Episode 16 | December 22, 2021
Aaron Rankin, Sprout Social Co-founder and CTO
Aaron shares an open and honest reflection on how growing up in humble circumstances shaped him into the person he is today.
- Growing up & struggles with money (1:41)
- How Aaron’s childhood informs his parenting (9:26)
- First jobs & early drive to hustle (13:18)
- Falling in love with computers (16:35)
- Some influential professional figures (25:34)
- Changes in how he tells his own story (29:36)
- Finding intrinsic motivation as CTO (45:33)
- Becoming an investor (54:53)
“I think that the story has always been the same, but I think that the way that I would have told it has changed over the years, and the reason for that is I think that just as I've gotten older, I've gotten a lot more comfortable with who I am.”Aaron Rankin
Luke [00:00:03] This is the Atolio Conversations. I’m Luke Alie. Today, we’re talking with Aaron Rankin. Aaron is a co-founder and CTO at Sprout Social, a provider of social media management solutions. In this episode, Aaron talks with us about his life, which goes from growing up in a household where money was tight and a source of strain to eventually co-founding a hugely successful startup. This is a longer episode than some of our others because we really take the time to dove into the stories behind some of the formative people experiences and ideas that have made Aaron who he is today. And I just want to say that I am so grateful to Aaron for his openness and candor in talking about his life and his story. So with that, please enjoy my conversation with Aaron. Aaron, thank you so much for coming on the podcast to talk with me today.
Aaron [00:01:11] Yeah, it’s really great to be here. I’ve listened to a few of your past episodes. You had some really exciting guests. I’m just excited to be here and share my story with the community.
Luke [00:01:21] Yeah, absolutely. So that stories, the stories are really interesting one. I’m really excited to talk about it. Um, let’s let’s really zoom out and talk about some of the more formative things in your life that that kind of have made you made you who you are today or taking taking you on the path that you’ve you’ve gone on.
Aaron [00:01:42] Yeah. And I’m happy to share my background. I mean, I think. Anyone, you know, as an adult professional trying to reflect on how they got to where they are, you know, it’s going be really hard to pinpoint exactly what that path was. But when I try to like reverse engineer it, you know, I think I go all the way back to honestly like kind of my earliest memories, you know? When I was five, my my mother got married, which means that for the first five years of my life, I was raised by a single mother she. She’s the first person, her family to their immediate family, you know, four of her parents. So where they’re going to college, she got into University of Pennsylvania and within a couple of years. Unfortunately for her, fortunately for me, she she became pregnant with me and, you know, dropped out and raised me as a single mother. She got married when I was five as I shared, and between her and my my non-biological father. You know, they I think just they really worked their butts off to try to support a family. I mean, there were times when my my father was working three jobs simultaneously, like, I really don’t know when he was sleeping and he basically was sleeping any time he wasn’t working. And so, you know, anyway, like if I go all the way back, I think the first thing I start with is like, I saw the struggle of my mom, you know, raising me as a single mother. My, my family, you know, as I kind of grew older, my family wasn’t poor. We weren’t poor, but money was always tight and money was the stress point in my family. If my parents thought about anything, it was this probably money. I don’t really feel like I had a deprived childhood. I think I had a pretty great childhood. But seeing struggle and as a kid, just feeling wanting, I think was something that that I knew, you know, from from very early on, you know, just I remember in my neighborhood just it was not something that I talked about, but I could. I was sort of very conscious of differences in people and status. You know it just in my in my in my working class neighborhood where I grew up outside of Philadelphia. Still, there are, you know, there there’s kind of disparities. I remember just, you know, kids at school wearing the cool new like years. And my family just buy me whatever, you know, whatever they can afford. Kids would point out when they had a nicer bike than you. Families have nicer cars and and and all this kind of stuff. And so anyway, I think what you know as it naturally, as a kid, you know, kids are always wanting things, you know, toys and so forth. And I think because I couldn’t just get that from my family, my parents wouldn’t just buy me anything I wanted. It really, I think, encouraged me to to build some self-reliance. If I wanted something, I was going to have to have to get it for myself. My parents weren’t going to give me an allowance or spending money or just buy anything that I asked for or so. So I think it really I think it really starts there
Luke [00:04:53] to to have that as a stress point. And for your response to that stress point to be something that comes from a place of self empowerment and self-sufficiency and self-reliance, like you’re saying. Is there anything that you think? Else in your childhood or do you feel that it’s more of just an innate quality to sort of respond to that stress with like grit and determination and self-reliance and that kind of attitude that that sort of perspective on it? Or do you think was there anything else from that from that early, early age that kind of comes to mind about kind of early examples or lessons or people that you saw that were kind of leading leading that?
