What I Wish I Knew: Private Equity Leaders' Advice to Their Younger Selves

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Working with hundreds of PE firms at Bluewave is definitely rewarding, but also pretty daunting and humbling. Not a day goes by when I don't reflect, telling myself, Wow, I wish I knew that before. Every day is something where I understand how far I still have to go. In this episode, we have a treasure trove of wisdom from prior Karma. School of Business episodes, where our guests share things that they wish they knew and could have told their 22-year-old selves.

First off is Andy Greenberg, investment banker and founder of Greenberg Variations Capital. In episode 35, Andy shares his perspective on Just say Yes. I think, just say yes. As things cross your field of vision, have a disposition to try different things. I guess the modern, fashionable way to say that might be lean in, but, of course, I mean it more fundamentally.

I did more sports when I was in junior high school, I got into high school, I was small, I gravitated to brainy activities, like to be.

The guy who is the lacrosse coach of my high school, he was a history teacher, came up to me after class one day. And he said the varsity is looking for a Coxswain. I just looked down my nose at it, I thought Coxswain was like glorified equipment manager on the rowing team. That's an example of something I really regret as I've gotten older.

I don't know that it would have been a life-changing event, but of course, as you learn about that sport and what that means, that would have been a terrific challenge for me. That's an educator, that's an example of a teacher looking at a kid and thinking he does okay in class. But this would be a good thing for him. I didn't say yes. We all get into those situations.

We recognize them more readily as we get older, but my advice for younger people would be, where possible, try to say yes. What would be an example of one of those times where you were going to say no, and you said, yes? That's an interesting question where I got into something that was totally outside of my comfort zone. I have never felt as prosperous as when I was a first-year law firm associate. Making $37,000 a year and leaving that job to work for a long-shot political campaign. That took a deep breath, and I did it with a buddy of mine.

I told myself that the chances that it would be such a failure that I ended up at Skid Row were small and did it. I think that's an amazing example. And then you were the secretary of Commerce of a founding state at age 30..

That's amazing.

Next up is Ed Heine, then an operating partner with Cold War Capital, now the managing partner of Line 5 Capital. In episode 32, Ed talks about the value of getting comfortable, being uncomfortable. I think, if you put myself back in that context now. So I was getting out of school, going into flight school. I think I was incredibly focused at that point in my life. Of like, you have to nail flight school, I don't know if you're familiar the way the Navy does, flight school is.

They don't want to stack the deck in any one community with, like everybody wants to go fly fighters, so the top 5 go fly fighters or whatever the number is. I don't know what the math is anymore. What they do is they quality, spread it out. But number one in every phase of their class gets to choose what they want. You go through these progressive phases, you go through ground school, and then you select training location, and then from the training, you go. Helicopters or fixed wing jets and fighters and all these different phases. So I knew, if I want to go to where I want to go, you have to be number one, period. That's the way you get it.

So I was extremely focused on that, but I think what I missed was that you never get done with that at that time. I learned it later is that you don't get your wings in the Navy. And then all of a sudden you know everything you know about flying, you know nothing about flying. You're remarkably dangerous still.

You don't get done with the training assignment, where you spend a year learning how to fly your particular aircraft from my KCF-18. You're very bad at it. Still, when you get done with that, you know. You go through three years of flying in a combat unit, and you spend all your time training and some of your time deploying and doing flights over, in my case, Afghanistan. And you get back from that and you think, Am I done learning? No, man, there's always something next.

And that's true now in my career, right? I got out of the Navy. And I spent a ton of time waking up at five in the morning, doing online courses, trying to, like, fill this business acumen. That I knew that I didn't have, that I needed if I wanted to be successful. You get into the private equity world and you're like, Wow, everyone's much, much smarter than I am. I really need to step up my game, maybe experienced in that area.

I wouldn't buy the smarter. Just the concept that you're never going to be done learning, you're going to be a lifelong student, so just settle into it and embrace that. I think that's great advice, and it's this whole concept.

