Interviewed by Linnéa Jungnelius
"As CEO, I gained a new appreciation for the velocity of decisions that a CEO of an early-stage company has to make… These decisions, in many cases, can be pretty existential for the company," says Rob.
"When you sit in a seat like that, you start to realize that there are really two to three things that matter. When I think about my role as an investor now, it's to zero in on those things that truly move the needle for the business.”
From professional basketball to private equity, Rob Delaney's journey is as diverse as it is impressive. Now Managing Director at Carrick Capital Partners, a growth-oriented investment firm, he is laser-focused on helping entrepreneurs scale their software and tech-enabled services companies, with a keen eye on the payments space.
In this dynamic episode of the Brilliant People Podcast, Rob joins host Linnea Jungnelius, Global Head of Marketing & Strategy at Acertitude, to unpack:
- Focusing on the critical few factors that move the needle in business
- Building unshakable trust with management teams
- Carrick's value creation playbook, showcased through DailyPay's meteoric rise
- The role of artificial intelligence in private equity and portfolio companies
- Maintaining peak performance and keeping your “monster" in check
Get ready for an insider's look at decision-making, scaling businesses, and thriving in high-stakes roles. Whether you're an investor, entrepreneur, or leader, this episode is your blueprint for success in today's relentless business landscape.
Pro basketball to private equity
Linnea: Rob, welcome to the show. Let's jump in with your backstory. Walk us through some of your career choices from professional basketball player for the Aalborg Vikings, to strategist at Accenture, and now investor at Carrick. How did you get to where you are today?
Rob: Happy to be here, Linnea. I would love to sit here and tell you that it was a series of well-thought-out decisions, but I think it's more about going through life, reacting to things that happen, and taking opportunities as they arise.
For me, basketball was my first love. It was what I cared most about growing up. I played in college, and it taught me a lot about myself and where I found confidence as a person in many ways.
I tried to take it as far as I could until I realized, "This is probably not going to last very long or take me very far." I pivoted to Accenture. Worked there for several years, learned a ton. Consulting is an interesting place to start your career because you get exposed to many different things. You don't necessarily get pigeonholed.
It was an incredible experience, but I realized after a few years, "I don't want to be a consultant for the rest of my life." So I went to business school, tried different things. One of the internships I did was with Carrick and I thought, "This is really clicking and something I want to continue to pursue." Since joining Carrick, I've made several different choices in my career as well. It's a story of seeing what's in front of you and reacting to it versus overly thought-out planning.
Linnea: That's great advice, because a lot of times, especially if you talk to people who are younger and trying to sort out their path, testing things, getting into it, feeling what's right for you, taking the things that you want to learn, and then you kind of go from there. But without getting exposure, you don't really sort out the path. No one typically has all the answers from the beginning.
Rob: There are few people, I think who know from a very early age what they're going to be or do. That's rare, and if you do, you're probably exceptional in that field. Tiger Woods knew he was a golfer at six, but that's uncommon. It's about being open-minded, flexible, and taking stock of what's happening, then following that path.
What makes Carrick unique
Linnea: And that path led to Carrick. As a true growth investor straddling PE and VC, you're very active in software and tech-enabled services. What drew you to that space, or what's kept you there?
Rob: There's a macro and micro view. The macro is Carrick's investment space: software and recurring tech businesses. That is an attractive, exciting area to be as an investor and entrepreneur. The micro is Carrick itself - the firm's fit, the people, and their approach drew me in and kept me here. I've been here six and a half years, which is a long time these days. It's a combination of their market position and who they are as a firm.
Linnea: I'm a bit of a unicorn too, having been here for 11 years. You mentioned fit - what was the fit for you, and what was it about Carrick's approach to building value? Can you explain how they operate?
Rob: Any private equity or venture capital firm claims a unique secret sauce and there's obviously overlap. What I liked about Carrick was their position in the investing world. In private investing, they're between early-stage VC, where there's no data, and later-stage buyout PE, which is heavily financial engineering. Carrick has some data when evaluating businesses, so decisions aren't purely based on sentiment, but there's still an early-stage element with risk to underwrite. I found that market segment very attractive.
