Parker Gals | Just Ask the Question (w/ Caroline Phipps, ParkerGale)

0:00In this one particular board meeting, I had a question in mind about a slide that came up like nine minutes into the board meeting. And I didn't ask it because I was like, I don't want to, you know, I don't want to sound dumb. Everyone did the pre-read.

0:13Cass: Everybody already knows. Right, right. And then 10 minutes later, somebody, an executive asked the same question. And then, you know, the response was, that's a great question. And then we spent 20 minutes talking about it. And I was so bummed that I had the question 10 minutes earlier. Yeah, this is a huge missed opportunity. And like this executive person didn't know it either.

0:50Cass: Welcome to another episode of the Parker Gals podcast here at Parker Gal HQ. you. Today I have with me one of our own, Caroline Phipps. How are you doing today, Caroline? I'm doing great. Awesome. And Caroline is coming to us from Philly right now while her husband, John, just graduated from Morton Business School. She's a VP on our investment team. How are you feeling today? I'm feeling great. I'm excited to be here. I love the Parker Gals branding. I think, I can't believe I haven't thought of that in five years. I've never thought of that. I never thought of that. I was telling Liz, who came up with the name, for those who haven't watched the inaugural episode with Liz and I, our associate came up with the name.

1:38Cass: I feel like you have to be maybe a little bit outside of it to come up with. And then somebody else recently said to me, oh, podcasts. And I was like, instead of podcast. And I was like, man, you guys are good with the puns. I feel like I'm too far in it now to take a step back and realize these things. I also, when I was deep into Twitter, back when Twitter was fun, I, you know how there was like hashtags for everything? I, for some reason, decided to like live tweet when live tweeting was also more of a thing. Me attempting to paint my bathroom of a place that I was renting because it was like horrible.

2:18Cass: and so I like went you know I was like in my 20s went to like somewhere to pick out Sherwood Williams to pick out some paint uh and I like decided to do this with champagne and so I like was live tweeting it and I forget like I like was putting like hashtag champagne and painting and like one of my friends at the very end of me painting and like taking pictures and showing the saga was like, Cass, champainting. Like, it was there for you the whole time. So maybe we'll go back in time and make that a thing. Incorrect it, yeah. But anyway, that's not what this podcast is about. This podcast is about Caroline.

2:59Cass: So Caroline, you studied accounting and finance at Indiana University. And you also played D1 soccer casually on top of doing everything else. And you were the captain of the soccer team. And during that time studying accounting and finance, so were you a double major? Were you just like, was one a minor? Yes, I was a double major in accounting and finance. Very casual. Okay, doing all these things. Honestly, like being in private equity and investment banking probably felt like a breeze by comparison. You're like, oh, what are people complaining about? Like we all have the same 24 hours. Um, and then you were, you started William Blair for two years in investment banking.

3:46Cass: And we'll probably get into this a little bit, but you didn't recruit within like three months of starting William Blair for private equity. you we we hired you well into your second kind of go around the sun your second year at william blair in december and you started with us in june yeah i started in at the beginning of that august oh that august in december yeah which is i mean we were on it that year i feel like you were um And that's called off-cycle recruiting, which is crazy. We hired you eight months in advance to nine months in advance, depending on the exact dates. And that was late.

4:34Cass: That's like all of your peers probably knew what they were doing a year ahead of time. Yes. Yes, some of my peers who worked in New York banks had their jobs within a week of hitting the desk in their first job. in investment banking. They had their next job for two years from then. Which is crazy because you're just like, how'd the first week go, buddy? Like, oh, I've just been at training. Right, exactly. Or I haven't even, I just booked my flight to go to training. I haven't even been to training yet. Which, yeah, we can get into a little bit about like how you thought about that in a second.

5:09Cass: But before we get to more of your career stuff, okay, so you are VP on the investment team here at Parker Gale. That's a little bit a hint of your background before that. Let's get to know you a little bit before we ask you all your hard-hitting career questions. So we're going to do the indication of interest section. And the first question that everybody here at Parker Gale who has met you for more than a day probably knows about you is what is your go-to comfort show? So this is very easy. My go-to comfort show is The Office. And that might sound like a basic answer. but that's why it's a comfort show exactly I think I've watched every episode of The Office probably five times or more one of the primary drivers a lot how many seasons are there of The Office oh I think seven okay maybe maybe for some reason there's like 10 in my head okay so there may be 10 there may be 10 we don't know I just don't need to know yes but yeah my siblings and I have just loved the show for so long so I think my sister and brother have actually watched it more times than I have.

