Phishing, AI Scams, and the Ever-Intensifying Cybersecurity War

Joining us today in the Sky Lounge is Antonio Pagano, founder of Wawandco and co-founder of Symbol Security. Todd and Antonoio discuss the importance of cybersecurity, focusing on the human element and compliance, the evolution of phishing attacks, and the role of AI in crafting sophisticated scams. Antonio shares insights on real-world cybersecurity incidents, the trends in cyber insurance, and the dynamics of running a business with a remote co-founder. Antonio Pagano shares his journey as a founder, discussing the challenges, successes, and the constantly evolving landscape of entrepreneurship. While Antonio is always challenging himself to learn and develop new skills and understanding, he also highlights the importance of balancing ambition with personal well-being, and that a grounded approach fuels both creativity and success.

ABOUT OUR GUEST

Antonio Pagano is a visionary entrepreneur from Barranquilla, Colombia, dedicated to making technology accessible and impactful. In 2013, he founded Wawandco, a software development company that builds efficient, high-quality solutions for US and European clients. With expertise in web applications, mobile solutions, APIs, and user experience, Wawandco has become a trusted business partner worldwide. Antonio’s drive to address modern challenges led him to co-found Symbol Security, a SaaS company enhancing cybersecurity awareness. By tackling the human element of cyber risk, Symbol Security empowers organizations to safeguard their assets effectively.Beyond these ventures, Antonio’s innovative spirit has birthed tools like Releaso, which uses AI to simplify product communication, and Retabler, which is designed to streamline data workflows for startups.While excelling professionally, Antonio remains a devoted family man who enjoys sports, outdoor activities, and spending time with loved ones. His story is a testament to how vision and determination can shape the future of technology and inspire meaningful change.

 

Contact:

antonio@wawand.co – symbolsecurity.com
antonio@symbolsecurity.com – wawand.co

Socials
https://www.linkedin.com/in/paganotoni/
https://x.com/paganotoni

Sometimes the constraints create the opportunity to find ways to do things and not having a lot of cash makes you think about how do you efficiently do things. So, yeah. I keep saying this and I keep talking about this with my wife. Like, sometimes what you don't get, gets you something. It may sound contradictory, but you get something from that.

ANTONIO'S TALES FROM THE SKY LOUNGE

Todd Merrill:

Hi, welcome to Tales from the Sky Lounge. It’s a podcast about business consulting and venture investing. We get out there in the world and we talk to people who are making it happen and we get their stories. 

If you could like and subscribe, it really helps us get our message out. So today in the Sky Lounge, Antonio Pagano. Hi, Antonio.

 

Antonio Pagano:

What’s up? Thanks for having me here.

 

Todd Merrill:

Yeah. Well, Antonio, who are you and what are you working on these days?

 

Antonio Pagano:

Yeah, well, a bunch of things.

 

Todd Merrill:

Ha ha ha. Loaded question. I know.

 

Antonio Pagano:

I’m the founder of a software development consultancy company in Colombia, which is named Wawandco. What we do there is we accelerate companies through technology and we help them maximize their potential to use this technology. And on the side, not so on the side, but taking a lot of my time or most of my time, I’m the CTO and co-founder of Symbol Security.

Symbol Security is a software. It’s a service platform that provides cybersecurity awareness to multiple companies. So, yes, I’m at this moment dealing with these two big tasks. Yeah. And enjoying, by the way.

 

Todd Merrill:

Very cool. Well, a lot to unpack. And you’re in Boston if I remember right.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

That’s where you are. It’s very cool. Stay warm, for sure.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Well, let’s kind of unpack it a little bit at a time. So, my favorite thing to talk about being a cybersecurity founder as well would be cybersecurity. So, let’s take that one first. So Symbol, what aspect of cybersecurity do you all go after or how do you protect your clients?

 

Antonio Pagano:

Yes, we are focused on the weakest part of any company. There’s a lot of cybersecurity, but we see a lot of pressure in the technical part of cybersecurity firewalls and networking and prevention systems that prevent attacks, but we are focused on the human part of the equation. We understand that as systems evolve and they become stronger, we play an important role in making the people who work in the company stronger, making employees aware of the danger that’s out there with cybercriminals and other threats. And we take an approach of facilitating the work of compliance teams through a platform that automates multiple processes for them.

 

Todd Merrill:

Okay. Yeah. And I think compliance is a lot of what’s driving cybersecurity, but you have to go through the training and all that stuff.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

But the worst thing you can hear as a cybersecurity CISO is, “Hey, man, click on this link. It’s really cool.”

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Or “I found this thumb drive in the parking lot.” Or “I got some weird email or text message.”

 

Antonio Pagano:

Yeah. And it’s evolving to the physical world. Well, you already mentioned the USB drive that would be the pandemics and the QR getting all that visibility that we know. Now, we also get attacks through QR. It’s called quishing QR.

