Santiago what's your backstory?

I was born in Argentina in 1987, so I’m kind of an old-school type of guy. It was a great upbringing, very familiar type of thing. Of course, Argentina has its issues that we know. The upsides is of course, but looking back, it was a simpler time. There was no access to technology or anything fancy—lots of limitations. But that’s pretty much what it is.

Argentina has a very strong European immigrant influence, so there’s this old-school work culture—sacrificing, working hard, all that. I did a lot of that. I started working when I was about 12 or 13, doing simple jobs to make some money.

Then I did a couple of years of college without much success as financially it wasn't that easy. I loved coding so I decided to try it out (this was in 2012), and that was my beginning as a professional developer. So I dropped out of college and started working. It was very hard to work back then, but I landed a job. I was one of the first people that I know in Argentina that worked for an American company. I was remote and we communicated using Skype. It was very limited, but that’s how it all started.

Now, I live in Italy. After selling my previous company, I was able to move here, which is a great place to live.

What does your company do & how did you come up with the idea?

DataWorks is a very simple platform. We focus on practical data science education. Essentially, we don’t create videos, learning materials, or books. We curate amazing projects for people to practice different topics. The idea came from something that’s already well-known in the industry.

We had a previous company called Remoter, a data science platform. It was fairly simple, offering videos and a little bit of everything. We got acquired by INE, an American company, and they’re leaders in IT training, specifically in networking, cybersecurity, cloud, etc. When they acquired us, we reached pretty high positions within the company, and that’s when we started learning about all the different processes in the IT training industry—something we didn’t know much about, to be honest. We discovered that there’s a huge lack of practical upskilling across all industries and segments. Whether it's marketing, networking, or data science, there aren’t many platforms that let you practice when it comes to IT training.

So, we created this platform, and the key thing is there are no traditional learning materials. It’s just practical projects for various topics. People can go in, practice with them, upskill, and once they hit a bottleneck, they have an assistant to help them figure out what they need to improve. This concept is very common in the industry. For example, in cybersecurity, there are platforms like Hack the Box, TryHackMe, and Immersive Labs. Essentially, you’re learning by solving problems.

We have two types of customers. The first is B2C—individuals who want to up skill through projects. They might have bought books or are paying for platforms like DataCamp or Udemy, but they’re missing practical projects to hone their skills. You can watch a thousand hours of video, but you need hands-on practice to do something with that knowledge.

The second type of customer is companies. They need to create a training plan and monitor how their employees are progressing with it. If you just have employees watching videos, you have no real way of measuring their skills or progress. So, what happens is that a manager will create a training plan with various resources—videos from DataCamp, books from O'Reilly, and Udemy courses—and then they’ll include projects from our catalog. These projects serve as a pulse check, helping the manager see how employees are progressing.

How did you get your first 10 customers for DataWars?

For us, getting the first customers was easy because we created a very compelling premium tier, and that’s usually what I try to aim for. You can get your first customers in multiple ways, right? You could potentially just literally find people on LinkedIn, try to email them, try to somehow reach out and get yourself 100 meetings, and from 100 meetings, you're going to get 10 customers.

I like to do the opposite, which is creating very appealing freemium tiers that create value for people. And from that mass of people that you are creating value for, some are going to decide to pay you back, right, in exchange for that value you have created, once you, of course, increase the value proposition with a paid tier.

So basically, we released DataWorth without a way to charge people. It was a completely free platform, and we did that for like six months. We increased the number of projects we had, tested the platform, improved the experience, just took six months without charging users anything. After that, we kept everything as it is, still giving people value, and then we added a couple of value-added options on top and asked for people who resonated with them to upgrade.

The key here is how we're going to segment these users because this is the most important thing. You can have a wide variety of users in your product, and they all serve multiple purposes, and not all of them, the purpose they serve is paying you.

For example, we have a wide variety of users. We could say we have, for instance, students, people in college or even high school, trying to learn data science, Python, pandas, machine learning, and all that. That type of segment, to be honest, is not a segment we're going after to get paid because they don’t have a lot of money. But this segment? They're extremely helpful in finding bugs, providing feedback for projects, doing brand awareness, they’re basically our best supporters.

Then we have another type of segment: people who are busy, working and want to improve their skills. So, you have, for example, an accountant who wants to learn how to use pandas. For that person, paying is possible, it’s not prohibitive. So then you have to create an offering for that particular person.

In our case, the way it works is you can save the status of your projects to come back later, which saves you time. And for that segment, people who work, you would usually assume that if you work, you have less time compared to students. So you’re trading time for money, and that’s when they decide to pay for the subscription because we’re going to save them time.

But this is the important part of segmenting, understanding who your audience is. Again, some chunks of your audience will not pay, and that’s perfectly fine for us because they serve some sort of purpose. Once you identify the areas that are going to pay, then you create a compelling offering for them.

