Tony Pietrocola: If you have conviction on something that big, so when you know you're in the wave of something like we are right now with AI, bet big, because you don't know when that next thing is going to come, right?
Drew Dinkelacker: Welcome to Bullseyes & Blind Spots, a series of The Marketing Accelerator Podcast, where chief executives share the pivotal decisions that define their leadership and the blind spots that reshape their perspective. Tony Pietrocola is the president and co-founder of AgileBlue, an AI native cybersecurity platform, and he's a seasoned technology executive with over 20 years of entrepreneurial experience. Welcome to Bullseyes & Blind Spots.
Tony: Drew, thanks for having me. Looking forward to it. And yes, I'm seasoned. I think that also means old, so yeah, I like it. It's a better way!
Drew: You could define that any way you like. Seasoned could also just be salty, I don't know.
Tony: I'll buy a little bit of that, too.
Drew: Yeah. So, let's start with a bullseye. Take us back to a time when you faced a tough decision and you really hit the mark. You knocked the ball out of the ballpark, man. What was happening around you? Why was it so impactful? Give us your bullseye.
Tony: You know, I don't know if there's one bullseye. I know there isn't in a game of darts, but I don't know if there is one in the game of leadership or business. You know, Drew, look, I think you know this as well as I do. I think anybody who has been asked this question... It's a great question, by the way... Would start with people. You've got to have the right people. And I think the only way you... Oh, you know how to always bring on the right people. You probably hired some wrong people in your seasoned career as well, right? And you can see the impact that has on your organization. So, I think that's always going to be one of them. I'll tell you the other one, and I think people pick up on this quick, delaying the inevitable. I think when smart people see you have trouble making decisions... It could be a small decision, it could be a large decision... But they know where you're going to get to, but you just can't get there. I think that also could affect leadership. And, you know, it's interesting. I wonder if you've seen that as well. If you can't get to that decision, does your team look at you and be like, "Well, are you really the leader?" Because the leader does have to make those tough decisions and then live with it, whether it's a good decision or bad decision. The last thing is, if you have conviction on something... And I stole this from someone, it's not like I created this, so don't give me any credit for it. I stole this. But all good stuff is stolen, right?
Drew: Absolutely.
Tony: If you have conviction on something, bet big. So, when you know you're in the wave of something like we are right now with AI, or maybe back in the day it was the internet... Whatever it might be, depending on how seasoned you actually are... Bet big, because you don't know when that next thing is going to come, right? So, if you bet big and you go hard, I think that shows that you're willing to take the, you know, take the reins as a leader.
Drew: Absolutely. Those are great, great, great bullseyes to hit. And so, I'm assuming you have bet big in your life on something you had conviction about. Can you tell us a little bit about that, when you bet big?
Tony: Well, my first company, we developed websites, and how I bet big is we started that company in 2001. It's a long time ago, as the internet was just getting cranking, right? But I was a systems engineer at Apple Computer. Back then we were called Apple Computer. Now it's just called Apple. So, to leave that type of role, that job... Steve Jobs had just come back, right, in '97. I got a job there in '97. To leave to start your own thing is scary. But you're betting big that you think, "Hey, I can do a great job. I can build something. I can do better than Apple"... Not necessarily as Apple, but you know what I mean. And so, you're betting big because, you know, the internet thing is going to probably last. Well, same thing now, right? When we started AgileBlue, we went to market in 2020. Machine learning, which is the predecessor of AI, you know... Generative AI is new, but not machine learning AI... And you bet big. You're developing a company that's going to differentiate the market you're in based on that. I think that's when you have to have conviction and go.
Drew: Well done. And it does. And this is why I find business owners are some of the most courageous people I know. You know, people don't think about... People who are outside of business don't think of the courage it takes to be a business, especially an owner. And you're betting big, and you're betting big with your life savings. You're betting big with other people's money.
Tony: Credit card balances.
Drew: Yeah, people just don't realize that. And it takes a serious amount of courage to take that on. And how was that... What was that phrase you used earlier on about the... Was it defining?
Tony: Delaying the inevitable?
Drew: Delaying the inevitable. You know, it's interesting because I've been in those experiences. One with a longtime client who had a longtime employee who was, let's just say, limiting the owner's access to information. And the owner...
Tony: Interesting.
Drew: Yeah, the owner's complaining about it to me, and I'm like, "Why is this person still on staff?" "Well, you know, he's been here since the beginning. He's kind of like family." And I said, "I've seen your kids work here. You would never let them get away with it." And so, what that was a blind spot, which takes us right into our next question. Every leader has blind spots, and you can't avoid them. The trick really is discovering them and accepting that it is a blind spot, not ignoring it. Can you share a time when a blind spot in your leadership, when it came to light to you, how did you discover it? What did it cost you? Tell us about a blind spot experience.
