. We quickly discovered that that's not what YC is about and that there is inherent value in the application process. It gets you to look at your company objectively and forces you to make a serious case on why it will be wildly successful. It's an exercise that puts a huge spotlight on your weaker spots and what you need to focus on.

Long story short, we got to the final interview, despite applying a couple of weeks past the deadline. Due to Corona, the interview was on Zoom and not at the YC offices in California, but the tension was nonetheless high. We were in lockdown back then, and this interview completely took over our minds for a couple of weeks.

I will never forget the moment I realized they would pass. "How will you grow this to a $1B business?" they asked, and despite all the preparation, we did not have a convincing answer.

I still don't have a convincing answer today, and that's okay. We're on a different path. We want to build a calm, focused, highly profitable company, and we are okay with this taking years. Walking slowly towards our inevitable success and enjoying the view, instead of trail running down a mountain to get to the prize fast or die trying.

After the rejection, I was about to call it quits on the funding initiative, but Fab insisted on trying with some other funds, maybe with someone better aligned with our philosophy. A fund that backs the Basecamp's of the world instead of the Instagram's. Enter Earnest Capital.

They invested in us, and to this day, I am shocked at how smooth, fast, and open the process was. Tyler got what we were trying to build immediately and had done its due diligence. It felt like talking to a fellow maker, more than your random VC.

While initially anxious about accepting the investment, I think we totally made the right call. The folks at Earnest are great partners for the long term, and the skin-in-the-game mentoring approach is fucking genius.

I honestly hope to join Earnest as an investor and mentor someday. What they are enabling is really amazing.

Focus 🧘‍♂️

We spent the rest of the year working on the product, launching multiple updates, and building in public.

We also onboarded new team members, worked on strategic partnerships (some still to be announced), launched a side project, and cleaned our slate for year of less by shutting down other projects.

We're now at 600 subscribers and $5k MRR, and 100% focused on Mailbrew. This is the solid foundation I hoped we'd have at the end of the year, and I am excited for what 2021 will bring.

I am under no illusion that we're done or a success. We still need to grow this project a lot, but we are in a much better place to do this than we ever were.

If we maintain the focus, determination, and uncompromising approach of this past year, 2021 will be an amazing year both personally and professionally.