Aaron [00:05:40] Yeah, I mean. It’s yeah, it’s it’s hard to unpack. I think there’s a couple of things here. One is being an only child for five years, I think, and with with the single mother who is busy all the time working. I just naturally developed a sense of sort of independence and, you know, both in terms of like entertaining myself and and also just wanting to do things for myself, like as much as possible. I mean, we lived with my grandparents and I just remember, like wanting to help out around the house as much as possible, cooking, cleaning, whatever it was and also for myself, like wanting to do whatever I could for myself, put on my clothes, tie my shoes, you know, bathe myself, whatever, whatever it might be. I just sort of wanted that, and I don’t. It’s probably somewhat in my circumstances. I don’t know, just not always having adults support me, I think, and perhaps just having some pride in, you know, accomplishing things on my own. But I think as I got older, this kind of combined with, you know, as I shared, just like, you know, being very kind of status aware and not having everything I wanted, you know, when I saw people who had achieved things, you know, meeting successful professionals every now and then, like, there weren’t a lot that I met in my life. But when I did, it was like such a stark contrast from other people that I had ever met that something I don’t know whether I didn’t know whether or not I really understood their story. I presumed that they just worked really hard and they studied really hard and were very disciplined. And that’s what got them there. Whether or not that’s true, I don’t know. But that was my. Interpretation of the situation, and I think, you know, as a kid, kids are generally not all that disciplined, and I think seeing adults accomplish things and presuming that’s how they got there, I think gave me some encouragement and catalyzed maybe a little bit of that in the way that I learned about things from as soon as I could. I, you know, I look for ways to make money for myself at the earliest age possible. I was trying to get a paper out. We had a local newspaper where kids deliver the newspaper and it was kind of an under the table job and I finally got one of those and I was 11, which was awesome. I got to make, I don’t know, thirty dollars a week or something delivering newspapers to, you know, that reported on high school football and whatnot. And and you know, when I was 14, I grew up in Pennsylvania. So when I was 14, I could get these things called working papers, which let me apply to some real jobs. I applied to our local convenience store, which for anybody in that area is Wawa is a very popular convenience store. But they said, Hey, you’re 14 years old. We’re not going to trust you to, like, run our cash register and stock our shelves. So I was reading the classifieds in the newspaper, you know, back then before kind of before the internet. And I saw this like ad for a web marketing role. It actually applied. I applied to that job and somehow somehow got that job making web landing pages for a dot.com startup. But bam and kind of getting ahead of myself.
Luke [00:09:16] No, no. I mean, so I want to get back onto to your journey. But while we’re kind of talking about these, these like early years in these kind of first steps, has this changed your perspective on how to like it, especially the story of kind of the circumstance that you came up? And has this changed your perspective on parenting as well?
Aaron [00:09:38] I don’t know if it’s changed. I think it’s I think it’s solidified my perspective on parenting. So I have two younger children, a seven year old girl and a four year old boy. And I think that the way that I parent and what I am encouraging them is very much just trying to replicate the way that I am, whether that’s right or wrong. I have just I see that that’s like my natural inclination encourage them to be independent. Help them feel confidence. And to celebrate when they’re able to do things for themselves. I mean, my seven year old daughter. This morning and for a couple of years now, she will make breakfast for her and her brother, and she’s just so, so capable, so independent and certainly like, I’ve encouraged that my wife’s encouraged that. But there’s something also innate, I think, in her and I don’t know if she got that for me or whatnot, but there’s just something about her where she, just like very much wants to do things on her own really takes pride in that. And so, yeah, I think that to you to answer your question. I think that’s it has influenced me. And the other thing is. My children are growing up in a completely different circumstance than than I did or than my wife did. My wife’s an immigrant and her parents came here with very little. So she, I think, you know, she had a somewhat similar view as a child. And I think that’s something that we struggle with is not not having grown up in a situation like my children are in. We’re unsure of how the environment that we’ve given them will shape them, and I think it almost. Forces us, it causes us to to go is maybe the wrong way to describe it, like at times to try to deprive them a little bit and and sometimes to make hyperbolic statements about their circumstances or a sort of untrue statements so that they feel that they’re worse off than they are, if that makes any sense. This morning, my son was washing fruit. He’s four years old. He’s not all that careful. He left the water on while he was just doing something else. And I like quickly was like, Maxwell, you are wasting water right now, buddy. We don’t waste things in our family. That’s, you know, that’s you’re throwing money down the drain. How are we going to buy food if you throw away all of our money? And I’ll say things like that to them suggesting that like, we’re right on the edge of poverty. And like, my daughter has really taken that to heart, and she understands that it’s not true anymore. But she’s still like she has taken these things to be tenants of how she operates. Like, we don’t waste electricity. We don’t waste money. We’re going to take care of her things. We’re going to be grateful for what we have. I didn’t need to be told that as a child, it was just like obvious. But anyway, so yeah, I think that it has absolutely shaped like parenthood.
Luke [00:12:38] Yeah, yeah. Sort of being able to still convey that sense of not taking things for granted. Yes, but not from a forced environment or forced circumstance, right? Or like a unnecessarily painful one. You know, if you’re if you’re able to avoid that. But that’s that’s I I’m really happy to hear that though, that that stuck with you, you know?
Aaron [00:13:01] Yeah, I mean, it’s just it’s built in. I can’t I can’t shake it.
Luke [00:13:05] Yeah. Yeah, yeah. Fair. Fair. Awesome. Also. Let’s well, let’s jump back on on on to your story, though. So yeah, you you started this. You landed this job doing this. This this web development job, right?
Luke [00:20:05] Wild. Absolutely.
Aaron [00:20:06] So just kind of weird.
