Leadership lessons, personal worth vs. net worth, and exiting 3 companies with Jamie Ahern (CEO of CarmaCare)

Jamie Ahern 00:00
I would rather have a C player today that's coachable than an A player that's not coachable, because you can turn that C player into an A player. We're almost guaranteed that an A player, over time, is going to be a C player, and there's no hope for him. So I think understanding the power of coachability and just being more susceptible to coaching myself, where, like, again, I was always a gloves-up, ready-to-fight kind of person, just understanding that it sucks to give tough feedback and to truly treat it like a gift is important.

Callan Harrington 00:29
You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Today's guest is Jamie Ahern. Jamie is the CEO of Karma Care. Prior, which I'm excited to go through, he's had multiple exits along the way, some time in hedge funds, and this is going to be a fun one to go through. Jamie, welcome to the show.

Jamie Ahern 01:04
Thank you so much for having me.

Callan Harrington 01:05
Absolutely. So tell us a little bit about Karma Care, and how did you get involved? And what are you doing for Karma Care?

Jamie Ahern 01:10
Yeah, so I'm currently the CEO of Karma Care. I'm a big believer, and hopefully, this will come out throughout the show, a big believer in falling in love with the problem versus the solution. So the problem that we're really trying to solve is that car repairs represent the number three driver of consumer debt in the United States. Something like six in 10 Millennials have foregone necessary car repairs, you know, and I've been spoiled. I've lived my entire life in Chicago and Manhattan, where, like, you can kind of get by without a car. For most people in the United States, your car represents not just a mode of transportation, it's truly your livelihood. So you can't keep a job, you can't feed your family without a car. Mix that with inflation, car repairs through the roof of 25% year over year, and with interest rates, you now can't afford to buy a new car, and so keeping your car on the road is more important than ever. And really, we're trying to solve that through a couple different facets. So our first product is really attacking the extended car warranty space. So if you think about the financial products that are really designed to help out with car affordability, you have car insurance on the one end that's relatively well regulated, relatively well saturated, and then extended car warranties, which have been turned into a meme. So it is just a lot of opportunity, right for the picking, really, to help out with everything that's not a collision with car expenses. So like you press on, car doesn't go on. What do you do? The second thing that we're really excited about is, especially launching this tomorrow morning, what we're referring to as the virtual garage. The virtual garage is something like three quarters of people from a recent AAA study, three-quarters of consumers in the United States have what they refer to as "repair phobia," that they have extreme anxiety taking their car into the shop. And from our perspective, after a ton of research, we believe the core reason for that is dramatic information asymmetry, where you have a mechanic that has gone to school for years and years and has practiced being a mechanic for years and years to be an expert in fixing cars, and you work as an accountant or as a consultant or behind a desk and a computer all day. You don't know the first thing about cars, but you need your car in order to survive. They tell you, X, Y, and Z is wrong, it's gonna be five grand. You say, "Thanks, here's my money." So the virtual garage, really, what we're doing is pairing consumers with licensed mechanics to virtually diagnose problems and give a loose cost estimate, just so you know kind of what's going on by the time you walk into a repair shop.

Callan Harrington 03:40
You mentioned, and of course, we had a conversation before this, and I was pretty blown away. I had no idea that that would have been number three. It makes sense when you think about it in hindsight; they're costly repairs, and what are you going to do? Your only other option is to buy another car or use other modes of transportation, which aren't going to be inexpensive or just not doable, depending on the city that you're in, as you mentioned. So that's super interesting. Now, how did this all begin? I want to make sure that I'd heard this correctly. Did you start at the Citadel when you were 17? Is that correct?

Jamie Ahern 04:17
Yeah, yes, I did. So do you want the Citadel story or the Karma Care story?

Callan Harrington 04:21
We'll come back to the Karma Care story. But yeah, starting at the Citadel, and for people that don't know, Citadel is one of the most successful, one of the, you know, most prestigious hedge funds, period. And you started when you were 17. How did that even happen?

Jamie Ahern 04:36
This is a good story. So basically, what had happened? I grew up in a very middle-class area. My parents were entrepreneurs, so when times were good, they were great. But there were obviously the other ends of that where, like, money was tight. And so we lived in a very kind of, like, middle-of-the-road type of town, pretty unremarkable. My dad would always joke the only remarkable thing about Sleepy Hollow, where I grew up, is how unremarkable it is. Just kind of like run-of-the-mill. Went to high school there, and I had graduated valedictorian, and so I had to give a speech. It was a pretty large high school. I think we graduated something like 600 kids or so, you have like their family, and typically, like the police and fire department and everything else would come. And so we were on, we were out at a huge park in our town, and I spoke, and about two weeks later, I'm of Irish heritage, and so my dad's idea, my parents' idea of volunteering is serving beer at an Irish festival in Chicago. His volunteering, so my dad's probably five or six beers in, and the fire chief, so the chief of the fire department for our local town, is also of Irish descent and is at this volunteer fundraiser at our local church. And he gets to the front of the line, like him and my dad are talking, and he's like, "Hey, I heard your son speak at the graduation, whatever, like, two weeks ago. What does he want to do when he graduates Northwestern?" And my dad's like, "Oh, he wants to work for a hedge fund." And again, I was 17 at the time. I started school early, so I kind of like skipped a couple grades and was really like barely 17 when this conversation was happening, and I had no idea what a hedge fund was. I didn't know Citadel, I didn't know what they did. I didn't really understand what the stock market was, but outside of that, no clue. And it turned out the fire chief's sister was like, the fifth employee at Citadel. And so I'm like, I move in, you know, a week or two later into Northwestern, and I get a call from this extremely senior woman at Citadel, the fire chief's sister, and she was like, "Hey, I heard, you know, whatever, my brother was speaking very highly of you. Do you want to come in for an interview?" And so I went down there. I think the expectation was for that to kick off like a junior year internship, like they typically do. But since, you know, Northwestern is just on the north side of Chicago, so it's only about a 20-25 minute commute all the way downtown. And so after talking to them a little bit, they're like, "Hey, is there any way you could just do stuff during the week?" And so I packed my classes, like, Tuesday, Thursday, and then come downtown, work there, like, Monday, Wednesday, Friday, weekends, whatever I could. And again, like my parents did everything they could to pay for tuition, but a lot of that fell on me, and so the fact that Citadel was willing to help out, it's like, yeah, no brainer here. Let's figure this out.