6:18But there, yeah, there's just something about it when I dissect why it's so relaxing and comforting to watch. The day-to-day nature of the plot lines and how they develop the characters and you feel like you know them makes everything feel so predictable. And also after you've seen it five times, it's extremely predictable. It makes it a little humor in like every 30 second bit. So it's just the best. And I will continue to watch it for an extended amount of time. There's no due date or end date on when I'm going to stop watching The Office.

7:02Cass: You're not sick of it yet. No. When you watch it, are you like, I know what episode I want to watch and that's the one I'm going to watch today? Or are you just like whatever's on or wherever I left off? So that's a good question. I think I go by seasons. Like sometimes I'll be like, I would love to watch season one and two, especially, you know, like sometimes I'll just start the first episode for fun because it's so interesting how it evolved from there. And other times watching like what people would say are the best seasons. So what was it like three to six or seven when Michael's in his prime a lot most of the time I'll just go to those episodes like go to fun run watch those episodes again yeah I do think there is something a lot of those like I feel like those 22 minute long comedic shows like I feel like there's a lot in that era of like parks and recreation and modern family yes like where the first season doesn't get appreciated until like they're like three seasons in like I felt that way about um the gosh now I'm struggling to think of the name but it was like with the Rose Motel and the oh yes Schitt's Creek yes like I kind of like hated the first season when I first watched it I was like why do people why why are people obsessed with it it it I feel like the office is the same way where like it takes a while to like get to know the characters and then once you know them like it's lovely and then you go back and you can enjoy like I remember that one I am not a serial re-watcher but I did go back to watch the first season of that so I actually enjoyed it the second time around because by the end of like the five or six seasons of that show I savored it and I loved it and then I like kind of got to go back and actually enjoy the first season because I like kind of hate watched the first season because I was like let me get to know these people and get through this but like totally yeah why is this who are these people what's going on I feel like the office is that way totally yeah I'm no no expert whatsoever in watching film or reality tv but I have noticed now now I try to identify what tricks they're using to get you to know or like the characters more quickly at the beginning so that you buy in faster yeah especially in reality TV, they'll pose like, here are the people you should be supporting.

9:30Here are the people that you shouldn't like. They don't want you to be neutral.

9:34Cass: Yes. Yeah. That's so true. And then what's something that you can cook without looking at a recipe? All right. So this is kind of a hard question because I don't really cook. I enjoy cooking, but definitely when I cook, I need a recipe. So one thing I've made for the last 10 years consistently, sometimes every day, sometimes just once in a while. It's a blueberry banana smoothie and I have the same formula every time. Frozen blueberries first in the ninja blender. First is very important. Then vanilla protein powder, then peanut butter, either powder or normal peanut butter. It doesn't really matter.

10:16Doesn't matter. A splash of milk, kind of any kind of milk you have, but just a splash. If it's too much, it's not good. And then sometimes I add spinach, sometimes not, depending on if I have it or not.

10:30Cass: Depending on spinach quality as well. Yes. Whether the spinach is wilted in the fridge or not. And then banana. And then you just blend it up. That's the stack in that order. I like add liquids too late, I feel like. yeah and i don't do don't do too much liquid because i like it to be like ice cream texture yeah you're like making an acai bowl yes yes and then i find i can't buy a smoothie that's better than it that's good so i recently read actually i think this was like the headline of an email it was like we have protein smoothies at home or something like that which is just like oh yeah Like I could just make this instead of spending like$15 on it.

11:15Yes.

11:16Cass: Which is the going rate, I feel like. Yeah. And when you buy them, they're way too big. Like I don't need a 32-ounce smoothie. No. Yeah. No. That's amazing. And you've done that for like 10 years? Yeah. Since freshman year of college, I've made it the same way. Yeah. So you were not only double majoring, playing D1 soccer and captain your senior and academic captain your junior year, if I remember correctly, but on top of all of that, you were making smoothies every day. Yeah. You and I had different college experiences. And then what is your perfect Saturday? This answer I know to my core is actually my perfect Saturday nowadays, but likely would have sounded really boring in the past.

12:05perfect saturday would be to wake up have breakfast at home with my husband and my daughter and my husband usually makes breakfast is he yeah is he and he's making yes he makes avocado toast with eggs exactly how i like it that's the best and then we would go to the farmer's market get some coffee depending on the season hot or cold very important you're like not you're not a serial killer who only has cold coffee no every day of the year no matter what it's dependent on the day yeah which one it is that's good and then yeah then the rest of the day we would just we

12:40Cass: would go to the park yeah go outside yes we would be in a big grassy area with a soccer ball and a blanket and and then we would have a big meal when we got home and watch a movie that's my perfect saturday that's amazing it is it is funny i when we were in i feel like same age toddler stage uh tyler was asked recently like by somebody like well what do you guys do on the weekends and he's Like we go on walks. Yeah. We go on really. The walk is the event. We go on really long walks. You can find us on a walk. And like the person was just like mortified because like they didn't have kids. And they were like, what do you mean?

