A (3:11)

It's good to be back on the show. I got my cup, too. So we're.

B (3:15)

Hell, yeah.

A (3:16)

We're in there like swimwear. This is great.

B (3:18)

It's like Red Bull. You know, everybody wants the Red Bull hats, but you can't buy them. You got to be sponsored in order to get one.

A (3:24)

Is that true?

B (3:25)

Yeah, you can't buy the Red Bull hat.

A (3:27)

I learned something. And we're 11 seconds into the podcast. That's a good. That's a good start today. Thanks for that.

B (3:34)

You're quickly becoming a fan favorite, so I'm happy to have you back on. This is your third appearance. One time I interviewed you. One time you interviewed me. Now we're going to have a conversation about what's going on in the private equity world and what you've been working on as an operating partner. And I think if we get to, I don't know, let's be aggressive. If we can get you on five times, I think we're going to have to get leather jackets like we're on.

A (3:58)

SNL and we'll, we'll get, we'll do the hat thing. But for us also, we can be just like Red Bull, at least in terms of style, if not profits. I hear they do pretty good.

B (4:08)

Well, for the benefit of listeners, can you give them a refresher on where you work, what you do, and some of the most common types of problems that you help portfolio companies solve?

A (4:17)

Yeah, for sure. So I'm an operating partner at Parkerdale capital. We buy B2B software companies from founders, and I mostly do everything related to sales and marketing and strategy in the portfolio. So you catch me on any given day. That job looks very different, but it's everything from hiring executives to assessing sales and marketing organizations during diligence. To the fun stuff, which is figuring out what we need to do to grow faster once someone becomes part of the family. So that's the job in a nutshell.

B (4:48)

I feel like in many ways you're a go to market whisperer. You get a lot of reps at seeing what the good companies do, what the not so good companies do, and you have some tips and tactics to help them accelerate.

A (5:00)

Yeah, I might prefer Customer Whisperer because I do think kind of everything revolves around the customer and I would hate to ignore my portfolio buddies in the customer success function. And that's super important. And I would say that's also the first place that we look with a new portfolio company is where is the untapped growth in the customer base? Because one, it's usually a little easier to go there first and two, the yield is better, especially if you're trying to make something happen with some speed.

B (5:26)

This is going to be important for some of the other topics that we hit on today. For context, how many companies does someone in your shoes typically have responsibility for?

A (5:35)

So I did count as part of my prep for this episode, and there's nine right now, which some could argue is, is too many. I do try to pick my spot so I'm involved in more shallow ways with some and deeper ways with others. But there are, there are nine right now that I'm involved with. And as I say that, it feels like a lot.

B (5:56)

This is a little off script already, but is it true that VCs, private equity investors end up spending the most time actually with the companies who are not performing? Or is that a misnomer?

A (6:07)

I don't think it's a rule of thumb. I mean, I think it's a function of several things. Like one, you don't get into this job if you don't like fixing problems. So if there is a big problem, you run to that just instinctually. I would also say sometimes, but not always, that's where a company wants the help and is pulling you in because they could use an extra set of hands or there's just a big challenge that they want help figuring out where to even start. But it's not just that. It's kind of a function of the personalities of the management team. I think it's a big function of the trust that you've built with that team for whatever amount of time that you've worked together. And yeah, it's, it's a function of like the challenge or the opportunity in front of you, which I think we'll talk a Lot about today. Like, that to me is the essence of strategy. Like, do you know what the challenge or the opportunity is? And I think from what I've seen, like, the teams that are willing to talk about that also tend to be the teams that are more open to accepting help to go get after whatever that challenge or opportunity is.

B (7:05)

This is definitely not a blanket rule or a generalization, but I remember one friend that I have who works in private equity, he said, one of the companies in our portfolio is going to return the fund. They're doing so well that I spend the least amount of time with them. It's just like we check in and we say, great job. Keep doing whatever you're doing. And he's like, it's a weird inverse relationship where I'm spending the most time with the companies, where we're probably going to maybe claw back to even on it. But it's definitely not the company that's going to 11x.

A (7:29)

I mean, it's something we talk about a lot as a team is just time allocation. Because it feels like you work in these cycles of 3, 4, 6 weeks at a time and you just get sucked into whatever's going on. And I do think you have to create a way to have some intentionality in how you allocate your time. And sometimes it's helpful to just stare at the portfolio and say, there's all these companies, like, where should we be allocating our time and where should we be over investing? This is one of those things where I feel like plans are useless, but planning is essential because that plan tends to go out the window whenever you have to hire somebody new or tackle some new challenge. But. But like, you do have to have the conversation because otherwise you're just going to be totally reactive to what's going on in the portfolio. I do think in some cases it's a situation where the squeaky wheel does get the grease. So, yeah, I don't know if that's true for everybody, but it is one of the things that they don't talk about when you interview for this job, which is you have to find a way to be helpful to multiple companies who have multiple levels of openness to accepting that help, who have multiple different kinds of challenges and opportunities. And how do you figure that out while building relationships with the management teams at the same time? It's part of what makes the job fun, but it's part of what makes the job hard too.