Callan Harrington 07:27
What was that like, doing that, being there at 17?

Jamie Ahern 07:32
So the other, I think, interesting dynamic or dimension of this is this is in 2007, so this is right before the financial crisis, and so I was technically there through the whole crisis. You know, at 17, I had no idea what a workplace was like. And so for me, that started to feel a lot more normal. And I'm sure there's a lot to unpack, you know, for a different question here, it's like, I didn't know any better. Like, that's what work was to me, was Citadel. And like, Citadel, yeah, it's, like, in hindsight, a very intense place. It's a very candid place, which I tend to do well in, where, like, people don't beat around the bush. They kind of, if you've got something to say, you say it. And so in a lot of ways, like, Citadel formed where it wasn't as much of, like, me being overwhelmed coming in, I was so young, I was clay, right? And like, they just kind of molded me into the Citadel archetype, and it worked. But it does tend to be, you got comfortable with a few things that I think in retrospect are maybe not normal, where, you know, I had a couple mentors throughout the process get fired, and there's no notice. They don't know anything. Like, I would just show up, and the desk next to me would be empty, and it's like, "Oh, like, where's, you know, John today?" It's like, "Oh, he doesn't work here anymore." It's like, "Oh, God, like, that's just how this works." And that was before the crisis. And then when the crisis happened, like, there were moments where I was getting pretty frantic phone calls, like, while I was in a final, kind of thing, of like, "Jamie, you need to get down here now. Like, things are falling apart. Like, this has to happen, like, yesterday." And so, yeah, I would, whatever, hustle through a final to jog downtown and get there and try to, whatever, piece things together. Obviously, at 17, I wasn't managing anything ultra-mission critical, but I did a lot of, like, the cash balance reporting and stuff like that to make sure that, like, you know, there was enough money to turn the lights on the next day. And so that was a wild time. I'm glad I lived through it once. If I never had to do that again, Citadel, I would gladly do again. Citadel, through the crisis, I would prefer to never, never do again. That was intense.

Callan Harrington 09:30
What do you think were some of the biggest challenges that you experienced and learnings that you had from there during that time?

Jamie Ahern 09:38
You know, a couple of things, and I've heard, I think it was Steve Jobs who gets talked about a lot in tech that, like, being lazy is a good thing, because lazy people will find creative ways to not do work, and oftentimes they'll get the work done. And so that really came through where, like, again, as a 17-year-old intern, I got the shit work. I was bottom of the totem pole. I got whatever, what everybody else didn't want to do. And so I think that helped me, sort of, like, approach problems a little bit more creatively, because, like, some of these things would be incredibly tedious, where they have to get done and they have to get done with 100% accuracy, but they're not fun to go through. It'd be like ticking and tying, like, you know, trade reports or something to make sure that, like, what the broker saw is like what we saw, and make sure that all lined up. And there could be tens of thousands or hundreds of thousands of rows to, like, go through all this. And so, like, you know, I started getting creative with, like, VBA and, like, writing whatever, like, small, stupid code in Excel to, like, do things quicker. And, like, it's like, oh, like, I'm actually getting rewarded for being lazy because I didn't want to do this. Not kind of being punished for not doing my job. And I think Citadel was definitely a place that, like, they gave you plenty of rope, no matter who you were. Where, like, the expectations were very clear, and the upside was very clear. Where they were very generous when, like, bonus season came around, etc., but they were also very—the downside was very clear, right? Like, and it wasn't about how hard you worked, it was purely outcome. And so it's not about face time or anything else. It was purely outcome-driven. And so if you performed, you got rewarded, and if you didn't perform, no matter how hard you tried, you got fired. But at least you knew where you stood, right? There was never any guessing. And so I think I've had to learn how to, like, soften some of those corners a little bit. But certainly, when I left Citadel, I was pretty rigid in how I thought because it was like, well, if you're doing well, you get paid, and if you're not doing well, you get fired. That's just the way the world works. And I realized after that that's not the way most of the world works. That's the way, like, a very small sliver of the world works.