Carrick has some data when evaluating businesses, so decisions aren't purely based on sentiment but there's still an early-stage element with risk to underwrite. I found that market segment very attractive.
I think we are unique in a few ways. The first thing is how concentrated we are in terms of our investments. Unlike early-stage VCs making many high-velocity investments yearly, we make few, focusing on areas where we have deep expertise, where we’ve spent a ton of time — and that is by design.
Second, we blend art and science. We have operational capabilities and get heavily involved throughout the investment lifecycle, but we can also step back. We're not over-engineering or strictly following a playbook. This approach makes us somewhat unique in our space.
Involvement across the deal lifecycle
Linnea: Totally. Let’s get further into how you get involved across the investment lifecycle. What roles do you play at different stages?
Rob: Pre-investment, we're heavily involved in sourcing, evaluating, underwriting, and executing deals, which is an intensive process taking months.
Post-investment, we focus on helping management with the "two to three big things" or "pivotals" that truly move the needle for the business. With early-stage businesses, tons of things are wrong and need doing but few things really matter.
We're heavily involved in these key areas post-investment, particularly where we have expertise or prior experience. Our approach isn't a rigid playbook. We don't show up and say, "Here's how you fix this segment of your go-to market." It is a set of principles adapted to each company's unique situation.
Linnea: You talked about being supportive in the process. How do you make the process collaborative rather than dictatorial?
Rob: Our approach is naturally collaborative due to our mix of minority and control deals. Obviously, when we're not in a control position on the cap table, we don't have the authority to dictate anything. And that would never be our approach even if we were in control.
In control positions, we view our role as advisors and facilitators. We do not invest in companies where it's like, "Hey, we're going to run this business." That's just not our playbook. We're not set up to do that. It's about building a relationship with the management team where they trust us, and that gives us license to help them in those areas, those “pivotals” that I've been talking about.
Building trust: accountability, not agreeability
Linnea: Any tactical suggestions for building great relationships with management teams?
Rob: It starts pre-investment with how you approach deal negotiations. Deal negotiations can often get hairy. A lot of times emotion comes into it on both sides. So, how do you comport yourself during that process? What knowledge are you bringing to the table? Are you showing sincere engagement in the company and understanding what they do? We try to invest in areas where we've spent the time to understand the space.
Post-close, it's about building trust. The interesting thing about trust is that people often associate it with how friendly we are. Friendship brings closeness. It is true that trust can be a byproduct, but that's not the first principle of what builds trust.
Excessive agreeability between parties can often be a ‘silent killer of trust.’
In fact, excessive agreeability between parties can often be a "silent killer of trust.” Think about those board meetings where everyone comes in exchanging pleasantries, nodding, and high-fiving. However, once the meeting concludes, they go back to their respective corners saying, "Well, these guys are screwing up this and they're screwing up that." And then the entrepreneurs and management team are saying, "Well, these board members, they don't know what they're talking about." I think that happens a lot in these relationships.
For me, it's not necessarily about building a friendship on agreeableness. It's actually about: do they trust me? Do they believe that I am always approaching the situation with intellectual honesty? Am I accountable? Am I going to do what I say I'm going to do?
I think that you can build up trust over time, even if you don't agree on everything. In fact, I would argue some of the best relationships I've had in business and in sports were actually kind of tense. There was a lot of disagreement, but there was that mutual trust that each person was accountable and honest. That's really what builds trust and respect. That, then, enables you to disagree. That enables you to surface things where it's like, "Hey, we don't see this the same way."
When we do deals, the best thing you can do is align as much of the incentives as possible.
You're going to have intellectual disagreements and instances where incentives differ. We always try to align incentives when we sign up for these partnerships. When we do deals, the best thing you can do is align as much of the incentives as possible. Inevitably, incentives shift, something happens. So, how do you manage that? Well, you can only manage that situation if there's trust.
I would say that the thing we work hard to do at Carrick and I work hard to do is let the other side of the table know that I'm reliable, accountable, and honest, whatever the discussion or ask is. I think that goes a long way.