Luke [00:20:09] Yeah, for real, there’s just that like, it’s so funny. I think that’s so funny to hear that juxtaposed like also with what you were saying about like you just wanted a Nintendo and then you kind of get this other machine, but it still scratches the same itch somehow, and it just some and still then sweep you on this like really wild bath.
Aaron [00:20:27] Had I gotten the Nintendo or had I gotten both, I think I would have just played with the Nintendo, and I have no idea where I would have ended up, but instead I got this machine. And yeah, it was. It was the best toy I had. So that’s the one that I played with. You know, I think you might have asked about, well, you know, we were talking about circumstances and, you know, if there keep key people or, you know, inspirations, yeah, I think that it’s just reminded me, you know, as as I became basically playing with this ploy for a couple of years and having like my my parents and relatives become aware of the fact that I was like really into this thing. It started to become like part of my identity. I feel or that’s how other people saw me, like in my family. And at some point I spent a weekend visiting a relative is a guy who’s my mother’s cousin, so I think of him as my cousin. But you know, technically he’s my mother is my mother’s generation. He he was from San Diego, and he happened to be on the East Coast for a little while, doing doing some work, and he was a professional programmer. And so spending time with him, just like poured gas on the fire because I, first of all, he had really cool toys in the sense that like he had a proper modern laptop that had like a modem thing that would pop out of it and you plug a phone line in and he was dialing in and doing all sorts of stuff that I didn’t understand. And then on top of that, his lifestyle was just way different than my family’s lifestyle. He had he didn’t have a fancy car, but he had a new car. He lived in an apartment. You know, he’s this is like a temporary work situation. But the apartment he he lived in was much nicer than the home that I grew up in. I remember there was some comment that weekend about my my one of my aunts said something to him about like, Andy, you know, why do you why? Why do you buy the fancy napkins? And he was like, I studied hard so that I could pay for these fancy napkins. And I was just like, That’s amazing. Like the fact that you have the discretion and discretionary income. So I just, I don’t know. Upgrade your napkins that just like, really made it clear to me that I need to work in software engineering because that’s what he’s doing and it’s working for him. And I love this computer stuff. So like. I didn’t mention, but like growing up, I was like obsessed with baseball, and for a little while, all I wanted to do was be a baseball player. But, you know, I quickly realized like I wasn’t athletic enough to do that. But then having this love of computing and then seeing him have this great lifestyle and also seemingly like loving his work, it was just like so obvious to me that that’s what I wanted to be when I grew up. So I feel I feel really grateful that like all these things came together and it was clear to me because I mean, I. I think most adults don’t know what they want to be when they grow up, but somehow I just knew it was just so excitingly obvious.
Luke [00:23:41] Yeah, and it was a combination of things. It was a combination of your circumstances, followed by seeing somebody living out a certain example of it, but also just you having type one fun, like enjoying doing your own, like playing with that stuff, right? Exactly. And so it really just came together as a way for you to follow it. That’s so and it’s but you also and then you also further than that, you took the initiative to then like, do something like apply to this web development job, right?
Aaron [00:24:10] Yeah, that was so ridiculous to. I mean, literally like, I see this ad in the paper and then I jump into Microsoft Word and they had all these templates of documents and stuff. And first of all, I just wanted to play with all the software on this new computer. So just being able to use word for real was exciting to me. But to apply to this job, I had to build a write a resume. So I created a resume for myself, and I think I put like Paper Boy on there. And, you know, I shared like the fact that at my church I was doing like avy work and whatever I could sell about myself, I sold. I wrote a cover letter like, and I like to apply for these jobs. I just did that. And I think that they actually I don’t know why they even called me, and I guess they just didn’t have enough people to play this job. But I remember like going into that interview and, you know, my mom drives me there and escorts me into the office. And I think the the people at reception that were there to greet me, like, understood that I was a kid. And you could just tell that they were just amused by the whole situation. But but they weren’t doing it to just, like, have some fun like, I think they were actually at least I received it as like they were seriously considering hiring me. And so, yeah, what a great experience for a child. Like, it’s a big confidence booster. I think
Luke [00:25:33] so. And you described like a couple of more jobs that that followed that as well. Yeah, there any were there any people or any stand up not to say like, Oh, there’s one person who like you have to single out isn’t like that, but like, you know who who comes to mind in terms of really influential figures during those those times?