Callan Harrington 11:39
Yeah, you've brought up a couple of interesting points. I think that when you mentioned, in particular, kind of that forced creativity, I think one of the things that I found, and I've heard this from other people, is when you have constraints, you're more creative, if that makes any sense, where we have this box around, when you've got a blue ocean and you can go anywhere, it's actually harder, in my opinion, to be creative in that. But when you have these constraints, which is why, you know, and I think it makes a lot of sense when they say how some of the best companies were started in a market downturn, you're going to get to the root issue, and you're going to be really creative at solving that root problem because you don't have the resources to tackle all the problems. And it sounds like that's pretty similar to the experience that you had with that. Is that right?

Jamie Ahern 12:22
Yeah. I mean, Citadel obviously had a ton of resources, but being low man on the totem pole, like, I couldn't hand off my work to anybody else. I had to do this. And yeah, there was nobody else I could tap into or anything like I was the, like, last stop. And so, yeah, like, I've never actually thought about it from that perspective, but, yeah, you're probably right that it was driven by I had more work than I had time or patience to do. So, like, how am I going to come up with a way to get it done?

Callan Harrington 12:50
I'm interested, how much did that help you later in your career? Like, that piece in particular, that kind of forced creativity to solve a problem?

Jamie Ahern 13:01
You know, it's funny, I was texting with a mentor, actually, over the weekend, and you had mentioned I sort of made the announcement. Made it, like, LinkedIn official, the equivalent of, like, Facebook official, I guess, that, like, I am at Karma Care. One of my mentors reached out just to congratulate me and whatever else. And he said that I was one of the more resourceful people that he's ever worked with, and I took that as an extreme compliment. You know, I've never thought about it through this lens, but now that I'm thinking about it, a lot of it probably did come from Citadel, where it was such an interesting culture because it had nothing to do with FaceTime. If you wanted to work two hours a week and your portfolio was up, you still got paid. And that was fine. And it really was, at least back then. I don't know if that's changed. I mean, this is 15 plus years ago, but back then, like, it was very much like it only mattered what you were able to produce, and not how much, how hard you worked, or how much you worked. And so, yeah, like, I do think that probably, I probably have carried that forward with me, where even now, like, I'm probably not your stereotypical CEO, or even at, like, COO, for that matter, where, like, I like to write code. I like to get into databases. I like to, like, I can barely speak English, but it's not going to prevent me from, like, trying to write copy and, like, send out emails and, like, I definitely tinker. But I feel like I got that bug from Citadel, where, again, that behavior was rewarded as long as it had positive outcomes.

Callan Harrington 14:24
Yep, makes sense. You're getting paid for your performance no matter what. So you left Citadel, and then you still stayed in kind of the finance space. What did you do after Citadel?

Jamie Ahern 14:34
Yeah, so a large chunk of my time at Citadel was while I was still in college. And then I graduated, they moved me up to New York, and they had really spun up. And this might be getting, like, too finance-heavy, but there's sort of, like, the buy side in finance and the sell side in finance. So like, the buy side initiates a transaction. So like, they either want to, like, buy or sell something, and the sell side basically makes it happen. So like the buy side would be a hedge fund in most cases, like a Citadel or Bridgewater or like even a lot of the Fidelities, Vanguards, whatever, are all usually buy side shops, and the sell side is more like your investment banks, your Goldman Sachs, your Morgan Stanleys, your UBSs that, like, make what the buy side wants to do, just make it happen. Citadel, because a lot of this was just post-crisis, Citadel thought there was a big opportunity in the sell side. So kind of like Citadel to, like, start to eat some of Goldman Sachs's lunch kind of thing. And so they spun up an investment bank that they had positioned me into. And after about a year, it became very apparent that Citadel had too much of a brand within the hedge fund world to really be successful as a sell side. Because sell side, like, the most important thing is that the buy side trusts you. If they don't trust you, and so like, if you've got a big hedge fund working with Citadel as a sell side, it's like, well, how do I know you're not just gonna, like, feed this back to Citadel, the hedge fund, and, like, crush me. And that was a hard thing, I think, that they couldn't really overcome. So they ended up folding that division, and I got fired. And so was looking around, was in New York, was reasonably happy there, and did find my way to another hedge fund, actually, from the head of the trading desk was another Northwestern alum, and so we've kind of networked our way into that. And like, he's like a big brother to me, we are extremely close, but yeah, brought me on to a much smaller hedge fund. So that was, call it, about 20 people in the front office, so like, making investment decisions, and we managed, I think, at our peak, around like 1.8 billion in assets. But really just, again, super lean, like 20-person team, and that was mostly Asia-focused, so kind of Japanese tilt, but really kind of like pan Asia.

Callan Harrington 16:50
Let me ask you a question. What was that transition like? You were at Citadel, one of the largest hedge funds in the world, rose up the ranks quickly, were there through college? And then it's interesting, because it's exactly what you just described, how this was this culture of you may have a great person that you work with, and then they're gone. What was that like for you? You experienced that, and then you go to a smaller fund. What was that transition like?

