Speaker 1it's important for them to understand how they and their organization got there, which is they got there not because they were great leaders, but because they were really good at doing the job, doing the work, doing the analysis, doing the presentation.
Speaker 2I'm Ted Seides, and this is Capital Allocators. My guest on today's show is Matt Spielman, founder and CEO of Inflection Point Partners, an executive coaching firm that works with leaders primarily in investment organizations. Matt first joined me on the show four years ago, where we discussed his path into executive coaching, inflection points in his career, and his GPS system that aligns an individual's goals and helps execute on them. Our conversation this time around builds on that foundation with what Matt has learned. We explore the challenges of leadership at the top, the personality dynamics that shape investment organizations, and the essential role of feedback, empathy, and appreciation in managing people. We discuss the evolution of Inflection Point from one-on-one coaching to firm-wide leadership systems, and the role artificial intelligence may play in scaling his work going forward. Before we get to the
Speaker 3interview, a quick announcement. We've set new dates for our Capital Allocators University. Those dates are December 3rd and 4th in New York City. Later in the year is just a better time of year for this gathering. It's post-AGM season, travel starts to wind down, it's right before the holiday crunch time, and it's a great time for Capital Razors to reflect on their previous year and plan for the year ahead. December 3rd and 4th in New York City. CAU for IRBD is a closed-door gathering for Capital Razors to connect with peers, learn from allocators and other experts, and really share their experience. You can learn more at CapitalAllocators.com slash university. Thanks so much for spreading the word about Capital Allocators University for investor relations and business development professionals. Capital Allocators is
Speaker 2brought to you by AlphaSense. Here's something for you. Most AI tools today are very good at sounding right, but can you actually trace it back to a filing transcript or specific passage? Or are you just trusting the confidence of the output? For allocators, that's not a minor concern. A missed filing, incorrect source, or context that gets lost somewhere in the retrieval chain aren't edge cases. They're how decisions go wrong. AlphaSense is the AI platform built specifically for this. They own the content. Over 500 million curated documents from broker research and expert transcripts. To filings and earnings calls. And they own the retrieval layer on top of it. That means every answer can link back to an exact, verifiable source. Because the answer is only as good as what's underneath it. And with AlphaSense, you know exactly what that is. See it for yourself. Try a free trial at Alpha-Sense.com slash Capital. That's AlphaSense.com with a hyphen in the middle slash Capital. Capital. Capital allocators is also brought to you by Morningstar. In a sea of data, you need to know what you can trust. Morningstar's data, analytics, and research helps bring clarity across public and private markets, connecting independent research and data into the tools and AI platforms you use every day. So insights are easier to spot and act on. Morningstar. Nothing in your way. Visit Morningstar.com slash GameOn to learn more. Capital allocators is also brought to you by Juniper Square, the operations partner trusted by the leading private market GPs. One theme that keeps coming up on the show is GPs that build the strongest and most durable relationships with LPs are the ones that have both strong returns and strong operations. AI raises the stakes on operations. And having Juniper Square as your operations partner helps ensure your data is organized, accurate, and accessible so you can unlock operational alpha. That's why thousands of GPs trust Juniper Square. Learn more at JuniperSquare.com slash Capital Allocators. Please enjoy my conversation with Matt Spielman. Matt, great to see you. It's great to be here, Ted. So you've been at this for 10 years now. What have you found works?
Speaker 1People really grab onto systems. And structure. Executive coaching or professional development, by nature, can be a little bit squishy. What I tried to do is provide a system that people can grab onto and say, we're in this part of the system now. Now we're in this one, and now we're in this one. Now the structure combined with this maniacal focus on outcomes and achievement and results also rings true for a lot of the folks who grab onto it. They get a lot out of it, a lot more than they thought they were going to get.
Speaker 2When you put the system in place, what types of outcomes is the system driving towards?
Speaker 1Determined by the individual and or the team. We often engage executive teams or even offices, but it's determined by them. It's certainly not something that I come in or my team comes in and said, this would be a really meaningful outcome for you. We can give background or context. We've had thousands of coaching sessions. Hundreds and hundreds of game plans. These are some of the things that people aim for, but it's really driven by them. The outcomes can be somebody wants to advance to the next level. Somebody wants to raise a certain size fund. Somebody wants to launch a new type of initiative. Somebody wants to open up an office. Somebody wants to acquire a sports team. They can be lofty goals, and we complement that with things that are going on in their life. So it could be in their family, could be at home or out of the office. That's a really important focus of ours. Recognizing that they're not robots, which can't just show up and compartmentalize all the other facets or pieces of our life. We do have them set goals for non-work related outcomes.