B (8:44)

Time allocation part is so difficult. And okay, so you work with nine companies right now that can go up or down. I ask that, Paul, because operators like myself, maybe we're a little paranoid, maybe we're a little selfish, but we inherently think that our investors are just thinking about us all day, which just isn't true.

A (9:03)

Not all day. I mean, that would be impossible, right? I don't know what the, you know, one divided by nine is as a percentage fraction. I'm not doing a case interview live on this, on this podcast. But yeah, I would say it's always there in the back of the, of your mind, but you have to work on the thing that's in front of you or you go insane. Right? Because the context switching can be a tiring part of the job. But again, it's also like the energizing part of the job. There's always something new to work on.

B (9:28)

Do you assume for the most part that the executives at your portfolio companies are doing their jobs?

A (9:33)

Yeah, we do assume that you're doing your jobs because otherwise the stress of thinking about that in the converse situation, that would be unbearable. I think we do assume that people are doing their jobs. We do assume that people have entered into these roles intentionally and we do assume that you kind of know what you're getting into in an investor backed business, but that it's hard. Actually, one of the things that I did after our last conversation is I went back to how I'm positioning hello operator online and I just thought about like, who is this for and why does it exist? All this time I've been writing for both investors and investor backed executives and I've been writing about leadership and operating philosophy which is related to, but not quite the same thing as like the frameworks that you use to operate a business. It's like a mix of frameworks and mindsets. But the reason that I've written so much about that is because it's so hard, right? Like you're in this business, you've got a CEO that you've worked for or maybe you are the CEO and that's even harder. You've got your team that you work for and work with and then you've got these investor folks. So you're in this like Bermuda Triangle of people who all want different things from you and you're constantly trying to find this balance. So we wouldn't have put you in that situation if we didn't think you could do the job. And our assumption is you want to do the job well and you are doing the job well when we're not watching. Right. Unless you give us reason to think otherwise.

B (10:57)

It totally is a Bermuda Triangle. And I've always thought that about hello Operator, without putting a label on it, that you're writing for the people operating within the Bermuda Triangle.

A (11:06)

That's absolutely what it is. And like, it's funny like sometimes I struggle to figure out is this inbounds for the blog or not? And what I'm trying to do is tackle like there's problems that the business has and those are know, figuring out how to grow, figuring out how to cut costs, figuring out how to make the business more valuable because that's what you were hired to do by your investors. There's figuring out how to build a great team because any job in an investor backed business at the management team level is too big for one person. So you need to assemble a great team or you will fail full stop. And then there's like an ambition or a trajectory component too. Like you want to move up and maybe you want to run one of these things one day or maybe you want to work for the investor someday. So how do you use this as a stepping stone so that yeah, you can build a more valuable business as you go, but so that you can position yourself for whatever you want the next thing to be. And if you're thinking about all three of those things at the same time, not only is that challenging to figure out, but it's emotionally draining and you need like a headset to put on that helps you orient to the right way to tackle that challenge and helps you balance all of the asks on your time and attention. And the cool thing about it, and one of the reasons I've been writing about this for six or seven years now is like it's an unsolvable problem. There's no perfect answer for how to do it. And every company is different. But I do think there's some, some frameworks and some lessons and some stories that can help you. And that's what I try to write about.

B (12:35)

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A (15:57)

I was gonna ask. Yeah.

B (15:59)

A serial cfo and he now runs his own fractional CFO firm, which I refer people to all the time. And we were riffing on this concept of the Bermuda Triangle. I think he called it the Triangle of Doom, which we were joking that it was kind of negative. But from the CFO's position, you have the board, you have. Just because I have to bring it back to me, right?

A (16:16)

All about me. Please do, please do. It's your show.

B (16:18)

You have the cfo, you have the board and you have the CEO. You definitionally, as a cfo, report to the CEO, but you also have a fiduciary responsibility to the board.

A (16:29)

Correct.

B (16:29)

And then you occupy the weakest position within the triangle because there's always information asymmetry on what the CEO and the board are talking about. And then you also have to watch out in terms of what you say to each party because they may be saying something about you. So I do think the cfo, I know other operators also operate within more nuanced spot within that triangle, but it's hard to navigate.