Aaron [00:25:50] Well, yes, you know, that first job was 3Com was great. And ultimately, when I like, I shared when I was in high school, I got a job at this company, e cal. And there are just so many awesome influences there. So this is like I know, 98 99 e cal was just this like really hot Philadelphia startup. So you go into their offices and there’s just so much energy, so much excitement. They had a ton of venture funding, like from my perspective, they were just crushing it. And when I first got into this company, like I didn’t know anything about corporate environments, I didn’t understand hierarchy. I didn’t really understand roles, none of this stuff. But it quickly started becoming apparent to me like, who is important or who the boss was? And that made me very curious about these people. And so as a programmer, I got exposure to their CTO, who was one of their founders. And just this idea of like this is an engineer who created this company was just very intriguing to me. Like, I really want to understand whose person was and what they did all day. The other half of my role doing I.T. work, I just I’m just running around the company, fixing people’s computers, setting up computers, whatever, and I would spend a good amount of time with the executives in particular. Like I spent some time working on the CEO’s computer from time to time. And I was just really intrigued by who he was. And just it gave me some understanding of, like, I don’t know, entrepreneurs and business people in the backgrounds that they might come from and just hearing the way that they would talk about their business hearing just regular hallway banter. It was like this whole, I don’t know. It’s like it’s like I walked into this world that I thought was completely new to me. And so I don’t want to say that like, I spent tons of time under their wings and they were like very personal mentors. But. I think I just had this personality where I was always looking for. Like, drawn to role models or like looking for role models. And being in that environment, I mean, I encountered so many, but I was acutely aware of like the founders and the executive team, and they were just different adults than any adults I’d ever met before. Not to disparage my local community, but I grew up around it. Like I said, a lot of working class folks, you know, tradesmen and so forth. And they were they were talented, but these people were like, intellectually talented. Like, the idea that they would express were just like on a new level. And so anyway, I think that. That their influence not only excited me about just working in software, but I think that that to me, if I go all the way back, that was the first time I ever thought about the idea of starting a company, and I don’t think I thought about it as like, I’m going to go do that. I thought about it as these people did something that I’ve never thought about doing. And. I find them very appealing and and and interesting and. And I think it just. I don’t know at some point I think that that turned into something more. Definitely not at the time was I thinking, I need to go start a company. But but their example stuck with me, for sure.
Luke [00:29:36] It’s kind of a weird question. You have like a very you seem to have a very clear kind of sense of this, this sort of path in this narrative for yourself. And I was curious if your the way that you’ve told this story about yourself and about your kind of upbringing and circumstances in these these steps that you’ve gone through your life, whether or not that story that you’ve told yourself or that that version that you kind of see in yourself, if that has changed over time or.
Aaron [00:30:08] I think that I think that the story has always been the same, but I think that the way that I would have told it has changed over the years. And the reason for that is I think that just as I’ve gotten older, I’ve gotten a lot more comfortable with who I am. And I also think that, like having any level of professional success has given me the confidence to be open about my background. I think what this is something that I’m a little bit ashamed of, but like when I was younger, I think I didn’t want to admit where I came from. I, I, I saw where I came from as being so different from where I wanted to be that I was so afraid of admitting that I could be somebody different. I just socioeconomically. I just saw myself as jumping from one segment or one kind of class strata to another and I didn’t want. People to think I didn’t belong. I didn’t want them to think I was not one of them, and so I almost hid from it like I would just not talk about it. I didn’t want to share it. I was. I didn’t want to bring friends home, things like that. And again, I’m just saying that I’m a little bit ashamed, but at some point, I don’t know. I just got to the point where I just didn’t care anymore like I. Felt good about enough about myself and comfortable enough myself that I realized, like no people will judge me for who I am, not where I came from or something, but but it goes all the way back to like I was sharing in the beginning as a kid. Like, I just remember being judged for not having the cool shoes. And so like, even in that environment, you know, you’re not necessarily being judged. I just grew up around and in these with funny enough, like in these like very humble circumstances where even there, where everybody was pretty much socioeconomically the same people wanted to be different. And um, and they would make you kids would make you feel ashamed of not having as much as them, even though like nobody’s comparing like net worth, there’s something there, just like your shoes aren’t good, so you must be poor and I’m going to pick on you for that. So, yeah, to answer your question, I definitely have said it differently over the years, but I didn’t. I didn’t necessarily lie about my circumstances. I just wouldn’t share about it.
Luke [00:32:21] Yeah, yeah, yeah. There’s definitely a certain irony to, you know, having the hunger to get those new shoes drive you to finally get them. And then by the time you get the cool shoes, you’ve probably learned enough along the way that you’re kind of like, Oh, these shoes actually don’t even matter that much, you know?
Aaron [00:32:40] Yeah, yeah, exactly. Yeah. I mean, even back, probably the time I was a teenager, I just didn’t care as much. But yeah. But there’s also I think some of it was just like this feeling of of of shame or something or, you know, wanting to fit in. But another thing was just that I was always so forward driven that I didn’t need to look in the rearview mirror or even share that I was just focused on like, what’s what’s what’s about to happen, not what has happened. Yeah, it’s just kind of built into me too.
Luke [00:33:15] Yeah, absolutely. Well, so let’s talk about where that kind of let’s go back to the kind of, yeah, where we were, we kind of left off and where where did that forward momentum kind of take you after after those, those jobs?