 

Todd Merrill:

Yeah. Okay

 

Antonio Pagano:

So somebody changed a QR that was in a public place and then a lot of people scan it and go to the danger site.

 

Todd Merrill:

So, like at a restaurant, you had the QR code on the whole thing.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

And then somebody, some bad person takes a sticker that looks just like the bar and then just sticks it right on there and it goes to the middle kind of site or something.

 

Antonio Pagano:

Yeah. Or even worse, there are these payment QRs. I don’t know how common are certain areas that there are these payment QRs. Like, somebody takes advantage of the opportunity and just puts his own QR on top of the original one.

 

Todd Merrill:

And then you get all the details.

 

Antonio Pagano:

Yeah. You paid to the wrong person.

 

Todd Merrill:

God, man. Okay. Yeah. People are always the weakest link in cybersecurity for sure.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Well, how did you get into that? You’re a co-founder. What was that foundation story like with you and your co-founders?

 

Antonio Pagano:

Well, yeah. So it was more of like, yeah. So, I have a background in cybersecurity. I studied systems auditing as my specialization. It’s like a postgraduate in cybersecurity. And I was running Wawandco. At some point, one of our clients introduced us to a person who was connected with the channel for distribution. And he wanted to do something on the phishing side of the training for cybersecurity. And we started talking and I don’t know, things clicked. We became co-founders and started it. We’ve learned a lot of things. Right now, it’s not about phishing.

In the beginning, phishing was everything. Maybe the node floors or other big players at the moment were not as big as they are right now. And there were not as many players, but we were trying to gain a space there. And then we shifted our approach towards a more human-centric one. Towards one that allows also to create efficiencies through automation for different actors in the game. Not just the employees in the company, but people taking care of those cybersecurity awareness programs. And that’s where we are right now. Trying to accelerate the processes within our cybersecurity awareness program.

 

Todd Merrill:

Do you feel phishing is evolving? I started a company in 2008 to go after a more robust login experience using cryptography. We got in front of some interesting websites, like adult dating, that kind of thing. And they had very serious problems with people, I guess catfishing is the word. They’d go get an anchor from Russia, get their picture, and then make that their headshot, and then they would try to get you to pay $500 for a plane ticket somewhere.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Is that still going on? Has it gotten more complicated?

 

Antonio Pagano:

Yes. It has evolved, definitely. And there have also been a lot of measures taken by the providers to counter-attack phishing. So it’s harder these days to train people also. As a provider, one of the challenges we have is that every provider, let’s say Office 365, Google, they are putting a lot of controls in order to prevent phishing from coming in. So when you’re going to send training to prevent phishing, they are going to say, “Hey, this is phishing.” And sometimes it’s too hard. So that to me shows that the kind of attack that the actual delinquent is doing is more sophisticated because they’re finding ways, maybe through the use of AI, maybe through the use of other tools, to put those emails in the inbox and get the people to click the links.

 

Todd Merrill:

Okay

 

Antonio Pagano:

So yes, it’s evolving to a point where there are a lot of countermeasures that are being taken by the providers. But on the flip side, the malicious actor is also doing a lot of other stuff to get people to click the links.

 

Todd Merrill:

So you said AI.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Are people using these language tools to go in and carefully craft individual … yeah, so it used to be the game was, you know, somebody sent out thousands of the same kind of email. Dear, first name, but they were the same. With AI, are they able to rotate around and carefully craft a message?

 

Antonio Pagano:

Yeah, because one of the signs of a phishing email is the grammar or how well-written the email was. Some of these malicious actors are not native to the language they’re attacking. But with AI, they can not only translate the message but make it sound natural. And that makes things harder. So yes. And also, variations on domains, like typosquatting, I think is the name for this. They buy a domain that’s very similar to the actual one. And you click on it, and they put a page that’s equal to yours. So yeah, AI would facilitate all of those things. Yeah, probably not with a provider, I don’t know, like OpenAI or Anthropic, but they would use their own version of Ollama or something like that.

 

Todd Merrill:

And so you’re seeing that now, where the scams…

 

Antonio Pagano:

…yes, we’re seeing where the scams are becoming more sophisticated. Yeah.

 

Todd Merrill:

Are they surveilling the inbound and then adjusting the message in real-time? Is that happening yet?

 

Antonio Pagano:

Not that I’ve seen, you know. But probably they are doing that. Probably they are reacting to that sort of behavior because at the end of the day, social engineering in general, not just phishing, takes advantage of our behavior and just uses it to whatever they want.

 

Todd Merrill:

And then you have any crazy stories? You know, I’ve always heard of the CFO getting pinged, the old Apple iCard scam. Oh my God, you gotta go right now. It was like when crypto was kind of early. You know, you got to move this stuff real quick, and then it’s gone.

 

Antonio Pagano:

Yeah, the one that comes to mind is we had this big client who we’re working with, and they’re very proactive in what they do. They train their people, they monitor domain variations, and so on. And at some point, they are working with a contractor, and this contractor sends them somebody out of the blue within the same thread, jumps in and says, “Hey, we’re changing the payment details. So hey, please pay for these new payment details.” And the team was so well-trained that they identified that this was not from the same domain. The difference was there, and add just a single letter in the domain.

