We left our day job in late 2018, and we started traveling and enjoying the new freedom of being entrepreneurs right away. But while we enjoyed this new lifestyle, we weren't really excited about the (very slow) growth of our company.
It was 2019 and our core business then was Boxy Suite, a Gmail client for Mac. It was paying the bills (and the plane tickets) but that ramen profitability was starting to linger a bit too long. Luckily, 2019 was also the year we started working on something new: a better way to get your favorite content, unplugging from feeds. Mailbrew was born.
But a new product in private beta and dreams about adding more zeros to our MRR weren't cutting it. We wanted more, that's why we left our job in the first place.
Francesco had an idea: let's give ourselves an ultimatum.
We both agreed that the opportunity cost of earning a minimum salary and scraping by, while being top-tech talent, was starting to get too high to make sense.
So the idea was: if in 6 months we're still barely paying ourselves a minimum salary to live in Milan, we should go back to a normal day job.
Even the idea of going back to a day job for me felt like seppuku, but he was right: if we want to accelerate our growth, we shouldn't look for hacks and shortcuts. We need skin in the game, we need to keep ourselves accountable. We need to make it this year, not next year, not in 10 years.
The milestone to hit wasn't a specific number, like 10k MRR. We just felt that "making it" was about having steady revenues to pay ourselves comfortably, leaving some buffer in the company to invest, and eventually hire, and finally have some peace of mind.
We basically said to each other: if we're still scraping by in 6 months (18 months since quitting our jobs), it means it's not working.
Having an ultimatum already helped us make a big decision we wouldn't have made otherwise: we decided to not pay ourselves anything for a few months, and instead invest in a productivity boost and lifestyle improvement. Enough working in bars, searching for wifi, trying to stay away from bad music and loud voices, let's get a couple of desks at a WeWork.
So that's how 2020 started: with an ultimatum, no salary, a mission to make a new product work, and a couple of nice desks to be more focused and productive.
The next few months are history.
We put the finishing touches on Mailbrew with the help us our first beta testers, while we put Boxy Suite on maintenance mode (it was still making ~$5k/month). Focusing only on Mailbrew and finally working side by side every day had a huge impact on our productivity and put us on the same page on everything.
In March we were finally ready to launch Mailbrew, but we have a curse that whenever hit an important milestone or we're ready to launch something, we're not in the same room. So when it finally came to launching Mailbrew in March, a global pandemic that you're probably familiar with started, and so we launched it from our homes, in lockdown.
Still, with the launch of Mailbrew things started to change for us.
We finally felt we were not the "Boxy Team" anymore: Mailbrew received amazing responses, comments, feedback, and it was clear it was going to become our core business if we gave it a fair chance.
To maximize our chances of real success, we applied the Barbell Strategy by betting big on Mailbrew (high-risk) while de-risking with Boxy Suite and little consulting on the side, and giving some space to side-projects as well (as smaller, but riskier bets).
In hindsight, giving ourselves an ultimatum gave us the right amount of urgency, and clarity, to say no to lots of things, ship faster, focus our attention, and fine-tune our bullshit detector.
It was a drastic way of saying: this is not a joke, we either make it or we don't.
Besides the ultimatum, there are a few other things that helped us become sharper and better entrepreneurs this year, while also improving our general wellbeing.
We started giving more honest and ruthless feedback to each other, always speaking our mind and making sure that weak and bad ideas don't sneak their way in our roadmap out of sheer confirmation bias or fear to offend the other person.
We kept trusting our guts when we feel like we have a strong intuition about something. Finding the balance between pragmatism and intuition is one of the biggest struggles for entrepreneurs, but it gives the greatest results when you get it right.
We've decided to take our first investment. We still feel bootstrappers at heart, and the reason we eventually made this choice is because we chatted with Tyler Tringas, founder of Earnest Capital, and realized how perfectly aligned we were, and how their model is structured around founders that care about their freedom and ownership. I can't even imagine working as hard as we're working now without the peace of mind and confidence of being in the Earnest network, getting their mentorship, and knowing we finally have a safety net in our bank account.
We both focused more on finding the right work-life balance. We often take breaks from work, long pauses to think, long walks, respect each other time, and always try to reduce sync work in favor of async work — in fact we slowly settled on a 50/50 async/sync schedule. Focused mornings at home, afternoons at the office. Even when we were back in lockdown, we started reducing notifications and pinging each other in the morning by default.
All in all, we've decided we want to build a calm company where work is modeled around our life, not the other way around.
One year has passed since Francesco proposed the ultimatum, but it feels like a decade. We started 2020 feeling lost and without purpose, disenamoured with our core business, and we're ending it with a clearer growth path, working on a product we're excited to use every single day, and enough money in the bank to work without the insidious background noise of anxiety that things aren't working out.
It's not like the ultimatum itself saved our company. It was the realization that we needed to hold each other accountable, stop delaying important choices because of the commitment they required, and start focusing on things that matter while cutting back on noise and distractions.
The same principles we're enforcing in our work, we're enforcing in our private lives. If there's a disconnect between how you work and how you lead your life, it's impossible to feel truly at peace and content with either.