From employee to bootstrapper to financial freedom
By: Mauricio Morales
Tags: Startup, Financial Freedom, Lifestyle, Remote Working, Nomad

From employee to bootstrapper to financial freedom

I recently started to fulfill my lifestyle expectations. I’m now able to live wherever I want and move whenever I want, working remotely and having a flexible work schedule while running digital products that create recurring income so I don’t have the complicated uncertainty of those early days as an entrepreneur.

I’m just beginning this journey, but it’s already a few years since I started to walk the walk and having a retrospective look at it allows me to share a few thoughts and stories with you in case you’re planning to do the same.

I went from employee to bootstrapper to achieve that financial independence, without raising a cent from venture capital. I believe the learnings I’ve got throughout this process have made me a more solid and resilient person.

Exploring ideas

I’m always full of business ideas and I’ve been like this since my early days. The fact is that most of us don’t execute on those or if we execute we don’t have the necessary patience to continue pursuing them.

And patience is as important as the execution itself.

Today’s technology is making it super simple to try out ideas and explore their potential, nowadays you can find software as a service for almost anything, whether you want to test an e-commerce, online service, or some productized service with recurring subscriptions.

Exploration of ideas is inexpensive and I think there hasn’t been a better moment in our digital age to start a business than it is now.

This exploration will make you fall (even more) in love with your idea because you see it makes sense, or will help you get the relevant information to make a decision of discarding it.

There are so many ways to test ideas right now (that should be another post) but the key message here is that you should act. This will lead you to seriously consider starting your side hustle.

Starting the side hustle

When I was going to start my side hustle I was packed with ideas. I wanted to explore as many as possible to see which one had the most potential.

This was back in 2014 and I started researching and exploring the ecosystem and I found the (then fresh) concept of startup studios or venture builders. This was the Aha! moment for me.

There was this nice concept or creating a kind of laboratory where a team can explore different ideas and then you spin off the successful ones. As a passionate entrepreneur I saw this was a model I could pursue at least for that phase of my life, because I just didn’t know which idea to bet on and I wanted to make sure that I was going to make a good decision on that.

By the way, at that time I was living in Madrid, a splendid city.

Credits to Mike Swigunski for this photo. I’m just not that good with the camera.

Making a bet

As the laboratory initiative was clear to me, I decided to make my bet, still as a side hustle, I invested 20K USD from my savings into this concept and accepted that for the upcoming months everything I was making from my salary was not going to any saving accounts but invested in the business.

I wasn’t a good friend of loans and credit cards, so I also decided that everything I was going to try had to be done without borrowing money.

This is how I allocated the resources.

The framework for picking the first ideas to try was important, although now that I see it was very imperfect. The 3 selected ones were: a marketplace for pop-up stores space rental; a cooks/chefs marketplace to get cooks at home; a food delivery service for healthy food with plates designed by great chefs and nutritionists.

Surround yourself with a great team

Finding the right entrepreneurial team with a passion for exploration was my next challenge, it took me around 6 months to find the first lead developer. I ended up in all kind of meetups and online communities and broadcasting some messages to the University where I studied. A professor helped me share those messages across tech communities where I eventually found the first candidate with the skills, and more importantly, the attitude and willingness to try this out.

During those 6 months I managed to write prototypes for some of the ideas, when the first developers joined I already had a simple base for the projects, the proper technical framework for prototyping was in place and the ideas were defined at a high level. By the way, we named it Rocka, as we were putting the first stone for a business (stone or “rock”, did you see what we did there?).

We spent 16 months building, testing and experimenting with the ideas, but none of them worked out (the reasons why could be another post). But it was not a waste of time, in the end we managed to assemble a team for experimentation, we shared the same energy and we had that Laboratory mindset.

The only problem is that we were running out of money. I was actually running out of money personally. I didn’t know how to raise money fast nor was very interested.

We needed to find another solution. And as crazy as it sounds, this is when I realized that this should not be a side hustle anymore. I needed to commit even more and make a bigger bet.

Focus on revenue

The team was full of product builders and we had great methods to build software and try experiments quickly. We were constantly being asked by friends and businesses whether we offered this experimentation as a service, and we always said no, until then.

If the market needs product experimentation, why don’t we offer this? We then created the venture builder as a service and worked with entrepreneurs and bigger companies who wanted to launch startups. We got a nice contract that gave me peace of mind for at least 1 year so I could focus on the business.

We focused on revenue but always had one thing clear: we don’t want to be a consulting company. We continued exploring ideas! Running our own hackathons 4 times per year, we continued building and running our experiments.

As a remote team from our inception, we realized that remote work is unique and we were facing pains, from mental health to team collaboration and synchronization.

Those pains were the triggers for some of the ideas we built in our hackathons. Among many ideas we got into:

A collaboration toolkit for automating daily updates , standups, executive check-ins: we were tired of synchronous meetings and wanted to replace those with technology. This is DailyBot.

, standups, executive check-ins: we were tired of synchronous meetings and wanted to replace those with technology. This is DailyBot. A meditation and sleep app, in spanish: most of our team speaks Spanish as their primary language and we didn’t find good apps for this audience. This is Bambú.

Notice that at this point we’re running a services business which brings enough revenue to be sustainable and some extra cash for us to continuously invest on experimenting. At some point we managed to have a team of 5–6 people fully focused on experimenting, and another 6–10 focused on the services-based revenue. I ran all over the place, from CEO to product to development, those were interesting times.

Betting on the best bets

We had two products that 1) we were using on a daily basis and found great value on them, 2) were standing out from other experiments we ran.

We decided to make the next bet: close gracefully all the services contracts and put the focus on our products.

We spinned off another team for the meditation app, a team focused on content generation and growth. And the main team spinned off to become DailyBot.

A transition like this one is never as simple as it sounds, in my personal case I’ve experienced anxiety and stress but I worked with coaches and top psychologists to overcome fears and challenges.

This bet turned out to be the best decision we’ve made. We introduced a self-service subscription model to DailyBot and started to grow MRR at a 2 figures rate per month.

As it is a product that helps remote teams and makes WFH easier, we had a high volume of registrations and subscriptions because of the pandemic. We know about the many businesses that have been suffering during this 2020 pandemic and that’s why we’ve been committed to help them.

We found our products to be highly valuable for remote workers during these times.

Closing

This is the story of how the proper exploration and execution of your ideas drive you somewhere. Making the right bets will get you where you want to be. This may take years and there are no shortcuts, although of course talent matters and there is always a luck component. But luck and talent will not work if you are not in the right place, so, start now.

I like sharing what it is to build a business as a bootstrapper, follow me on Twitter [@maomorales] and let’s stay in touch.