13:19Cass: Like what else are you doing that day? And he's like, that's the day. It's almost all of the day. And a lot of times the walk is, yeah, it's more of an event than what we're actually going to. Yeah. Like we might get coffees on this walk. like we we're gonna have to find some kind of grassy area the kids will point at cars and tell you the color of the cars the whole time and it's delightful actually yeah I know it's so silly but like it is it is funny I feel like Liz is gonna get different answers because she's interviewing associates I feel like than I am I feel like my answer so far for like VP and up is like pretty consistently.

14:01Cass: Like it's a little boring, but I love it. Yes, but it's ideal. Yes. All right, let's get into career.

14:13Cass: So what drew you into private equity? I will start with saying that my brother-in-law, who's about seven, six or seven years ahead of me in life and school and all that, he went to Indiana University as well, did the investment banking workshop, which I can get into more later, and then did investment banking after undergrad, and then he went into private equity. And you knew your brother-in-law well by this, like when you were entering college. And you're one of four. Yes, I'm one of four. I'm the third child of four. And my older sister really set the bar extremely high when she met her amazing husband freshman year in the dorms.

14:59Cass: So many kudos that your other siblings are going to be like, you're spending this much time on an in-law. You better be talking about me. Okay. Yeah. So yeah, she met, they met freshman year and then have been together ever since. Um, so I, I've known him since I was probably like 13. And then by the time I went to IU also, I've, you know, followed in my sister's footsteps. I going to IU, I knew he was, you know, he was in investment banking and then he did private equity and I knew he loved it and he thought I would like it a lot. So that was kind of in my head. But of course, as a college student and then as a new, somebody who just started in their first year in your career, you know nothing, which I would have admitted at the time and I know still now.

15:46I didn't know anything. So I wanted to do my first year, one, because I just was like, I want to know what the job I signed up for is. And then also I really loved William Blair and I love the people there and I wanted to learn from them and they were brilliant and awesome. So I did the first full year at Blair thinking like, I'm not going to respond to a recruiter email.

16:12Cass: Which was probably tough in and of itself because I feel like recruiters are just like ding, ding, ding, ding, ding, ding, ding, ding. And yeah, like, oh, and there's social pressure. Yes. Of like, what are you doing? What are you not doing? Right. Yeah. Pressure to determine the rest of your career. And we already have jobs two years from now. Now, Caroline, what are you doing with your life? You're like, I'm just like trying to figure out what tomorrow looks like. and like how to do a good job. Yeah. Right. And learning things like as simple as how to access the drive, you know, or how to do a, create a good PowerPoint slide.

16:51That's actually a professional level and not college level. I still haven't figured that out, honestly. Right.

16:55Cass: I just go to Paul's office and I'm like, can you, I did my annual meeting slides before he did his this year, which was a huge mistake because you know what I did this morning is I went in there and I looked at his and I was like these are so much better can you let me know when those are on the drive and I will steal your same format he has the consultant's touch but also a Paul touch on top of it that's just like a premium I know slide like he doesn't he doesn't mind like he actually prefers that I keep his yeah consistent instead of like having to sit through me. So yes, please do take my format.

17:35Cass: Please do take this. Like, please, yours are horrendous. It's objectively the better way to think about things.

17:43Exactly.

17:44Cass: Okay. So you, you kind of like, were like slow burn for relative to investment banking. You're like, I'm going to try this out for a little bit before taking a job a weekend. Were you focused on, remind me, were you focused on anything at William Blair? Were you kind of all over the place in terms of industries that you were working with? So I was in the services and industrials group, which was grouped together at the time. And I, so I spent some time on some industrials deals. And then most of my time ended up being with the commercial services group. So we did deals like environmental services, facility services, construction services.

18:24So yeah, it was services and not tech like at Parker Gale, but extremely interesting. And I really liked it.

18:30Cass: So you did that for a little bit and then you were like, okay, after a year, I'll like maybe start responding to these recruiters. Like what kind of, what did you learn a year plus going into your second year, a year and a half in where you're like, okay, you know what? Like maybe I will explore kind of doing that more traditional path of like two years of investment banking. And then I go into private equity. Yeah. I felt like I learned for myself that I wanted to do PE when I got so much exposure to when we were on sales when Blair was on a sell side mandate and we were speaking on the phone with lots and lots of private equity firms to sell the company that we were engaged to sell I often found it was so interesting to hear from the VPs and associates at the private equity firms it was so interesting for me to hear their questions about the company that I was working on because I had been working on that company for maybe six months.