Linnea: I'm hearing a few things that are important: emotional intelligence; candid communication; and laying things out on the table, but doing it in a way that's elegant and constructive. I'm also hearing a focus on depth of knowledge, being in a position to share helpful advice, and making sure that you can be uniquely supportive. And, of course, do what you say you're going to do, right?
Rob: Accountability, it's huge. In any relationship, but especially in these situations. You'd be amazed how often I talk to entrepreneurs or management teams or other investors and where they have interactions where lots of money is invested, lots of time is invested over periods of years, and there's no accountability on either side towards each other. People pick up on that relatively quickly. It's very important.
Mastering CEO decision velocity
Linnea: That's a critical point. Now, let's shift gears. You spent time as CEO of Infinia ML, an early-stage software and intelligent document processing company in your portfolio. How did this experience alter your perspective on investing and value creation?
Rob: We could talk about this all day, but the place I would start is that I gained a new appreciation for the velocity of decisions that a CEO of an early-stage company has to make.
I've never been the CEO of a larger company, but I would imagine it's somewhat similar but different. You've got experienced lieutenants around you, people who you're constantly going to for advice, both internally and externally. You've got all of that.
If you are building an early-stage company, oftentimes one or two people are making an incredible amount of decisions on a daily basis. And these decisions, in many cases, can be pretty existential for the company.
One, that's hard in and of itself. Two, that brings tremendous stress upon a person. I always had respect for entrepreneurs, but it really changed the geometry of how I thought what that person goes through and the information filter that they have to handle daily.
Where that translates is, as investors, what we have to do is build these maps of businesses. Oftentimes, that looks like a financial model, decks, and diligence reports.
When you sit in the seat of running a business, you learn quickly that the map of the business is not reality.
There's this famous philosopher, I can't recall the name, but he had this theory that a map is not reality and people need to be careful about that. That was never more apparent to me than when I became the CEO of that company.
As an investor, you constantly are trained to think through the business in terms of the maps that you build. But when you run the business, it never goes that way on a day-to-day basis.
As an investor, you constantly are trained to think through the business in terms of the maps that you build. But when you run the business, it never goes that way on a day-to-day basis. It's one of those things that is hard to grasp until it smacks you in the face.
Linnea: Haha, you don't say.
Rob: Yes, shockingly, right? It's one of those things that is hard to grasp until it smacks you in the face. Great entrepreneurs know that intuitively. They develop that sense for their business.
I'm not a great entrepreneur, but I think when you sit in a seat like that and do the bare minimum of introspection, you start to realize that, "Wow, the map that I have created for this business is not actually what matters, what makes it succeed, or what makes it move forward."
What I started to learn in running the business is there's really two to three things that matter, in any given moment, and these things are dynamic. And these two to three things are what I should spend the majority of my time on or what I should ensure my best people are focused on. That really changed my perspective on investing.
When I think about my role as an investor now, it's to identify those things. Can we correctly identify what those things are in that business? That can be hard to do if you're not running the business. I'd argue in most cases, pre-investment, you can't fully do that.
So, then you have to back into it. You have to ask, “do these entrepreneurs or management team, do they know? Do they at least think they know what the things are that matter? Or do they have a hundred things that they're spending their time on all the time?”
You can look at that and then you can start to underwrite the management team and say, have they at least zeroed in on, like, "Here are the things that are really moving the needle for us"? Especially if it's a one product, earlier stage business.
And then post-investment, you can start to monitor like, “do they have the right things? Are they focused on the right things?” And then you can help them execute those things, or shift, or re-underwrite. "Actually, this thing doesn't matter that much."
Investors often miss that. It's easy to miss that, the importance of that structure, especially when you're looking at mountains of spreadsheets and data. You could go down a 10-day rabbit hole about some element of the P&L, but you always have to pull up and say, “does this actually move the needle?”