 

Todd Merrill:

Wow!

 

Antonio Pagano:

How did they do it? That’s probably another story. But the customer came to us and said, “Hey, we thought we were monitoring our domain variations.” And we said, “Yes, you are.” We looked at the history of notifications we sent to them, and that domain variation had changed an hour before the attack, and we notified them immediately, but the response time for them was not the best. But it was good and a good validating point for them to use this domain monitoring service that we had, and it helped them a lot. Yeah.

 

Todd Merrill:

Just looking at simple things like did the domain change, or is this something a little off?

 

Antonio Pagano:

Yes

 

Todd Merrill:

So you’re looking for super subtle things like Bank America.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Wow! And then so do you coach people on employing business controls? Like, if it’s over $100,000 or $10,000, the CFO agrees to walk down the hall and talk to the CEO or do it on Slack or some other channel.

 

Antonio Pagano:

Yes, that was actually the trigger. That was a trigger for the payment person or the controller. She saw it and she was very smart and said, “Oh, I know that this is a big deal. I cannot just pay this guy to account.” We got to go through the process. So, it helped. Again, it was good because it helped validate that it works and it made us gain a lot of credibility with this big client. So, it certainly felt great.

 

Todd Merrill:

There used to be this thing at some of these hacker conferences, the Wall of Sheep. So if you got hacked at the conference, your name would go up there. But do you have something like that, but for the opposite, your successes like this one? Like your top 10 best prevention stories?

 

Antonio Pagano:

Yeah, I would say that this one is like the 5th one. There are some critical that I cannot reveal some of the details because I will be in trouble.

 

Todd Merrill:

Yeah. Wow! Yeah, that’s always fun. That’s a fun part of being a cybersecurity company, I guess. Do you have exposure to the insurance part of all this cyber insurance? Are you seeing trends there? It seems like it’s gotten like a year, year and a half, two years ago, it’s everything kind of tightened up a little bit.

 

Antonio Pagano:

Yes. Yes.

 

Todd Merrill:

Do you have an idea why that was so?

 

Antonio Pagano:

I think it’s very visible how sophisticated the bad actors have turned into. And how much evidence we have on that in different movies. You can pick any name of big company being leaked or something like that. But, you know, what’s interesting about that is that we see the pressure to use our product from two angles. One is compliance, like compliance mandates you to do some things. And the other one is cyber insurance. So cyber insurance is getting a style that they are now requiring programs for cybersecurity awareness, programs for different aspects of cybersecurity. I mean, I see that being a trend and not going down. That’s going to be tougher every time.

 

Todd Merrill:

So, like a SOC 2 or something like that drives it.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

And then also, you know, so people have to get cyber insurance because they have an investor, they have a big customer that requires it, something like that.

 

Antonio Pagano:

Yes

 

Todd Merrill:

Okay. Very cool. Well, so how are you and your founder doing running a business? Are you in the same city or are you virtual away from each other?

 

Antonio Pagano:

Yeah, we’re away from each other. My co-founder is in New York City. So, we talk almost all the time. We keep talking. Yeah.

 

Todd Merrill:

So lots of Slack, lots of phone calls, that kind of thing or?

 

Antonio Pagano:

Yeah. We recently moved to Basecamp.

 

Todd Merrill:

Okay

 

Antonio Pagano:

Yeah. And it’s working very well for us. Yeah, we do a lot of like async work and meeting kind of work. I mean, meetings are unavoidable. We have to meet. We’ve got to see each other every day, I would say. And talk about things that we have to polish and everything. So, it’s great.

 

Todd Merrill:

How often do you go up there or does your other founder come down to you?

 

Antonio Pagano:

We see each other, I would say, five times a year at least. Well, at least we would see each other four times for the board meetings that we had. But beyond that, we see each other, I would say, two or three more times. So maybe eight times a year we see each other. Yeah. Anytime I have the chance, I go and say hi. The connection, I feel it’s important. Having that connection between founders. There’s something about virtuality that abstracts human connection or parts of the human connection. And I find that it’s really important to stay in contact. Maybe there’s a cultural aspect to that. Yeah.

 

Todd Merrill:

I think there is, absolutely. I don’t know if it’s just like a country culture. I think it’s a company culture. It’s important. People that stay connected and make time to go see each other tend to do pretty well. It’s hard to get mad at somebody that you know you’re going to have to be in the same room with. But sometimes, it’s very easy if they’re just on the other end of a computer, just to go that jerk. So are you guys backed by, did you take outside funding? You said you had a board.

 

Antonio Pagano:

We’re not. We are 100% bootstrapped.

 

Todd Merrill:

Good for you.