Like, life's a journey, it's not a destination, and every time I thought I got to a destination, it was a bigger hill. Yeah, 22 year old me totally was thinking like, flight school is the destination, and then, Oh, getting out of flight school is the destination. That, oh, no. I was like, I've got an investment banking analyst job, out of college, I've arrived.

And then, like the great story is, I thought I was such a hotshot right out of college. And then I still had to get my parents to sign for my cell phone and back it. Because I like humbling, I'm like, all right, you know, tail between the legs. And then you get those experiences over and over again, and when you get comfortable with that, then it just becomes part of you. And so I think that's such tremendous advice.

Yeah, I think the tighter way of saying is just getting comfortable, being uncomfortable, and it's something I talk with my boys about. I've got 11 year old, nine year old boys and just talking to them often about just be comfortable, being in uncomfortable situations.

Matt Cole, managing director of SBJ Capital, shares in episode 31 how his 22 year old should embrace the journey. It's a great question and to be able to demonstrate sort of perspective. And what have you learned over the course of your career? And here I am, in my mid 40s, I've been at this for a while.

And as I think about it, I realized me at 22 I wouldn't have listened, it would have fallen on deaf ears. And, you know, I mean, as I just think about my route to PE and to some extent, my somewhat non-traditional path to getting here. For me, it was just embracing the journey and the successes and failures and everything in between. You know, that's been the reality for me. And I think the best, or the biggest lesson learned for me is more than what I've been learning more recently. Is to just have accepted that because it wasn't a direct path. There were a lot of ups and downs, but it got me to this point.

And I think I'm at the right place and I'm extremely excited about what I'm doing now, excited about the firm that I'm part of. And it was a journey getting there. I think that is a great mindset to have and a really hard one. And you know, that's absolutely one that I wish I had as well. Because it's so easy to just to be, you know, put the blinders on and run and run and run.

And I think I probably went through kind of an existential crisis because I've been working my entire life to become a partner at a really good B firm. And then I got there and I said, Wait a minute, I don't even remember the journey here. And I've been chasing this one thing. And then you get it and you're like, looking left and right, yeah.

What do I do now? And I never took time to smell the roses, and part of that's probably just my DNA. I can't help but just keep on pushing things, but boy do I wish I did that.

And I'm trying to find the grace in my life to do that better now, and I still have a hard time. It's a constant lesson, I won't sit here and pretend that it's all I've solved the riddle, it's a constant battle.

So I completely appreciate where you're coming from. I had different visions of where my career was going to go a couple of times. I'm really excited about where I'm at now, but that was not. It was not always obvious that this was going to go. It's like this whole idea that life's a journey, not a destination.

In episode 27, Scott Phillips, managing director at Oryx Capital Partners, shares with younger Scott. The value of resilience, you know, I think there's. And it gets back to that same saying, we just said this too shall pass. Is resilience, I think people that have resilience. And then flexibility to really adapt to the situations presented to you and maximize those opportunities. I think, you know, early in my career, I kind of, you know, I had some challenges that may have may have always me. Or how do I really get through this and really learn resilience over time? Where you really realize, you know, difficult times happen, those are difficult times of opportunity, of real growth and development.

And if you can learn resiliency and flexibility, then I think that that proves very successful later on. So that's that's my two cents in terms of, you know, if I were to tell myself a little earlier, you know. Embrace the tough times, the rough times, because that makes you sharper and better, and that is, you can really maximize opportunity during those times. I think that's great advice. And you know, in this kind of day and age, there's so much about trying to take the pain out of everything. And everything's got to be good and happy. And maybe culturally, in the U..S.

Everything's going to be smile and no one wants to know that. There's tough times. And and I think going back to your first point about, like, having that winning mentality, yeah. And everyone thinks, you know, going back, or even the flywheel, right? Everyone thinks when something's humming and it's all good. It was all easy.

Yeah, you know, but the reality it. It's going through a lot of losses and a lot of like, in winds and everything in between. To get to something where that flywheel is moving at a hundred miles an hour. And I'm like, this is great, but what it really takes to your point is so essential is that resilience is it's nothing is easy to start, yeah.