19:28Months ahead of time. They're just seeing it for like 10 minutes. Yeah. And then 30 minutes. And you're like, oh, I didn't think about that this way. Exactly. Yes. So I was very intrigued by the way that they thought about deals in general, about companies in the space in general. Like how did they know to ask that question? That was such a good question that I didn't think of. That drew me to knowing I wanted to do that role.

19:54Cass: Yeah. And you probably met a ton of different versions. I mean, you're selling a business, you're talking to a ton of different firms, you're probably starting to figure out, you know, what kind of firm would I want to work at? And what kind of firm would I not want to work at? Definitely? Yes, yes. Which I don't know how you I feel like you probably can tell that by the way, like people show up on a call. But like, I don't know, how did you how did that kind of like inform what you were thinking when you're like, okay, I kind of am interested in going to this other side, Like what kind of was that mandate?

20:27Cass: Like what were you looking for that may have been different if you were looking for it right out of school? Yeah, I learned through being at Blair that I really, through working with many different teams and then also just the firm culture in general, was great to where people would treat you with respect. and have, you know, before starting a meeting, they would ask how you were, just do simple things like building connection and not treat you just like a number or a cog in the wheel. So I liked that a lot and I didn't want to move away from that. What I saw in many of the meetings with private equity firms when we'd be selling companies is firms have completely different cultures where sometimes they would just approach a management meeting without any of that and just cut straight to four hours of hardcore questioning.

21:18Cass: Yes. You were in on the spotlight. You were like, I'm grilling you. Right. And then our client, who was the management team, afterwards, I would hear from them like, that was a brutal experience. Yeah. They didn't want to work. But like for the right price. Yeah, right. And oftentimes, though, they would tell the bankers like, we didn't like those people. so and you know even hopefully they don't bid the highest hopefully they don't the highest yeah yeah so I saw a lot of that and then yeah just through the interactions I just knew I was looking for a place where when where people treated you like a person first and did interesting work and I was like maybe that's too much to ask I didn't know at the time you know but when I found Parker Gale.

22:07I absolutely found that. And I, one, I mean, one of the few things I noticed right away was that people were paying attention on the Zooms because I was interviewing during COVID era and we at Parker Gale do panel interviews, which means several people are involved from Parker Gale.

22:26Cass: You'll have like, you'll have like four people from Parker Gale and then Caroline on the other end. Yeah. Yeah. Which feels intimidating, but at the same time I was my first thought was oh they care about this meeting they're paying attention to the meeting yeah and they're they all they're all on it and they didn't yeah reschedule six times or cancel last second on me and you know which is or there's not like six people on the invite but only one person showed up right right so I felt very respected and I was like I know that they would treat me this way if I was working with them and you don't get that at other firm sometimes.

23:01Cass: So yeah. Yeah. Yeah. That's interesting. Okay. So you're at this like kind of influx point that we're talking about here from IB to PE, but what about like going on this path at all? Right. So early on in your career, kind of who helped inspire you? You talked a little bit about your brother-in-law kind of, Hey, maybe you like this flavor of investment banking. So then like, maybe you tried it out. Like how, if we think about like mentors or we think about like getting down that path because that is also like a path that people do take but like you don't it's like if you know you know and if you don't you don't and then like it is kind of a hard leap on top of by the way playing soccer and doing all these other things who helped kind of inspire you to go down this path and can you talk a little bit about what they did and how that thought process worked and kind of where it led you.

23:59Totally, yeah. So the person that comes to mind is Professor Haverly at Indiana University, who's still doing great things running the investment banking workshop and other programs. But when, so I knew about the investment banking workshop through my brother-in-law. and then once I got interested and joined I met with Professor Haverly and immediately just knew he was somebody I looked up to and I think just throughout the program it's for context the workshop is and I think it's it's evolved over the years but yeah at the time it was a combination of a club and a class essentially so it was a big commitment to be a part of you would take courses with the cohort of people that were in it each semester starting sophomore year and then you also it's not just one class right wow it was yes and sometimes it was multiple classes each semester that you would take with that cohort of people and then you also had commitments almost every weeknight of the semester going to firm presentations for like banks that we're recruiting.

25:10That's why you needed that protein powered blueberry smoothie. And I would often show up to the events after practice with my hair in a ponytail in business formal. Oh my gosh. Which wasn't a good look at all, but I just had to do it. It was a look. You were remembered.

25:30Cass: You were memorable. Yeah. I had to get my name on the attendance sheet. So you didn't get kicked out of the club. Exactly. So anyways, throughout the years, because it was about two and a half years that I was involved in that program, Professor Haverly is such an inspiration in that he, I think he cuts through a lot of the noise of what you hear as a college student. And I think is an increasing trend of what college students experience, which is pressure for what are you going to do after this? And you have to decide now and you have to be the smartest and the best and involved in the most things.

26:04And there's a lot of social buzz and pressure about like who's getting what job. Yeah.