Speaker 2Once you set that process in place, having worked with lots of leaders at this point, and particularly in asset management, what have you found are some of the characteristics of who these really great leaders are and what they go through? It was after probably it was the
Speaker 14,000 coaching session mark. I sat back, began to reflect, and some themes emerge of some of these leaders, these managing partners, these CEOs, these managing directors, et cetera. The one ironically that sits at the top is that it's really lonely at the top. Oftentimes an individual or a partnership team, they have things in their head that they're thinking about that they can't share with anybody else. And they've exhausted all the other things that they're thinking about that they can't share with anybody else. And they've exhausted all the airtime they have with their significant other at home. And that person's thinking, I don't really have somebody else to talk to about this. And these are fairly meaty, meaningful things. And they often walk around and there's an element of pangs of loneliness. There was one of our clients in phase one of the game plan system, the diagnostic stage. I walk into his office and he said, Matt, I know you have this GPS thing. I just want to talk to you for the next 30 minutes. I've been carrying around a bunch of stuff. I can't share it with people here at work. I can't share it at home. I just need to talk to somebody about this. And that's where the light bulb went off. I began to look at some of my other folks and other partners, and this is a real common theme.
Speaker 2What's an example that you could share of something that someone at the top is coming to you and they just can't talk to anybody else about?
Speaker 1We have a major departure that we're working through. We don't have the details finalized, so there's nothing to announce yet. But this is weighing on my mind. This could impact some of our efforts that we're working through right now. I need to talk to somebody about this to begin to strategize what, when, what do we say, but they can't share with anybody else.
Speaker 2What have you found of those same people, they have those types of challenges, that the best ones do really well?
Speaker 1They're really clear on their why. One of the things we do early on in the engagement, in the relationship, is I really want to get at what is it that drives them. It's generally beyond the fund size, it's beyond the returns, it's beyond all the stuff that people see. There's generally something that goes back to, well, I came over from another country and I came here with nothing and I want to prove to myself and other people. We don't quite go through the Toyota Five Wise for those who studied the Toyota Five Wise in that case, because that could be a little bit annoying, but we do get down to at least two or three, potentially four. And if you understand what it is that drives you, some of the things that could really weigh us down, actually we have the power to work through them. This was my observation, but this was echoed well before me by Nietzsche, by Frankl, by Simon Sinek, where they say, essentially, the people who have their why can work through almost any how, and then I added, can accomplish almost any what. What I have found, the commonality is when I begin to get at what is it that really drives you, what do you value, they have an answer on the tip of their tongue. That was an interesting observation for me, because not everybody does, which also means they're more resilient and they can bounce back from some of the things that they face every single
Speaker 2day. When that why is apparent to the individual who's leading, how does that then translate to building an organization or working with an organization to achieve some common goal that may be specific to that individual?
Speaker 1Because that is specific to that particular person doesn't mean that's what drives other people. What really needs to happen from there is great leaders set the course. I believe that to be the core purpose. And Jim Collins, who wrote Good to Great and Built to Last, wrote this really great HBR piece about defining your company's vision. And he talks about what do you get up out of bed to go do every single day, and that's your core purpose. And that could be the company's core purpose as well. But that needs to translate it to some kind of vision. What is it that we want to do? We want to maybe raise a certain fund size by a certain timeframe, something that we're going to bring about. So that's setting the course. And leaders need to set the course. Leaders need to tell the folks on their team and across the organization, here's where we're going. Yes, they can get input from their leadership team, and they can do a little listening corners, but they need to set the course. Exceptional leaders in their conversations, interactions with people can kind of get at, what is it about that outcome that drives them? What drives them every morning when they get out of bed? The people on their team who are running deals, they're going to experience hiccups, hiccups along the way. And it's going to be a different why for that individual and for all individuals than it is for him or her who's leading the organization.
