CEOInterviews.AIAnthony Caiafa - Leading Teams From 3 to 3,000 People

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Anthony Caiafa0:00

Be humble. You've got to remain humble because I've been in plenty of situations where, like you said, that person who reported to you and you just weren't very kind, they're the one you're asking for an investment in something. So it's definitely a big thing to take away.

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Interviewer0:21

There he is. Look at that hair. Is that some COVID hair? Did you actually put water in it today?

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Anthony Caiafa0:28

Truthfully, my wife was like, 'So you're just gonna do that?' And I was like, 'I guess that means to change it.' No holes in the t-shirts, that's it, man. It went from a professional headshot to now I feel like you're a music producer, or a snowboarder, or a car salesman. But I just haven't been going to the barber. I used to go every Saturday, then I stopped. It was getting bad, so I shaved it.

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Interviewer1:09

Are you guys still pretty locked down? Jersey's going up, Jersey's on the rise.

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Anthony Caiafa1:15

Jersey's definitely in the cases are all going up, and schools are shutting down all over the place. So we try to keep it, because we have two little kids and my wife's pregnant, so we try to keep it like, no thanks.

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Interviewer1:34

How old are your kids?

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Anthony Caiafa1:35

Five, three, and then a couple months.

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Interviewer1:41

That's amazing. This morning, right before the show, I was texting my wife because as I was getting ready, I went to throw away my floss into the trash and there was an empty pregnancy test box. So I texted her, 'Hey, is everything cool? I saw this in the trash.' She was like, 'Oh, I was just cleaning this morning.' I was like, 'Okay cool.' We've got two little ones, three and one and a half. But I was like, she had a lot bigger laugh than me.

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Anthony Caiafa2:16

Yeah, because you're just like, 'Oh wait a second.' Yes, I was like, 'I don't want to be the sleuth, the investigator here, but I've gotta ask. You can't not ask when you see an empty pregnancy test box in your trash can.'

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Interviewer2:27

So is this your first podcast?

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Anthony Caiafa2:30

No, not so. Throughout the years, I've done talks, so not my first. But I think it's the first one in a little bit since I joined SS&C. This is the first time I've done it just because it's been so busy.

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Interviewer2:55

Do you listen to other podcasts? Are you a fan of them?

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Anthony Caiafa2:58

Yeah, I like Joe Rogan. I like his style. I think after the Spotify acquisition, it's interesting because his content is random. He doesn't really take sides that often, so it's interesting to see some of the stuff going on. Another podcast, Barbell Shrugged, and there are some tech ones that are pretty cool. I just try to listen to as many as I can.

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Interviewer3:29

I did notice after the Spotify transition for him, I started seeing some guests that I don't think he would have had on, like authors of books. It's like, I get it. A lot of love to him, way to land hundreds of millions of dollars as a contract and not have to run that sales process anymore.

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Anthony Caiafa3:53

It's interesting. I was reading how they're starting to try to silence some of his content because they don't necessarily agree with it. I'm very curious to see how it shapes up over time. But look, $100 million, if someone came and said, 'Hey, we'll give you $100 million for your podcast,' you'd be like, 'Yeah, I think we could do that.' It's interesting. If you have a $100 million or $300 million check in front of you, your brain just starts figuring out every way why you could take it. It's a no-brainer. More power to him.

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Interviewer4:48

I haven't heard of Barbell Shrugged. Is that a fitness podcast?

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Anthony Caiafa4:50

Yeah, it's a cool one. A couple of guys talk to different people in the weightlifting world. They discuss styles, methods, eating philosophies. The recent one about Tom Brady's TB12 was interesting. You just throw it on in the background when you drive, and it takes your mind off things.

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Interviewer5:25

Are you into fitness? What do you do? Do you work out, lift weights, run?

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Anthony Caiafa5:30

Yeah, I run a lot. I used to do strongman competitions years ago. Not like some of these guys who are a little too much, but we used to travel around and compete in different small competitions, which was a lot of fun. Way before COVID, I converted my garage into a full gym based on equipment from closed gyms. I have stones, yokes, farmer carries, squat racks. So literally on the other side of this wall, as soon as I'm done during the day, I pop right in there. Me and my wife swap, and then we'll both be able to get it in for a little bit.