26:09Cass: And you're like, wait, how can we all be the best? Right. And then you start to get disoriented, I think a little bit on what actually matters. And Professor Haberley instills in every student in the program that like first and foremost, what matters is integrity and humility, which I've totally kept through, you know through my time and my career I think about that all the time and it's helpful to hear because you get you know you could get in situations where totally different messages yes otherwise yeah totally he would instill confidence and still does in us as college students to not be afraid to reach out to alumni to talk to them and be grateful for all the time they're giving you but also like you have something to offer which is hard you know that's also like a confidence boost you kind of need because when you're at a giant school with thousands of people and everybody's so great and so smart they're like oh how am I you know what am I going to offer this alumni who's 10 years older than me on a call but um yeah the confidence to send a cold email and get on the phone with an alumni you've never met before definitely came from him and all my peers experienced that.

27:25And then also he encourages everybody to give back once you are an alumni. So yeah, I actually met my husband in the investment banking workshop, which is an extremely nerdy thing to say, but we met there and then you were

27:43Cass: spending so much time together that it makes sense. Exactly. So yeah, shout out to that professor for also running a matchmaking workshop. Exactly. Yes. Yeah. We have thanked him before for that. And I think there are several other couples that came through the workshop, which is so funny. Yeah. That's amazing. Okay. So now you're kind of often on the receiving end of those calls. What do you get out of them? So you were saying, hey, he gave me the confidence to realize that I had something to offer. When you are on the receiving end of those, you know, however many years later, what do you get out of those kinds of phone calls when you do get them?

28:31Cass: And you probably, what students probably don't know is you like, you get a lot, but like compared to how many you could get, it's probably not that crazy. Like reaching out is still worth it. Totally. Yes. Yes. I agree with that. And I used to get a lot more as, you know, when you're an analyst at an investment bank, you get so many emails. Yes. People are like fixated on that first step. Like, how do I just get this from here to there? Totally. Yeah. That's a good question. I enjoy all the conversations. I think I'm always extremely impressed with how many things they're doing. Like, like you're.

29:07Yeah. Same. Yeah. Even because, you know, I, I feel like I was very, very involved. I was very involved with my soccer team and I was very involved in school and the workshop and outside of that, not many other things, but to be clear,

29:22Cass: like there's no, there's really no time to be. Right. There wasn't more time, but yeah, students today will be involved in so many things and they'll be, you know, starting a company or they'll have so much insight into a certain industry that they've been looking into or reading about. Yeah. So I admire their excitement about different things that they're involved in and also about their future. Yeah. I always encourage them to be themselves too. Because I think tied into what I was just saying about the workshop and Professor Haverly, I always felt like, oh, no, am I going to have to not be myself at some point to get a job or to do well on a job?

30:07And I was very, I was kind of scared that I would, you know, even sending a cold email, sometimes you're like.

30:12Cass: People do that and people do that. And I like, I remember straight out of school, like my roommates, I lived with like two other girls, like for most of my 20s and like, and had different roommates, most of them college friends and being like, and hearing them especially covet times i mean by by covet times it was just listening to my husband on phone calls which was also interesting but like if somebody did take a work call or i saw them in like a work setting for some reason i was like this is a different person yeah this is not my friend this is like a different they're just like completely like new mask on like now i am work version of me yeah like oh and i probably to some extent did a little bit of that right like straight out of school.

30:56Cass: I was just like, I am a pencil skirt wearing like accountant, and this is what I must look and act like, but that's exhausting. Yeah, it's exhausting. And then also, I realized once I got a little bit older out of college, you're not, you're kind of not fooling anybody. And I think, I'm sure people older than me think that about me today and my age people today. But yeah, they, like, I know what the college experiences like so you don't have to it's okay pretend like you're a professional robot yeah yes I know I like probably when I do talk to college students which is more rare I feel like yeah like you're usually talking to people who are like a couple years behind you looking at the next rung so I'm often talking to like younger professionals but if I ever do talk to college students I'm like so out of the mix where I'm just like just have fun yeah just have fun like There's plenty of time for not fun things or to be very serious, but don't forget to have fun.

31:56Cass: But I think you can also have fun and do things that are beneficial for figuring out what you want to do in your life, in your career. Okay. And then speaking of learning and all that stuff, fun stuff back in school, what is something – so we're always learning and our careers are always evolving. what is something that you figured out recently that you wish somebody told you earlier? So for this one, I think I relearn it. I've relearned it every year since being at Parker Gale. So it's a little bit different of an answer, but in my first or second year, I realized that you can and should ask questions.

32:43And that was, that changed my perspective on work. I think before then there was a thought that if I'm asking certain questions, it's going to sound dumb. It's going to sound like I don't.