Building teams and seeking a certain delusional quality
Linnea: One thing which comes through in every single conversation we have on the podcast is focus, figuring out how time is best spent. We only have so much time, so we've got to work backwards. What do we need to accomplish? How are we going to get there? How are we going to resource that? Let's talk more about one part of that map, which is the talent piece. We all know getting the right CEO and team in place is critical to achieving whatever it is your map tells you to go do.
So how do you go about getting the right team in place and enabling them to succeed? I know you're quite big on personality assessments, so dive into some of that for us.
Rob: Well, it's funny, sometimes I would have thoughts to myself when I was the CEO of Infinia ML, the biggest part of my job is probably just making sure these five or six functions have good people running them, and that I'm then clearing the path for them to do what they do.
That's a hugely important thing, especially when you think of it in the context of what matters for my business. That doesn't mean you can be derelict in the basic blocking and tackling of running a business. You have to have the right people in place, and you have to be able to delegate to those people to do those things.
We invest at various stages. Some of the companies we invest in are earlier stage where it is very much a key person or two. Oftentimes we're holding the business till they get to a stage where, "Oh, now we have 400 or 500 employees." So it looks different, more corporate.
As we're investing, a big thing we look for is whether the leaders of the business have the self-awareness and adaptability to start letting go of functions and delegating. Is that within their personality? If it's not, it's not necessarily a deal breaker, but we view our role as helping them see that, understand it, and identify the right people to bring in.
As we're investing, a big thing we look for is whether the leaders have the self-awareness and adaptability to start delegating. Is that within their personality? It's not necessarily a deal breaker, but we view our role as helping them see that, understand it, and identify the right people to bring in.
In addition, we run extensive personality assessments on character traits pre-investment. We don't do that because we have some spreadsheet on our drive that says, "Well, we don't invest in these kinds of people." That's not it.
We do that because it helps inform how we work with a person, how we get through to them, and who they should put around themselves. We're very much using that to drive, "Okay, here are the gaps in your business, here are your strengths, your weaknesses. How do we find the right people to put around you?"
What I would argue is, in the earliest stages of the business, you have to have a strong CEO or leader, whatever the leader of the business is called, that person has to have certain qualities. Entrepreneurs have to have a certain delusional quality to them. They have to be incredibly hardworking, visionary, all that.
You can get to a certain stage where, especially if the delegation is done correctly, actually that next layer is far more important, where it's like, who's running these functions? Are they very good? And do they understand what their mission is? That becomes, in my opinion, more important as you get to that next stage of the business.
AI impacting PE, or is it?
Linnea: Yes, empowers the entire value creation. One of the new capabilities many are talking about building today is artificial intelligence. How are you using AI? And how is it impacting your portfolio companies today? I know you have some views on this.
Rob: Look, I think the first thing is always, when I hear AI ... Infinia ML was an AI company, it was a machine learning business. It was actually originally started at a lab at Duke University. I think oftentimes when people ask that question, my first thought is, what do you mean by AI? AI is so many things. AI is this huge catch-all for type of computing.
So, there's no real answer to that because it's like, “how are computers affecting your business, or the internet?” It is this huge category. For me, when I look at the types of businesses we would invest in, I think this is the types of businesses most people are looking at in terms of working for, investing in. It's not about, “are we developing or creating some type of AI that is unique?” It's about, “have we identified where in our business there is a particular type of artificial intelligence that we can harness?” That focus. Sometimes it's an incredibly small thing. The impact might be large, but it's like an incredibly small function.
That's how I think about it when I look at companies. You're a business, you're not an AI company. There are very few AI companies that are going to succeed. Right now, I think there's one AI company that's actually making all the profits: NVIDIA. It's about how can you take this technology that is a major platform shift, particularly if you're talking about large language models, generative AI, how can you take that and find the points in your business where it makes an impact? And then harness it effectively, because you may not be set up to harness it. You may have to do all kinds of groundwork before that.
Linnea: Right. Pinpointing how it can be most impactful, whether it's efficiency, time savings, automation, replacing or upskilling resources, wherever that is. And then implementation, harnessing it, is incredibly important.
Where do you see this going? How is generative AI shaping the private equity landscape specifically in the coming years?