 

Antonio Pagano:

Yeah, at least for the moment. Our cybersecurity company is six years old and we haven’t ever taken outside money. We thought about it at some moments, but we figured out how to optimize things and to grow the income from our clients and from different sources of revenue, which is something interesting. Sometimes the constraints create the opportunity to find ways to do things and not having a lot of cash makes you think about how do you efficiently do things. So, yeah. I keep saying this and I keep talking about this with my wife. Like, sometimes what you don’t get, gets you something. It may sound contradictory, but you get something from that. And I think in terms of funding, we’re still on the side of not chasing money. But I don’t know, maybe we get the appetite later. We’re not close to that.

 

Todd Merrill:

Yeah, and you know, money’s not for everybody. And I think if you can bootstrap carefully and do exactly what you’re saying, is grow intentionally.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

You build a lot more solid company, maybe because you have to, but I think at the end of the day, a solid company is a solid company. And that’s the goal of everybody, right?

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Whether you have a whole bunch of money or just a little bit. And you’re in Boston, so you’re kind of in a hotbed of founder activity. Do you come into contact with other founders? What do you think the landscape is like right now?

 

Antonio Pagano:

Probably through my other company, I get a lot more connection with founders because we help them to accelerate the company experience that we have at Wawandco. So yes, I’m always in contact with other founders, learning from their experience and sharing my experience with them, so yes.

 

Todd Merrill:

Let’s talk about Wawandco. You’ve been doing that for a while, so how did you get started with that? And maybe back up, what is it at first?

 

Antonio Pagano:

Yeah, for sure. So Wawandco provides software development teams to different companies. And that includes design, quality assurance, DevOps, and of course, programming. Yeah. I started that 12 years ago, and I say 12 because it’s turning 12 years in two days.

 

Todd Merrill:

Oh, wow!

 

Antonio Pagano:

Yeah, we’re celebrating.

 

Todd Merrill:

Congratulations!

 

Antonio Pagano:

Yeah, thank you. I started Wawandco, probably I was working as a developer. No, I was, yeah, I was working as a developer at a company. And then I got the opportunity to work with a US company as an architect. And I got that opportunity. And that company that I went to work with ran out of money. They were funded, but they ran out of money. And I had to figure out, well, what I was going to do after that. So, I started consulting. And through that consulting, I was able to grow my client base to the point where I started hiring. I took an approach that’s unconventional. So, I hired people from college, who didn’t have expertise, and I trained them on the things that I was going to use them. Use doesn’t sound very good, but use them to help me with. And well, to this year, that person who started still works with me and we’re very close friends. And that’s how everybody in my team has come to us.

So yes, it’s unconventional that it has worked to create a culture that’s very tight in the sense of being connected, that encompasses the same values,and so on. So yes, that’s how I started it. And yeah, these days, I’m not as active as a CEO as in the beginning, but still very connected with what we do, still attending a lot of things in the company and running a business, growing it as we go.

 

Todd Merrill:

And where are most of the developers?

 

Antonio Pagano:

Yeah, most of our developers are in Barranquilla, Colombia. That’s the north coast of Colombia. Yeah.

 

Todd Merrill:

It would be nice to be down there today. I mean, Atlanta, it’s minus something Celsius. Yeah, it’d be cool.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

So do you have a staff down there in Colombia that helps you?

 

Antonio Pagano:

Yeah

 

Todd Merrill:

And then how did you kind of start from one guy to build out this team of people?

 

Antonio Pagano:

Yeah, you know, it’s interesting because your role as a leader starts to shift as you go. And it shifts because you start encountering two variables that change. The first one is the number of people. And the second one is your expertise with people that you have. So, you start with, as I mentioned, with somebody that didn’t have much experience. And it was just one person. So, you got to do more like very close follow-up with them. Like, “Hey, what are you doing? Do it this way and so on.” But as they grow, you got to switch to a mode where you give freedom to people because they have experience with things. You don’t want to be in the middle. That’s that variable.

And the other thing is the number of people. So, if we are three or four people, we have contact with everybody. But at the moment, we’re 45 people. And it’s really hard for me to be in touch with everybody. But I still try and find skip level meetings to catch up and so on. At any rate, it’s impossible to manage people. I think there’s a variety of requisite law which states that the… maybe I’m going too technical here, but there’s a control law that says that in order for a system to be controlled, the controller entity needs to have the same parts, plus one than the control entity. So, the controller needs to be more complicated than the team being controlled. So, a person cannot control another one because you have the same number of parts. And now talk about five people. Controlling in terms of humans is an illusion. Anyways, I may have gotten too technical.

 

Todd Merrill:

Yeah. It’s interesting. We talked about this with another crowd earlier this week. You have culture and as a founder, you pick the first couple people.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

So your corporate cultural values are going to inherently be involved in those selections. Right?

