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Why I Fail a Lot

One of the hardest and most critical decisions in business is choosing what to work on.

There is no clear answer, no magical recipe that tells you if a given idea “is worth it” for YOU or not.

It is a complicated question because it raises many other hard questions:

Is it really a good idea? Most business ideas look great from the outside, but as soon as you start working on them, you understand why no one has done them before. Not because other people are stupid, but because it is just harder and more complicated than you think.

Is it worth doing it? As soon as you start working on an idea, you start seeing how difficult it is to sell your products. Even when you do sell them, sometimes you get disappointed by how few people are willing to buy. And even when you are in a big market, you may get surprised by how expensive it is to acquire those customers—is the margin worth the effort?

What about the opportunity cost? When you get to the reality of things and properly understand the market, your product, and the unit economics, you may start asking yourself: is it the right thing to commit years of my life to, or is there something better? Sometimes it is not even about only the finances, it is about self-worth, mission, legacy, and all the other stuff that matters to you.

As you can see, you can easily overthink this question and simply get stuck, give up too easily, or even worse, end up working on something that you truly hate.

From my own experience, I think the best way to deal with this decision is to simply take action and fail fast—JUST DO IT, like the Nike famous slogan.

Why? Because it is a very complex equation with a lot of variables, and the best way to deal with those types of equations is to minimize the unknowns by taking actions: Actions = Insights. Get insights about the business, but more importantly, about yourself—about what you really want, what you like or hate, what you are good at, and what you are bad at. The only way to get those insights is by taking action.

But as you may already expect with this approach, you are going to fail—sometimes miserably—especially in the early days. But that’s fine. It is the price of learning the skills, the mental models, and the way of thinking that allows you to make much better decisions in the future. And believe me, “what to work on” is a very high-leverage decision, getting it right has a huge ROI that’s worth the price.

The way I try to operate around this theory—again, not sure if it is the best one, but it has been working for me so far—is this:

  1. I try to stay clear and maintain a list of subjective criteria for what kind of business I want to be in. For example: consumer only (not B2B), niche markets (no VC), highly automatable operations, etc. Anything that doesn’t meet those criteria means too much overhead and is not worth it.
  2. I try to maintain and develop a personal leverage profile that can act as my unfair advantage for anything that I do—things like skills/knowledge, network/distribution, market positioning, etc. I try to always find an idea that leverages this unfair advantage; otherwise, it will be too hard for me to execute.
  3. Then, when an idea comes up, I just evaluate it (subjectively) against my business criteria and leverage profile to see if it is worth exploring (not necessarily doing). If the answer is yes, I will just do it with a few rules in mind:

If it works, I scale. If it doesn’t, I just kill it. Both ways lead to a learning that ends up in my business criteria and leverage profile (development roadmap).

Let me give you an example. It is a story of my most recent failure. It may sound obvious to some of you, but this is what it is.

It started with something I noticed in my own building. Many people are looking for extra parking, and there are others who are not using theirs. A very classic asset under-utilization problem, which historically gave birth to the largest marketplaces in the world.

The idea was to build a website that matches someone who wants to rent an extra parking space with someone who has a spare one. In order to stay closer to the transaction, ensure recurring revenue, and add more value, I also offered contracting, payment collection, and payout services. When it came to distribution, I relied on in-building displays and promotion.

If it worked, it would become a cash-printing machine which fits perfectly with anyone’s business criteria (not only mine). It also leveraged my connection with buildings/real estate, making GTM (Go-To-Market) easier.

Well, the problem was painful, so adoption was smooth. I was able to secure a few contracts by posting in Facebook groups. However, in order to scale, I needed to gain trust and promote within the building. This is when I faced the difficult reality of the gatekeeper, who was the building management: It is not allowed to advertise without permission. And in order to obtain their permission: 1) you need convince them (as it was nice to have for them), and 2) offer revenue share as an incentive.

It was a bit of a disappointment. Then I met with a building manager who was suffering because they didn’t have visitor parking. It was a very painful problem for them as their guests struggled to find parking on the street. They were willing to sign up as soon as I could support hourly/daily rental with no revenue share.

At this stage, it became a real business with real traction, as I could simply build an app to facilitate that. But as I started working on it, I ran into the reality of: 1) buildings without visitor parking are a very small market, 2) there were a lot of operations/regulations headaches, where security and access create huge friction which wasn’t clear upfront. This actually failed my business criteria as it had so much overhead and issues that I didn’t want to deal with, especially when you look at the TAM size and the profit you get in return—it actually took me time to accept that.

I ended up deciding not to proceed. It was obviously a hard decision as it cost me money and time, but failure is the path to anything that is great. I learned a lot about property management as a space, but more importantly about myself. I learned that I really hate operations, but I also realized that I am still good at B2B sales, as I was able to quickly close the deal with the building I mentioned earlier (even if I didn’t do it for a long time).

Overall, I am satisfied, but it is still very painful to fail. The way I try to see it: if one out of four ideas works, and that means starting one real business a year, I’m doing well.

The most important thing for this approach to work is to simply afford to fail, which requires a strong support system and a safety net that I discussed in the Work Smart, Think Hard article.

You can always execute and fail faster. I chose a quarter as my timebox because I have other commitments on the side. While you can definitely move faster, the risk is failing too early. This is where clarity on your business criteria plays a key role.

But you know what? This approach gets easier over time. The more success you have, the stronger your leverage and support system become, and the better your judgment gets. This makes the journey much less stressful and more enjoyable—to the point where you start doing it for the sake of doing it, like serial founders do.

If you are serious about entrepreneurship, you need to stick around to fail enough in order to succeed.

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