Rob: I don't think it's shaping the private equity landscape in the coming years. I think it's shaping a ton of things in our world, including a ton of companies that private equity firms will invest in that will be impacted. I don't think it's necessarily going to shape the private equity landscape, even if you think about how we could apply it to our business as investors.
One of the greatest challenges with effectively gaining advantage using AI is if you have a differentiated dataset. Part of the reason our business is still somewhat artisanal is that there is no data on private companies. There is no real public data beyond a company’s website and LinkedIn. Once you get to know the company, there is data on it, but oftentimes it's not a ton of historical data and you don't have a big dataset to compare it to.
Public markets investors have been using AI for decades. It was one of the first real use cases of AI, dramatically impacting things like trading. In the private markets, I'm not sure I see a scenario in the near term where we can use AI to make vastly better, more informed investment decisions, which ultimately is one of our main goals.
I do think it will largely impact how we synthesize and analyze information. That can impact everything from the amount of money we spend with third parties to due diligence work to how efficiently teams map companies and understand market spaces. There's going to be impact there, but I also think that will be table stakes.
All the good firms will do that, so you compete away that advantage. It's not like any of us are going to develop some proprietary algorithm that is better than our competitors have access to. It's like I said before, “where can we take it and harness it?”
There are businesses that have a unique data set or workflow advantage when they harness AI, which creates a competitive moat. I'm not sure I see that in private equity.
There are businesses that have a unique data set or workflow advantage when they harness AI, which creates a competitive moat. I'm not sure I see that in private equity.
The DailyPay portfolio company story
Linnea: Bringing this all together, we've talked about how you approach value creation, teams, and technology. Walk us through how all of these elements came together through the DailyPay deal and success story.
Rob: DailyPay is a company based here in New York. They are pioneers in something called earned wage access.
Earned wage access is a solution where a company sells through employers, so they'll sell to a large employer, and then that employer will offer DailyPay as a benefit. And the benefit is, if you sign up for DailyPay, you can get your paycheck advanced far earlier than payday.
The overwhelming majority of people in the United States are paid bi-weekly or semi-monthly. Shocking to some people, although it shouldn't be, that is wildly insufficient for most people's cash flow needs.
You could make the analogy to an early-stage business often where cash flow depends on when the money comes in the door and then that's how they grow their business. Same way people are trying to grow their lives.
The way that payroll is structured in our country is insufficient for most people to live a less stressful life and grow their life.
DailyPay offers this service. It is wildly popular, and we could tell as we invested, but our thesis underpinning why we thought this was an interesting space goes back to years of experience in the HCM and payroll space.
One of the founders of our firm was an HR entrepreneur and built an HR outsourcing business. We've recently made another investment in payroll. Payroll is a specific area where we spend an inordinate amount of time and understand all the market dynamics.
History of payroll
Not to get too into the weeds, but the history of payroll is interesting to understand. Payroll was a way for the government to deputize employers to tax citizens. Because originally, taxes were mainly tobacco and alcohol. And then obviously citizens said, "Well, taxes should be a little bit more progressive." So, we introduced income tax.
But how do you implement an income tax on tens of millions, hundreds of millions of people if you're the government? Well, they realize the way to do it is through an employer. This is why payroll exists, because then, you created sort of a ledger where the government could consistently and understandably levy taxes.
Because of that, payroll was kind of one of the first fintechs, and computing and all types of technology has gone to the payroll space early, or it's always been an early adopter.
I think what people don't realize is, because it's just such an embedded way of life, what that's created is a system where individuals are essentially floating an interest-free loan to their employers. If the first day of your pay cycle is today, you'll get paid in 14 days. So you're giving 13 days of interest-free credit to your employer for the work that you did today. That doesn't make sense.
But because the system is so old, because of the way it's been set up, because there's so much inertia and complication in our tax code and in the way payroll is administrated, that's a pretty embedded thing and it's not going to change anytime soon.
There are certain areas where people do get paid faster. Uber drivers generally get paid every day, but that's a little bit different because I'm paying for the trip, and then that money, small percent of it is going to Uber, the company, and then the rest of it is going to the driver.