 

Antonio Pagano:

Yes

 

Todd Merrill:

So, after you pick the first couple people, at some point, you can’t control everything or you can’t influence everything. You can’t be everywhere. And then something happens around 20, 25 people. Maybe more, maybe less. And then that second-generation hires that third generation.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

And then as the founder, you’re going to start missing some of those processes just because there’s just a lot going on.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

And then that’s when it either… like, you’ve got very strong cultural values and you did a good job and everybody is kind of aligned or not. And then it starts to spiral. Do you feel like you made it through that second wave hiring, the third wave successfully? Or did you have any challenges with that?

 

Antonio Pagano:

Yeah. I have a lot of challenges.

 

Todd Merrill:

Yeah

 

Antonio Pagano:

I come from a very technical background. At that point, I haven’t done management school. So, I was maybe taking agile methodologies and training a very busy client on that. But I had a lot of trouble letting things go, and as a founder, I can tell that that’s a common issue with friends you have. I’ve seen it in many founders, especially if it’s a solo founder. Like, you can see how it’s hard for us to let things go. But at the end of the day, I noticed that my team was doing a better job than me trying to do five things at a time. So, it was not smart for me to be doing that job. So, I think it helped me a lot to have an amazing team. I have to say that. Just the fact that I am splitting myself between two companies shows that I can delegate stuff with them, and the company is going to grow amazingly. But I can tell that it’s important, and hiring becomes a really important piece of the puzzle when you get to a point where you want to delegate. You have to feel sure that you’re delegating to people that are capable of doing the job that you’re doing better than you doing five things at a time.  And I’m really thankful for having that. Quite honestly, that’s something that’s great for me. I really appreciate that in my team.

 

Todd Merrill:

Did you have any help in terms of a peer group or a mentor when you were first getting going?

 

Antonio Pagano:

I did not, you know, and that’s probably because I err on the side of not being social. I’ve been listening to different podcasts and I found that that’s a very useful way of learning from the experience of others, from the errors of others, and maybe not falling into the same traps that they fall into. So yes, I didn’t have at the moment any help. I don’t know, a coach or something like that. But I was maybe listening to very top voices and taking things from here and there, mixing those beats and finding ways to do it better every time. I wish I had a peer group that would tell me, hey, do this, do that, this won’t work, and so on.

 

Todd Merrill:

So, with Wawandco, you mentioned you work with a lot of different founders.

 

Antonio Pagano:

Yes

 

Todd Merrill:

Do you want to share any wisdom there, what you see?

 

Antonio Pagano:

Yes

 

Todd Merrill:

You’ve been a founder, you’ve been another founder, right? So now you see these young ones and then they’re kind of doing the same stuff. You’re like, “Oh man, here we go again.”

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Do you help them? What advice would you give them?

 

Antonio Pagano:

Yes, we help them a lot in trying to be out as soon as possible. Like, to be out in production, out with your customer, and learning as soon as possible. If I have to share a piece of wisdom, I would say that you get to cut as much as possible from your B1, just to be out and gather as much feedback as possible from the market. At the end of the day, you could go out with the greatest product and they can say, no, we don’t want that. So the sooner you’re out, the better you’re going to be because you’re going to get more feedback and you’re going to be able to learn from that feedback. And if we transition that into, I don’t know, finances, it’s better to lose, I don’t know, $100K than losing $1 million. You better fail fast instead of delaying that. Even though I don’t think you have to fail, you can make it.

 

Todd Merrill:

Figure it out fast and then iterate.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

It used to be fail fast, fail forward was what everybody said.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

But if you do it right, it’s not so much failure. It just takes a small step, we need to adjust, take another step, adjust.

 

Antonio Pagano:

Agreed. Yes. I think it’s a failure when you don’t learn from what you’re doing. When I say learn, maybe for at a personal level, it’s essentially not learn, but as a team, if you don’t include what you’ve seen out in the market into your platform to make it better. Like, if you are just sending things out and saying, no, it doesn’t work, you fail. But if you take the input that we’re getting and making that feedback get to your app, then you are learning, you’re growing, and it’s not like you’ve lost what you’ve done. Yeah.

 

Todd Merrill:

Who are these founders? Where do they come from? How do they find you?

 

Antonio Pagano:

Well, it’s different. We have different sources for this. Website is probably where we get most of the requests for help. But we also get referrals from a lot of our clients. Most of them are very happy with us and just recommend us and say, “Hey, we have this amazing team in Colombia. They can help you build this and that.” And that has worked very well. But we get a lot of business through our website that works very well. We haven’t invested much in paid advertisement, but we get some good number of deals from there. And it’s growing. So we’ll keep doing what we’re doing there and try to keep improving it to grow a little bit more.

 

Todd Merrill:

So who’s starting companies these days? Is it young people right out of college? Is it older people that have been in the corporate world? Do you see a lot of repeat founders?

 

Antonio Pagano:

Yes, there are a lot of solo founders. That tendency is getting bigger and bigger. And I say that because we get the chance to work with people in communities where they just hire us for tasks on platforms that they have built by themselves, but they’ve grown it to a point where it’s impossible for them to make a sale. Maybe they are focused on marketing or other areas of their business. So yes, we’ve seen a tendency on these professionals that are trying to make an extra income to an app that does this leader niche thing. And then all of a sudden that leader app turns into a business in itself. And they start shifting away from their work into making their first main income stream, this application. And that’s when they have to hire the pros and say, “Hey, help me with this, help me with that.”