32:57Cass: I needed to research all of this stuff before this conversation. I should know it. So I'm not going to ask anything. Yeah. I'm ashamed that I don't know this basic thing. Right. Or what I think is a basic thing. Correct. Yeah. So what I learned probably about a year, year and a half into being an associate at Parker Gale was I just started realizing that in meetings, especially in this one particular board meeting, I had a question in mind about a slide that came up like nine minutes into the board meeting. And I didn't ask it because I was like, I don't want to, you know, don't want to Everyone did the pre-read.

33:38Cass: Everybody already knows. Right, right. And then 10 minutes later, somebody, an executive, asked the same question. And then, you know, the response was, that's a great question. And then we spent 20 minutes talking about it. And I was so bummed that I had the question 10 minutes earlier. Yeah, this is a huge missed opportunity. And like this executive person didn't know it either. Totally. Yes. So I have learned, I feel like every year I learn that same lesson in a different way. And now, like this past year, I've been so much better at my job, I think, because I'm able to, I do prepare and then I'm able to make the conversation more interesting and progress things more by asking what I don't know.

34:28And what oftentimes then other people actually don't know either. Or there's just like a ton of assumptions. Yes. Yes.

34:36Cass: On both sides that like, if you don't ask the question, it might be even the most basic, like I was on a meeting this morning and one of our colleagues was like, well, have you talked to this? Have you talked to the person about this issue? And they're like, no. And like, what a very simple question. Like there's an issue that we're talking about involving an employee that we're trying to figure out like this answer to this data question. Right. And it's like, yeah, well, that employee will get back to me with the question that I had. And it's like, well, you have to have you talked to them about the problem?

35:11Cass: Like, oh, no, I haven't. So sometimes it's just like, oh, yeah, I'll do that. We should do that. Totally. Yes. There's just yeah, I also learned that lesson all the time. I've also had that same thing happen a million times over where I'm like, I don't know this, but surely everybody else in the room knows this. And then somebody else asks that question and you're like, oh, like, and then it leads to a great conversation. Well, yeah. And, and like, I made this assumption that was completely wrong that everybody else already knows this and I shouldn't ask. And it led to a great, exactly per your example, like 20 minute, like, this is not just like a good question.

35:55Cass: Here's the like one sentence answer. It's like, no, this is actually really meaty. So you would have missed out on it, right? Okay. And then what are you most interested in or excited about right now in the industry? And for us, that's tech and private equity. So you could take that either way. Yeah. So you know this extensively because we've been working together on some stuff, but I have really enjoyed the last six months playing with AI tools as the start. And then now what I'm most enjoying is figuring out how to actually best use AI tools in my day-to-day. So of course this is what everybody in the world is doing right now.

36:42But I found it so interesting to figure out what it's good at and what it's not good at. And yeah, just how to get really efficient

36:52Cass: with using, for example, Excel plugins as a little analyst for me to, when I know exactly what I want to do, to like maybe take a first pass building something. Set up the template. Here's the format. Or to audit something that I've done and would just like a second look at. And then I think for tools like Claude and OpenAI, there's so many use cases for being like a research assistant, but then learning all the areas where that's not good at being a research assistant and how, where you need to audit and continue to be skeptical. That has been so interesting for me. So I feel like you were very early, even for our firm, who I feel like was generally kind of early because we're in software, right?

37:47Cass: We're like in, when I talk to other friends who are maybe in industrials and other things, they're like, AI, like, I don't really know what's going on over there, but like, we're starting to figure it out, I guess. But it does also make sense to me that you were, you were kind of one of the folks spearheading, I feel like here of like, I'm going to try out, I'm going to speak to all these tools, all these different vendors, see what they're offering take you know well have you know my note taker take copious notes um but i also it makes so much sense to me too because like you are like queen efficiency for those who don't know caroline the only time you are you have such a sunny disposition and you have a great attitude which is just like obviously amazing qualities to have as a person um the only time that i will see you even like hint at having like like being upset about something is when something is inefficient yes yeah that is true like this could have taken 10 minutes less like than it did and like it just like makes you die inside so i feel like you are very primed for the age of ai like you are in the right potentially in the right you know decade yeah i haven't thought about it like that but you're totally right that is yes and I think why I'm so now that I think about your history is like oh yeah you were juggling all that you had you had no choice but to be efficient yeah and show up in business you know formal professional with a ponytail because that was the efficient option right so we're maximizing time yeah yeah which is clearly what we're doing on this podcast right now so exactly yeah you're gonna you're gonna be like 10 out of 10 enjoyed being on the podcast however here's some show notes we could have made this way more efficient if like maybe you didn't talk as much you would never say that no no um okay and then what is speaking of the private equity industry, what is a commonly held belief about private equity that you disagree with?