But businesses that have lots of employees, their system is set up where you're working for me and I'm only paying you every 14 days. That's great for my cash flow as the employer. It's actually critical for a lot of businesses.
As we looked at that and thought about the inertia of the gig economy, companies like Uber, and the challenges people are having with labor, particularly turnover, something's got to change here.
Sourcing DailyPay
We had been following the industry for years, and we kind of think it's an inevitability. So now it becomes about evaluating, who do we think is going to be the winner or one of the winners? So that's how we got to know DailyPay.
As we dug in further, we became enamored with, one, the difference they're making in people's lives, but two, the power of being at that point of liquidity for people. So if people are engaging with this service, one, they're getting access to their funds faster, but two, there are so many other possibilities that you can create by being that person or being that solution that helps them with their cash flow needs.
We had monitored the company for a long period of time and we spent a lot of time evaluating, and I think we demonstrated our understanding of the payroll space. It's interesting.
I think the best innovations usually come from industry outsiders.
I think the best innovations usually come from industry outsiders. Because if you've been in payroll your entire life, you're almost not going to be able to think of, "Well, how would I fix this?" The people who run the DailyPay business are industry outsiders. We look for that in these companies when they're coming up with really innovative ideas.
What we bring to the table now as an investor is that we are more of an industry insider. We know the space, so while we wouldn't have been the ones to come up with the solution to solve the problem, we can help them navigate the world that they're in. That's been one of the ways we've added a lot of value, post-investment.
Scaling DailyPay
Linnea: From here, let's talk about how you acquired the business. Clearly, you had paid attention to it for a long time so you knew where there was potential.
What were the tenets of the value creation plan? And how did you go about executing on some of these transformation work streams, the two to three areas of focus that you describe?
Rob: An important point here is that don't own a majority stake of this business; we're a minority investor, we're one of the largest shareholders in the company. We're on the board, so we are heavily involved.
What we identified were two critical areas for the company. First, I talked about this sort of inevitability in the market. What we saw is, demand is coming whether you are ready for it or not. So one of the things that we identified day one, pre-day one, before we invested, is there's a bunch of infrastructure that needs to be stood up in this business so they can actually service the demand.
That's an under-talked about thing. Sometimes demand is there, but the company isn't mature enough to service it. It would break the company.
That's an under-talked about thing. Sometimes demand is there, but the company isn't mature enough to service it. It would break the company. This is things like, do I have my customer support function? Do I have the scale in my customer support function? Do I have the scale in my technology infrastructure? Do I have the capital markets function in place?
This company had unbelievable growth over a three- to four-year period, which I think would have broke most companies.
There's a really complex capital markets function where DailyPay is advancing funds to millions of people. So that's a thing where, "Oh, this is a nice idea. If I was only doing it with one company, it wouldn't be that hard. Now I'm doing it with thousands of companies. How do you manage all that?"
So that was the thing we identified, where the idea was great, the innovation was there, the team was eager, but there was a mountain of demand coming. We worked really closely with them on setting up that infrastructure to scale.
The second thing was understanding, now that we've become this vital benefit for millions of people, and we are at this interesting point of liquidity, what else can we do for the customers?
That's where we've spent a lot of time with the company. Can we help customers access their pay earlier? Help them pay their bills? Help them get better offers at other businesses? Help the employers do things like manage shifts and workers more efficiently?
So there's all these things that are kind of offshoots of that sort of leverage point, the company's original product that we've stepped into to help.
Linnea: That's great, a true focus on customer needs. What's been the outcome of all of this? And how was the team critical to facilitating that success?
Rob: I'm not going to talk about specific numbers, but what I can say is, from a growth perspective, this company is unparalleled in its peer group. Even in the broader market, you'd have a hard time finding a company with a similar growth trajectory.
The cool thing about the team and this company is the quality of the middle management layer is as good as I've ever seen. They have people running functions in that business who are just exceptional that probably wouldn't even make it into a board deck.
I think there's a bunch of reasons for that. Such a successful company makes it easy to attract people, but it is also the mission. It's rare that you can work for a company that is this successful and also has this big of an impact on millions of people. They've been able to attract and build out a team that is as good as I've ever seen.