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Interviewer6:19

I'm pretty big into fitness. This past year, my big thing was foundation. I wanted to build a strong foundation after having kids and such a crazy work schedule. I said, 'I'm gonna give myself five years to build a solid foundation.' I started by monitoring everything, tracking all my calories and macros in MyFitnessPal. I did nothing except track for the first couple weeks, then started changing based on that. I've been consistently tracking for almost 360 something days now. I weigh myself every morning at the same time. I got to really understand how my body processes food. When you actually weigh all your food and understand the exact nutrients going into your body for an extended period, you get a completely different understanding of nutrition. That's important because nutrition affects your mood and everything. It's also discipline.

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Anthony Caiafa7:42

It takes a lot of discipline, especially with little kids. They have snacks galore. It's super difficult to be like, 'Okay, I know if I eat this, it's gonna add x amount of macros.' But that discipline really does help transition into a lot of different things. You also have to test and understand what works for you. I'm very similar. A lot of these guys who lift heavy say, 'Carbs, carbs, carbs,' but for me, that doesn't work because my body doesn't accept it well. I get sluggish and tired. Discipline and learning pivot very well into leadership.

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Interviewer8:44

Did you always do this, or was it stress from work that made you start a healthier lifestyle?

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Anthony Caiafa8:53

No. Throughout high school, I was your typical person sitting on the computer for a hundred million hours a day, not paying attention to anything else. Health was not it. I smoked cigarettes, the whole thing. Around 20 or 21, my doctor said, 'Dude, if you continue this, you're just gonna die.' So I thought, 'Well, I probably don't wanna die.' I turned everything around, hooked up with some people who had a similar mindset, made some friends, and that's kind of it.

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Interviewer9:36

Were you programming in high school?

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Anthony Caiafa9:38

Yeah, in high school and even as a kid. I started doing a lot of this stuff in fifth or sixth grade. That's when VB was cool and online gaming wasn't as cool as it is today, but it was still pretty cool for us. The movie 'Hackers' originally got me into that era, and then I quickly realized it's not as visual as this, but it's still kind of cool. It just took off from there.

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Interviewer10:10

Did you end up going to college for this, or did you go right into the market?

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Anthony Caiafa10:15

I went to school for a little bit. When I was at the school, they didn't have a good Linux program foundation, and their online school system was pretty bad. So I helped pivot into building it with them. Eventually, they were like, 'Well, you can't really go to school here anymore since you're building the system.' I said, 'Okay, whatever.' From there, I just pivoted and took off. Lately, I've been finishing out the degree, not because I feel like I need it, but because I only live one time. If it's something I want to get behind me, why not? I gotta try as many different things as I can.

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Interviewer11:01

I was surprised you didn't graduate with every possible degree the college could issue.

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Anthony Caiafa11:07

My attention span is like, I like being able to jump in and be more hands-on and learn it. Sometimes I think if I would have focused on it, where would I have been now? But I do want to finish it, and that's what I've been working towards. It's just something to do.

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Interviewer11:32

Did you finish? No, but I was rooting for you. I was alluding to you being in the database of their system, helping them build their systems, and just issuing yourself a Doctor of Veterinary Medicine.

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Anthony Caiafa11:43

At some point, someone will give me an honorary doctorate, but I'll wait for that day.

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Interviewer11:49

That is amazing. So you go through college, you build these systems, you get really into building systems. What's your first major job?

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Anthony Caiafa12:00

I had a bunch of them. Way long ago, I started in an internet cafe in South Jersey. We were helping people fix computers, running Counter-Strike leagues, stuff like that. It quickly pivoted into a babysitting job because parents just dropped kids off. I left and went to a couple of different tech companies. I would say my first real tech job was at Publisher.com, focused around online photos, which got bought by Shutterfly. From there, it was startup after startup. The one that brought the most experience and was most interesting was DigitalOcean. We started that with next to nothing, and now it's a massive player in the cloud market.

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Interviewer13:11

I was a big fan when I saw that you were a site reliability engineer at DigitalOcean. I was using them to deploy some Ruby applications, and they were super useful. That was my introduction to the pipeline build deploy. I then got into Heroku and fell in love with that. But I love the branding. They were one of the only people doing that at the time.

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Anthony Caiafa13:49

It was a wild ride. A lot of really smart people came through that place. One thing we focused on in the beginning was simplicity and marketing. The UI/UX was key to that success because what was under the hood wasn't as glamorous as what everybody saw. Over time, it got better as we grew and attracted more intelligent talent. It was a lot of fun. We started in a tiny little room with a bunch of folks hammering away on things. Sometimes my wife laughs because I would come home after four or five days sleeping in the office, deploying code before a venture event. It was a different time, but a massive learning experience, building thousand-server data centers in hours.