DevOps is an area where that becomes very natural. You can put your app in, let’s say, a tiny platform, but then would you grow even though like, what file to deal with this amount of sense actually that you’re getting off? You built the app for one thing, but you didn’t built it to scale that way. And that’s when we help them. We allow them to grow. And also, I help them concentrate on what they like doing more, like the core of a business or other things that they definitely rock on.

 

Todd Merrill:

You have been in business for a long time, almost 12 years. Do you have a sense of the flow of venture investing? It seems like it kind of slowed down a little bit post-Silicon Valley Bank.

 

Antonio Pagano:

Yes

 

Todd Merrill:

Is it turning around yet?

 

Antonio Pagano:

It is turning around. I say this for the two sides of the coin that I’m playing, let’s call it that way. I see it as a one-on-one call. We’re getting a lot more like, hey, I want to build this or I want to invest in this platform that I have. I want to grow and so on. Or I was raising last year but now things are looking different. I’ve seen this. And on the simple side, we see how you touched on the topic of receiving capital or getting investment. We’re getting a lot of requests for like, “Hey, we want to put this amount of cash in your business.” Where like, one year ago, if we were to go and chase some cash, that would have been impossible. Yeah. So, it’s kind of flipping back to a more actively seen kind of world. And I think it’s natural with interest rates going down and so on. That’s going to make the market a lot more active for investment, for acquisitions and so on.

 

Todd Merrill:

So, with high interest rates, you can make a decent amount of money in a safe way. So then, therefore, why chase riskier investments? Okay.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

And then now that the interest rates are coming down, everybody has got to go up the risk curve a little bit and that’s the theory.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Okay. That makes a lot of sense. Yeah, let’s hope 2025 is the resurgence of venture or at least, you know, what I see is a lot of smaller companies starting. So, nobody is chasing that huge check right now, the people are doing exactly what you’re doing. Get started, throw a little bit of money in with your friends, and then kind of start small, grow slow and methodical, and then make a nice little business.

 

Antonio Pagano:

Yes. And when you think about it, it’s an effect of not having… somebody said that the free money, it’s no longer there. Like, there’s no more free money. So, everybody wants to optimize and since they’re starting these companies bootstrapped, and there’s more of a tendency on that just because it was hard at least last year to get money from VCs. So, the tendency was to just build your company with whatever you have, like smaller companies, and let’s grow it slower but let’s grow it. And now maybe with the new tendency to split back a little bit, we see a lot more investors in that company.

 

Todd Merrill:

You’re involved in two different companies which is amazing, right? Two continents and you got all kinds of interesting things going on. How do you handle all that? Are there days where you just go, man, I just want to go ride my bike or you just want to stop for a second?

 

Antonio Pagano:

Yes, definitely, there are days like that. There are days where, I mean, it is what it is. You get crazy with the amount of things. But I say that I had an amazing team and that’s I would say my treasure. I have a team that’s very well-equipped to help me with things that happen to me every day. In both companies, I have a great team at Symbol. Symbol is amazing, and the same at Wawandco. And that helps me delegate stuff and free myself from the pressure that would be handling those two ones.

Quite honestly, I thought this was going to be harder for me with two companies, but I found a way to be present in both companies and it’s working very well. I found a way to be supported by my co-founder and just being there, being the backbone of the platform, like being there to keep things running, keep things working very well while he runs the growth operation at the company, like growth and sales. We complement each other very well, and I’m also very thankful for that. I’m really enjoying it.

 

Todd Merrill:

So, what are you going to do for your third company?

 

Antonio Pagano:

I don’t know. I first need to get rid of one or two.

 

Todd Merrill:

Yeah

 

Antonio Pagano:

Like, I don’t know. The hard thing is I don’t see myself going out of any of these because I really enjoy it.

 

Todd Merrill:

Yeah

 

Antonio Pagano:

Part of me still wants to be producing products, but another part of me wants to help other people and learn from the different experiences of shifting technologies and doing stuff.

 

Todd Merrill:

Are you intentional about blocking out certain times for your personal life?

 

Antonio Pagano:

Yes

 

Todd Merrill:

How do you think about that?

 

Antonio Pagano:

Yeah. I’ve been very good about that since the beginning. I copied that from the Basecamp guys where they say like at 5 pm, it’s over, you are not worth it. I kind of took that literally. That doesn’t mean that I’ve never been after 5 at the office, but there are cases where you have to stay or Saturdays where you have to jump in and fix things, especially if you’re a founder.