When I say that, I'm not just talking about the senior management team, I'm talking about that next layer. We talked about this earlier. You start out and it's like, the two to three people, founders are doing everything, but you get to a point now where you have over 500, where it's like, what does that next layer look like? At DailyPay, it's truly exceptional.
Linnea: We've seen that a lot too. You come in, you upgrade the leadership team first and foremost, but great CEOs, then they'll dive in and dial up the layers deeper into the company. When you get all of that humming, gosh, you can do extraordinary things.
Let's get off the work topic now. What things do you do outside of work that allow you to show up as your best self every day?
Rob: I try to have a reasonable amount of balance in my life. It's depends on the time. It fluctuates. Certainly, in those years when I was the CEO of Infinia ML, there was less balance. For lots of people, careers are demanding. I try to be deliberate about creating that balance.
There's the things that are for self and health, exercise, all that. And then for me, it's family. Spending the majority of my time with my family is a critical component in being able to show up and be my best self. I don't think there's any rocket science to it, but I think it's about finding the right balance.
Sustaining performance and taming the "monster" within
Linnea: A lot of these jobs are very intense and require a lot of time, frankly.
So if you think about that, is there any advice perhaps as you think back on your time as CEO, which maybe was the most demanding, how did you do that in a way that allowed you to sustain peak performance?
Rob: I have different view of this now that I'm removed from that experience. I still work in a demanding job, but the pressures are different.
People who work in high-intensity, highly demanding professions, there's something in them that has driven them to that point. There literally is a monster in you that enables you to push through things.
I would say that all of us, especially people who work in high-intensity, highly demanding professions, there's something in them that has driven them to that point. I like to refer to it as “the monster.” There literally is a monster in you that enables you to push through things, be extremely determined, competitive, hardworking, ambitious. Part of that is the ego.
I talked about this when we were talking about entrepreneurs. Oftentimes I actually see a somewhat delusional quality in these entrepreneurs. That's kind of a good thing as long as it's kept in check. The delusional quality can be part of the “monster package.”
In order to sustain a high-level of performance though, you have to have a methodology for keeping the monster in check, because otherwise it'll run your life and take you to a place that's unhealthy.
You have to have a methodology for keeping the monster in check because otherwise it'll run your life and take you to an unhealthy place.
Your relationships will break down, your health will break down, you'll lose sight of what matters. It’s not as easy as like, "Oh yeah, just do that." I had to be deliberate about it. What are the things that I do to keep that in check and to constantly be introspective about who am I right now? What is driving me? What am I doing with my life on a day-to-day basis?
For every person, it's probably a bit different what their process is for keeping - I wish I had a better word from it - but keeping the monster in check. If you're able to do that, that enables you to have a lot more sustainability versus big peaks and valleys where you burn out, or you have all these things bubbling up in your personal life that are hard to deal with. Whatever that is for you, have a process for keeping the monster in check.
Inspiration and asking the "why" questions
Linnea: We're going to have to add monster quality to all of our scorecards for entrepreneurial CEOs.
I think there's something in that. First, you've got to have the awareness. How am I living? And how am I going about my work?
And coupled with that awareness, back to your point about having a map, you develop a map almost for yourself. You have to be pretty disciplined about how you spend your time, where you dedicate your attention, and with whom.
Speaking of monster CEOs, are there leaders and people that inspire you and energize you?
Rob: I would say no. Part of this is because we live in a world where a person is valorized – or everybody says has tremendous virtue in the public eye – and five years later, has some huge downfall. I hesitate to look at people and put them up on that pedestal who are well known in the public eye.
I could point out 10 people in my life who are not well known, who would be the people who I find inspiring. It's people who you're dealing with in your day-to-day life, family members, friends, parents, people who you see who are just, "Hey, this is a person, they've got four kids, and look at the job they're doing with their kids and their job." That's where I draw inspiration.
Linnea: If you think about those handful or two handfuls of inspiring people, what are the common qualities?