Speaker 2It feels like that can get complicated. The more people you have in the organization, the more there's an element that feels like a therapist trying to figure out what is it exactly that each person wants. When you've seen people figure that out well, how do they
Speaker 1make it work? What we have found is an organization can have a game plan. Here's the vision, statement. Here's what it is we're working towards here. We're setting the course. Here's our organization's core purpose using Collins' parlance, and this is why we're doing what we're doing. And now it's up to all of you to identify what do you need to contribute to that in order to bring those outcomes about and be really clear on your why and the meaning and the consequence for what we also call the so what. If the goal is the what, then what's the so what? Why is that important? Everybody has their own individual game plan. What may seem maybe a little bit complicated is actually quite organized when it's put into action.
Speaker 2Asset management in particular is notoriously about managing money and maybe not as effective about managing people. When you first are talking to someone, so you're not embedded in the organization, you haven't worked through a lot of the processes, what do you see in the holes of people understanding how to lead others that are in these seats that are running their business? First, it's important
Speaker 1for them to understand how they and their organization got there, which is they got there not because they were great leaders, but because they were really good at doing the job, doing the work, doing the analysis, doing the presentation, asking the right questions at the management presentation, not because they were able to lead a deal team. That's where we start. I understand why you're not necessarily a good leader. There's generally a nodding and laughing and a smiling and a smirking of understanding, yeah, that's not what we're really known for. So we established that right at the outset. And then we go through these people because they've also invited us in. They're committed to continuous improvement. Those people who are the most busy and had the busiest schedule and they were traveling all over, they were the ones who were voracious to read the books or the articles and to have the conversations and they kept all the coaching sessions. That was inversely correlated. They were committed to learning developing and growing because they also recognize what's going to separate their organization from another organization is what people call the soft stuff. But sometimes the soft stuff can be the hard stuff and that's the human stuff. Do you have the right position, the right role, with the right training, with the right compensation, with the right feedback? So we go through a leadership framework that has been built over the last 10 years and then built on the shoulders of all the books and articles and then my 20 years of being a leader. And we go through and we activate each one of those leadership principles.
Speaker 2Some of the key roles you hear about in that activation starts with that hiring process. What have you found are some of the ways that you help these organizations with their hiring
Speaker 1practices? What I have found is the hiring process seems to work pretty well. There are a lot of terrific executive search firms that are out there and there's tremendous amount of time, energy, and financial resources spent on that hire. Where companies drop the ball, is they could do a much better job of assessment of during the interview process, going into data and looking back on past successes of, let's say, hiring a CEO for a portfolio company, what has worked and layering on those successes into the hiring process. I've noted that not all of the firms are actually doing that. And there are several executive coaching firms who offer assessment work. Here's where they really drop the ball. You hire, you spend months, time, money, and you extend an offer, negotiate, lawyers are involved, et cetera. Okay, start date. The first 90 days, 100 days are the most important and acutely vulnerable time in executives' tenure. The companies view it as it's a done deal. Okay, we hired, they're going to start, and let's get them their passwords, their computer, and all that. And there's the bathroom and you're off and running. You actually got them to the 20-yard line. Now you're in the red zone. It has to be a fully built out, structured first 90 or 100-day process that they have to activate in order to give that person the chance that he or she is going to succeed. What are some of the most important aspects of that 90 days? There's an inherent tension between they've hired me to take on a leadership role, so there are massive expectations of me. In our world that we work in, it's on a very short time horizon. And at the same time, there's a lot that I don't know. I need to learn. So listening to people, making sure we sit down, talk to everybody to gather vital information, but also ensure that the body accepts the organ. That initial process can be very scripted and structured, and it should be. There should be intentionality with the questions that are asked. Who you see, when, do you see them in person, do you see them over the phone? All of that, building bridges, gathering information, being accepted by the organization is often overlooked or is given
Speaker 2short shrift. And the assessment part before. Before the onboarding piece, what types of tools go into trying to understand if you have the right person for the right role?
Speaker 1There are several assessments that are administered and different organizations have their either proprietary tools or they use other assessments. It's usually some deeply involved six to seven hour interview, asking all sorts of questions and then layering it over a database of other bits of information. And then there's a couple of different types of assessments that go into trying to understand if you have the right person for the right role. And then there's some of those assessments that go into trying to understand if you have the right person for the right role. Like that, to try to give us the greatest chance that we're going to hire the right person, because as leaders, we are casting directors. We need to put the right person in the right role.
Speaker 2When you've done an assessment, what are some of the ways that personality types impact what happens in an investment organization?