Aaron [00:33:30] Yeah. Well, you know, I mentioned my my mother’s cousin, Andy, my cousin Andy. He was on the East Coast, not really East Coast, but he’s on the eastern side of the country, coming from San Diego, doing a stint with Carnegie Mellon University in Pittsburgh, Pennsylvania. And when I spent that weekend with him, it was in Pittsburgh. So I grew up in Philadelphia, which, if you’re not familiar with Pennsylvania, is three hundred miles from Pittsburgh, so very far apart opposite ends of the state. Culturally very different. I had no exposure to Pittsburgh. And so when I when I spent that weekend with Andy, I shared, you know, just how it just made me made it clear to me that I wanted to grow up to be a software engineer. And he introduced me to Carnegie Mellon University and not coming from Pittsburgh to know a thing about this place. He was like, If you want to work in software, this is the kind of school that you need to try to go to. And so that just made me aware of CMU, and I came to appreciate and learned CMU was just on the cutting edge of computer science and engineering and had been for years and was just a highly respected university in that space. And so that, you know, when I eventually applied to college a couple of years later applied to Carnegie Mellon, I I was a good student, but not a great student. I would just do the minimum I could to just kind of get an A or B, and I was happy with that. And basically, if I did the minimum to ensure that my mom wasn’t on my back. But but no more because I really did not enjoy the subjects that were being taught in school. So I didn’t know that. I didn’t think I would get into Carnegie Mellon, but I I somehow I did. I think I just just gave it in. And so I was very fortunate to be able to go there, and I just feel like I owe so much to that experience. I mean, I learned just an immense amount in class, but I probably learned even more, you know, outside of class. Again, as I said before, like, I’ve just I’ve always been so sure I was younger. I was just like very impressionable about the people. I was very selective about the people that I wanted to be around, but I was very impressionable in just being with them. And so, you know, I just I met some awesome people, their students, professors, et cetera. It was just such a challenging and rigorous place which really like pushed me in that way. Like, you know, I couldn’t I couldn’t just kind of I couldn’t. I couldn’t fake it there, like I couldn’t high school. But in going through that challenge, going through that rigor, like I think it was also a very confidence building place, you know, and exposed me to just such a kind of broad and diverse set of people and backgrounds. But they all kind of had this common thread of working hard and being ambitious. And so, so anyway, you know, while I was there true to form, despite having just like a crushing course load, I still hustled there. I mean, I ran a little website development consulting business where their local Pittsburgh organizations that needed like little web apps and websites, and I would build them for them. And I I did lamp programing for research groups on campus and all sorts of stuff like that just to keep earning money and frankly, paying for my college. I mean, my parents didn’t pay for my college. I took out loans, so I didn’t need immediate cash. But but I still, I think in college I was earning 20 or 30 grand a year coding and just by like, first of all, like trying to like, live a greater lifestyle than I should have been living in college. Meaning just like going out to restaurants more and just wanting to feel like I was an adult, but also like paying down my loans as quickly as I could as well. So anyway, I think the esthetic, you know, certainly the education, but the the experience and the people that I met there were just so kind of influential. It, you know, I think also, Kim, you just. Opened a lot of doors career wise, and you know, the first of which really was when I was a junior, I got into one of the most prestigious internships in the country, which is called IBM Extreme Blue. Not a lot of college kids want to work for IBM, but extreme blue was just like was highly, highly, highly respected and I was able to take part in that program. And I mean, besides the work experience, I just met really incredible people through extreme blue who I still stay in touch with to this day and have shaped my career in so many ways. You know, that extreme blue experience also led me to start my full time career after college at IBM. I chose that job only because it paid the best. This common thread early in my life of just wanting to earn more, and maybe that wasn’t. I think I learned within a couple of years that wasn’t the best reason to make that choice. That was when I started realizing it wasn’t just all about money. But that experience. I think even though it became clear in a year or two that it wasn’t the right role for me, I needed to go through that to see that I needed to see what it was like to. I mean, this was a very technical role, but it involved no programing, and so right off the bat, I’m like, Wait a minute, I wanted to be a software engineer. Why am I doing this? Oh, because it pays better. All right. Oh, because it lets me work with execs all the time, do I? And that feels like it makes me feel like I’m important or something. I think it started making me examine kind of extrinsic versus intrinsic motivations for the first time in my life. I was always seemingly intrinsically motivated, but it was always tied to intrinsic things. And so it worked. There was a harmony there. I wanted to earn a lot of income, and I knew that software engineering can do that, but I loved software engineering. But at IBM, I wasn’t doing that. I was doing stuff I didn’t like doing. And so I think I had to go through that experience to know that it wasn’t right for me and in particular, like I wanted to build things and I wasn’t doing that there. The other thing IBM really showed me was, I knew that if I wanted to build things, it wasn’t the right place to do that. I saw that there were really awesome at research and laboratories, but not commercializing those innovations necessarily like in many ways. I think there’s a lot of parallels between IBM and Xerox Parc. Like, so many awesome things have been invented there that you wouldn’t even realize, and it’s because other companies have figured out how to bring them to market successfully. But but anyway, going back to that, that internship with IBM. The connections that I made there led me to the role that I went to after IBM, which is with this really buzzy Boston based startup and DECA, one of the people that I met at the internship, suggested that I apply to and deca. He was working at