Rob: Common qualities? I go back to the people who have found the process for them that works in terms of “keeping the monster in check.”
When you meet them or when you observe them, you get a sense that they are asking themselves the question of why. Why am I doing what I'm doing? Why am I spending my time the way I'm spending my time? Versus being impulsive and driven by desire or ambition.
You can tell when somebody's asking that question, in the way they live their lives. I can think of, off the top of my head, three or four people I know and family and friends who are like that. So those are kind of the people I look to more.
Certainly, I love to read about entrepreneurs and there's certain things they do that I find very inspiring, but for me, it's difficult to be personally inspired by them because I don't know what their reality is like.
Linnea: That resonates with me. What you're describing is people who live quite intentionally and in how they go about accomplishing their personal and professional missions.
They've set some goals, or they're trying to accomplish some things, and then they shape their lives in a way where they can then go and do that. It's cool when you see people achieve big things, often it's because they've named them and they go after them.
Favorite books and podcasts
Rob: Yes, and sometimes it's not goals. Sometimes it's like this is a way of being, this is the way I want to be as a person. In many ways, that can be more inspiring than achievement.
Linnea: Totally. We're getting close to the end here, but I do want to ask you about other sources of inspiration in terms content, books, podcasts, quotes, whether it's on private equity, artificial intelligence, leadership or even some of the things we're talking about like living a principled life?
Rob: I spend the majority of my reading time on social psychology, behavioral psychology, and veering into how our neurology and biology impacts who we are, what we do, and why we do what we do.
- There's a guy named Jonathan Haidt who's written a bunch of books about youths today and how the social psychology of the world they're going up in is impacting them. That's interesting. I also like to read about how these things impact entrepreneurship, business, and sports.
- Michael Lewis, I like his stuff.
- Some of the good biographers out there like Isaacson and some of the books he's written, or storytellers, I'm most interested in that topic and then generally how it manifests in areas like business, sports.
- Moneyball is a good example of that, right? That was a good book. That to me is a book about psychology and how it really impacted the way people ran baseball teams forever. There was a sort of embedded way of thinking, and it's like there was a reason we were conditioned to think the guy who got up at the plate and just looked like an all-star baseball player was the person that we should draft. They just reinvented a totally different way of looking at it.
There's lots of examples of that, and I'm always interested in that angle. So that's what I spend a lot of my time listening to and reading about.
Linnea: I recently spent two days at a board member event and notably most of the topics were about psychology, people dynamics, and communication. How do we better relate to each other? That’s what drives effectiveness. These sorts of things. It is a fascinating area. If you looked at my bookcase, you’d find plenty of Isaacson and Lewis on there.
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Defining Brilliance with Rob Delaney
Linnea: In each episode, we like to define brilliance in a few ways, being that our mission is to unleash human potential. I'm going to hit you with a quick lightning round, if you could please fill in the blanks…
Rob:
 | Purpose is... | the thing that you will consistently sacrifice for. |
 | Leadership is... | cultivation, not curation. |
 | Success is... | impossible to define in my opinion, but what I can tell you is, success should be treated not that differently from failure. |
 | Brilliant leaders are... | courageous and calm. |
 | I perform at my best when... | you already know what the answer's going to be...when the monster is in check. |
Linnea: I love that answer. Rob, that was so fun. It was great to have you here in the New York studio, thank you. We'll have to do it again sometime.
Rob: I really enjoyed it. Thank you for having me.
Linnea: Thank you to Rob Delaney of Carrick Capital Partners for joining us on today's episode. I hope all of you walk away inspired with new ideas for how to build strong portfolio companies, strong teams, and strong mindsets. And thanks to you, our listeners, for tuning in.
That's it for this episode of the Brilliant People Podcast. I'm Linnea Jungnelius. If you found this conversation valuable, be sure to subscribe, rate, and review the show, and follow us on LinkedIn for the latest insights on how to lead and perform at your best.
Until next time, stay brilliant at work. And keep the monster in check.
For more Brilliant People content, check out the insights from Ben Humphreys, Senior Operating Executive at Monomoy Capital Partners.
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