Speaker 1Some of your audience may have taken the Myers-Briggs type indicator launched in 62. Really wonderful assessment. But the footnote to this assessment or any other assessment, it's just how it's used. I have somebody who's on my team, has her PhD, administers the Hogan and several others. And her favorite way to administer one assessment is to go to the MoMA. She's really into art. And she sits down with her partners and she asks them questions. What do you see here? And she ties what the person is looking at to get at what that person values, what that person sees. What I see is that the person is looking at what that person values. And I'm looking at what that particular like is Myers-Briggs. In this amazing profession, financial services and asset management, I have noticed there are a couple of things that jump out. One is if there's a certain dichotomy called thinking or feeling. Thinkers, it's how they prefer to make a decision. And they look at a situation, they step back, they analyze the situation and they render an objective. Okay, this is what we should do. The feelers, they look at a situation, their preference is to jump into the situation. And they look at the situation, they step back, they analyze the situation, almost like walk in the shoes of the person, place, thing, or whatever is happening there. The general population is 40% thinkers, T, and 60% feelers, or F. In my 460 profiles, 80% thinkers and 20% feelers. Now, if we actually just only looked at investment professionals and not professional services like IR, it's probably more like 88 or 90% thinkers. That means that these organizations could be colder, a little bit tougher. They may not be thinking about what some of the employees are thinking about, like, hey, I just went to a meeting. Somebody on my deal team is probably hungry for that information and probably would really help them. Their instinct is not necessarily how are others thinking about this? How are others feeling? What energy can I expend in order to bring them into this?
Speaker 2That sounds like a lack of empathy. Feeling sounds like you're walking in someone else's shoes. What What does that do to an investment organization that is so dominated by the thinkers?
Speaker 1It's not necessarily a lack of empathy. These are preferences. Just like you have a preference to write with your left hand, you can write with your less dominant hand, and you could even develop it over time. It doesn't mean it's a fait accompli and that I'm not going to be really empathic. This is merely an energy expenditure. If you expend the energy, you could be wildly empathic and walk in somebody else's shoes. But when times are stressed, I likely don't expend that energy and I go into something that's more natural and more normal. What I have found is in these tougher environments where the tea is really playing out, some of those leadership principles fall away. I may not be as clear about setting the course of, I'm leading this deal team. Over the next three months, we're going to do this. These are the key milestones. They don't actually spend the time or the energy to do that. They also may find. Meeting with the people on their direct reports every single week, which is what I advocate, and that could be five or 10 minutes, but every week, oh my God, really? I got to meet with them? I get that pushback all the time. And if somebody, let's say they work over the weekend, have really good analysis, they present in the Monday morning meeting, I may ask them, hey, did you walk up to that person afterwards and say, hey, like really good effort there. I know you worked hard. No, why not? It's just not something that they're naturally thinking about. The cardinal rule of being a great leader. is appreciating deeply. That is one of the areas that is most often overlooked. One of the books that I tell these voracious leaders that I work with who are constantly hungry for reading articles and books is read Dale Carnegie's How to Win Friends and Influence People. It's not really how to win friends and influence people. That sounds very contrived. It's really about how to connect meaningfully to others. And in the book, he has several hundred meaningful quotes. One of which is the deepest human principle is the craving to feel appreciated. And I think if you manage through that lens and that lens alone, as you walked about the day, you're going to improve your leadership capability by 51%. You're already halfway there to being a great leader.
Speaker 2Really curious what other characteristics you've seen permeate investment organizations.
Speaker 1There are four dichotomies. So I mentioned the T and the F. There's a fourth one. It's J or P. So J is judging. It's how do we prefer to go about the world? And J is a very structured, regimented, scheduled. The people who go on vacation and day one is plan this and day two is plan this. P is the other side. We're not really sure where we want to go on vacation. Let's just go. We'll determine what we're going to do that day when we wake up. And that's the P, judging or perceiving. The general population is 55% J and 45% P. A slight scheduled, regimented, structured versus a little bit more pressure prompted, flexible, spontaneous, impromptu. Okay. This world is 75%. 25% J, 25% P. So the other dichotomy is extroversion versus introversion. It's about 60, 40. But when we combine, let's say an E, extrovert with somebody who has a T preference, which is they're hard driving and they're making tough decisions and not necessarily bringing somebody along their decision-making process and filling them in along the way, and they're driving to get stuff done and knock something off of their list, they could miss some important information. Somebody may come and say, "Hey, I just got this note. There's some good bit of information here." And this other person may say, "We already closed. We already sent that email." Sometimes the best information comes at the 11th hour. And we may have to be a little bit spontaneous and flexible to actually get the best results. I constantly remind people of that. We're going to take a quick break in the action to tell you about Ridgeline, the investment management platform built for firms who are rethinking how work gets done. You're at your desk looking at a line graph. behavior replicated in the future.