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Interviewer15:02

Was DigitalOcean building their own hosting equipment or using a cloud provider?

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Anthony Caiafa15:07

No, we did everything. We would buy whatever gear came in. We looked at it very commodity-based. We would just look for cores, memory, and storage. If you came in at the best price for that gear, we would buy loads of it. We had a ton of automation behind the scenes that helped us stand up data centers and racks. You could stand up a full 48U rack in seven to ten minutes. We did some really crazy things on the networking side too. The networking team was really strong. At first, it was just me and a few people, but then we hired some really smart talent who helped scale it up.

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Interviewer16:02

How has site reliability engineering evolved? That must have been at least 10 years ago at DigitalOcean. What is it like now? Do you follow it still?

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Anthony Caiafa16:16

Yeah, I still follow it. We hire a bunch of different SRE types. I think it's more specialized at this point. We have an overarching SRE organization, and I have a ton of different writings about how I feel these organizations should be built. We have people with focus areas: infrastructure side SREs that are networking-focused, database-focused, big data-focused, or cloud-focused. It's evolved, but people are still trying to form their own opinion on how to deploy it. They've gone through the 'oh yeah, this isn't as easy as the Google book says.' It's not one size fits all, and people are starting to realize that. But the talent is there, so it's definitely growing still.

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Interviewer17:19

I met this startup a few months ago doing something really cool in site reliability engineering called Gremlin. Have you heard of them? Do you like what they're doing?

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Anthony Caiafa17:31

Yeah, they have some cool stuff and some smart people. We have a couple of folks from DigitalOcean who are over there working on the platform.

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Interviewer17:44

Very cool. It's a small world. All the great people kind of collect together, and the relationships between them, even between guests, I find out different people know each other. It feels like such a big world, but then it becomes really small. That underscores the importance of reputation and being a good person because whoever is your direct report today may be the investor tomorrow.

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Anthony Caiafa18:08

That's interesting you say that. I do think that is something young engineers should really understand. I didn't know that as a young engineer. I was very bullish, very argumentative because you just want your opinions to be heard and be in the front of everything. When people ask me, 'What's the one thing?' I say, 'Be humble. You've got to remain humble.' I've been in plenty of situations where that person who reported to you and you weren't very kind, they're the one you're asking for an investment in something. So it's definitely a big thing to take away.

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Interviewer18:52

So where are you at today? You're at SS&C Technologies, right?

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Anthony Caiafa18:55

Yeah, SS&C. As a quick high level, we are a very large organization in the financial services industry. Publicly traded, 23,000 to 26,000 employees globally, 162 offices. We're a big organization.

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Interviewer19:19

What's the problem you solve?

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Anthony Caiafa19:22

We solve a ton of different problems. Our product portfolio is massive. Our goal is to make sure that no matter what vertical you're in in the financial services industry, we can jump in and help you from end to end. We're essentially the plumbing of the financial services industry. Our services range from middle office, front office, and back office accounting, fund management, fund analytics, risk analytics, full BCP/DRS, virtual data rooms, BPO automation, everything the customer needs, no matter what vertical they're in.

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Interviewer20:12

Who is the usual customer? Is it mostly banks and funds, or do you get small family offices?

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Anthony Caiafa20:18

Everything. Big investment banks, big banks, middle-size hedge funds, small hedge funds, high-frequency trading shops, private equity shops, venture capital firms, small mom-and-pop shops, family offices. You name it. We also have an entire health area, SS&C Health, so we do a lot of pharmacy transactions and automation for different insurance providers.

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Interviewer21:02

I think I was talking to a company called Change Healthcare a long time ago, and they were explaining the process of prescriptions and the finance business model. For me, I geek out over that type of stuff. Understanding complicated systems, I can geek out just as hard understanding a code base as I can understanding somebody's business model.

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Anthony Caiafa21:21

They are one in the same at the end of the day. Financial services and healthcare, most of these things, you're just processing transactions at a high volume and reliably. Especially in financial services and healthcare, you can't just drop transactions because that's either millions of dollars or somebody's life. That's something we've focused on for a long time, especially since I walked in here: resiliency and stability to make sure we can process everything accurately.