How did you ensure your product met your customers' needs?

To confirm that our product matched what customers needed, the key was what I mentioned earlier: we created a compelling free tier. This got a lot of people signing up and trying the product, and from that, we were able to figure out what people valued the most. We ran multiple experiments to finally get to the product we have today. Some of the things we tried were based on hypotheses—we thought, "This is going to be great, people are going to love it," but to be honest, nobody liked it or used it.

So, the key for us was launching early with a MVP free. That gave us a huge volume of users, which was crucial. Then it was just a matter of listening to feedback, making improvements, and so on. Once you start selling, though, you realize it’s not that simple. It’s hard not to get caught up in trying to fulfill every request from paying customers.

That’s why we always made sure to keep a strong base of free users. When paying customers would say, “I’d buy from you if you had this feature,” our response was pretty straightforward: if we didn’t think that feature was important for our large pool of users, we weren’t going to add it just for one person. This approach was really helpful in the early beginning.

How did you get your first 100 customers?

For us, it really comes back to the freemium tier—having a large volume of users, creating a great product, building a community, and, most importantly, constantly engaging with your users to improve that. The way we reached our first 100 customers was simple: we built a product that was viral. People just started sharing it with each other. You'd find it on Reddit, LinkedIn, and everywhere in between.

From there, we used a pretty basic bottoms-up strategy. We focused on B2C users, people who might not even be paying for the product yet, and looked for opportunities to upsell. So, you'd identify someone using DataWars at a specific company, maybe through their email or activity, and reach out to them. You’d say something like, "Hey, I see you’re using DataWars and it looks like you're really getting value from it. Your company could be paying for the premium option." And that was pretty much it.

We also did a lot of partnerships with some publishing websites that drove a lot of traffic our way. And honestly, that was it. The key to success for us was creating an amazing product, offering a compelling free tier, fostering a community that encourages sharing, and then trying to upsell from there.

What distribution channels did you try that didn't work?

Well, I think this is probably a pretty common answer, but anything paid, whether it's advertising on traditional social media channels or digital channels, just didn’t work for us.

Maybe it’s because we’re not good at it, or maybe it’s because we don’t have enough money, but any form of sort of advertising didn't work. We also tried a few good newsletters that we read and subscribed to, but those didn’t work either. I think part of it might be about the segment we were targeting, but the biggest issue by far was with paid digital marketing.

You’re competing with some of the biggest players out there. It’s just too crowded of a market. It’s much better to have your initiative. We did have a few good ideas, but yeah, paid advertising on traditional digital channels just doesn’t work. And it makes sense why, it’s all about competing with so many others, both in terms of the offering and the bidding. So overall, it wasn’t the best.

What tools have been the most helpful in growing your business?

The key for us was probably that we started using LinkedIn fairly early on, and YouTube as a distribution channel. That definitely helped. As far as how we work, since we’re all engineers, we use a lot of Airtable and Google Sheets, basically, a lot of structured tools. I also use Excalidraw quite a bit. Being engineers, we go from complete chaos to something much more structured, like a table. So we’ll start brainstorming, drawing all over the place, and then eventually that chaos has to fit into a table. It doesn’t matter what it is, it has to fit into a table with relationships.

In terms of distribution, YouTube and LinkedIn have been essential. For day-to-day work, Airtable, Google Sheets, and Excalidraw are my go-to tools. I also use Loom a lot to avoid meetings, and we use Discord for our community, which has been really helpful as well.

How did you make the transition from a side hustle to full-time entrepreneurship?

For me, this question is fairly simple to answer, and probably a bit different. I'm very good with risk. I won’t go into the whole story now, but back when we sold our previous company, we were financially independent enough that we could afford to not have a salary and start a new company. But before that, when I was living in Argentina and working as a software developer for a US company, I was making very good money. I was also super resilient and cheap, and because of that, after six months of work, I was able to save enough to live for two years — or even less time working.

For me, it was zero risk. I worked and made money, and the key here was reducing expenses — being cheap and austere. That was the approach for me. But also, I like risk. I don’t have a problem with it. In reality, there's no real risk. People think there's a risk, but there isn't. For example, I saved for six months, which gave me enough to live for two years without a salary. What’s the worst that could have happened? I would have run out of money, gone back to work, and maybe lost the opportunity cost of not earning a salary for 12-18 months. But in the grand scheme of things, that didn’t seem like a huge risk.

To be honest, the risk doesn't really exist the way people think it does, especially in today's world. For me, it was simple. The key is to keep costs low. If you start working and begin to increase your cost of living, the more you increase that, the harder it’s going to be to leap. I've met a lot of aspiring entrepreneurs, brilliant people with great ideas and the willingness to do the work, but they've put themselves in tough financial situations, like having family expenses or spending on vacations. I know that can be hard to get out of.