Speaker 2Most of the time, when we think about giving feedback to someone on the team, we do think about improvements. This is feedback so they can get better. That frame of, I'm going to show you all the positive things, feels like it might leave out the critical things that someone's getting wrong. What are the best ways of addressing challenging situations? So
Speaker 1this is one of the leadership principles, which I take more of the coaching approach. So people don't misinterpret that coaching is not directing. It's not prescribing. Doctors prescribe. Advisors advise. Consultants tell you what to do. Coaches actually engage you in a conversation and ask you questions like, what were you thinking about there? What was happening there? How did you prepare? How might you think about it differently next time? The answers that you're going to get is you would probably tell me, I probably put a little bit too much pressure on myself, or I could have spent a little bit more time Sunday night. But if you ask, open-ended questions, try to avoid the why. Why put somebody on the defensive? Ask how or what questions. How were you thinking about that? What happened there? How do you think it landed on the room? What might you do differently next time? What have you done in the past that's worked really well for you? How can we replicate that here? You'll probably get at some of that stuff that didn't work, and then you can really dig into it. But the other person is realizing it, like, oh, that makes a lot of sense to me.
Speaker 2I want to grab onto something, you mentioned, of this idea of you recommend that leaders meet with people on their team once a week. What are some of those other tools in addition to that on the day-to-day basis when someone's going about leading a team that you recommend? The day-to-day basis and meeting once
Speaker 1a week, you raise that, and often people roll their eyes a little bit. I'm like, every week? The data indicates this, and one of the people that I follow and read quite a bit of his work is Marcus Buckingham. And Marcus Buckingham, from the Gallup Organization, wrote one of the best books on business for my money. I think it's called First Break All the Rules, and it was based upon research that he and the Gallup Organization did in 400 companies, 80,000 managers, and these are the things that great managers do. He's out there saying, you need to meet with your people once a week. And if you say to me that I can't meet with my people once a week, I may get into, why not? And they say, well, I have 20 people. That's too many people. The six to eight is the sweet spot. Well, let's just even take the 20. I still think that that person can meet with his folks once a week. And it doesn't have to be an hour conversation. It could be knocking on the door, popping by, say, Ted, what do you got going on this week? What are your priorities? And you say, well, I got this, I got this, I got this. How could I be of assistance to you? It could be five minutes. So much happens in that five minutes. One could be the manager may say, maybe you shouldn't be working on that because we have this presentation on Friday. I just got this new bit of information. Let me share that with you. Maybe that'll adjust your week. It also messages to you that you matter what you're about to spend 40 to 60 to 80 hours on. I actually have line of sight into as your manager. That means going back to the deepest human principles, the craving to be appreciated. That means that I've taken the time to understand where you're now going to spend your entire week on. And then I offer my assistance and I could potentially help you accomplish those items and make it a really successful week for you. If we have these set-ups, if we have these set-ups, set of goals that we have for ourselves, and they're generally, whether they're six months goals, one year goals, and they can be longer. We do a winning of the day, whether it's the night before the morning of our prompt is what would make today a winning day? I pulled that from Wrigley field, Chicago Cubs. If they win, they hang the white flag indicating to the entire city that the Cubs won that day. What is your version of hanging the flag of a winning day? What are the three or four things you're going to do today that would, advance the ball down the field? We don't always accomplish everything in one day, but we either start something, we continue something, or we conclude something. But we really want to be intentional about how we're going to spend the time in front of us, or if we do it Sunday night or Monday night, the next day. This really micro focus on the day, working in service of those six or one month goals.
Speaker 2If you're going to take this exercise of winning the day and start to use it every day, what are the ways that are more effective in writing down what it is in service of what you're trying to accomplish?