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Interviewer22:03

I had a financial software company before I did the podcast. We were doing retirement analysis, withdrawal strategies against tax brackets. We put in tons of financial products and modeled hundreds of thousands of scenarios. Looking back, it was a three-year blur, but when you see the suite of tools, it's unbelievable. I sold my interest and started the podcast. I was curious, do you guys get into the data feeds over there, or do you just provide services?

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Anthony Caiafa22:59

Everything. We have every data feed you could imagine coming in from markets and exchanges. We have a whole business called FIX that hosts FIX infrastructures for customers, live exchanges that people can transact on. You mentioned retirement; we're actually one of the largest companies that host all the retirement accounts for some of these large organizations. All the account information is housed within SS&C. The data is so rich. We bought a company called Algorithmics that does portfolio risk assessments, feeding all that data in and looking at portfolio information to calculate risk based on what positions you're going to take. It's definitely really powerful.

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Interviewer24:18

I liked a company a while back called Riskalyze. They had a cool culture and branding. Branding wins me over nine times out of ten. If something's beautiful, you want to walk up to it and experience it.

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Anthony Caiafa24:37

It's really important. You could have the coolest technology under the hood, but if the front-end app is like, 'What is this?' I'm just gonna ignore it.

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Interviewer24:50

One thing that caught my interest when you were talking about how large it is and you have a large product portfolio, you're building this stuff because you have data and you're connecting things. If a new product were to come on the market, how does the information flow given the size of the organization? Where does the back signal go off that says, 'Hey, our customers, we should build this product now because this is emerging in the marketplace?'

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Anthony Caiafa25:24

There are so many different ways because of how large we are. The way our organization is structured, there's constant feedback. We built something called pods. Pods are a way that different folks from all walks of the different business units can come together and share information. For example, if one large customer uses one product set, and we find out through conversations in these pods that they're looking at other product sets we have, those groups come together, talk, host meetings, and put together additional feedback from the customer. They build a strategy around how to address it. That's honestly how a recent product around customer data platforms came about. We had so many different customers, and everybody came together and said, 'Hey, everyone's asking for this particular thing.' We can get requirements and general feedback and start building it. That leadership funnel and organization structure is powerful and key to the success of a lot of these things.

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Interviewer26:59

So it's happening amongst the executives, baked into the culture?

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Anthony Caiafa27:01

Oh yeah. It's in everyone's best interest to make sure our customers are happy. The more we collaborate, the more the customer feels that we're one large organization instead of 50 small organizations.

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Interviewer27:23

When the idea comes up to build this new product based on customer feedback, what's the process to get funding for that within the organization?

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Anthony Caiafa27:29

It definitely depends. It could be where we take one or two or three people off any other given project and say, 'Let's start scoping this out and put together a prototype or an MVP, very small, very narrow scope.' We'll get some feedback from the customers, and if they like that, we'll start putting more teams, more people, more money behind it. We don't want to be in a situation where we have a ton of pet projects and nothing ever comes to fruition. We really focus on starting small, getting something functional out the door in a very small amount of time, getting customer feedback, and if it takes off, we hit the races and put the money where it deserves to be.

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Interviewer28:25

I love that day one mentality. I heard Bezos in a number of interviews, and he constantly talks about how everything they do, they start really small.

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Anthony Caiafa28:37

SS&C, and this is one thing that drew me to the organization, is such an entrepreneurial company. Anybody's ideas, any direction you think you could take to make the customers happier, it doesn't matter what level in the organization you are in, you can bring it up and essentially start forming a product around it and build an entire ecosystem organically around your idea. There are not many companies that offer that level of autonomy. The big thing here is that we are a meritocracy. A lot of people say they are, but we truly are. Bill Stone is our founder, and he is as accessible as any other person at that level. You could email Bill at two o'clock in the morning. He may respond, he may not, but most of the time I get responses. You don't see that often. We're willing to try just about anything because it's whatever is going to help our customer. His heart's in it. He likes what he does, he's living his dream. He and our CEO, Raul Canwar, are so involved and open to listen to just about anything. That's what makes people really drive to change things. Change can happen at the drop of a dime, and that's really cool to see.

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Interviewer30:20

Founders still being at the company is one of my biggest criteria for my personal investment strategy. I agree. I'm a founder myself, I have a company under 20 people. I know what it would be like with a board running it versus a founder. It's never the same.