And there's going to be, you know, you know, this kind of trajectory through humanity, where people think it's like, you're happy or sad. It's really a continuum of change and flux and it takes resilience to get there, and I think it ties really nicely with what you're talking about. This whole winning mentality is you got to have resilience.

You got to have it, yeah. I mean, the only other knowledge I have is also a Texan live in Texas, right? So, you know, I got an opportunity to coach my son's flag football team, and, you know, football is big in Texas.

Yeah, it's on the lights and everything else. And you know, we make it all the way to the championship and we lose. And by the way, only the first place team gets a trophy, yeah.

So it's very rare these days, yeah, very rare. So it was a good lesson for my son. Is you want that trophy?

Well, then you've got to work twice as hard next year as a team and that's. That's the kind of that resilience you got to teach and learn, I think over time. So it's going to be an analogy I have on that one. I think it's a great piece of advice and that'll be something I write down. Because you lose perspective, all these little things that kind of lead to, you know, that continuum of kind of satisfaction in the world.

Yeah.

Next up operating partner Cici Zhang shines a light in episode 22 on Quote Unquote How everything will be okay, and to quote unquote, take the call I mentioned to you. I've loved writing, I've kept journals and things like that throughout my life. So I think one of the fun things about that is. I can read my 16 year old journal entries back then on something like a Myspace or a live journal or something like that.

And reading about all those stresses and just so much high school emo, whatever you want to call it, fears and stresses and emotions. But then then I can read my 20 something year old journals and go back and be like, Oh, it's 20 something year old Cici can say to teenager Cici, everything will be okay. And then 20 something year old Cici is going through all these stresses. That at the time feels like the biggest thing in the world. And then, you know, at this point, you know, 30 something year old Cici can say to 20 something year old Cici. Everything will be okay. So hopefully that gives me confidence that no matter what is going on right now, because at every point, there's always different stresses.

I hope that 10 years down the line, I can continue to say to myself, like, looking back on it, things will be okay. I think the other thing I would say to my 22 year old self. And a piece of advice that I, you know, I'm really passionate about getting more women into private equity, more women in finance. And a piece of advice I always give to young women is, and young people in their career in general, is always take the call, and by take the call, I mean, take the headhunter call. Because I think a lot of times I wasn't looking to leave my role at the time, but I took the call and then I learned something new.

And I was able to compare it to what I was doing and saying. Actually, like, I'm very happy where I am, and so I was deliberate and intentional about staying where I am. I feel good about that versus it's just inertia. And so I always say, take the headhunter call because you'll learn something about a new company or how you feel about that. And one way or another, it helps you make a more informed decision about exploring something new or being intentional about your choice to stay.

Yeah, I really like your two perspectives there, and I remember there's this great Garth Brooks song from I think the 1990s that was. Some of God's greatest gifts are unanswered prayers. And as I think about all the things I wanted, you know, as a kid and grew. And it's like, and then I look back, it's like, Ooh, thank God, I didn't get that dream. So, but what a gift that you've given to your future self to be able to see that progression.

And it goes back to kind of the things that we were talking about at the beginning of the podcast. Is like, if you have the audacity to listen to the universe, it will take you where you need to go. And I remember that was when I was going through my whole, you know, I'd worked my whole life to become a partner at a PE firm. And then I get to this point where I just felt like something was missing. And that was like, I had this ratatouille moment where I was like, Oh, I thought I was gonna be like, dad and build a company one day, and then I had this idea for the company.

And I was going through this existential crisis and I talked to my brother, who's the most in touch with humanity of all my siblings. I'm one of six kids, and so Tim, my brother, really kind of gets the way that humanity works versus my more linear, logical self. And he just kind of said, Hey, you know, if you listen to the universe, it'll tell you where to go.

And my first reaction was like, that sounds a little huggy. But it's also hard to listen to the universe, right? Because you can hear a lot of different things. And you don't know your own what's going on in your own mind, like, parse through whatever lenses and things that you're listening for.

