The Meaning of Money
Chapter Seven
The Person, Not the Paper
Mark Sullivan on why the surest returns come from trusting the people you back
Read the transcript
Hello, and welcome back to The Meaning of Money. I'm excited to have with me Mark Sullivan from Lineage Capital. We're going to have a really fun conversation and a deep dive on a couple of different things here. Welcome, Mark. Thanks. Thanks for having me here. Mark, one of the things that people often talk about is financial capital in the investment business. But long ago, ironically, it was Michael Milton who got me focused on the importance of human capital. And one of the things that really strikes me about your model is just how much you focus on owners. Share with the viewership a little bit about your model and how you pick the people that you're investing into, because I think you have a very different model, and the degree to which you really take a bet on the person. We do. Our firm solely focuses on partnering with owner-managers. So 100% of our investments, we're partnering with typically the founder. Sometimes the business is transitioned to another owner, an individual or family or something. And where we're really different, the real focus for us, is owners who believe in their business, want some liquidity, want to stay involved, and really care about their business. Our model, I think, is fairly uniquely tailored to those folks, because we allow them to get significant liquidity while letting them keep control of the board of directors. So even if we own 60% or 70% of the business, they get to keep board control, which is typically very comforting for them. A lot of people are concerned about bringing on a partner: What does that mean? What can they do? I've lost control of my business. And as you said, we really need to understand our partners before we invest with them, because we don't have rights that people typically have after we invest in the business. So understanding their motivations, what's important to them in and outside the business, is foundational to what we're doing in our model.
Will founders keep going after a big payday?
Let's talk about that for a second. I was talking with another founder of a venture capital firm, and he made the statement that the only thing that's guaranteed in a startup is that you will run into challenges. And I think that's a fair statement. Any time you're building a business, you're going to run into them. Very rare is the fairy-tale business builder for whom it's all rainbows. One of the other things he mentioned that was interesting was that before getting an exit, there's this deep hunger of, I have to make the business work, for a variety of reasons. But sometimes after an exit, there are new questions that can become nagging when you run into problems, like, why am I doing this still? Why am I messing with this? I've got a bunch of money in the bank. Why am I still putting up with this? Whereas before the money, you're like, I have to make it work. To the extent that you're giving significant liquidity to the founders that you're betting on, and given that you have a lot riding with them and need to see them continue through, how do you assess that risk? So it's actually been quite fascinating in that regard, because we're always thinking, okay, these folks are going to get a transformational new net worth, liquidity net worth, out of the business, and are they really going to want to keep going? For one, they're kind of self-selecting with our model, because we're requiring them to keep typically a 30% or 40% ownership. So they must believe in the business and think that they can have an impact. But what's really fascinating is that, for the most part, many of them say they're working harder than they did beforehand. And I think that is because of the partnership. They don't want to let their partner down, which has been really fascinating. We've not had anybody, even when a business goes sideways from time to time, we've not had anybody just sort of throw in the towel and say, I'm out of here, good luck. So either we're good at picking partners or partners are good at picking us, but it's worked out pretty well.
When a founder's strengths hold the business back
That doesn't mean we agree on everything every step of the way. Typically these founders have built their business, and what's made them successful, some of those things can also prevent them from getting to the next level. And that's where the rub can come. Often it's, well, why do I need a CFO? I've never had a CFO before. And if we collectively get the right CFO, they're like, why didn't I always have a CFO? What was I thinking? But if we make the wrong decision initially, it's, I told you we didn't need a CFO, this is just a waste of money. So a lot of it has to do with the moves we make together and how they work out. And then there are always people in the business who have extreme loyalty to other people in the business. Sometimes it's great that they have that loyalty, but the person they have a loyalty to may not be able to take it to the next level, and that's where you can also see some friction at times. But for the most part, the vast majority of our investments have been rewarding for them and for us, even with other challenges along the way. We've had businesses that stumble out of the blocks and then we get momentum, and vice versa. We're investing in businesses that have typically been around for 10, 20, 30 years. These are not venture businesses; they're kind of mom-and-pop, mainstream-America businesses.