Speaker 1Specificity or being explicit is really important. Checking in after the day, or certainly we have prompts at the end of the week, looking back on the week that was, what are the things that worked? What are the things that didn't work? What I have found is we do this for a month and then it becomes a little bit monotonous to do it every single morning. And for me to check in with them, it becomes a little bit rote and it becomes a part of the DNA of the day or the week. Gaming the system or writing something down that's too easy or that we know we can get through, that's not fooling anybody. We need to be honest and authentic with ourselves of what would be meaningful enough for us to advance what it is that we need to get
Speaker 2done. What's changed in what you've seen about what's made for effective coaching or ways that you've been able to help organizations that might be different from what it was a couple of years ago? Two things.
Speaker 1One, the initial six-month engagements, the way I started the business model about 10 years ago, has turned into six-year, seven-year, eight-year, nine-year relationships. Something very powerful happens when you go from an executive coaching partner to this leadership advisor where there's a tremendous amount of trust. And there's also a bunch of institutional knowledge that person could pick up on something that we had spoken about two years ago and doesn't have to reinvent something. The second is this starting with a founder or two founders. It could be that six-month engagement. They find real value in it. And then a bit of a light bulb goes off and say, I really would want my other people to experience this across the organization. In particular, that creating of the game plan or that document that they create, they're like, it'd be really great if our entire leadership team did one of these. And the individual leaders had one of those. So that landing and expanding over the years has happened where you start working with one or two people, and then it goes to five, and then it goes to eight. And what's really awesome in some of the best sessions that I have, when we sit around a table and we have nine people discussing, checking in on their group game plan, the executive leadership team game plan, or the London game plan. And people are like, oh, I don't know. I don't know. I don't know. I don't know. And people are talking about the things that are really working and the things that maybe are not working, the things that we can do better. I'm basically a facilitator of conversations that never take place without this construct. And oftentimes I'll get feedback afterwards and say, Matt, that was the most valuable hour of the entire month that we had. It's getting people together, asking potentially tough questions, them feeling trusted because there's a shared background in history. They're more willing to engage in maybe uncomfortable conversations that they normally wouldn't. All steeped in bringing about these stated objectives and outcomes. I did not foresee this 10 years ago when I started.
Speaker 2A lot of times, particularly say in the hedge fund world, you think about coaching, you think about the Wendy Rhodes character in Billions, who's inside the organization, having conversations with a bunch of different people in service of the leader and the organization. What have you found are the benefits and drawbacks of being an outside coach to an organization, and particularly the one where you are deeply embedded in for several years?
Speaker 1Well, first, I love that show, love that character. You're kind of like the Wendy of such and such organization. I see that as a compliment. And then I say, not quite. That character worked inside the organization. So she is an employee and she reported to the head of the managing partner, CEO, Axe. There can be something pretty powerful being outside an organization where intentionally a very different email address, may not be in every day. And there's a little bit more comfort, I think, in sharing information with me or one of the members on my team versus if that person were an employee of the organization. I know I felt that way when I was an executive and they offered coaching onsite versus I've been working with my coach for a really long time. And that was part of the reason. Somebody who didn't grow up in the system, who may not actually be, let's say, a deal partner or be an investor, how much can Matt or a team member, really understand about my day-to-day? That could potentially be a challenge. There've been several opportunities along the way to join organizations, become chief performance officer. And I think the independence, there are more benefits than there are negatives.
Speaker 2One of the things you touched on earlier was working with the LP community. How does that look different than your work in the GP community?
Speaker 1There are lots of similarities and there are lots of differences. I got a call from an LP. He was super excited. He said, Matt, the person that you've been working with, they got this offer to go to another endowment. It was a bigger opportunity. It was an advancement. And this person was excited about that. That promotion, developing people, yes, for your organization, of course, but also seeing the people who are on your team grow to such a point where they're hired away to a bigger opportunity. That's like a badge of honor versus on the GP side viewed as a scarlet letter. There are many reasons why people leave. But in not something that somebody would be calling me up and boasting about. That's a major, major difference. Why do you think that's the case? On the GP side, there could be, let's say, many deal partners. On the LP side, there's one CIO who's running that particular office. There are fewer opportunities as somebody elevates to take on a more meaty role. Structurally and systemically, there could be a whole order of magnitude, add a whole other zero to the amount of money that they would be allocating. That adds the complexity. There's a lot more people. There's more managerial opportunities, but within one organization, there are not so many places to go. On the GP side, there are many more places to go. You could have a really wonderful 20 or 30-year career as a deal partner. How about other differences? Similarly, there's that one unit, somebody who's leading that particular office. You have the junior person who's reporting to the next more senior person. That person's reporting to the other person. Especially more in smaller offices called 10 or 11 or 12-person offices. On the GP side, let's take the associate. They could report to three or four or five people. They could be working on three or four or five deals. The nucleus on the GP side, let's take private equity, is the deal team. Those deal partners are actually like mini-CEOs. All the more important to actually stress leadership across that organization because there are many leaders who are leading those deals, but there's not necessarily the same type of deal. There's not necessarily the same type of deal. There's not necessarily the same type of reporting structure on the GP side. It's quite different. If you ask a VP who they report to, they might be confused by the question. Which deal? What do you mean? Or you have a VP and associate who are working on a work stream here. You have a partner and a principal working on that team. They would be confused by that question.