So I think that's a really good point. And I think you're a great example of how the life is a journey, not a destination. If you keep on, you end up in good places.

In this segment, John Huon, managing partner with Compass Equity Group, discussed during episode 19 how he wished he had a deeper perspective on persistence during the early days in his career. One of them is just persistence. Whether it be during my entrepreneurial days or working in corporate America, it takes time, and I see it today. You know? Some of our team members will come in and they'll start their thesis research, and a quarter or two later they'll say, I think I'm ready.

I want to go buy a business and I think it takes a lot of time to become an expert in an industry. And so you have to persist and keep working at it and peel the onion back, as they say, and get smarter. And then sometimes when things get rough, you just got to keep working at it, had a friend tell me long ago. Just preserve the asset, right?

You don't want to lose the asset. Where? If you've invested $50 million and it goes down to 40, that's an unfortunate situation. But you don't want the 50 to go to zero. That's hard to recover from.

So that persistence when times get tough, when you're frustrated, is one of the things that I think is most important. And then I mentioned at the beginning of the conversation, I'm a little bit add. But we look for individuals that are curious, right? That curiosity to always want to be better, to love what you do, to read, listen to podcasts, to do the things that make them smarter, and enrich their intellectual knowledge about a subject over time. If you're looking at it as a job. And you have to come in and do some research about an industry that you're not so excited about, you're in the wrong spot. You need to find a different industry or a different job.

And so if people really become curious and become the subject matter expert in a niche, that's where I think they can really apply value. Whether that be a consultant or an expert. Or that's where you can really bring value when you're looking at a private equity opportunity to invest in a business and grow it. So persistence and curiosity are two things that I try to bring, and certainly I encourage for the team members we bring on board. I think those are two excellent life lessons that if you can just do those two things, nothing else are going to make you a better person with a more enjoyable life. So I very much appreciate that guidance, and probably something I'll tell my kids tonight if they decide not to listen to me anymore.

Yeah, do it while they're young, because when they grow up, they're done. Sadly, yeah, they're tweens and teens, so they really don't listen to me. But it doesn't mean I stop trying because of persistence.

In episode 18, Brian Adams, president and founder of Excelsior Capital, wishes he started owning assets a little earlier in life. Yeah, I thought a lot about this question over the last couple of years, and I'm going to give a simplistic answer, which is I wish I had known earlier. To just start owning assets, be it stocks, be it operating companies, be it real estate, residential, commercial. If you just were in the business of owning assets for the last 25 years, you've enjoyed massive appreciation, incredible cash flow. And I think we're in a world where things are just getting more expensive and pricing is not going to go back now. The earlier that you can get into the asset ownership business in whatever type of ice cream it comes in, the better off you're going to be. I wish I had understood that earlier.

I think that is amazing advice and one that I too, think I wish I did. It's really interesting as you think about people like you and people like me who are in the investment business so often. As I mentioned earlier, the Cobbler's kids have no shoes in how I manage my own personal life, which has ended up okay. But still, as you think about the full potential of what it could be. It's just those mindsets of being in the ownership business and having maybe a little bit of delayed gratification, particularly in your younger days. And what that would mean going forward, as things compound and accrue and build and grow? I think we all have stories, particularly those in Nashville, about, Wow, I wish I bought that.

Yeah, I mean, if you look at we live in a part of Nashville called Oak Hill, it's a residential bedroom community close to Green Hills, Belmede. It's a nice part of town. My father-in-law bought 20 acres in 1984, back when this was considered like the sticks, right? He has taken a company public.

He has had massive venture capital exits, like big multiples. We actually ran the numbers. Owning this property has been his best investment he ever made. That is amazing and that makes a lot of sense. Just what I've seen in Nashville real estate in six and a half years, I can't imagine since 1984..

I remember when I moved to Nashville in 2016.

I was like, Oh, I've missed it.