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Anthony Caiafa30:46

That's a good way to see it. If the folks that started it all bailed, then what's the point? You obviously don't believe in that mission. Sure, maybe you made your money and want to go make more money somewhere else, but if you believed in your product and your mission, you stick around. Bill's been in this since 1986, which is crazy. More power to him.

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Interviewer31:21

It's a hard thing to experience. To really wrap your mind around it, you have to spend time doing something you don't love, then find out if you're doing what you love, and then not give up, keep going, persist, let years go by. These are long lessons that take three to five years to learn. That's why experience is so important.

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Anthony Caiafa31:45

And then think about now. We're a 20-something-thousand-person organization that had to go 100% remote in weeks. That's hard. That's not an easy feat. We're still releasing quarterly earnings and doing really well. This time is crazy, and I feel like without somebody that's been attached to this for so long, I'm not sure if you would do as well.

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Interviewer32:23

I was talking with Harry, the CIO at Zoom. He was so chill and laid back when I asked him about how they went remote and handled COVID. He said, 'We just made it happen.' I wanted a better response. How did you guys do it? What is going on in your mind when you lead the technology part of a 20,000-person organization and you have to go remote overnight?

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Anthony Caiafa32:56

It was crazy. But I would have to say that the team I had around me, everything we did for the past 18 months, really had its time to shine. We were upgrading infrastructure, adding new features, new processes, new procedures, new tooling. It was definitely hectic. We didn't sleep for weeks. We were constantly online. Then into the second week, you have folks that normally would go into an office, and now you have to onboard them with laptops. That's hard because you still need to ensure security. I was out talking to almost every contact I had trying to source laptops. I think that was the most difficult piece. My team built 15,000 laptops in two weeks. That's huge. Zoom was a big part of it. I talked to Eric, their CEO, frequently and thanked him because going on to this platform really helped us with our remote strategy. We used Zoom rooms and hundreds of Zoom breakout rooms where folks could log in, get their problem solved, and hop back out. Our call centers were off the charts. I would definitely say our transition was really smooth because of everything we focused on previously, not in anticipation of this, but the teams came together and it's just really talented.

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Interviewer35:01

Eric's fantastic. He's the picture-perfect way for a founder to interact on social media. He's on Twitter, LinkedIn, jumps into support questions, responds to people, and it's actually him doing it. Their origin story is so cool. Did you ever get into it?

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Anthony Caiafa35:26

No, I won't go into it, but the 10,000-foot view is he was at a GoToMeeting type company. He was looking at this new technology, and they said, 'No, we invested in this other technology, so we're not going to modify the system.' He said, 'Someone's going to come out and do this, and it's going to kill us long term.' He left, got VC funding, and started it. He knocked their socks off.

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Interviewer35:58

That's kind of how all these ideas are born. Some of the largest companies of our time have very similar stories. Not everybody can see the vision. It's a skill that needs to be developed over time.

So you were at DigitalOcean, and now you're at SS&C. How did you meet the SS&C executive team? How did you end up there?

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Anthony Caiafa36:27

I was at Bloomberg before this. I did a bunch of different things at Bloomberg for a while: SRE, building teams, building strategies, building platforms, security architecture. Then I got hooked up with SS&C through a mutual friend. We had a couple of conversations, more than a couple, and it just made sense. They really needed somebody that had financial services experience but also a completely different set of experience, like the startup world, scaling systems in that way, to come in and have a fresh look at how we do tech, how we do engineering, and how to build these teams. I think that's one of the bigger challenges of this role.

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Interviewer37:26

What are your takeaways from building these teams? What have you learned?

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Anthony Caiafa37:34

Every day is a different lesson. Going through this whole thing, the emphasis on culture for us and for anybody is just so important. I used to ignore it for a long time and always thought, 'We're engineers, we'll get through it.' But nope. You have to make sure the people are happy. You have to make sure you can accurately assess their skill sets so you can place them in areas where they can be successful. You have to make sure that you're also, daily, something I do daily, and sometimes my directs aren't the happiest about it, but I go down and talk to anybody and everybody. I'll randomly message people on our chat software and just be like, 'Hey, how's your day going?' Whether they're a desktop support technician or a principal engineer, I'll talk to them, see if I can help, answer any problems. I tell them, 'Look, I've done all your jobs before. I've been there. I've done it. So I may be sitting all the way up here, but I still know a thing or two about how to do these things. Please use me.' I think that's been especially during this pandemic really valuable for them. Other things I focused on were putting together internal collaboration and communication things. We did Quarantine Creations, where everybody came together and showed something they did during quarantine that isn't computer related. Everybody voted, and they got Secret Lab and Oculus gifts. We did one for Halloween, and now we're going to do one around internal gaming teams. Community and culture, I don't care what anybody says, are some of the most important things you could do, especially in this role.