IndyCar. And so I landed the job there, and that was just that brought me back to my roots from from the Dot-Com startup scene because Indica was in 2005, 2006, that super hot startup. It was such a fertile place, just so much raw intellect, hustle, tenacity, founder, culture everywhere and not just among the founders like everyone at that company, was a builder. And frankly, like now, there are so many. There is an IndyCar mafia parallel like PayPal Mafia. There’s a bunch of unicorn and high potential companies have been founded by former and deckhands post, which just went public. The guy that brought me to IndyCar that encouraged me to apply to Dacca is one of the most founders salsa fi jellyfish shoe box. Like many others, including my company Sprout Social. And so anyway, I think IndyCar brought put me back on this path to like being being in the right place in a way, in a place that was aligned with really what I wanted, where where I could be happy. And. And the other thing is just like reconnecting me with. Some of that, like founder, experience, founder, culture experience that I had when I was a teenager, but add in deca, I was now at, I was now in my professional career. And theoretically, you know, this wasn’t something I was thinking about at the time. It theoretically was like now in a position to actually do something for myself. Start a company for myself. And it really just took the right circumstances. So during the Great Recession 2008 2009, the dynamic in Dhaka changed dramatically and especially for me because we haven’t talked about where I’ve lived. But like in Dhaka was Boston, Cambridge, Massachusetts based company. I was living in Chicago, and so it was harder for me to really be connected to the most exciting stuff in the company and around the time of the recession. And Decca did a big round of layoffs. I kept my job, but my role shifted dramatically, and once again I sort of lost the intrinsic motivation of what I was doing. I wasn’t working on the same profile of projects anymore. And so I kind of got into this like kind of pit of, you know, dissatisfied dissatisfaction. And, you know, ultimately, like during that time, serendipity connected me with Justin Howard, who’s my who’s my co-founder at Sprout. And and we just started working together on things. And that’s kind of what kind of what led to sprout. So it’s almost like. I had thought a lot about starting a company, but not always from the perspective of I’m going to do it, I just thought about it as this like really interesting ambition. But actually, this is going a couple of steps back. There is a period of my life around when I was working for IBM, where I was surrounded by friends who were similarly ambitious and as a hobby on the side, we’d always be pitching each other business ideas and like, we were just searching for things to build on our own. So. There have been these like kind of seeds sown in me, so to speak of, like just thinking about what could I do on my own? What business can I start on my own? What ideas are really worthy of that? I mean, we talked about this idea that we called Digital Locker where you’d have a digital. You’d have like this online website where you could store any files and content that you ever might want to store. Guess what? Like that became Dropbox? They’re just sort of any other ideas like that where like, we just. We we saw the opportunity, but for some reason didn’t go after it and start to say like, oh, like if we hadn’t done that, we would have, we would have become that, but. But looking back on it, it was clear that like we all wanted to, we all wanted to do it. But we couldn’t get it off the ground like we could just we could talk about it and be excited about it. But we didn’t have whatever catalyst that we was required. And so anyway, somehow with Justin, when we when we got together, something catalyzed us to take to go from that zero to one, so to speak, just in terms of like activating taking action on the idea.
Luke [00:45:36] I feel like there’s sort of a point where you’re talking about that difference between intrinsic and extrinsic motivation, where you realize that the it’s part of the intrinsic motivation was around actually like building things and kind of doing the actual engineering. I mean, but there must have, of course, been sort of a change over time, as you like decided to to start this other company where you’re like, obviously, when you’re a founder, you’re like, you’ll be building stuff, but you’re like building a company. You’re not exactly like coding and kind of building the stock for yourself necessarily, right? Yeah, it seems like there must have been some kind of shift in terms of like what you considered to be intrinsically motivating or or.
Aaron [00:46:15] Yeah, it’s really interesting that you frame it that way because it helps me actually to process what happened here because. Yes, when you are a founder, there are so many, and as an engineer, there’s so many things that you have to do that you have to learn how to do that are not necessarily just right, like writing this writing like literally coding, but the way that we started Sprout was different than that. We, you know, we Justin and I met serendipitously and we were just talking about, Oh, what do you do, you know, simple like normal banter, you know, talking shop, you know, what do you do for a living kind of stuff? And within like 30 seconds of him sharing what his full time job was, he started talking about, like how he was paying contract developers to just build him little websites on the Twitter API. And we just started talking about that and riffing on that. And within a couple of days, we are working together on similar concepts, and those concepts kind of pivoted and shifted until they became what what turned into sprout social. But when we first started working on this, it was just a project. It was just. Like Justin was so fascinated about what social media could do for business and like that was extremely exciting to me as well, and we are both excited about just what social media was doing to to to society and culture. And this is back in 2009 and particularly the intersection of that with business like what is this? How does this change the way that people talk to businesses, talk to organizations, talk to governments, whomever, whatever these, you know, repeat consumers and individuals talking to, like bigger organizations. It used to be very much like a push. You know, a big organization can just will push whatever they want, whatever messages they want to you, and you just have to take it in with social. It was like, now, no, now it’s a dialog and it’s all out in the open. So you have to be like, you have to be honest, otherwise you’re going to be called out for it. But for