Yeah, you always think that, but that's the thing is. Like, I would tell my 22-year-old self. Like, you read these articles about people flipping houses or buying coastal property or whatever and like, Oh, it's pricing has gotten crazy, I'm out. If you just put the money to work and then forget about it for 20 years, it's unbelievable.

Next up, Mohit Kansal, managing director with Clarivest, shared in episode 13 how he'd focus on skills development earlier in life, besides a string of stock tips. I would probably be less focused on the specific job or the brand, or getting that grade, but more about building the skills which are going to help you be successful in the future. I know it's extremely tough. I'm sure you're wired the way, say Sean Dugg, you know, he's an overachiever, you know, I got to get that grade, that job, that school.

But it's having the perspective to say, OK, at this point in my career, what are the things I need right? It's being able to navigate challenging situations, it's negotiation, it's analytics, as we talked about, it's big picture thinking.

It's developing relationships with people. Luckily, I think I kind of fell into learning some of these things. It wasn't by design, but you know, there's some things I wish I had spent more time on. When I was younger, maybe I'd been taking an outside sales rep job for a year, right?

Like, you know, maybe that would have been smart. Some stuff which doesn't necessarily make sense on the resume. Or you're like, hey, you don't think about in the day-to-day. But just take a long-term view to your career and life. And not be so focused on the next step and the next step. That's what I think I would tell my 22-year-old self if I had to go back in time.

Marshall Phelps, managing director with Midocean Partners, next puts his arm around younger Marshall and talks with him about being patient, working hard and investing in relationships. There's a bunch of things I would tell that young man, but from a professional context, what I would say is that be patient, right? There's two things. Really, be patient, you know? Keep your head down and you do good work, build relationships, and good things will happen.

I would drill down more on the relationships part, and I've tried to tell my junior and mid-level folks over the years about this point. This is a human-oriented business, and the relationships that you build are absolutely essential to your career arc. And the better you are at it, the higher you will go in your chosen profession. But there's an important caveat to that.

Some people collect relationships like trading cards, but they're bullshit or they're ephemeral. It's like you hear these people start talking of all the people they know, and it's such a turnoff, right? You know, the kind of people I'm talking about? So investing in real relationships, right? You don't have to be everybody's best friend, but try to give somebody. When you talk to them, try to give them some value as much as you're trying to take value from them.

And the other thing I always I would tell my younger self is try to develop those meaningful relationships with the people at your level, right? Because you're going to go through your careers together. So, if you're a young investment banker, build relationships with people in the private equity community that are your age, and similarly in corporates and otherwise. Because what happens is in 10 to 15 years. Those relationships that you build, that value exchange that you've had over the years, develops into a real trust-oriented relationship. And I can't tell you how valuable that is as you get more senior, because you can dispense with all. The who is this person?

Do I trust them? can I get into business with them? et cetera. And you can really get on to trying to make things happen, right? So, you know, as I've moved over to private equity, that's been a huge, huge boon for me. And that's what I would tell younger me. Build those relationships as meaningfully as you can.

I think that's spot on advice. And you know, we've been other than maybe the last couple of few years, we've been a tribal species for thousands and thousands of years. Yes, and life isn't necessarily transactional by any means, but certainly it is something where you get out of things, what you give in turn. And and that's in some ways the reason for the name of this podcast. It's just kind of this karma school of business and life, where just do good things with and for good people. And it spins in the right direction.

And and I, and I think you encapsulated that, you know, very eloquently there.

And last but certainly not least, Devin Matthews, partner with Parker Gale, shares some timeless wisdom about quote unquote being yourself. The early part of my career, again, I was an art history major from Suny Binghamton. I didn't have the resume you see in a lot of private equity firms. I moved out to Chicago get a P.h.D. in sociology.

My brothers were living out in Chicago at the time. I grew up in upstate New York, so I was living in a one bedroom apartment with my two older brothers. We had shared a bedroom for most of our childhood in upstate New York, so that was fun. And they were both English majors, working for Morningstar, the mutual fund company rating company, when it was quite small.