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Interviewer39:42

Do you drive that initiative yourself, or do you have someone on your team that's really strong in that area?

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Anthony Caiafa39:50

It's me. I drive it, but I take the feedback from the group. The way I built the team, my whole vision for my directs has always been engineers first but leaders after. I don't want somebody that's just a people leader. That's just not interesting to me. I need folks that can dive down into the weeds and understand the problem space instead of just delegating everything. I like to have good conversations. A lot of them come from so many different walks of life and companies that they have really good opinions on culture, collaboration, communication, and how to build these things. That's where our pods concept came out of, lots of thinking, reading, research, and getting feedback from the team, the business people, and everybody.

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Interviewer40:55

I like how you mentioned engineer first. They have that capacity to traverse ideas in a specific way, to look at things like schematics if they need to. That's a really useful skill. The first time I ran into a purely manager person, I was blown away. They almost took an 'optimism, it'll all work out' route. I was like, 'That's great, but we actually have to do the work to make sure it does work out.' That was my introduction to a new style of person. It stretched me a lot.

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Anthony Caiafa42:05

You gotta get along with everybody. For me, one of the big things is if I can't have an in-depth technical conversation with you or understand how you approach problems analytically, it's really difficult for me to understand how you could be a technology leader. I don't knock people leaders; I think they're super important. But when you're in in-depth tech roles, you definitely need to be able to talk to a lot of the problems. How do you translate what the business needs into a raw technical way of what we need to do to actually accomplish it? It's important. There's value in everybody, and it's really understanding how to learn the person and read the person.

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Interviewer43:16

Reading the scenario, knowing what each company needs, what each team needs, it's going to be specific. When people ask about team structure, I say it's heavily dependent on business model. The two-pizza teams, the A teams, however you want to brand it, you just have to do the work.

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Anthony Caiafa43:41

You gotta dive in. One size does not fit all. There are so many different parts of tech and engineering. When they're an engineer first, they bring a different perspective to problems. You're never going to have folks that are complacent with 'it's always the way we've done it.' If it's always the way we've done it, maybe it's wrong and you need to fix it and address it differently. You have to figure out a way to come up with a solution and get people behind you to help see your vision and build it.

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Interviewer44:24

Did we finish the story about how you met the executive team at SS&C?

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Anthony Caiafa44:35

I'm not sure, but as a quick thing, they were looking for somebody with a big financial services but also startup background. Raul and I had a mutual friend. He said, 'Hey, there's this company SS&C. I never heard of them, but he's a good friend of mine and he's looking for a CTO to come in and really shape the way technology needs to be at this organization. They don't necessarily just want a people manager; they want somebody that has the technical skills and abilities.' I said, 'Okay cool, I'll go have a conversation with them. It doesn't hurt.' Raul is the type of guy that when you meet him, he runs such a big organization and is very humble and very smart. The biggest thing for me why I came over here was Bill and the executive group. They were behind change. They knew change needed to happen. And it's history, I guess.

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Interviewer45:48

Where is Raul today?

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Anthony Caiafa45:50

He is the CEO. He runs the entire business. He's still engaged just as much as I am.

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Interviewer46:02

If we were to take your current way that you're spending your time and divide it into a pie chart with three sections, what are the top three ways you're spending your time?

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Anthony Caiafa46:10

I spend my time in so many different ways. Some of the big things for me, I traverse through so many domains all day long. I could wake up on any given day and focus on contracts, budgeting, building out new data centers, figuring out all the things that need to go along with that. We could be dealing with team planning, team structures, team organization, and what we need to do to build out the different products and platforms we're focusing on. Getting status updates from groups and going out to find technologies that would help SS&C grow, if we're potentially M&A-ing it. If you see our history, we buy a lot of companies. I'm spread really wide. I'll be with customers. My week to week is very variable. Nothing is consistent.

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Interviewer47:43

It's like you're a founder. I was talking the other day to my wife. She asked if I would ever go work for anybody. I said probably not. If they gave me a large bucket of cash and said go do what you want to do, then I would. I like getting to do that. Negotiating real estate contracts is actually kind of fun.