That line gets blurry if you are a founder. But I’ve been very good about saying that at 5 or 6 pm, I get to be at home. I don’t remember a day that I haven’t read to my child. Maybe if I’m traveling, but if I’m at home, I’m always waiting for them to sleep. I have the pleasure to do that and I’m thankful for having that. But yeah, I think I’ve been very intentional about that and when it’s needed, it’s also noticeable that it’s needed and there’s no question. Or I haven’t had, I don’t know, like my wife saying, “Oh, you’re all the time in the office.” No, that’s not me. I’ve been with the kids. I’ve been at home, thankfully. And I really enjoy it.

 

Todd Merrill:

You feel like that takes the pressure off or recharges the batteries in some way?

 

Antonio Pagano:

Yes

 

Todd Merrill:

And then when you’re at work, you’re 100% because you’ve already taken care of the family and recharged and had a good time.

 

Antonio Pagano:

Yeah. And beyond that, there’s also the sleeping routine. If you don’t take care of yourself, it’s hard to take care of anything else. So, sleeping very well, doing exercise, whatever you do, if it’s cardio, if it’s weight lifting, whatever you do. I think it’s important because it can also de-stress you from whatever you have in the office or in the rest of the world. And also, it’s important to, as you mentioned, to recharge. So, yeah. I think that, as I said, having those constraints helps you focus on things when you are working or when you are at life, even though for a founder it’s really hard to make that line not blur because we will have different events that will pull you away from whatever you’re doing.

 

Todd Merrill:

Do you have a favorite sport that you grew up playing or are you involved with any?

 

Antonio Pagano:

Yeah, I grew up playing. I was very active in sports, you know? I’m a child of two gymnastics teachers.

 

Todd Merrill:

No kidding.

 

Antonio Pagano:

Yeah. So, I was very active in sports since my four years, I would say. And my father took this approach of multidisciplinary training where I took different sports as I was growing. And then, at the end, I decided to pick one. And I decided to play volleyball even though I’m not really tall.

 

Todd Merrill:

Okay

 

Antonio Pagano:

I’m actually normal size to go that way. But I played a lot of volleyball. I played baseball. I did BMX. I did a lot of sports in my young age. And I still do some volleyball there. My wife also used to be a volleyball person. She was part of a national team. She’s kind of the star of the house on that side. Yeah. And I’m surrounded with a lot of people that play sports. My team, my uncle, also is compounded by many people that play different sports.

 

Todd Merrill:

Okay.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Yeah. A lot of successful people have some kind of sports background. What do you think it is about sports that helps you be successful in business?

 

Antonio Pagano:

Yeah. There’s definitely a connection. I tend to say that I learned more in playing on a team sport than being on my MBA. And I kind of sustained, to some degree, that’s kind of real. My top management lessons come from my experience in sports. And then when I get to like, I don’t know, MBA or starting postgraduate, then I solidify those learnings through theories or through other things. But I can see how cooperation, how being part of a team, understanding that you are just a part of a system that’s bigger than you, and that you got to behave in the sense of the wellness of that system will definitely play a good part in the success of some individuals that have the chance.

Now I’ve seen individuals that play individual sports and also have that mentality of chasing things, of being very disciplined about themselves, or of like self-respect or respect to the work that you have to put into things. I think there’s something there and I’m definitely going to repeat the formula with my kids. I don’t know if they’re going to be entrepreneurs or what they’re going to do, but I think it serves very well as a foundation.

 

Todd Merrill:

Yeah, teach you how to work hard, teach you how to take coaching, teach you to be a part of something bigger than yourself. Those are all great values.

 

Antonio Pagano:

Yeah, I agree.

 

Todd Merrill:

Let me turn around to MBA. When I was a young technical founder, we had a software company and we did IT outsourced administration, like way back in the day. All of us were nerds, right? And we all met in technical jobs and then kind of in spite of ourselves had some success. But we’d always fight about all the non-technical marketing, the business, the finance, advertising, how much do we pay each other. And then we figured it out. I got an advertisement for Emory, Executive MBA and it was like, here’s the subjects we cover. And I thought, holy crap. Like, that’s what we’re missing right there. Did you have a moment like that where you took, why did you decide to get an MBA, and then did it unlock some things for you like it did?

 

Antonio Pagano:

Yes, yes. So, I decided to take an MBA after what was probably eight years of existence. And some of my colleagues or classmates, I have to say, they asked me, why are you here? And I was like, well, I have to explain. I was reading at the moment Ryan Holiday’s Ego is the Enemy. And one of the things he mentioned is that you got to be always in that apprentice position. Reel choice #3 And I thought to myself, like, hey, if I think that I know everything, then I will not learn. So, I decided to go there and I actually learned a bunch of things. And interestingly from parts that I didn’t expect, from sections that I didn’t expect, from interactions that I didn’t expect, I learned so much, but just putting myself in the position of learning. And I think that’s important. That’s key. Not just for like, let’s say, education, but also for a founder. You cannot think that your hypothesis, that the thing that you’re putting out on the market is correct. I mean, it’s a fact that you got to validate that. You got to learn from the market. You got to incorporate what you learned. And take that with humility and like this. Redo your hypothesis and go again and learn again. Yeah. I think it’s important.