that, for a long time in the beginning of our of our history, I think we didn’t realize we had a venture scale business on our hands or what that even meant, and we were just building this thing that we believed in. And I mean, for the first nine months of us working on Sprout, it started as kind of a side hustle like moonlighting gig. We weren’t even thinking about taking funding. We’re just building the app. So it was just building and. At some point we made some awesome connection with the team at Twitter, and back then Twitter was like twenty five people and we made a connection with the person who was running the Corp Dev team reporting to Dick Costolo when he was CEO. And that person was excited about what we’re doing because they were thinking about what is what is Twitter for business, what does that really mean? And we wanted to just be open with them about what we are building. We’re like, we don’t want to be competitive. So tell us that this is something that you’re going to do because like, you’re just going to you’re going to bulldoze us if we’re in your path. And anyway, that that relationship quickly turned into them, saying, like, you guys realize what you have in your hands here, you need to like, we are just two. At that point, we had brought two more people into the group and we had four co-founders and we were not talking about taking funding. We weren’t even talking about how we’re going to monetize. We had a free beta going with two thousand people in the app, and that Twitter contact was like, Look. You need to take funding if you’re going to take this for if you’re going to do this for real. Someone else is going to crush you because they’re going to they’re going to take venture funding and build a big team and do this a lot faster than you can do it. So if you care about this project, you need to take funding if you need help with that here. We’re going to connect you with Ron Conway and Chris Sacca and all these valley angels. And we’re going to help you with those intros so that so that you actually do it. And that’s what turned into it becoming, you know, a typical venture backed, high growth, fast growth startup. So, so anyway, long way of saying like, I think I got a gentle introduction to it because to me, it just started as a software side project and me getting to do the stuff that I really loved doing, but had enough time also getting exposure to the fact that we were building something bigger than an app, whether or not we thought about it as a business that could earn money or just. Something that other people would derive value from. By the time it became that the air time became obvious, it like this should be a start up. We need to build a team, you need to take funding. It was like a baby. You know, it was like, Okay, this is our child. Like, we care about it. And whatever it will take to make this successful, we’re going to give it that. Whether that means me giving it code or me giving, you know, helping find it engineers or whatever it might be.
Luke [00:51:21] That’s so interesting. Yeah, like that. Yeah, right. I can totally understand how that shift in motivation, like takes place so organically where it goes from this it depends on like you get into it for being for the sake of of of one particular exercise or one particular action. But then it takes on a life of its own and then it becomes so much bigger than that. And then it just has. And then it’s just like, doesn’t matter what’s on the plate, you just want to like, make it work, right?
Aaron [00:51:48] Like, that’s right. That’s right. And I think that that that’s just like for us, that’s what’s kept us activated and engaged for eleven years now.
Luke [00:51:57] So it wasn’t, you know, you didn’t find it hard to like, step away from the code and like, you know,
Aaron [00:52:02] well, actually, I mean, I would say that I did. It took me a lot of years to step away from the code. I mean, I remember I used to even tout when I’d be interviewing engineer, is it like I’m still coding and I don’t have any plans to stop? And at some point it just had to stop and it wasn’t even like I made it. I realized that in retrospect, I realized, Wait a minute, I haven’t written code in like two weeks. I don’t even have the idea open on my computer. Like what’s going on? And then I realized then I would try to fight back against it. Like, No, I’m going to code. I’m going to set aside time on these days and I’m going to do it. And then I realized like. I couldn’t I couldn’t contribute at a level that. That really upheld my commitment to the teams that I was coding with, or if I tried to live up to that commitment. I would let something else fall generally like in my personal life. And so I was either like letting my team down or is letting my family down. And and eventually I realized I was also just not doing the job that I was supposed to be doing that nobody else was doing, which was being the CTO. And I think I had to figure out what does that even mean? How like, what does it mean in this circumstance? And at some point I just realized, OK, any minute that I’m not coding or any minute that I’m coding, I’m not doing the rest of the things that I should be doing as a CTO and and like, I have to come to terms that like which, which is more important, which one of my more aligned to where can I, how can I contribute more? And I think also sometimes reconciling like again, back to the motivations like where am I intrinsically motivated? I love coding. I could be intrinsically motivated to code forever. And there’s a lot of things that I do or have had to do as a CTO that I’m not necessarily intrinsically directly motivated to do like those activities. But what they what they contribute back to the team or what they contribute back to the company and is like second order effect is where I am intrinsically motivated and have to really try hard. Remember that because if I don’t do whatever is right in front of me that I’m not excited about, will jade me and make me want to go do this? Like, you know, it’ll it’ll cause me to go and look for something and seek something that gives me more give more pleasure like coding or having a technical conversation, whatever it might be. So motivation is so powerful. And if you can figure out really how to like, it’s like wind in a sail like you can just like, capture the right way, then then it can really drive you. But if you don’t, they can your sails going to, you know, flail around and you’re just going to be stuck.
Luke [00:54:51] Would you say that that’s like your your kind of work is like an investor and that kind of stage, what was that kind of start to that phase like? And I’m curious to hear how like your your sense of self and your motivations had kind of influenced that particular chapter?