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Anthony Caiafa48:09

I love it. I'm negotiating contracts all the time. One thing to know about SS&C is we own our data centers. They're 250,000 square foot facilities, big 30-megawatt facilities all over the place. When I tell you my days are very all over the place, busy, and crazy, it's the truth. You have to run and be able to understand so many different verticals in business and technology and how to bridge them correctly. It's a lot of fun.

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Interviewer48:59

Have you gone down the rabbit hole yet of DNA-based data storage?

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Anthony Caiafa49:05

No, what is that?

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Interviewer49:08

It is the future, my friend. I have been watching this little market emerge over the past three years from an MIT project to getting out of MIT, getting external funding, doubling and tripling. The one problem they have is the speed at which you can read and write data to DNA, but the density is pretty interesting. I think a football stadium worth of servers can be condensed down to DNA data the size of your hand. The business use case is long-term storage. These companies have backups on tape, and those are only good for so many years because they degrade. They have to recopy them. It's a money pit. If you had persistent storage that would last hundreds or thousands of years, that was the concept. The barrier was the speed of reading and writing. This spin-out built all this technology, and now they can write Wikipedia content in a very short period of time. A few weeks ago, a major Fortune 50 company's CTO left to go work at their startup to take the product to market. The company is called Catalog DNA. It's pretty cool.

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Anthony Caiafa51:04

That's pretty cool. These types of businesses are pretty awesome. There's not many things in our generation that are overly awesome. Obviously, some of the stuff SpaceX is doing is really neat. Some of the other ones aren't that interesting. Facebook? Yeah, grandparents love Amazon.

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Interviewer51:47

My son the other day, I didn't even realize it. He knows what my wife orders him for Christmas because he'll go to Alexa and say, 'Alexa, show me the deliveries.' He said, 'Mommy, what's this toy?' I was like, 'Oh boy, we gotta unplug it.'

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Anthony Caiafa52:10

They are smart. The Alexa stuff, David Zbitski, one of the tech leaders over at the Alexa project, I've talked to him a couple times. One of my favorite takeaways is you can ask Alexa, 'Why did you do that?' and she'll actually tell you.

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Interviewer52:28

Really? I'm gonna do that. 'Why'd you do that, Alexa?' She's like, 'Because I love you.'

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Anthony Caiafa52:39

The Zoom thing is new. We've been doing Zoom birthdays, Zoom this, Zoom that. We had a Zoom birthday party right in the middle of the pandemic. I said, 'Everyone want to be quiet for a minute? I just want to tell everybody something.' I said, 'Alexa, order me a thousand batteries.' And you hear everyone's Alexa going off, 'Which batteries would you like to order?' It was pretty funny. I messed everybody up.

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Interviewer53:18

That's crazy. I want to get into a couple more leadership things. I have these prep calls and come up with questions, and then after I get to know you, I want to hear what you think. What are you learning right now as a leader from a tech or leadership perspective?

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Anthony Caiafa53:49

From a leadership perspective, especially during this pandemic, one of the biggest things I've been learning is that checking in on people is really important. The mental health of individuals is something I never thought about. Now knowing that there are people stuck inside their homes, not going anywhere, not having anybody around them, those are the types of people to check in on. Being able to change somebody's day even the slightest amount is monumental. Being more personable, getting down and letting people know they can come and talk to me, and focusing on them, I think is one thing I've learned big time from this. We could talk about being an inspirational leader and all that, but I don't think it's as important as making sure you realize you put your pants on the same way as every single person. Nobody's better than anybody else. You should make sure people know you're there. I think that's really important, especially as a leader.

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Interviewer55:19

I love that you say that. I was thinking a lot about spending time with somebody. You mentioned earlier you reach out and talk to people. Caring builds trust and relationship. It's like a bank account because you can spend that. I noticed there's this currency you build with people. Sometimes I'll be slacking and go to type a message, and I'm like, 'I don't have enough social currency to be doing this with this person right now. We need to get on a call because it's been five days since I've had a personal call with them.' I know they're going to interpret this the wrong way because it's text and lacks context.