A (16:53)

Yeah, for sure. And like the game of who gets to know what when is one of the most exhausting parts of being in that triangle. Right. Like, you've experienced this, you've been a CFO and you've felt that tension between like, does the CEO need to know this? Do the investors need to know this? Does someone on my team need to know this? And you have to be very deliberate about how you handle that. And what's the Ben Horowitz book hard thing about hard things for CEO? Like that's the hard thing about hard things for CFOs is like there is no right answer about who gets to know what when, but you are going to have to deal with it. And so having a framework or a rule of thumb or even like a story from somebody else that just validates the right way to think about it is really helpful. And there's not enough of that stuff out there.

B (17:35)

I want to tie this back to how you work with CEOs, CFOs and other operators and how you think about your relationships with portfolio companies. I know you love them all, but do you have favorites?

A (17:47)

I mean. Yeah, I do. Everybody does. And if, if your investors are telling you differently, they're lying. And I would say my favorites are not always the companies with the best results. There's companies I absolutely love working with. They're going through rough patches or dealing with big challenges. And it's the relationship that we built, but more like their style of how they have a conversation about what's going on and what needs to happen that either gives me energy or takes it away. And I've done some wr about that. That's kind of the setup for, for this episode. But everybody has favorites in every walk of life, and your investors are no different. The question is, how do you become a favorite? And what puts you on, like, one side of the line or the other? Which is kind of what we're going to talk about.

B (18:30)

Maybe we can start with reporting and communication. You can take it in any direction you want. But I assume there's a way to, to come correct to your investors that make it an easier on ramp to have a conversation.

A (18:42)

Yeah, for sure. Is this a Kellogg thing? I think he said Templates build trust.

B (18:46)

We love to, to quote the great Dave Kellogg of kelblog fame, I think it's templates build agreement.

A (18:51)

Yeah, I like templates build trust. It's got a. It's got a nice meter to it. So maybe, I don't know, shout out to Dave, wherever he is. Just talked to him the other day. I think the first thing that just makes it easy and makes the board conversation, or just the check in or whatever, the, the meeting on the calendar that's usually recurring and usually involves some slides or Excel or both. Whatever makes that go better is if you can prove to us that you can throw a lasso around the business and get it under control and present it to us in the same format with the same visual transference of information that is a signal to your investors that you have things under control. And it also enables you as a management team to take a very important step, which is you stop talking about the data and you start talking about the business. And so what I mean by that is like we've all been in a review or a board meeting where people start asking definitional questions about the quantitative stuff that's in front of you. Like the classic example is what's an mql? Again, like, how are we defining that? Or what's a sales accepted lead? Or like We've all got trauma response to what I just said, so sorry about that. But some people never get out of that. And like every board meeting there's a snag or a record scratch moment where you spend 30 minutes going down a definitional rabbit hole about a metric. And that can be annoying, but like that is a signal to your investors that you have not defined how the business works and you have not created agreement with the board, that this is how we're going to talk about stuff. And I feel like that is a very important interlock. Nobody tells you how important it is. But the really good operators, intuitively or through experience, know that that's really important. Because the minute you get agreement on like this is the template, these are the definitions, this is the slide you're going to see every single time. You get to start having a more fun conversation about again, where are the challenges and opportunities and what you guys are running into is the business actually getting better using data that we can trust as the source of truth and what should we focus on next and what do you need help with? Everybody has felt both of those situations. Whether you're CEO on down, you've all been part of a meeting that just went totally sideways because nobody even knows what we're really talking about. And you try to get to like a center of gravity and it just never happens. And we've all been part of a situation where things are clear, things are standardized, all the static has been taken out of the definitions and that second one is so much more fun to be a part of because you can usually obviously see what needs to be worked on next. It's like, oh, we talked about how we define win rate and we've looked at that for the last eight quarters and it's getting way worse in the middle market and it's getting way better in enterprise. Let's draw a red box around that middle market win rate and talk about what your guys plan is to improve that. And when you do that definitional exercise, the fun part is like what needs to be fixed usually becomes pretty obvious and the way that you fix it usually isn't that hard. Might be a lot of work, but like it's a solved problem. In the world of business, the problem is a lot of teams never get there. I'm in love with the teams that do the work early to get there.

B (22:10)

I had a faux pas on this in my second ever board meeting. So we knew that we wanted to have a discussion around if our sales efficiency made sense and our unit Economics made sense to have someone physically walk into a shop to try to onboard them as a customer, send a person in, right? And so I brought all the materials for it. I brought this CAC payback slide. And it was like that record scratch moment, like. And somebody from Insight, I remember said, how are you calculating that CAC payback period?

A (22:38)

Danger Will Robinson.