40:00So I think my answer to this is likely highly biased to the fact that I've worked at Parker Gale for five years. And that's my only experience working in a private equity firm. But I think it's commonly understood among like executives and folks who work in PE that the relationship between a company's operators and the PE firm is a little bit stress inducing. Yeah. And it's kind of like a top down. The private equity firm has to have a lot of tension.

40:35Cass: Yes. Private equity firm tells the operators what to do. And often maybe they wouldn't want to do it that way. They make them report things that they wouldn't necessarily report. And it's just additional work, you know, work creation and a source of stress for the operating team that could slow things down. In my experience at Parker Gale, I would hope the management teams feel this way too, but I think we are a lot more collaborative with our management teams. So sometimes if, you know, if we're asking for certain additional reporting or analyses, we're often really working with them on it so i would hope that they feel we're more a source of leverage or support for them versus a source of more work and just stress yeah period yeah i feel like you're really good at that for example if you're like hey we need to start reporting on this one thing can you tell me where like what's the best source of information for that oh it's HubSpot.

41:38Cass: Oh, it's, you know, your instance of this of NetSuite or whatever. Hey, can I help you? Like you, you're like, what's the next step that you're going to have to take to like audit what we have? Let me do that for you. Let me help you with that. Let's look at the data together. Versus like, hey, have you thought about raising prices? We should raise, I'm going to put it in the model that you raise prices by next quarter. Right. Even if that's not going to fly with your customer base. we're gonna do it yeah so if if it's not that you'll have to figure something else out to get us to this revenue number in three months so good luck good luck um yeah we i i tend to agree i think i actually heard from uh i was at a dinner last week very unsolicited i was talking to like a student at booth who was like oh yeah in my legal class like the lawyer was working against parker yet or something like that i don't i i don't have specifics i wish i did and and apparently we got like this glowing review of like like an incredible private equity firm to work with because like we were like so kind and i was like i don't know if necessarily we want the reputation for like the lawyer that is like litigating or like is doing a deal against us to be like they're so nice but apparently uh our reputation precedes us in the legal world a little bit enough to like get because sometimes i like talk to students and i'm like oh interesting that you've heard of us how have you heard of us probably the podcast or probably some kind of form of content and like And he was like, no, you guys have a podcast.

43:25Cass: And I was like, how did you hear about us then? So I'll take it though. I'll take being a nice firm to work with for sure. We are now at the closing call. This has been fun so far, but let's wrap it up with some questions about you. So what is the best book you've read this year? Great question. So. With all the abundant time that you have. Right. For reading. So I had read the book, The Rose Code, with my book club in Chicago. You have a book club? Shout out to my book club. Wow. Yes, it was a book club with women in private equity. So we had a lot of fun. What? Yes. That's amazing. Did it come out of Peak?

44:16It did, yes. Private Equity Association of Chicago. ago. I met my, what I call my first adult friends in that group. And then we started a book club, which is very fun.

44:27Cass: Oh, that's amazing. Yeah. Okay. So that was, this is not the book you're saying was the best book though. It's related to that book. Right. Yes. We read the Rose Code, which was phenomenal. And it was written by Kate Quinn. She also wrote a book called the Alice Network, which I'm almost finished with. I cannot say I finished, but that is the best book I've read this year. It's historical fiction. And she writes a lot of times in the first person from the perspective of strong female characters. And they're so interesting. She's very creative. And it's fun that it's historical fiction because I feel like I'm learning.

45:07And it's really interesting.

45:09Cass: Yeah. Yeah. All right. That's a new one. I haven't heard that one yet. So that's good and now I'm jealous of this book club yeah I always want to be in a book club but then I'm a bad book club member because I've like joined a book club in the I've joined two book clubs since coming to Chicago and then I like get salty about the picks though like I'm a bad book club member because like yeah because you actually read the book but I'm like why did we choose this like non-fiction thing about like who voted for this the way that it has worked at both of these was like everybody submits things and then it's like drawn from a hat kind of thing it's not necessarily most popular pick which i would like more i think i like i like a popular pick versus like we would get some obscure things that i swear like just like one guy in the corner like submitted and wanted to read who didn't even show up that month um so we're all like why are we reading this so um and then the my the most successful attempt i've made at a book club has been just with two girlfriends so it's just been like easy to like kind of agree on things and we just each take turns picking something yeah but we've kind of fallen off the horse and meeting is easier too meeting is easier because it's just three people but in a weird way meeting is harder because you need a quorum like you can't just have two so and honestly like if my friend who is in this book club of three ever listens to this podcast which you probably won't i would be okay with her knowing that i of the three we have a very flaky friend who cancels last minute all the time yeah which makes it really hard it makes it really hard To find motivation to finish the book when you know the book club meeting is going to get moved.