What advice do you have for founders in the earlier stages?

The first thing, kind of obvious, is learn to code. It doesn't matter who you are or what you do, you have to learn the basics of coding. It’s going to be how we interact with the world over the next 20 years. Back in the 1900s, to drive a car, you had to be a mechanic, right? And today, anybody can drive a car.

Learning how to code and understanding how machines work is really important because, even if you don’t write your own code, you need to understand how it works. If you're a marketer or a business person, that's perfectly fine, you won’t sit there and write code yourself, but understanding how it works is crucial.

The second thing, as I mentioned before, is that there’s no real risk. In reality, there's no risk. So try to decrease your cost of living, get rid of the boundaries and attachments you create for yourself, and make the leap. Try it out. Build your network early on, it’s really important.

One last piece of advice, which might be less common or even a bit contrary, is: don't start your startup too early. To be honest, I started my startup way too early. I was too young, I didn’t know what to do, I didn’t know how to sell, I didn’t know how to network, and I had no network. So everything felt like an uphill battle. If I could do it all over again, I wouldn’t have started my company so early. Of course, it’s easier to say that now, in hindsight. When I was there, I just couldn’t imagine working for another company. But I think working for a company you really like, ideally in a promising industry, is the best way to build your network, become financially independent, and most importantly, understand how to work. It’s not just about learning how to build and sell—it’s about learning how to get up in the morning, do the work, deal with people, and handle things like sick days. You also get to see what the real problems are in a given industry.

So, if I could give myself one piece of advice, it would be: don’t start too early. We often think the goal is to be a millionaire by the time you're 30, but that's not necessarily true. It could be true for you, but the real goal should be to not rush things. Focus on building a network, learning how to work, and understanding different industries and their problems. Then, when you’re ready, you can jump into creating your startup.

What drives you to do what you do?

For me, what drives me is impacting people and doing something fun that I enjoy. The most important thing isn’t financial; it’s about creating a real impact and interacting with people. In our case, we have a lot of students who are progressing with our tool, which is great to see. We’re also hiring a lot of junior people, so it’s not just about impacting our customers but also about impacting our employees. We've built a strong organization that allows them to grow and thrive.

At the end of the day, impacting people is what matters most to me. I wake up every day thinking about who I’m going to talk to. It's not just about having a conversation like you would over a coffee. It’s about what I need to improve, which customer I have in mind to get feedback from, or what I can build specifically for them. It’s also about what my employees are working on, like if someone opened a pull request and had issues with this or that.

So yeah, the most important thing for me is having an impact on people.

What's an unpopular opinion you have about entrepreneurship?

Well, I think two things. First, as I mentioned before, I don’t think it’s best to start too early. The best entrepreneurs are made after 30. The second thing is that entrepreneurship is a very tough industry, and it’s managed by VCs. It’s unfair in the sense that you can create a great product with a real need, but if you’re trying to go it completely on your own, it’s really hard to do things right without external help. It’s just not an easy path, and it’s a tough environment. That’s why building a network is so important.

I don’t think VC money is as crucial for creating products or funding good companies. In fact, it could even be detrimental. VC money is just a way for bad entrepreneurs to make money. Sure, it can help with distribution, marketing, and scaling, but that’s really an inefficient way to go about it. Great products are created with less money, not more.

So, I see VCs as playing a game to make themselves richer, rather than actually helping create better products. And, honestly, it tends to favor the worst entrepreneurs. If you want to do things right, you should stay away from VC money, at least in the beginning.

Those are my unpopular opinions.

What do you do to keep sane being a busy entrepreneur?

I'm a very resilient entrepreneur given I grew up in Argentina. We're poor, we had nothing, you know, I ran away from the country because it's safe and everything. So today, to be honest, I live in Italy next to the mountain, I get up every day, and I have my desk, my perfect setup. I don't have a problem working 14 hours per day. I don't know that thing about burnout.

But still, what I do is I enjoy, of course, time with my family, and my friends. I enjoy a lot of sports, like snowboarding. I moved to Italy in the middle of the month and exactly because of that, I wanted to snowboard. So I think sports is the key and also, of course, personal relationships and people and families.

Which experts or entrepreneurs do you recommend for learning how to grow a business?

I like following people from 'small' startups that are technical. I usually find one startup, Google the Founder, and try to listen to any podcast they've been on. For example, I did that with 1Password (Dave Teare is the founder) or with ProfitWell (back when ProfitWell was 'small'). The founder, Patrick Campbell, although not technical, is extremely smart and insightful.

Any quotes you live by?

"People overestimate what they can achieve in 1 year, but underestimate what they'll be able to accomplish in 10 years."

Your links + socials

Santiago's LinkedIn

Santiago's Twitter