B (22:40)

Dude. Next. Next 30 minutes. Yep. Not fun. Just debating how that was calculated for a marketplace business with a SaaS component. We never got to the point of if we could now deport like, the. I hate when people say strategic, but the strategic conversation of if we wanted to hire people to walk into these shops. And we ended up being like, why don't we come back next quarter to discuss that? And so I was like, I'm going to footnote the shit out of how this is calculated and standardize it and send it to people beforehand. Because I was, like, embarrassed that, like, we were debating the merits of how a metric was calculated rather than like, the big moment. I wanted to have to be able to go back to the CRO and CMO and be like, we can now do this. Like, we didn't get to it.

A (23:18)

There's two levels that you have to hit to solve that problem. I've written about this in something called how to build your data diet. I think is the title of the. Of the article. Data is not there just because we love data. We like to nerd out on data. Data is there so you can have the most honest answer to a question possible. Because, like, everybody knows what the questions are. There's no argument about the questions. Like, for. In my world, it's how much pipeline are we creating? How much of that pipeline are we converting? What are the key deals? What's our coverage for this quarter? Like, all the, all the questions are exactly the same. The problem is everybody is on a spectrum of, like, how quantitative and how honest are they in the answers? And like, if you're answering those questions with feel or anecdotes, you're just opening yourself up to tons of questions about, like, why aren't we more exact? And how much should I believe? But if you answer those with metrics that you've agreed on for how you calculate them and what the edge cases are, you're in a situation where, like, we're not talking about definitions anymore. We're talking about how we're doing and we're talking about the next thing that we need to fix. So my advice for CROs, but I think it applies to pretty much every function is you should build your data diet with your CEO and ideally with your investors. So instead of saying, well, what do you guys want to see? Which to me is a signal that someone doesn't have a strong opinion about how to track the business. Not a good sign. You get to a one page menu where you say, okay, every week we're going to show you this. Every month we're going to show you this. Every quarter we're going to show you this. Left hand side, here's the questions we're asking and right hand side is here's the metric and the calculation that answered those questions. Are we good? And if you do that, one, you get extra credit right off the bat because not a lot of people do that step. But two, you get to have that conversation usually in a more intimate setting, usually in more of like a fun intellectual sparring match. And three, you come out of it with agreement where you say like, okay, everybody hold hands and jump. Because these are the definitions that we're using to talk about the business going forward. We're good? Okay, we're good. Let's go.

B (25:19)

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A (28:59)

There's a bunch of signs. I mean the templates thing is, is a big one. Like if, if you look at the game tape of, let's say it's Q4 and you look at the game tape of board meetings from Q1, Q2, Q3, Q4, and you just, you didn't have a hobby, and you spread out all the slides on the floor like McConaughey and True Detective, and you looked at all of them, and if they're all different slides in different order, that's not a good sign.

B (29:23)

And you can tell when they pulled them, like, pull that one from kickoff, pull that one from the all hands.

A (29:28)

Yeah. So if you're, if you're just, like, doing the greatest hits of slides you've used elsewhere, that's not a. That's not a good sign. And it's also a sign to me that the board meeting is a weird thing. And in some cases, it's a little performative and theatrical. And we try for that not to be the case in our portfolio companies. To me, you should be going through the exercise that results in a good board meeting, like every week or at least every month, which is, again, going back to your data diet and reviewing either a trend line or some other way of laying the data out, asking yourself, okay, what is the insight here, if any, doing the McConaughey exercise, but in a more productive way, saying, okay, out of all the data that I just looked at in a consistent way that I look at every month, where is the biggest challenge or opportunity on my team? And picking two or three of those things and going to attack them like that, to me, is the workflow that results in a really thoughtful conversation in the board meeting. And if the format and the order and the actual data points that you're doing that with change every month or every quarter, you're being a little schizophrenic with how you're thinking about your business and you're not in command. So I don't know. Board meetings are. The importance of them are overemphasized. I mean, it's very important for us to have good governance for our companies and have a good conversation every quarter. But we're meeting with our companies way more often than that. And the folks who have figured out that there's seven or eight drivers that really are going to make a difference to making this a more valuable business in my function. And I look at them in a consistent way. It's obvious when you talk to them without any materials, but it's also obvious when they share materials with you on a screen, because it's the same templates, it's the same order, and it drives a conversation that isn't show and tell of the data itself. It's. Here is the challenge or opportunity that arises from that. That's what I want to talk about. And by the way, as investors, that's what we want to talk about, too.

B (31:30)

And if you're going into a board meeting and you're preparing for this mic drop moment, good or bad, you have also failed the TAS test going into the board meeting because updates and discussions, it shouldn't be. Well, we got all this bad stuff. Let me just package it up and I'll drop the atomic bomb, you know, in Q4. Yeah.