Speaker 2How about some of the maybe non-obvious similarities of working with an LP organization compared to a GP?
Speaker 1Failures in communication, dropping the ball in communication. Is universal. GP, LP, and at every other organization as well. Ambitious leaders take on too much in their plate. They don't delegate as much as they should. They're not communicating the vision as often as they should. They're not meeting with their people as often as they should. These are commonalities that we see both on the GP or LP side. That notion of delegation, that's one of the hardest things. One of our principles is let go to lead. While they principally were the ones who were doing the work as they were elevating, now they're doing the work through other people. And that's a commonality on both sides. And that's one of the hardest things for them to let go of. Mahatma Gandhi said, there go my people. I must follow them for I am their leader. We're not Gandhi. And the folks that we work with are not Gandhi. What is it about that statement? What is he saying there? And I need to lead through these people who I've spent a lot of time hiring and training and developing. And I have to believe in them and I trust them. And I need to lead from behind as hard as that is. That is a universal challenge that I see.
Speaker 2If you look at where you are today with Inflection Point as a business, how do you think about applying all the leadership principles to where you are and where you want to take the business from here?
Speaker 1I spend a lot of time on figuring out the course. So one of the 10 leadership principles is setting the course. This space, professional services, it's such a dynamic space. So I apply the same lens to me. I have this amazing group of coaches and I probably don't do it enough, but I try to appreciate them deeply. I try to be really clear about here's our tools. How could I be of help to you? Here's the game plan system. Am I providing enough training to you? Am I communicating enough? I try to be a student of the game as well. That whole delegation piece is a real challenge for me too. These become really, really difficult for me to do. Really meaningful partnerships. I just can't let anybody in on these relationships. So it can become a real challenge. And part of my game plan, which I happen to be just staring at my game plan now, is about putting some of these tools to work. I have to remind myself of that.
Speaker 2One of the things we've talked about is this distinction between working in the business, being a coach and working on the business. And it's something that you see with investment organizations all the time. How do you advise, your clients, to figure out how to manage their time so that they both can maximally be investing, working in the business, but then also doing what they have to do around the organization, working on the business?
Speaker 1It becomes part of the goals that they work on, that phrasing, working in versus working on, or living among the trees versus seeing the forest. And we need the time to reflect, especially on investment theses. And how are we thinking about how are we thinking about how we're going to manage our time? And we generally set objectives and goals around that. And it's stated one column of the game plan might be much more macro focused. Another column of the game plan might be much more micro focused. As annoying as this may be, we actually work directly with them and their executive assistant. We go in and calendar time for this working in versus working on. This is time that's dedicated to doing this. This is time dedicated to doing that. So we get as granular as programming the calendar.
Speaker 2I'd love to close with where we started and hear a little bit about the why and the vision that you have for Inflection Point for the next 10 years.