47:09Cass: The book club meeting will get moved. It will be getting moved multiple times. And so what me and the other friend have decided, me and the other friend are moms, and we're like, we already put on the calendar that we're going to this book club, that if our flaky friend flakes, bless up Marla, you know it's you. If Marla flakes, we will still get together and like have chips and margaritas or something because like we already like have bookmarched. Like this night is ours. We won't talk about the book. We'll wait. But like we are still taking the night off. I think so. I love that. Yeah. We keep the book club strong, but it's not quite.

47:48Cass: I don't know if I could call it a book club. Yeah. Yeah. Our ratio of books to meetings started to decline over time where we would meet more often than we would discuss a book. the book you're like oh shoot we should we should reschedule to actually talk about the book next time we're like next time when everybody's finished with it oh no see i will say what worked out really well with the first one was like if you show up and you didn't finish reading the book like you like we're still gonna talk about the book like it they were on it yeah They're like, you are, it's going to be spoiled for you.

48:26Cass: Yeah. Yeah. But like, we're not waiting. We're not waiting around, which I liked. Okay. And then what is your go-to karaoke song? Do you have a go-to karaoke song? Oh, I feel like there's an easy one. I don't know if you sing it though. I know where your head is going. I actually would say, no, it's not Sweet Caroline. Everybody does always play it, though, and sing. They sang it at my wedding, which is really fun. I probably wouldn't have had an answer to this except for this weekend. I was on a walk and decided to do karaoke. A karaoke trolley passed by, which I have not seen except for in Nashville.

49:13and they were singing Breaking Free from High School Musical, the whole bus, and bringing so much joy to the entire street. And everybody I was walking past was actually smiling. And I was like, I can't not smile at this. This is amazing and hilarious and the best energy to be spreading in a downtown area. And I realized that would be my go-to karaoke song now because I was in like the prime target market for High School Musical.

49:43Cass: yes I was just I was just a little too old for it but I still loved it and you had to secretly love it because you couldn't you kind of secretly loved it and then like you would like see like talk to somebody who's like oh I loved it too and you're like so excited that like you could I like similar to something we were talking about before I feel like it's so important to like nerd out on stuff and be okay with it and like the thing that I probably hate the most a quality I hate the most when it happens in people is when somebody like yucks somebody's yum because like it's not socially cool to do something or whatever like don't do that to people don't do there's enough of that in the world like just let I don't know how old I was was I in my early 20s I don't know and like singing breaking breaking free maybe yeah but like yeah don't yuck my yum like just like it's way more interesting to be actually interested in something than it is just be a nerd it's like so everyone else yeah yeah it's just like lovely okay and then the last question if you weren't in private equity what would you be doing instead?

51:00All right. So this, I have a very specific answer for this and I have no qualifications whatsoever. This is good. Then yes, it's a good start. Yes. I would love to be, I think, an optometrist in another life because I've always had really terrible vision. I've had contacts since first grade. And so I go to the eye doctor every year and every year it's the best experience ever. I love going to the eye doctor. Why? The eye doctors seem so happy and they correct your vision and they give you your context. Have you been to multiple eye doctors? All of your eye doctors are happy? Yes. Yeah.

51:41Cass: Maybe it's just been this like one eye doctor you've had for years that is just like a very happy person. No, it's like every, I've been to probably in the last five years, I've been to three different eye doctors based on living in different spots. And they're all happy. Yeah. And they're happy and they're chill and they're cool. And they do a great job correcting your vision. And then you leave. You leave happy. And I'm a happy customer because I have new glasses and new contacts. You leave happy. I mean, what I can see better. Yeah. Yeah. And I have no, I haven't taken a biology class since high school.

52:15So I have, again, no qualifications whatsoever. That's okay. No idea what their actual job looks like, but the experience as a patient is amazing. Every time I come home, like in another life, I would be an optometrist.

52:27Cass: Yeah. You're like truly making people, like if you fix something that's like been off and they've had bad vision, I can imagine like there's just like instant gratification and satisfaction in your customer base. That would be nice. Totally. I feel like a very similar adjacent profession in my brain as not a person who's a doctor is like dentistry. It's the opposite. Right. People are stressed. Yes. And then they leave the dentist appointment being like, yeah, like my teeth are a little bit like smoother and maybe I got some fluoride or whatever, but like overall, overall, I'm like, like grumpier or like I did.

53:05Cass: I'm not satisfied. mm-hmm yeah I agree interesting all right well now we know well I learned something new see you told me that you wouldn't surprise me with anything and guess what I'm surprised um this was very fun thank you so much for coming on the podcast yes of course this was so fun we'll see you next time on Parker Gales amazing thank you so much Cass

53:36Thank you.