A (31:49)

If you are viewing the board meeting as a dumping ground for the evidence of everything that you've accomplished, or illustrative examples of all the things that someone doing your job would produce in the time period we're talking about, that's not good. And I think you need to reconsider the relationship that you have with your board and probably with your work, too, because this is not about proving to us that you're doing your job. It's not about, look at all the things that I've accomplished. It's what is the thing that is keeping us from the business, that we are supposed to be in your area of the business, and are we addressing that thing or not? I will sometimes get a feeling of impatience in board meetings that are not going as well as they should be because we're six slides in and there's a lot of stuff that's happened and that's great. I can tell that people have been working 40 plus hours a week. Fantastic. I have no idea what the obstacle is that's in our way or what the opportunity is on the horizon that we're running towards. And that's what makes me nervous if I don't know what those things are.

B (32:53)

That is so well said. And there is this performative aspect of board meetings. There is this undue pressure I think we do put on ourselves. And I was actually talking to my wife last night. She's always made fun of me about how serious I take these things, how, how. And what she really gets upset about is I get frustrated. Like, if someone goes to, like, make a smoothie in the other room and I can vaguely hear it during a board meeting.

A (33:15)

Turn off the ninja. Let C.J. talk.

B (33:17)

I was interviewing somebody yesterday. My wife left one of our children home with us while she went to pick up the other one and she walked in on the podcast and luckily I can, like, say, hey, I'm really sorry about that. Let me just try that again. The person I was interviewing, he said that doesn't happen at my house because I have a lock on the door. Because my son, who's 5, walked in with his Legos during a board meeting. So I was telling my wife about this because I'm like, see, I'm not the only person who's crazy about board meetings. She's like, I don't get it, though. Like, you know these people. And what I tried to explain is that you may only have 12 hours a year to truly make a good impression on someone who determines a lot about how much you get paid, what your role is, and your scope in the company. And it sounds crazy to say that, but not all hours are created equal. Now you should have a relationship with someone like you, Paul, who's an operating partner who you can come to, and then you have more times to recover. But, like, it's not the same thing as me showing up and saying something stupid or having my kid walk in when I'm with the Rev Ops person I deal with every day. I only have 12 hours, I feel like, to make a good impression, we.

A (34:16)

Frame that up in our management team onboarding. So we. We just closed the deal. We have the management team in either their office or ours. And Devin, our founding partner, likes to give this speech. It's a good speech. And it usually starts with, our average hold period is 5ish years. That's four board meetings a year, 20 board meetings. Let's not waste any of them. And we actually take people through. Like, this is our philosophy, which we're talking through a lot right now. But, like, good board meeting, bad board meeting. And we recognize that part of our job is to get all that definitional and template stuff out of the way as early as possible without getting in the way of the business. So that there's no guessing game of what we want to see. If somebody asks me what I want to see in a board meeting, I know I screwed up because I haven't helped them templatize how they think about things, and I haven't taught them, like, what we like to see. And more importantly, we haven't translated those templates into the handwriting of the business because every. Every business is different. You. You said something too. Like, there's like, an undue performative nature to a lot of. And I actually think there's a simple tactic that executives can use if they're a little brave. But I've never seen it backfire, so I'm gonna share it with you, okay. Asking for permission. So when your section of the board meeting comes up, and you can do this ahead of time too, but if you find yourself Sucked into a vortex. And in a board meeting, this is something that you can do right off the bat. I'm happy to take you through all the slides that we hopefully set you in advance that talk about how we're doing and where we're focused. But with your permission, I would actually like to spend about 70 or 80% of the time on. On three big topics because I think they're really important. And I'm going to ask you for resourcing on one. I'm going to ask you for your input on another. And the third is just honestly really challenging and complex and involves multiple functions. And I just want to have a debate about it. Is that okay? So you tell me, like, how many times have you seen executives start they're part of a board meeting with, like, a proposed allocation of time and asking permission versus just like, oh, no, now it's my time to share the slides, and I'm going to do the show and tell with the slides. Unfortunately, like, I've seen the latter happen way more often than the former.

B (36:31)

I haven't maybe once, maybe twice. But people get tunnel vision, like, this is my time. Here's my deck. I have rehearsed it. Yeah. And if you can take yourself out of that, it's big.

A (36:42)

And. And again, the McConaughey exercise of taking your board slides in your barren studio apartment with no furniture, putting them on the hardwood floor and staring at them and saying, so what? That's what you should be doing is laying those out on the floor. Not. Not actually, but if you want to, that's totally fine. And asking, so what. What is the most important thing I want these people to take away? What is the most important challenge that I'm tackling right now? What is the most important opportunity that we're going after? And, like, what is the synthesis? That's what we're hungry for, is the synthesis. Like, yeah, we appreciate that you've put the storyline of the business out for us, but if there were two or three things you want us to leave with in terms of the things that really matter, the things that are keeping us from the business we're supposed to be, what are those? And I don't like when I have to ask that question in the board meeting, and it's very clear that person has thought about it for the first time, you should be thinking about that before that meeting ever starts. Otherwise, you're. You're in trouble and you're missing an opportunity. To your point, because, yeah, you might only get 20 sessions with these people. And the best way to make them count is to overallocate your time to the shit that matters.