Aaron [00:55:09] Yeah. So in the last 18 months, I have started investing and I work very closely with my wife on this work. She comes from a technical background as well spent most of her career in finance, but also started a company and was a CTO for a little while in that company, as has since exited. And so anyway, we worked, we work on this together, and I think what got us both interested in doing this was this feeling of like. We want to give back in some way we and as a combination of things like want it, it was around the time that, you know, Sprout had iPod and my lockup period had expired and so I suddenly had some liquidity from Sprout. And one of the first reactions I had was like. I just felt like so many people, not necessarily always explicitly, but so many people had helped me and supported me and influenced me along the way. And also taking a chance on our business and giving us capital that it just felt like the right thing to put some of that back in into the into the ecosystem. And I just felt really strongly about. About investing for that reason. But I also quickly realized that what’s a lot more, a lot more valuable in capital is is that human support and. I think I had a number of great conversations with entrepreneurs while I was mentoring at a local incubator. It made me realize I think this is maybe funny to say, but like I didn’t necessarily know that I could be a great startup advisor or mentor. And I’m not saying that I am a great one, but I had some conversations that were really energizing for me and where the entrepreneur shared that like, they were really helpful to them, and it wasn’t like I had to have the answer. I didn’t have to solve their problem. Sometimes I just had to be a shoulder to cry on or someone to commiserate with, or someone to validate what they’re already thinking. And just having that person to talk to you was so helpful that with the investment work, it was a combination of I want to give forward some capital, but I also just want to give forward any expertize, any experience positive or negative that I can share from the time that I’ve had so far to sprout. And I think that while I’m still very much engaged at Sprout in the last few years, I started thinking like, What else can I be doing? What else do I want to be doing in life? And how else can I be? Contributing just to the world and just one of the small ways that just keeps coming up in my mind was like, I want to help with investment, I want to help share my experience. It’s the thing that I know that I can do. It’s the thing that I know that I can share. I have it. It’s in the same way that I’m sharing my story right now, like this is easy for me to do because it’s just my life. And similarly, like sharing experiences from people is easy to do because it’s just my life. I don’t have to feel like I’m. I think, you know, a lot of like a lot of people, I definitely have bouts of imposter syndrome and like feeling like I’m an expert. I’m not always comfortable with that. I’m always comfortable feeling like, Oh, I am absolutely an expert in the space and I can share my opinions. And they’re absolutely valuable because I’m so skilled. I generally don’t feel that way about most topics. There’s a few things I feel like I’ve really learned them at a deep level, and I just love sharing what I know about those things. But those are like two out of a million topics that we could be talking about. And so I think just realizing that simply sharing what you’ve gone through can be really helpful that that feels so easy to do. It’s just telling, telling what has happened more or less. And so, so anyway, that that’s kind of how I how it how I’ve gotten into gotten into investing. And right now, it’s it’s I’d say it’s pretty small scale in the sense that it’s a it’s a it’s a side hustle. It’s it’s it’s pretty passive. We’re not really actively sourcing deals, but we get connected to a lot of really awesome opportunities like like working with the team at a taglio in the future. You know, we’re where my wife and I are starting to think about, like, could we do this on a bigger level? What would it take? Would we need to build a team around ourselves to to support that so far, because it’s been passive, we’ve been really focused on just like the areas that we know best, which is around B2B software. And I am very I would love to continue supporting B2B software entrepreneurs, but there’s a lot of other missions out there that are really motivating to US climate. Health and a number of things, education and so forth. And we would love to figure out ways to just contribute more to these spaces, but but we do feel like besides just needing more support, we also just need to learn a lot about these spaces. We don’t have the experience or expertize to contribute directly. And so anyway, I’m taking this a little bit too far, maybe. But but investing is something that that we want to be doing for a long time, and we would want to figure out how to do it at a really excellent level.
Luke [01:00:38] Yeah, absolutely. No. And I think that what you’re saying about like areas of expertize and finding your own way to kind of contribute, I mean, I think it is also interesting that you would say that you’re only really consider yourself more confidently an expert and just a couple of couple of topics. But I do have to say that I really admire just how much reflection and consideration and thought that you’ve put into just understanding yourself and your own kind of inner world and workings and motivations in a really, really, really appreciate you talking with me today about that and and I really hope that, you know, I know that I took a lot away from from your kind of conversation here in your story today, and I hope that some of our listeners did, too.
Aaron [01:01:29] Yeah, I mean, I hope so, too. I mean, thank you for letting me share it. Thank you for giving me a great space to just reflect on it. So much of this just kind of came out as we’re talking. It’s not often that I’m really thinking, like I said, thinking backward. I’m oftentimes just thinking for. But, but I think it’s helpful to really know, to study for everyone, to study their own journey, to really think about how they got to where they are and to consider just how to how to help that, how to how to let that help them shape where they want to go. Yeah. So anyway, you know, again, thank you for letting me share. I hope that some of this was helpful to the audience again, either whether it’s, you know, giving giving them some, some some insights that could help them or just validating what they already have considered and just needed a second opinion on.
Luke [01:02:22] Yeah, totally. And I totally agree about just the idea that we tell ourselves our own stories all the time, right? And just the value of being able to do that and reflect and see your own story and other people and let that affect your own, I think is so valuable. Yeah, awesome. Aaron, thank you so much for talking with me today. I really appreciate
Aaron [01:02:43] it. Yeah, yeah. Thank you. Thank you so much, Luke. I appreciate the questions, and it’s been a great, great time here.
Luke [01:02:53] Thank you to Aaron for the conversation. Thank you to Tom Tierney for the music. Thank you to Jamaal Titus for the production to help. And thank you for listening. We’ll see you again soon.