Jamie Ahern 17:18
Honestly, more seamless than you might expect. The biggest difference, I think, between those two shops was, for me, twofold. One, realizing the world wasn't just the United States. That was like, probably the biggest eye-opener, where, oftentimes I was actually working overnight in New York. So I'd work kind of like, 4 p.m. to 4 a.m. every once in a while, and you're dealing exclusively with people in Hong Kong and Singapore and Tokyo, and it's really kind of all over. That was pretty cool, where I feel like that was definitely one of the bigger—and they were very generous with, like, trips over there to, like, get to know your counterparts. And so spent not a ton of time, but a decent amount of time in Asia that I think really opened up my worldview, where it's not just the U.S. And then, two, the culture was still performance-based, but I likened it a lot more to, like, a patriarchy, like a family type of system where, like, because we were only 20 people, like, I knew the Chief Investment Officer, like the head guy, like, reasonably well. I sat right out in front of his office, and like, he'd say hi every time he walked in and out. And like, we knew each other very well. Whereas, like, I didn't know Ken Griffin at Citadel to the same degree, because Citadel is huge, and so it felt much more like a family. And like, I felt like he always had my best interests in mind, and like, they were always very fair in compensation and like also gave me enough leash to hurt myself, which thank God it didn't go that way. But there were moments where, again, at this point, 23 years old, I had discretion on a couple of hundred million dollars, where they would say, like, you can do whatever you want, up to whatever $100 million or $150 million without calling me. If you want to go bigger than that, give me a phone call. But like, otherwise, you do you, kid, which was, like, pretty cool. But again, I think it felt like, again, my boss felt like my big brother, and like the head guy felt like, you know, father figure or grandfather figure type thing.

Callan Harrington 19:15
So you were in finance for almost seven years, and then you went to tech. So before we get into the story of how you got into tech, why make that leap? Because, I mean, just kind of talking like that, stating the obvious, you're already in a hedge fund. You know, hedge funds typically, you know, as you had mentioned earlier, but for some of our listeners, you know, a lot of people start on the investment banking side as kind of a springboard into private equity or a hedge fund. You were already in the hedge fund, which means you had a fast track to make more money than you could spend. Why change? Why make that total change altogether?

Jamie Ahern 19:53
Yeah. So I think to answer that question, I should probably answer the question of, like, why I got into finance to begin with, outside of purely happenstance. Like, yes, the opportunity very much fell in my lap and I jumped at it, but a lot of it was okay. I'm graduating with a fair amount of student debt. How do I get out of this as fast as possible? And to your point, like, hedge funds pay well, right? And so that was the easiest way for me to pay off my student loans and be totally debt-free by 21, 22. And so the first couple of stops in my career journey were, honestly, I didn't have to give a whole lot of thought to because I was purely immersed. It's like, whoever's going to pay me the most, that's where I'm going because, like, I don't want to be in debt. And then really, ACQ also kind of had this very—so Citadel, again, I got fired. ACQ had this very obvious moment in time where I should be looking for a job, where not to go into too much detail, but Japan had a big event in 2013 that the markets went all over the place, and basically, we were on the wrong side of that. And so we went from, you know, close to a $2 billion hedge fund down to, you know, $400 million, which is still a lot of money, but we had infrastructure built around a $2 billion hedge fund. It's just hard to, hard to maintain. So my CIO basically folded the shop. So it wasn't like, I personally got fired, but it's like the company ceased to exist. So I had to find something new. And that was, like, the timing of that was interesting because I was now officially out of debt. To your point, I was making more money than I candidly knew what to do with. I was starting to, like, buy houses in Chicago as, like, investment properties and things like that, that, like, didn't—it was cool. And I was, like, again, in retrospect, very glad I did it. But, like, it also—you—I started to think a lot more about personal worth versus net worth. And it really came down to—and I got to be careful, my wife's in the other room, and she runs a bond portfolio. She's very much in that world. But it kind of came down to, like, my sole existence was to make extraordinarily wealthy people a little more rich. And yes, I got compensated very handsomely to do that. But at the end of the day, like, am I really making an impact? Am I really, like, positively changing the trajectory of other people's lives? And I couldn't get over that hump, and so I decided I didn't want to build and I did want to get into tech. And my biggest concern was like, well, I'm a finance guy. I've been trading Asian derivatives and, like, subprime mortgages my whole career for, you know, six, seven years at this point, what do I have that any tech firm would be even interested in talking to me about? Which is really probably feeding into your next question a little bit, like, how to get there? Another, in case you can't tell, Northwestern was extremely defining in my career, so I was at a Northwestern, like, New York Northwestern alumni event, and happened to strike up a conversation with a guy, ironically, who was the mentor that was texting me over the weekend. He was the founding data scientist at Netflix, and so the whole, like, recommendation engine, like, "you might also" was kind of his brainchild. So

Callan Harrington 22:53
This guy has taken hours of my life.