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Anthony Caiafa56:10

I hear people say, 'Oh, I do office hours.' It's not the same. Just because you sit on a Zoom and answer a couple questions, people are struggling. That's why I do those little things and reach out. I do these little competitions for the group. One thing I'm doing now, completely on the side, is working with our different vendors to source a handful of PS5s and a handful of new Xboxes. That's cool. If people can find a way to compete for those things internally, how many places are handing those things out? Even if I have to go buy them myself, I'll go buy them myself just so folks know we value you.

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Interviewer57:06

It's one of the best investments you can make. When I'm taking care of myself, the quality of work I'm producing at the rate I produce it is vastly different than if something's not working at home. Having relationships that are healthy and good at work can definitely help you get back in the zone or realize everything's going to be okay around people who care about you.

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Anthony Caiafa58:08

It is. I think also understanding that it should go without saying, but I don't think it does in most cases, everybody's a human. Everybody has their own problems. Nobody's problems are bigger than somebody else's. You have no idea what somebody's going through that given day. Even dropping a 'hello' or 'hey' changes things for people. Especially people in these big roles, you get a CTO that drops in, manages thousands of people, and just says, 'Hey, how's it going?' It's important.

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Interviewer58:51

It's hard to remember that too. We get to have a lot of awesome people on the show. One thing I'm realizing is this is a lesson you just learn over and over: everybody's just a person. You and I get off this and go do the rest of our lives. It doesn't stop. We're just doing our next activities until we come back next year and have another conversation. Sometimes you forget that you are the CTO and you can go talk to somebody else, and they think that's a cool thing. If you were to think about yourself like that all the time, you would be somebody nobody wants to spend time with.

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Anthony Caiafa59:38

That opens with being humble. We went from talking about macros and working out, pivoting into leadership and discipline, and then you can pivot back to focusing on being humble. You walk into a gym or go outside and run. 150 pounds, 135, whatever it is, it doesn't care if you're a CTO or Jeff Bezos. It's just there. It's about being humble and understanding that at the end of the day, we're all just a billion cells trying to figure it out for a little while.

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Interviewer1:00:17

Preach. I love it. That's why I have such a high respect for discipline. When I see people who have discipline, I like being at the gym and being around those people because we are doing the difficult thing. It's equal to all humans. It doesn't matter if you're a girl and five foot three or a dude and six four. The discipline is the discipline, and it's hard. You can see how long they've been doing it too. I've been doing it for a year, but I go to the gym. Look how big that person is. They've been doing discipline for 10 years.

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Anthony Caiafa1:00:58

There's so much motivational things to listen to around it. Talk about discipline yesterday. My wife, she's pregnant, so she comes to me and says, 'It's time for me to work out.' I said, 'All right.' She said, 'Or we could just go to Chick-fil-A and eat Chick-fil-A.' I was like, 'Damn. Let's just work out and then get Chick-fil-A.' It's important that you don't shut it down and that you kind of play with it. 'Oh maybe, but we should probably do this' versus 'no,' because then my wife would just cry and hate me. You gotta cater, man. Know your audience.

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Interviewer1:01:33

I'll tell you what, it definitely pivoted quite a bit after I had kids. You look at things really different. I think it really happened after I had my daughter. It was like, what happens if somebody talked to my kid that way? I'd be super pissed off. Your compassion definitely grows, and your patience grows tremendously. Trying to get a three-year-old dressed or to eat dinner, it's like, the most beautiful thing is how raw it is. I like to compare it to computers of the 1960s, the size of a room, you can see the transistors and touch everything. It's so obvious what's happening. As they get older, they become microprocessors, and you can't really tell what's going on. But the emotions, the negotiation, it's amazing.

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Anthony Caiafa1:02:47

It's crazy. She doesn't know what I do. It's great because it just doesn't matter to them. They're like, 'Yeah, okay, well that's cool. I'm still going to throw this macaroni at you.' I'm like, 'All right, no problem, dude.'

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Interviewer1:03:04

One thing that's interesting that I didn't know when I was younger and that I know now is famous people are not famous in their everyday lives. When your name's on the marquee and you're on the stage talking to thousands of people, you're experiencing that in that moment. But then the event's over, you drive home, and you go to the grocery store. It's just life. You get in your car and press the pedal the same way everybody else does. That's why you gotta be humble. I've met some people along the way who are not humble, and it's very irritating to sit around and hear people talk about themselves for hours on end. Who knows what will happen tomorrow. It's not promised.

Anthony Caiafa - Leading Teams From 3 to 3,000 People

About Anthony Caiafa