Tony: You know, it's a good question. I think the average person probably has, you know, a bunch of blind spots, both professionally and personally. I think definitely... I think there's two in my career as a leader that I continue to have to work on. Number one is definitely empathy. Not that I'm not an empathetic person. It's just sometimes you're flying at the speed of light, and you can lose that sight of empathy and putting yourself in the position of... Maybe it's someone on your team, maybe it's a customer, maybe it's a prospect, and your personal life could be, you know, your spouse or kid... And you're just not understanding, like, "Why don't they understand this? This is the way it has to be. What the heck?" Not understanding maybe that other perspective, which helps you become a much better A, leader, and B, person. And we all want to be, you know, decent people. That's something I always have to work at. Not because I'm not empathetic... It's just you're flying a hundred miles an hour sometimes. You just don't consider it. I think the other blind spot is people support what they help build.
Tony: And this was said to me a while ago back at Apple, meaning if you think you can do everything, if you're this micromanager... "This is how this has to be done. This is how this is going to be done"... People are going to do it because it's a task, it's their job. But you're probably not going to get a hundred percent out of it. It's going to be okay. And what are you really doing for them? If you say to someone, "Hey, here's our goal. I don't care how you get there. Let's get there legally. Let's get there. Here's the goal," and then you let them go, you're going to get the best. Why?
Tony: You gave them the goal, but you didn't tell them how to do it. Whether it took them two things to get to it or forty, they thought of it, they were critical thinking about it, and they solved the project. They're happier. They know you're not a micromanager, and you've laid out a big goal for them to hit. I think you've just created a tremendous scenario. But I do have to remind myself of that just about every day of the week to just lay it out. And these people are great. They'll go get it.
Tony: And that ties back to your hiring good quality people that you can delegate that to and have confidence in that delegation. So now, here we go. Here's the fun question. This is the time travel question. If you could sit down with Tony Pietrocola 20 years ago, what wisdom would today's Tony pass on to yesterday's Tony about career, about personal life, about hopes and dreams back in the 2000s? What would you tell him?
Tony: You know, I'm sure there's a million ways this could go. And I don't know. I think there's a lot of ways this can go. But I'm going to say this: I think you have to live every day very hard. And some days that might mean working 20 hours a day. It might mean taking a day off to spend it with someone you love who needs that time with you. It could be shutting down that laptop at night and working... Helping your kid work through an algebra problem that you have to Google, but you're not going to tell them you Googled it. You want them to think you're smart. I think it's just living that life hard and not just being maniacally focused on one thing. You know, I'm a huge fan of Elon Musk, and he'll make you believe... And you read everything about him, and obviously the guy's incredible... But he does believe you need to be maniacally focused. I'm not that guy. Obviously, I'm not Elon Musk. I think the point is, whatever I'm doing, you've got to do it to... I mean, just go all at it, whether that's work for that block, whether that's family for that block.
Tony: Maybe it's even out golfing with friends or something for that block. Whatever it is, you go hard at that, be very focused in what you're doing. And that is something in my life I've had a very difficult time with. So, I would tell my young... If I was a younger guy, I would tell him that. Maybe I'd be a little bit different today. I've just realized that probably over the last number of years.
Drew: Being present, whatever it is that you're doing, being present.
Tony: I love it.
Drew: That's really good and hard when you're dealing with all kinds of issues. Now here's a side question. What would Tony from the 2000s think of where Tony is today in 2025?
Tony: Oh, I... You know, I'm going to be very candid on that one. I think disappointed to some extent. I'm one of these guys that had ridiculous thoughts, dreams, aspirations, all that good stuff. From a business perspective, I think from a personal perspective, very happy. Raised two incredible daughters. So, I think that's the most important thing that I have zero regrets on. I'll Frank Sinatra that one a little bit. Zero regrets on that one. Maybe business-wise, a couple of misses here that I think we could have cleaned up. But, you know, I'm 51, so I've got some runway left. So, I think we're going to do amazing things at AgileBlue. We already are. And whatever the future holds, I think will be fantastic as well.
Drew: Tony, you've got plenty of runway left.
Tony: Let's hope, my man. Let's hope.
Drew: I can tell you that. No doubt about that. Thanks so much for sharing your journey, the bullseyes that gave you confidence, the blind spots that shaped your growth. Your candor and insight remind us that leadership isn't about perfection. It's about learning, it's about adapting and staying true to what matters most. Are you a growth-minded chief executive setting big goals for the future but a bit unsure about how you'll get there? I've created the Bullseyes & Blind Spots Accelerated Guide just for you. Only 16 pages, this guide asks eight revealing bullseyes and blind spot questions that will reveal truths that your marketing team can't or won't tell you. This is a leadership upgrade in just 16 pages. Visit bullseyesandblindspots.com for more information. That's bullseyesandblindspots.com.