B (37:55)

60 hours in 5 years sounds like a lot, but it's not.

A (37:59)

It's not.

B (37:59)

Paul, I'm gonna ask two tactical questions here. Super tactical. And then, then I want to move on to simplifiers and complicators. How many days before the board meeting should the materials be sent out?

A (38:09)

I don't know enough time to read them. I don't have a. I don't have a strong.

B (38:14)

But a week. From my perspective, I'm giving you a lot of time to come back with a lot of questions that I'm going to have to go back and forth with before. Like, I do think too much. There is such thing as too much time. But then I also don't want you to have to review it over pancakes and the La Quinta Inn the morning of the board meeting.

A (38:31)

I, I'm, I'm thinking about this answer for the first time, so bear with me. But I, I think it's like a balance, right? It's, it's enough time to read and absorb it, but not so much time that the information and the story in the deck has gotten stale. So for me, go to market nerd. If you send me a board deck a week in advance, I'm going to ask you how much the pipeline has changed and if those deals have closed. And like, there's. Good point. It depends on your business. Yeah, like, it depends on the pace of the business. The pace of the business is very slow and you're closing two or three enterprise deals a quarter. In my world, it might not matter if you send it a week before, but for most businesses, I think night before is fine, couple days before is great. I think it's a conversation again, asking for permission with your investors. Hey, how long do you guys need to spend with the materials to absorb it and feel like you're walking in with most of the context that's in the deck. That's a great question to ask. And when you guys agree on it, you don't have to wonder anymore. It's great.

B (39:32)

Second question, should you send the entire deck of what you're going to go over or just what you want people to concentrate on ahead of time?

A (39:40)

I'm not sure I have an opinion on that. I mean, I think it depends on what you start to knit together over a couple of quarters. Like, again, if you've started to templatize the board deck and there's some operating metrics and you guys tend to focus on big discussion points instead of kind of the functional show and tell model. Every company's different. But I again, I think that's an agreement. I don't think that's a best practice. You should create that agreement with your investors. And if stuff's a little chaotic and the framework changes, I think a good measure of your relationship with your investors is like, do you feel like you can have that conversation or not? That's a question to ask the investors too. Like, are you creating the environment where your management team can come to you and change the structure of the board meeting because they think it's appropriate? If they can't do that, like, you got to work on the trust between you and the investors, in my opinion.

B (40:28)

Well said. I want to get to one of my favorite frameworks that you have, and it's simplifiers versus complicators. Who are they and how can you tell which one you're dealing with?

A (40:39)

The fun thing, I don't know if I have to answer this because the fun thing about this article and this concept is people intuitively know what I'm talking about.

B (40:46)

When I can bring it, I can think of each. I can think of archetypes of each. I think of people I've worked with for each right now.

A (40:51)

So don't, don't name names. But I'm very curious for you, like, what comes to mind when I think of simplifiers and complicators because we've all worked with both of them and we all know like what the behaviors look like and how different it feels to work with them.

B (41:04)

More importantly, the complicator is usually also the person who wants to get on the phone to do the work in real time because they don't want to do the work. The complicator and the energy vampire, they live in the same house. They're roommates.

A (41:16)

There's the Venn diagram. Might be a circle in that. In that case for sure. That's funny.

B (41:20)

I can think of a lot of complicators who. A complicator typically will keep asking for more data. They want to have perfect data, but they also don't agree with the data a lot of the times. And then a simplifier, what comes to mind first for a simplifier is someone who's able to pull out the one variable or the one component that matters. So to give you an example of a simplifier in a negotiation, one of my favorite all time business heroes is Sam Zell. He basically created the idea of the real estate investment trust.

A (41:49)

Yep.

B (41:50)

He did hundreds and hundreds of deals. I think he sold his company to Blackstone or Blackrock for like, $60 billion.

A (41:57)

He did pretty good. Yeah.

B (41:58)

Yeah, he did really well. And I remember he said, I've done a lot of deals, but in every deal, there's really only one question that matters. And a simplifier will find that one question, whether in a negotiation or you're trying to figure out how to allocate resources. And they will ask that, and they won't stop until they get that finished.

