Before you start: At the beginning of August, I’ve interviewed Daniel Araújo, Attentive’s CEO. Books, podcasts, startup life and growing pains, nothing was left untouched. This is the first chapter of a 4-part interview (yeah, Daniel can talk a loooot), and I hope you enjoy reading it as much as I’ve enjoyed being part of it. – Ana

Hi Daniel. First of all, there are some questions we cannot escape from. Can you tell us a bit about you and the path that led you to Attentive?

I’ve studied business and after the first year in college, I’ve realized that I would eventually want to create my own company. I was already a geek at the time, so I knew it was going to be something in the technology area. I also really wanted to live in different countries before that, so I hopped a little bit in 3 or 4 countries. After spending five years in Google, in Dublin and London, I realized there was a very specific need and a new trend in the sales department, something I was starting to be very very interested. In many conversations with Pedro, my brother, and with a good friend of ours, Luis, we’ve started cooking this idea in 2015 and decided that all of us would leave our jobs and start working on Attentive full-time.

That specific need that led to creating the company came when I was working with sales teams at Google. I saw that everyone was spending a lot of time just trying to enter data into the CRM. Managers hated it because they never had their projections right, sales reps hated it because they wanted to spend time selling, not updating the CRM, and sales operations hated it because they were designing the process and nobody was following it. So, everyone was frustrated – if you look at other areas of the business, things ran smoothly, but in this particular area, things were not going very well.

The trend that we were witnessing was that software should be much more proactive, instead of reactive, and live everywhere, not just on web pages or a mobile app. It should be wherever people are, infer many of the things people need to do manually and just ask for permission.

So, I think we’re still in the first inning of that. In the next 10 years, there will probably be as big of a shift as databases were in the 80s or 90s, that created companies that are now leading the way. The next set of companies is going to be the ones that can create a software that is proactive, that comes to you instead of the other way around and can infer what it should do and ask for your permission to do it.

We started to fall in love with this idea, we saw that in sales, specifically, there was a very very clear need to develop this, so that was how we started to work on Attentive.

You’ve tried different paths for Attentive, now leading to something much more structured. But you’re not rolling with the original idea, right?

I think the big vision I was telling you about remained the same, but the way we were using the product changed many times. And it is still changing: not in the past 6-9 months, but before that we’ve changed many times… Even the pitch that we gave at TechStars last year became just a slice of the product that we have today.

So, definitely, there were a lot of iterations on how to do this type of software. We tested pretty much every single section. Should we do this proactive infer type of software to B2C or to B2B? Inside B2B, is it for sales, is it for marketing, for researchers, for analysts, for sales reps? We’ve learned a lot in the process, we knew the idea was still there but we were trying to find out the specific burning need that we could fix.

Throughout these 2.5 years we found areas were Attentive was not interesting at all, areas where it was interesting but it was just a nice to have, we found the last one was it was more of a vitamin and not really a painkiller, and now we found what I think is a real painkiller and it has a lot of room to grow as a product.

That’s part of being in a startup, this trial and error process. How does it feel being the CEO of a promising startup?

It’s great, it’s a roller coaster most of the time, as we have to develop a perspective that is able to question things all the time. However, it’s super fulfilling as well, it is a fantastic path to grow on a personal level. I love what I do, every day, and I think it doesn’t matter if we’re on the highs or in the lows, we’re always learning. If I focus on that, I never get frustrated and I can just concentrate on doing the job well.

How do you learn?

From every source I can! The main source is my team. By far, the most effective way for me to learn is relying on other people that already tested things and can bring other experiences that I don’t have. I have my own way of thinking, I’m just one person, with one perspective, one background. Multiplying that by a team, that’s a lot of available knowledge!

The second source for me is mentors. Over the past two years, clearly, that was one of the best ways of learning I had, personally. It is incredible how much you can rely on people that are not with you on a daily basis but can teach you so much by bringing an outsider perspective.

The third tier would be books, reading, videos, everything I can get my hands on. I always try to have a “how should I apply this” perspective, instead of just consuming information – which I did for a long long time. I try to make it applicable, to learn “right on time”, for example, if I’m planning a fundraising, I’m going to read a lot about fundraising and try to apply it as quickly as possible.

Do you think a curious mind and multiple interests have anything to do with success and entrepreneurship?

It does, but it is a double-edged sword. You see this in so many entrepreneurs – and I clearly suffer from that as well – we’re always fascinated and super interested in the things that we’re reading about, or the trends that we’re seeing, and we want to apply them, we want to ride that wave all the time. It’s good because you have to have that mindset in order to create something, but, on the other hand, you also must be focused on top of that. And I think that is super hard.

Going back to the many iterations that Attentive went through, it is difficult to know when to stop and refocus or continue pursuing something. That, for me, is something that you get over time and it’s not perfect, but it is fueled by the curiosity. It’s harder to find that balance than it is to be curious.