Speaker 1Let me start with the why. I get up every morning and I'm really clear that I want to ignite careers and energize lives. If there is a fist pump in my client or a team or an organization that can be expressed, that can be expressed. That's what I'm aiming for. I'm hungry for that. To ignite careers and energize lives. The form that it takes is still going through. What this Inflection Point looks like in five years is still in the larvae stage. We have offsites and there's revenue numbers that we're aiming for and certain number of clients and engagements that we're aiming for. But the why, what drives me and hopefully what drives the people who are the coaches on my team is to really work in service of others. And selfishly, that's my fuel. The letters we see of, hey man, that was really helpful, or Matt, that was one of the most helpful meetings that we had, or we're able to close that fund, or I attribute some of my success to getting promoted. We don't do it for that, but it certainly feels good. That's igniting that person's career, energizing that person's life, and whatever version of a fist pump that that person has, that's what gets me out of bed in the morning. It'd be interesting to see where it goes. The last nine months, I've been in the months, I've been heavily on the AI front. We have so much information, 5,500 coaching sessions, 600, 360 degree review, interviews that I've conducted and gathering information, and some of these observations that I'm sharing with you. There is a version of this that not only continues to generate insights, because it's already helped me, those 10 leadership principles, for example, we swam in the data and using AI to really help us swim in the data. But also, can AI provide that prompt to each one of our clients about, hey, what would be a really successful day? Your goal was the following that you stated. What are the three things you're going to do today that are going to work in service of that? And that's driven by an AI, maybe on your phone or a person's computer, and we're in the developmental stages of that. I'm most excited about that. It's going to be a sort of joke. It's like inflection point GPT. That's the next incarnation of this. But why we do it will never change. All right, Matt,
Speaker 2while I have you, I want to get a chance to ask you a couple of closing questions, a little different from the last time. What one thing do most people not know about you that you find interesting?
Speaker 1I have a real passion for cars and specifically driving cars. So I'm on the racetrack, not often enough. I've been 30, 35 times, mostly at a Lime Rock race park in Connecticut. And this obsession started in 2009, 2010-ish. I love the feeling and the sensation of driving. It's really an exercise in physics. And I also changed my own oil, Ted. A lot of people don't know that.
Speaker 2Which two people excluding your spouse have had the biggest impact on your professional life? It's key that you excluded
Speaker 1my spouse because Sharon has been massively supportive of me. My coach of 15 years, Peter Hazelrig, has had a profound impact on my professional career. I started working with him in 2010. I had a fantastic job with wonderful people at MTV Networks. And I started working with him. Together, we outlined the path to ultimately get closer to my why. I still meet with him regularly. The other person is one of my professors from one of my certification programs. Her name is Margaret McLean Walsh. And she sadly passed away a few months ago from a really aggressive form of cancer. She doggedly pursued me to come back and complete all the elements of the Columbia coaching program. And on the last one, I had to write a thesis, like a 30-page paper on something that I was really interested in and passionate about. A peer-reviewed paper with footnotes and some research, and people had to read it. That paper became the first paper that I had to write. It became the basis for the game plan system, for the ACHIEVE goal-setting model, the acronym that was created, and ultimately the book that came out of that. I'm actually not so sure. If she did not reach out to me, some of them would have, but not all of them would have manifested. What's the best advice you've ever received? Very simple, but you don't get something for nothing. I also grew up a drummer, and my idol growing up was Neil Peart, the drummer for Rush, who's considered the Michael Jordan of drumming. He wrote all of the lyrics for Rush. One of their songs is something for nothing. I've gotten here and get to do what I get to do every single day because I've worked really hard. I put in the time. And as I tell people, when I transition from executive to executive coach, I wanted to do it the right way. And they say, well, what's the right way? And I say, I want to learn everything about coaching and the coaching conversation, the science behind it. And I got certification after certification. So I could look my clients in the eyes and say, yes, I've worked. And yes, I'm driven to do this work. I enjoy the work. I work just as hard as my clients and they work really, really hard, but you don't get something for nothing, period. What brings you the greatest joy? In the professional context is seeing people bring about the outcomes that are on their game plan. It is the greatest feeling because it speaks to impact. What we did, the time we spent together, the machinations that we went through to create some of these things and the time that we put in to do those prompts and to check in on the stuff and to calendars. The work that I do, I want the work to matter. The more that we're able to achieve and bring about of things that are meaningful and consequential to them, that means we're doing stuff that has impact.
Speaker 2If the next five years are a chapter in your life,
Speaker 1what's that chapter about? It's inflection point GPT. I'm working with developers now and it's going to be an AI compliment and it's going to be infused in the work that we do, making our lives easier. And better at what we do and making a massive difference to the clients that we work with.
Speaker 2Well, Matt, thanks so much for sharing all your insights. My pleasure. I loved being here. Thanks for listening to the show. To learn more, hop on our website at capitalallocators.com, where you can join our mailing list, access past shows, learn about our gatherings, and sign up for premium content, including podcast transcripts, my investment portfolio, and a lot more. Have a good one and see you next time.
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