A (42:16)

Yeah, I like that. That's actually my number one thing. Like, I think this comes down to three core behaviors. It's answer the question, it's find the problem, and it's do the work. And the best simplifiers that I've ever worked with or been mentored by, they go three for three on those things. And I think the first one, in a lot of ways, is the easiest. It's also in. In some ways, the least common. And this goes back to a good board meeting. Like, I think Dave has a blog post on this, too. That's the first rule of. Of working with senior executives. Like, answer the question. I've even seen people express this in an acronym, which is atfq. And ATQ stands for answer the question. You can figure out what the F stands for. Every question that you're going to get asked by an investor or by an executive at your company, you can answer it directly, or you can take them on a ride around your entire part of your job and everything that's going on, and spoiler that that person does not want to be taken for a ride. They just want an answer to their question. I think there's a great Clayton Christensen quote that goes without a good question. A good answer has no place to go. And so I do think senior people are good at thinking about what's going on and trying to ask good questions. And so, in a way, I think answering the question is good manners, because you're kind of matching the effort that they've put in to putting that curiosity out there, and you're answering it with, like, a stick, the landing point. And complicators just can't seem to do that. And I would also say, like, complicators don't point out the problem. They talk about how much work's being done. They talk about how hard it is. They talk about the complications. This is especially true in sales. Like, you ask a complicated salesperson what's going on with the deal, they Will walk you through the entire three book epic of all the stakeholders and all the meetings and all the interactions they've had. But they won't, to your point, tell you about the thing that matters in the deal and if that's getting addressed. Yeah. And then complicators don't tend to turn in stuff on time because something always gets in the way. It took me a while to find language to describe it, but now that I do have the language, it's something I talk about with our leaders a lot. But I, I use it in interviews a lot. It's the number one thing that I test for.

B (44:26)

Salespeople can be the best at complicating things and they can be professional complicators and their whole weaponry is using words.

A (44:35)

Right.

B (44:36)

They know how to take you on that ride, but also feel like they're appeasing you. Be likable. And as a cfo, my weapon is numbers and I'm never going to win the word versus word battle. Have you ever caught yourself in that vortex?

A (44:51)

Oh yeah. And like recovering sales guy right here. Right. So I grew up in that age like doing prospecting over the phone before all this tech stack stuff got got crazy. And you learn how to draw people in and you learn how to connect. And if you've been in sales for more than a few years and you haven't made a hard jab, step into some other function, you know how to do that. And as a result, me being on the other side of the table now trying to assess salespeople, it's probably the hardest job to assess for because so hard salespeople are good at selling and in an interview the product is them, they're good at selling the product. And you kind of, you'll have these out of body experiences sometimes in sales interviews where the person is three or four minutes into answering a question and I can just picture myself like floating above my body saying, he hasn't actually said anything yet, but he's been talking for four minutes and it sounds good and I'm like nodding my head and falling into the trap. And luckily I've been, I've been good at keeping myself out of the trap. But it's, it's very challenging and you have to have ways to cut through all that stuff and figure out like what has this person actually done? How good are they at generating results? Do they actually know what they're doing to generate those results and will that transfer here, Getting that out of salespeople can be really hard.

B (46:06)

I had this Friend. His name's Bob Bobby. And he would be telling a story. We'd be in high school, driving from one part of town to the other. It would be seven minutes in, we're on the other side of town, and he's still just telling the story. Like, he can't stick the landing. And finally, my buddy Baker would just go, get there, Bob. Get there. Get there, Bob. You can. You can do it, Bob.

A (46:26)

Get there, dude. Get there. The hard part is we're rooting for Bob, too. Like, we're all, like, we. We want him to get there. And it's just. I think it's a lost art. Sticking the landing is a lost art. By the way, that's actually a cue that I used to use with my teams at Bain. So before we go into big presentation, I would literally not only say, stick the landing, I would physically emphasize it by saying, stick the landing. And I would tell them to think about a gymnast going off the vault, hitting the pad, making that noise, and sticking the landing. And that's how I wanted people to emphasize the point. Because when you do that, people pay attention and they take that forcefulness of the communication one. It's a clear sign you're done. Somebody else can jump in, but it's a clear sign that, like, you've thought about it and you're willing to put yourself out there in a little bit of a vulnerable way to make the point and then to see, like, what do you guys think? Do you agree? Do you disagree? Let's have a conversation.

B (47:20)

Well, why is answering the actual question such a lost start in business communication? Is it because we're hedging?

A (47:25)

It's a hard question. Let's see how articulate I can be with this, because I have a lot of feelings for it. I'm not sure I have the words for it.

B (47:32)

Okay.

A (47:33)

I think there is, in a lot of cases, a misplaced understanding of what's going on. When someone asks you a question in a business setting, you mean what they.

B (47:44)

Mean by their question. What's behind their question?