And they were like, Oh, this is great, I get paid, you know? It's interesting enough. I'm learning something new, but, you know, kind of was a means to an end. So I saw that and I applied for a job at William Blair and Company, one of the toniest white shoe investment banks.

There is still a pure partnership. One of the few left, like a mini Goldman Sachs. At that point, a few hundred employees and I got hired by the head of research to help him cover the video game industry. So here I am, 22, getting paid $25,000 a year, which was pretty darn good for me to play video games and write. Research, public company research about it.

And my brothers were like, what the heck, that's a job. And he was really kind to me and he was a blue blood. East Coast Yale Dartmouth, M.B.A. He was a rich guy.

And I was raised in a union household, the very Irish Catholic family. That, like, when you do well, God punishes you for it, so don't do too well. Watch out for rich people. This guy was so kind to me and kind of guided me through the first part of my career. So what I did?

Early in my career, though, I had kind of adapted to that, where I was like, Okay, don't be yourself, be this version of the young William Blair guy in the suit and tie. And, you know, as an art history major, I was a bit of a pretender. So I kind of, like, was like, don't show them too much of who you are. You're not a Cubs fan or a White Sox fan.

You're not a Yankees fan or a Mets fan, you're nothing, you're what you need to be in that room. At that time, I was good at connecting with people.

My dad was a therapist, I know how to talk to people. I was a middle child, like I was the, you know, I was the comedian of the family. So I could connect with people, but I was, and I could connect with them authentically. But I certainly was like, playing the role of, you know, investment banker.

And then I moved into private equity and I'd even more opportunities to interact with people and I could play that role. Not until, like my, maybe my late thirties, after I had a couple of kids and some confidence. And probably when I met Jim Milbury, my co-founder, I was like, Oh, I can just really be myself, and that's probably going to be a lot.

Well, it felt better, I was tired of being somebody else and that's when things really started to take off. So if I look back, I mean, I had a good run for those first half of my career. But the second half has been way more fun and a lot more authentic, and a lot less stressful. So easy advice for an old guy who's kind of made it to say, Oh, yeah, be yourself.

If I had been myself from the get-go, I may not have lasted at William Blair, but I may have wound up somewhere even better. Sooner, we started Parkergal, so people didn't have to edit themselves at work. And I edited a lot of myself for the first chunk of my career. Just to, like, stay safe. Because I was getting paid well, and I was making a lot more money than anybody in my family ever had made.

And I didn't want to screw that up. But once I kind of settled in, so my 20-year-old self was like, You're going to be fine, it's going to be fine. Be yourself and trust your instincts rather than you know, kind of play the game. I think that's great advice and certainly resonates on a number of levels.

I can remember, throughout so many iterations of my life, having kind of imposter syndrome, growing up in a similar kind of Irish Catholic clan. Showing up at this really nice high end college where I was like, Oh, I wonder if they're going to figure out if I don't belong here. And then getting into this investment bank and realizing, Oh, they're going to find out I don't belong here. And then private. And each time I would realize, Oh, I'm just as sharp as these people, and if I just be myself, it's so much easier.

And as we talk about, even like that narrative in your mind that goes and spins and spins and spins. That's certainly something I wish I figured out a lot earlier in life. And you know, it's this whole idea. If you make life simpler, it becomes simple. People want this work-life balance and stuff, and it's like, No, I think it's a life balance. Because if you've put work and I'm stealing this from a friend, Ben, if you've putting work on the same level as life, that's pretty sad.

And then, you know, kind of bring home to work with you. I didn't do a lot of that early in my career, so I don't think people knew exactly who I was. I thought they thought I was funny and maybe smart, a good co-worker, but I'm not sure they really knew who I was. So maybe I cut off some paths along the way.

If I could go back, be myself early in my career and wind up exactly where I am today, I'd be very happy. I just finished Dan Pink's The Power of Regret. He did a big study on regret, which hadn't been done before. Yeah, I'd say that's definitely something I regret, it's probably. I was a little bit playing the part for a while.

And when I stopped doing that, you know, things were good and things just got better.

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