Jamie Ahern 22:57
Very much, and he's really good at what he does. And, you know, him and I started talking, and he had just gotten poached at this company LearnVest in New York, which is kind of like financial planning for the everyday American, not just for, like, your hyper-wealthy folks. And, you know, we met at this event, but we kind of stayed in touch. And he started recruiting me as a data scientist, and he was really the one that helped translate for me. Like, I'd always called myself a quant in the hedge fund world because I like numbers and was, like, whatever, could code enough to cause problems. He helped me understand, like, the rest of the world has a word for that. We just call it data science instead of quant, but it's really, again, similar to, like, me trading subprime mortgages is actually kind of similar to me trading Asian derivatives. It's actually quite similar to me being a data scientist in a tech firm. It's all the same underlying skill set just applied to a different problem.

Callan Harrington 23:53
So you made this change. That makes complete sense, you know, that you're doing the same stuff for the data science world. How was that transition? What was that like, going over to the tech space from finance?

Jamie Ahern 24:02
That was big. So again, I was able to keep most of my sharp corners, even at the other hedge fund, because, like, we all kind of grew up in the same forge, if you will. So we all kind of looked and acted similar, and then I got into tech, and that's totally different. I remember, and I'm not proud of this, I remember it was like maybe my second week at LearnVest, I actually made one of our designers cry because I was coming off, like, way too aggressive. And I didn't mean to, like, that was just where I grew up. And, like, that was how we spoke to each other. And, like, again, you didn't sugarcoat things, you just hit it. And I remember, I think we were talking about, like, something that, at the time, I lacked respect for that. Now I've realized is probably some of the most important things that you can do in the business. To me, it was always a formula with a problem to solve, right? Like, you put x dollars in, you get y dollars out. As long as y is bigger than x, you're good to go. And a lot of the branding or messaging or, like, user experience stuff, like, all fell on deaf ears with me because it's not where I grew up. I didn't have a background in it, and so that was hard because I had to, one, learn to deal with people that weren't as psychopathic as, like, me and my hedge fund brethren. But then, two, I had to learn respect for stuff that didn't have a mathematical answer to it, that is a little bit more, like, softer and qualitative in nature, and find respect for it. That hurt a little bit, like, again, everything I'd ever known to that point, like, I still could do my day job. But in order to be successful, kind of at a higher level, I had to learn to deal with different types of people and learn to have respect for different types of things that previously, like, I just never encountered.

Callan Harrington 25:40
How did you go about doing that?

Jamie Ahern 25:42
You know, I think I'm a very skeptical guy by nature. So I actually kind of remember this. I got in a whatever, like, tussle with somebody about, like, a UX product experience type thing, and their response was like, "Okay, let's just test it and see what happens." Sure enough, their recommendation dramatically outperformed. It was like, okay, like, even if I can't see it just yet, there is a qualitative reason why we're doing these things that may come as a second, third, fourth order of effect. And I'm used to seeing things in a first order effect. Like, you do a thing, you see the change. That gave me a lot of confidence that, like, okay, like, I need to shut up and I need to listen a little bit more to people that know what they're talking about, and I can keep score, right? And I can watch and I can make decisions around that. At that point, I kind of shifted out of data science and more into growth marketing, which, again, are very similar for a lot of reasons, but that's really where, like, yeah, sometimes, like, the color yellow does have a big impact, right? Depending on how it's implemented and where it goes, or changing small words in copy has a really big impact. And just like watching that, measuring that, and finding respect for other people's universe. But it really took—and I, again, I wish I could say, like, that is just native to me, that, like, I respected everyone's opinion and respected everyone's job and everything else, but I had a hard time seeing that until I saw how it impacted my world and sort of what I looked at.

Callan Harrington 27:05
That's probably one of the biggest things to start up. In general, you could model out a lot, but it's more about what are these processes that we have to be able to test and see what's going to work? And some of that is just blind trust. Now, you guys grew LearnVest really fast and ended up having a pretty significant exit. What was that like for you? What kind of impact did that have on your career?

Jamie Ahern 27:23
Yeah, again, you sort of alluded to this, but to state it maybe a little bit more explicitly, like, I took a pretty major pay cut going from finance to tech. And what was cool is, like, all in a hurry, it kind of caught me up. Over the last three years of sort of, like, foregone wages, had I stayed in the finance world, it caught me up real quick and kind of in, like, one check. So there was really, like, a couple of elements to that. One was actually selling the company itself, and at that point, like, I'm not going to pretend like I was in every room, but I was certainly in, like, the squad team that was trying to, like, put together a lot of, like, the diligence stuff, and, like, I did have a counterpart at Northwestern Mutual, who ended up buying us. So I did have a counterpart that I was kind of, like, trading emails with and, like, trying to, you know, whatever, like, round up a lot of the data for, and that's where, like, I gotta be careful how I word this because I don't want it to come off the wrong way. Data can tell stories. It's not—data doesn't lie, right? But, like, there are many different interpretations of basically the same data set. And so especially in an environment like that, a lot of it is around, like, okay, this is the data set. How do we have it tell the story that we want it to where? Again, in finance, like, I didn't view it as much like that. In finance, like, there was a right and wrong answer. It was my job to find the right answer. In tech, and you sort of alluded to this a little bit with, like, the branding side, but it also was probably doubly true for, like, when you're trying to sell a company, the data can tell multiple different stories. And so, like, how do we make sure we're telling a story that's consistent with, like, the world that we think our potential acquirer, you know, views? And so that was fascinating, just to go through, like, those couple iterations of, like, well, how do we make this say what we want it to? And then the second piece was, it's so hard, and I don't think anyone does it well, understanding equity as a junior or, like, mid-level employee. Really, really, really hard. And there are some platforms out there that, like, do start to get there, like Carta and, you know, some other platforms, but like, at the end of the day, like, unless you're friends with the CFO, like, you really don't know what your equity is worth, or what it could potentially be worth, and understanding dilution, and, like, liquidity preferences, and, like, all sorts of other stuff. Like, what's crazy is, like, I came from—I traded options before, right? And I traded subprime mortgages. Like, I've traded really complex financial instruments, and, like, I didn't understand my equity that I was given, so that was kind of new to me. And I think through my kin process, I learned a lot more. But even then, like, I went from zero to a little bit, like, still was very eye-opening, where the exit money was good, but certainly not what I was expecting to some degree. And then the third piece was actually the integration work of, like, working with a very different company that had 150 years of history and tenured employees and, like, just dealt at a scale that was hard for us to think about, and the culture clash there. Both cultures were great for what they are, but they're different because they're different stages of a company, right? So I think, like, how to navigate that and how big companies think, etc., I think was helpful, but I did realize that it's—I'm probably more cut out for the smaller companies than the bigger companies.