So maybe I sidetracked the conversation with that but the reason was particularly that I was reading at the moment Ego is the Enemy, and that book, maybe think about that like, hey, I can put my ego on the side and learn. And thankfully that worked a lot. And I keep that in mind that whenever we are not in a position to learn, it’s hard that anybody will teach us anything.

 

Todd Merrill:

So, once you get to that executive level, you have so much inbound information. You have to process it so quickly. Your brain just doesn’t have a lot of time to go back and read a business book or watch a podcast or something. Do you find that that’s true? And how do you replace that? I know you probably read a lot of business books early. Do you still read a lot of business books?

 

Antonio Pagano:

I do. I do. I do read a lot of books. And I try not to push myself too hard. I read 20 books last year. So, I’m constant. I’m there pushing every day five, six pages and that takes me to what I want to be.

 

Todd Merrill:

Okay. So just a little bit at a time and then you always have something you’re kind of in the background learning.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Which one are you working on now? Or do you have a book?

 

Antonio Pagano:

I’m currently working on Nassim Taleb’s Fooled by Randomness.

 

Todd Merrill:

Okay

 

Antonio Pagano:

I want to read his five-book series. It’s really interesting because he talks in a way where he’s a statistician or mathematician and he talks about the randomness and how it’s included in different areas of our life. But the way the book is presented is more of a conversation that he’s having. He’s talking in a very natural way but focuses on many topics that we see everyday, and like how we know that randomness is there. That beyond doing all the good things that you have to do, there’s a little bit of randomness that we will play. So, yeah.

 

Todd Merrill:

Makes life interesting for sure.

 

Antonio Pagano:

Yeah, yeah.

 

Todd Merrill:

Well, yes. Tales from the Sky Lounge is all about travel and getting out there in the world. Do you have any great travel stories you want to share with us? I know you have a couple.

 

Antonio Pagano:

Yeah, yeah, yeah. Maybe this is like a short travel story but at some point, one of our clients at Wawandco was a party solutions company, software as a service. And they got a request from the FBI because somebody had dropped a bomb. They suspected that that person was in one of the parking lots they managed.

 

Todd Merrill:

Oh, man!

 

Antonio Pagano:

And they knew that we have cameras there. So they wanted to see if in our system we got something. Not me directly, but one of the guys told me like, hey, let’s review, and we started reviewing. This system has a lot of OCR for license plates and so on. The guy came on a car, just parked in front of the parking lot, but he didn’t come into the parking lot with the car. And we could not capture the license plate. And then we were like looking at the video, so what’s happening there? What’s happening? What’s happening? And then one of my teammates said, “Well, let’s see what his gesture is.” They started looking at cultural art. We moved into like detective mode.

 

Todd Merrill:

Ha ha ha!

 

Antonio Pagano:

And they started analyzing their gestures. And they say, “Oh, I know what’s happening. This guy is coming on an Uber. This is an Uber car.”

 

Todd Merrill:

Okay

 

Antonio Pagano:

I’m like, okay. So, from there we told that we thought that was an Uber. And two weeks after that, we got the email from the FBI saying they captured the guy.

 

Todd Merrill:

Okay

 

Antonio Pagano:

They called Uber and said like, “At what time, at X time somebody left at this place, can you determine who was it?” And the list was displayed. They called the person and ________.

 

Todd Merrill:

Wow!

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Very cool.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

That’s a crazy story. How often do you make it down to Colombia? Is that an interesting travel experience?

 

Antonio Pagano:

It is. I have to say that there’s a lot to see in Colombia and a lot to miss as well. Yes, it is. I definitely invite people to visit Colombia. There’s a lot of amazing things to see. So yes, I move between the two sides and I try to be connected with my well-informed team. So, they come when I go. And then that’s how we kind of run. But we stay in touch. So, I keep going there and I keep talking with them and in constant contact with them.

 

Todd Merrill:

You like connect through Miami? Is that like halfway?

 

Antonio Pagano:

Yes

 

Todd Merrill:

Yeah. Okay. Very cool.

 

Antonio Pagano:

Yeah

 

Todd Merrill:

Antonio, it’s been great having you on the Sky Lounge today.

 

Antonio Pagano:

It’s been great. Thanks for having me and I really appreciate your time.

 

Todd Merrill:

Yeah. How can people follow up with you after this on the internet if they want to get in touch with you?

 

Antonio Pagano:

You can find me on LinkedIn at paganotoni or Twitter, the same, at paganotoni or you can find us on the websites, symbolsecurity.com or wawand.co.

 

Todd Merrill:

Bye for now.

What is the Sky Lounge?

Tales from the Sky Lounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.

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ABOUT OUR HOST

Todd Merrill, Interim and Fractional CTO, CISO

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Connect with and learn more about Todd here:

email: Todd@SilverbackCTO.com
phone: +1 678-521-5305
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