A (47:46)

What's behind their question? So if you're in a situation where there's not a lot of trust between you and the other person, and someone asks you a direct question about the performance of your part of the business or the thing that you're supposed to be responsible for, it's easy to take that in a way that seems like an accusation. It's like, wait, is this person trying to expose me? Is this person trying to make a point? Is this person trying to you know, and then what you do there is like, you put up your dukes conversationally and you say like, I'll, I'll show them. And you typically get into a situation where you, you talk about how much work you're doing, you talk about how much progress you've made, you talk about how hard it is, you talk about how hard the team is working, and you, you kind of treat it like a defense attorney treats evidence. You're like, here it is. Can't convict me. But in a situation where you can either bring yourself to trust the person or you've built that trust ideally between, between both of you. And it's built on like, mutual vulnerability. And you've kind of seen that, like, hey, we're both want the same things and we're okay making mist and making false moves. It's like, oh, they just, they're curious. It's easier to take that as a curiosity than a signal of mal intent. I don't think it's as much of a lost art in business communication. I think it's a. It's a bit of a missing component of business culture in a lot of companies is they haven't taken the time to build that mutual trust and vulnerability so that people know that when they ask a question, someone else is typically trying to help them solve a problem, not expose them for something they're not doing. Does that make sense?

B (49:17)

It does. And this is what I wanted to gear towards a close and discuss is the act of naming the problem. I feel like the most mature people in a business setting, especially in a board meeting, are not afraid to name the problem. Can you just give me your perspective on, like, when you've seen people step up and just say, this is what we're dealing with. What do you feel when they say that and how does it make you respect kind of what they're working on?

A (49:41)

I get pumped. My saying that people do impressions of me and make fun of me for, but I will not stop saying it, is, you can't fix a secret. And it's true. You can't fix a secret. And so I think it is a tremendous signal of confidence in yourself as an operator when you're willing to say, that's broken, that's behind. We tried that, that didn't work. And here's what we're doing next. Like, the best operators understand that if you're batting.300, you're in the hall of Fame in baseball. I don't know if it's lower or higher in business, but it's pretty damn close. You're going to make some mistakes. Everybody knows, especially in the world of investing. Like, we invest in imperfect businesses on purpose because we think we can help them reach whatever business they're supposed to be. Like, we used to use the phrase full potential at Bain. The way you get to full potential is not by, like, perfect scientific optimization of processes and people and technology that's already pretty good. It's, how do you do it? You do it by fixing broken windows and tightening loose screws and, like, helping each other along the way. And so if people are posturing, like, nothing to see here, everything's fine. That, to me is like, glowing white hot, that there's a problem there and I gotta dig deeper. And if an executive is saying, you know, we have one big problem in our way right now that we haven't solved and it's X, I immediately respect that person more because what have they just demonstrated to me? They've demonstrated that they've done the work to look at all the data and their function. They've taken a stance, which is inherently a vulnerable thing for a human being to do, especially in a situation where there's multiple faces staring at you on zoom and silently judging you. And they've opened themselves up to say, like, okay, well, what are you going to do about it? I don't think board meetings should be dramatic, but I do think board meetings should have moments of vulnerability where both investors and operators say, this is what I haven't figured out yet, and this is what I need help with, and this is what's coming next if we don't fix this. Because again, you can't fix a secret. And if I leave the board meeting wondering, like, what the actual problem is or what isn't working, well, I know it's there. It just makes me nervous that I don't know what that thing is.

B (51:56)

There you have it, folks. Paul, this is always a pleasure. Anything you're working on that gets you excited.

A (52:01)

Lately, there's stuff in all nine companies I'm talking about that that's exciting. I won't get into it here. I will say I'm starting to do more writing. Not only a hello operator, but at the blog@parkergale.com we're putting more and more content up there. We're investing in the podcast using some of what you're doing CJ as inspiration. So folks will start to see some of that. But if you're not subscribed to the funcast, you can find us anywhere. Podcasts are sold PE fundcast. There's already some great stuff there and there's going to be way more of it on YouTube, so that's what I would say people should watch out for. And yeah, if these ideas resonate, all my stuff's over at hello Operator on Substack. It's free. It always will be. Not going to stop. I love writing it and I love talking about this stuff with you. So I appreciate you having me on.

B (52:45)

Can't Stop, Won't stop. Thanks dude. This is always fun to jam with you.

A (52:49)

Yeah, I appreciate it.

B (52:50)

Ear on the Numbers is a mostly media production yelling an intro by Fat Joe Artwork by Meg Delesandro. Show is executive produced by Ben Hillman. Nothing said on this podcast is intended to be business or investment advice. It's the sole opinion of me, a guy who feeds his dog way too much ice cream and has a history of net operating losses. Lol. If you like this podcast, hit subscribe and give us five stars. It will take like two seconds and our algorithm overlords love it. Drink water, call your mom and have a great day.

A (53:18)

Peace.