Callan Harrington 30:33
What you brought up about the equity piece is so important. And anytime I was looking at a position, whatever it was, I sent it to my attorney, and I paid a lot of money to have all of that reviewed. And I also probably took the risk of the company saying, like, you know why? It's almost like thinking, "Why are you sending this to an attorney?" And what I said was, like, because I've been burned by it before. Like, I don't know what these little pieces mean. I don't know what these little triggers mean. And I tell everybody all the time, it's like, send it to an attorney. Have an attorney review it, look at it, have them try to explain it to you. I agree with you, if you've got a friend that really understands it, then you can ask more intelligent questions about the investors that you're taking on and why you're trying to do this. How are you in position? How are you benchmarking? And those are questions a lot of people are afraid to ask, but I will tell you, the further you get around your career, you have to, and sometimes you almost have to be burned by it. You almost have to be burned by it to be able to tell other people, "Here's what you should do." And man, do I wish I would have done this differently.

Jamie Ahern 31:35
And to be super fair, none of that was, like, LearnVest's fault, nor, like, you know, I've also been burned a couple of times. It's never the company's fault. They're not doing anything on purpose. They're not hiding anything from you. It's more like my expectations were misaligned. And so I think, like, could I have negotiated differently on the way in, had I had perfect information? Like, yeah, maybe. And by the way, I did have perfect information. I just didn't read the 50 pages of documents to, like, get to the perfect information. But it is a point very well taken that I think there are so many different ways to structure these things, and there are so many things that, like, from a tax perspective or estate planning or whatever else that you need to do upfront that saves you a ton of time and headaches later, you fully, fully agree.

Callan Harrington 32:24
And I think you bring up a good point. I don't, and I would agree with that as well, that none of the companies—I don't believe that they had set it up in a way where, and actually it's probably more favorable. It's just, yeah, I didn't know. I didn't know what I didn't know. And they could have even told me that I just didn't know, and you're so excited to take the job, it doesn't even matter. You're just going in, you're like, "Oh, this is great." And then afterwards, you're like, "Well, I gotta sit to my attorney, right?" So makes total sense. Then you went to LiveWatch after this, is that correct?

Jamie Ahern 32:57
Yep.

Callan Harrington 32:57
And why did you ultimately join LiveWatch from LearnVest?

Jamie Ahern 32:57
Yeah. So when Northwestern Mutual bought LearnVest, obviously, like, that was a non-trivial check that I got where I had some extra money to play with. And I started doing—again, while I was working at Citadel, I bought a couple of houses. And so still, like, was into the rental property stuff, but I started to get, like, more and more into tech, and wanted to angel invest, and wanted to kind of be a part of that community a little bit better. So I did end up investing in a company based here in Chicago. And one of the guys I was kind of, like, investing alongside of—it was sort of like a friends and family type round, but there were only five of us that kind of filled up the round. And one of the guys I was getting really close with throughout this process is still a very good friend to this day, a guy named Dan Aronson, who, at the time, was kind of the number two at LiveWatch, and he had made the decision to go be a number one somewhere, and so he was looking to kind of backfill his role. One of the things that Brad, the CEO at LiveWatch, had kind of charged Dan with was, like, "Hey, can you help me find a replacement?" And so Dan and I had gotten pretty comfortable with each other throughout this diligence process where he kind of floated the idea. He knew I was from Chicago, still had a lot of family back here, and put me in touch with Brad. And that was kind of a match made in heaven. You know, Brad's a fascinating guy. So Brad is a professor at Kellogg, in addition to operating a series of businesses, and he was really the first guy that I'd ever met that studied leadership as a discipline, and it really showed in how he ran a team and how he ran a meeting and how he ran a company. And so that was very eye-opening for me, where, again, like, I'd seen some phenomenal success, both at Citadel in the hedge fund world as well as LearnVest, but never met somebody who's so calculated with leadership as he was. Not only is he a really good, natural-born leader, he's just also studied it and put in the hours to become a great leader. And not to say that the other people that I've worked with weren't current, it was just he was special. So learned a lot from him, and sort of throughout the negotiation process with him, there were a series of retention bonuses and things that Northwestern Mutual put in place that did make me a little more expensive than probably I was candidly worth. And so, you know, Brad having the relationship with Kellogg was like, "Hey, what do you think about you getting your MBA, and I'll sort of help out with that process in payment as well." And so that's what also kicked off, like, again, me kind of coming back to Northwestern now for an MBA really through Brad.

Callan Harrington 35:31
While you were there, and you had this opportunity now to learn from a really good leader, how did that change you?

Jamie Ahern 35:37
I think, in a variety of ways, fortunately or unfortunately. You know, I have had to fire a fair amount of people in my career, and I think it was really Brad that helped me shift that thought process a little bit. I was always terrified about the person that I was firing, and I think what he helped me understand is it's usually not about the person, it's usually about the rest of the team that they're impacting. And so, like, you're actually making everybody's life better, including the person that you're letting go, by doing this. And that's maybe the more extreme version of, like, feedback. And understanding that, like, feedback and coaching is a gift, especially as I've progressed in my career, receiving tough feedback is hard. Giving tough feedback is harder. And so I think, like, truthfully believing that, like, when you receive tough feedback, that's not easy for the person telling you that, that you really should treat it like a gift, and you really should treat it like—again, not to say that all advice is great advice, but to really think hard, because it took a lot of courage for that person to tell you something. And candidly, like, if they're giving you pointers on how to grow, it's because they care about you, right? And so, like, receiving tough feedback is usually from a place of, like, love and respect more so than it is a place of, like, disappointment and hatred. But that was something that really kind of changed the way I thought about leading teams, and the way that I thought about building teams and hiring and firing and, like, just the importance of bringing in—I would rather have a C player today that's coachable than an A player that's not coachable, because you can turn that C player into an A player. We're almost guaranteed that an A player, over time, is going to be a C player, and there's no hope for him. So I think understanding the power of coachability and just being more susceptible to coaching myself where, like, again, I was always a gloves-up, ready-to-fight kind of person, just understanding that, like, it sucks to give tough feedback and to truly treat it like a gift is important.

Callan Harrington 37:29
Oh, man, that is so well said. It is tough. It's really hard delivering tough feedback. But man, you are right. If you don't do that, then it sets a tone for the entire team. And I've made that mistake many times. It took me a while to catch on to that.

Jamie Ahern 37:47
Yeah, there's a phenomenal framework created by a Kellogg professor named Craig Wortman, called the two-by-two feedback matrix, or I don't remember what it's called, but two-by-two. Craig Wortman, you'll find it. He does YouTube videos and whatever on it, where it's basically creating a way, and it's especially powerful for feedback coming up. So to your point, maybe to say more explicitly, what I think you were getting to is, like, it's really hard to get feedback as the founder, CEO, like, top person at the company, because, like, you're used to giving feedback down, but it's really, really hard to get feedback back up. And so what Craig's framework does is it's a series of eight questions. It shouldn't take any more than, like, 10 minutes, and if it does take more than 10 minutes, you probably didn't do it right. Where all it is is, like, you say something you think you did well, I agree or disagree, and then I tell you something different that you did, that I think you did well. And then you tell me something that you want to work on, that you think you can do better. I agree or disagree. And then I have to tell you something different, that you can do better. And then we roll reverse, and then it's all turned back on me, and we answer the same four questions. But you're in a position where, like, you're not allowed to get out of this. And you do it every week, right? You're like, you're not allowed to get out of this. You have to give feedback.

Callan Harrington 39:02
I like that a lot. I've done some 360s where, you know, you do, like, the good, the bad, the ugly, but, like, I didn't like the ugly part because sometimes it wasn't an ugly. And I don't want to, like, force an ugly. That's a really cool—I am going to look that up, and I'll try to actually put that in the show notes as well. That's a really solid. I'm interested to look into that deeper. So you had this masterclass, and you just learned a ton when you were at LiveWatch. LiveWatch exited again, a common theme in your career, and then you go to Kin. And Kin is a rocket ship—I'm familiar because I've just had experience within the insurtech space. What were some of those challenges and some of those things that you guys found that's like, okay, when you made this change, that made a significant difference? What were some of those in your experience at Kin?

Jamie Ahern 39:50
So many in one, I feel like this doesn't get said enough. But even a rocket ship like Kin—and by any measure, Kin was a rocket ship—there are moments of, like, deep, deep despair where, like, you're pretty sure you're going bankrupt. And that is just, like, even as a rocket ship, that still happens. So, like, I think it gave me the confidence now, with perfect hindsight, that, like, no, there's shitty times you got to go through no matter what. That even building a phenomenal company in that short of a time still has some really, really dark days, and that's just part of the life that you signed up for. I think that was number one. Number two, I got to be careful, because VCs definitely don't like to hear this. But from my perspective, it's so much more important to build the right business and the right business model than it is to necessarily throw tech at problems. Great example is that, like, Kin does have a relatively high-touch sales process, where not all, but a good chunk of the sales process does have a physical person involved, right, to answer questions or, like, help move you throughout the process. VCs are like, "Okay, well, how do we automate that?" And, like, sometimes that's not the right answer, and that it's okay to have, like, a more high-touch sales process, as long as you're accounting for the costs appropriately and thinking about it appropriately. And especially with insurance, that was a very different way of thinking, where previously it's like, if someone wanted your product, you sold it to them, period, hard stop. Insurance is weird because the people that really, really, really want your product, you probably really, really, really don't want to have your product. And so there's this, like, weird push and pull that you have to, like, kind of tease some of those areas out. And especially as, like, the growth guy in the organization, like, that was something I had to get slapped around a little bit to be, like, it's not just about growth. It's about growing profitably. And again, this, like, second, third, fourth order impact that, like, maybe I was having a hard time four years prior understanding of, like, brand was even more so when it was, like, insurance risk. Like, yeah, dude, you can sell whatever, like, 1925 house on the beach in Miami, but like, we're gonna pay for it. And, like, whatever you're getting in premium is not going to cover the cost on this. And so that was a different way of thinking, that, like, not everybody should be our customer. And then, yeah, like, my team got way better, I think, than I was anticipating, where I had 200 plus employees kind of rolling up to me. And that was not, I think, anything that any of us had kind of planned for, but I did have to get really, really good at kind of, like, managing managers, and managing managers of managers, and knowing that that's just a different person with a different kind of, like, set of KPIs that they have to live up to, that also respond different, like, way differently, like you putting a ton of pressure on, like, your direct report doesn't always translate the way you want it to, down to the front lines.

Callan Harrington 42:33
I think those are all great examples, you know. So for our listeners, what Jamie's saying in the most simplified version, is when you sell insurance, and you're the carrier, you know, and you're responsible for paying out any claims if something was to happen that triggered that policy to pay, if you oversell in a particular area, let's just say beach houses in Florida, and a hurricane hits that coast where you had a lot of them, that could kill the entire company, because you have to pay all those claims, and you can go bankrupt really easy. Jamie, one thing I want to actually ask is, you know, you mentioned that even at a company that's super high growth by all times, you have these—by any measure, this is a super high-growth company—but there's still these moments of despair. And, you know, you've been in really high-pressure positions every single step along the way. How do you manage the stress?

Jamie Ahern 43:26
For me, I think you gotta get hit a couple of times. It's that, like, cult classic, like, I'm a huge fan of Green Street Hooligans. It's like about the soccer fighting clubs in England. There's a quote in it that's, like, "You gotta get punched in the face to realize you're not, you're not made of glass." And, like, it's kind of true. Like, you gotta get fired. You gotta blow up a couple of companies. You gotta, like—people always talk about it as failure to make it, I think, more palatable, but no, like, what failure means is, like, you gotta blow a company in half. And, like, everybody that you know and love, like, you just made unemployed, right? Like, that hurts to a different degree that, like, maybe failure doesn't totally encompass. Or, like, you personally have to get fired and be told flat out that you're not good enough to really realize, like, there's always the next day, and it really takes the pressure out of the situation. Like, yeah, you're staring death in the face, but you've been here before. You've died before. It's not that scary. It's really scary the first time through. Gets a lot less scary the fourth, fifth, sixth, seventh time through. And so I think for me, like, yes, it certainly added pressure to the situation. But I think all that meant was I can't miss here. That didn't actually change my thought process or, like, anything else. And I feel like that's another trait of leadership that, like, I learned from Brad. You can tell a seasoned leader from a more green leader. When times are rough, a green leader will try to jump at the problem and get really in everybody's business and try to solve it themselves and be the hero. A seasoned leader will empower their people, especially around that problem. Trust them to fix it, and if it's not working, find new people that can fix it, but you almost take a further hands-off approach when in really, really dire times as a seasoned leader, just knowing that you're going to be more of a distraction than you are helpful.

Callan Harrington 45:14
Fighting the instinct to get into the weeds and to trust your people. Right? The last question I want to ask is, you've jumped up all the way to the top now you're the CEO, right? If you can talk to your younger self and have a conversation with your younger self, your age, whatever age it is, totally up to you. What advice would you have for that person in that conversation?

Jamie Ahern 45:38
It actually has nothing to do with business. I went through a pretty rough patch after I left Kin, but before I started with Karma Care, where I had wrapped up my entire brand around Kin, and I had wrapped up my entire brand around being this, like, startup guy and whatever else, that, like, when that went away, I was very confused and lost on who I was. I think if I could say anything to my younger self, it would be to find balance in a much, much better way, and, like, not just purely chase dollars, because, God forbid you get it, and then, like, who are you? It was a very uneasy feeling for a while. I wouldn't say I'm all the way through that journey yet, but the importance of balance, I think, cannot be overstated, especially when you've seen a little bit of success where, like, you can just tie your entire existence around this company or this problem or this whatever, that may be extremely noble in pursuit, but if and when, like, it's time for you to move on, like, who are you at the end of the day, I think is a question I should have spent a lot more time thinking about as a younger person.

Callan Harrington 46:42
Jamie, I can't think of a better place to stop it than there. Thank you again for coming on the show, man, this has been great.

Jamie Ahern 46:47
Yeah, of course. Thanks for having me.