How mainstream businesses are actually using AI
I can't help but ask, because I know it's on everybody's mind: How are you seeing those businesses interact with AI today? I'm sure it's different for every company, but any thoughts on whether AI is living up to its hype, or it's overhyped, and where it's useful and where it's not? So it's funny. We had a board meeting with one of our businesses two days ago, and three months ago they were literally nowhere. We were like, you guys should start to look into this more, where it can be useful, how you can leverage it. And at the board presentation, every functional area, and we didn't know this was coming, every functional area was like, well, here's how we're using AI to improve the analysis, improve the data, improve processes. There's a part of the business, this is a children's publishing business, where the market does not want content created by AI. So we're very careful about that, because these are for grade-school kids. But generally speaking, they've really embraced it there. They kind of went from zero to 60 relative to some of the other businesses. The other businesses have gone more methodically at it. I would say just about every business, as it relates to the finance function and the analysis, and also automating some routine things like bank reconciliations, it may have made them more productive. I don't think it's revolutionized any of our businesses, and I don't know that it will, but it's definitely improving productivity and decision-making through better, faster analysis. I love hearing that. There's a lot of money and energy going into it, and the last thing you want is to hear that people are spinning their wheels and not actually generating results. So that's very positive feedback to hear. And like you said, it's just a tool; it's not going to get in every area, every business. And I think at the base level, you have a monthly subscription for 20, 25 bucks or whatever it is. The payback on that is quite good. If we were trying to do something broader and much more elaborate with much higher expense, we're not there yet. But for that, I think the return is quite good for improving productivity and analysis. And we're seeing it at our firm as well.
Using AI inside the firm, and not getting lazy
Oh, cool. How are you using AI in the context of your business? Yeah, so people are using it to enhance investment review. We get a memorandum in from the investment bank or something, and there's still a requirement to read it, but I think it can help with the analysis and the timing and the speed. Some of our teams have automated reporting from our portfolio companies; there's a monthly update, and it puts it in the format and does some base analysis, which has been quite helpful. So again, I think these are improvements to productivity and analytical capability and decision-making that are, I wouldn't call it a step change, but it's certainly helpful. Meaningful, but it's not going to put you out of a job. Yeah. And the key thing is for people not to get lazy and try to use it in place of doing the work. For someone new, we required a cover letter, to see if people really were interested in the job and how they thought about it. And I would say a very high percentage of the cover letters were written with AI without thought, and we just didn't go to the next step, even if the resume was really good. So I think you've really got to put the work in. It's irritating when you see that, and we all see it. When you're working with it, you can just totally tell from reading it. The difference between a truly personally written letter versus a generic output is just very different.
Where money helps more than people expect, and where it doesn't
So speaking of return on investment, I want to ask you about this. You've had a chance to work with owners; maybe you were the source of a big liquidity event for them, maybe they had one prior, or maybe together you went through one and you stayed in touch. A lot of people, especially before their first big exit, have a sense of wanting to achieve a certain level of wealth and imagining what that will do for them. And have no doubt, money is fabulously helpful for the things that money does. But it also sometimes happens that once you get that newfound wealth, some things get solved, maybe even better than you thought, and other new problems or challenges can arise. From what you've seen, and I'm sure it's different for everybody, and you've met some pretty interesting characters along the way, what are some areas of life where you've seen money help people maybe more than they were expecting? And what are some interesting problems on the other side that didn't go away no matter how much money you had, or became new problems that you didn't have before? Yeah, it's kind of interesting. I always ask the people we're partnering with, what are they going to do with the money? Have you been waiting to buy the beach house, or whatever they think? And it may be the nature of the businesses or the people, but very few of them, and we do stay in touch with them, have done something where their lifestyle or their life changes dramatically. I do remember one of the guys; he was living in a 1,200-square-foot house, and they bought a new house, and then he's like, I wish I had the 1,200-square-foot house again. We bought a 4,500-square-foot house and there's too much upkeep and all this kind of stuff. But generally, and maybe they're also private, I haven't encountered like, oh. A couple of people started foundations, things like that, which I think they're very excited about. And one person has gotten really involved in his state in school funding, and dedicated his time to helping them think through how they can improve the funding and actually manage the cash at school levels better than they do, because they don't even think about it. So there hasn't been a lot of transformational change that's visible with the people. You hear some stories about things they're glad to be able to do, like the charity, or they did buy a second home. But I think that's kind of it. Maybe we're dealing with the boring crowd that isn't doing too many wild things.
Purpose, philanthropy, and the freedom to give back
Well, you alluded to purpose, and I've always felt that true wealth is lived at the intersection of health, wealth, and purpose. When you're in the heat of building a business, and particularly pre-exit, you often don't have time to be super involved in the community or philanthropy in the way that maybe you might want. And one of the great joys, although discovered maybe after the fact, of having more financial freedom is the time to explore and take action on some things where you want to make a difference. And I have yet to hear anybody say anything other than, wow, that effort and giving back in that way, in something close to their heart, was one of the best things I've ever done. To a T. The return people get on truly just doing it to make a difference, not trying to get a contract from it, or a connection from it, or a visible board seat that'll help them network, but just truly trying to make that difference, whether it's a combination of sweat equity or giving money, if it's a cause somebody feels strongly about, the returns are off the charts. But what's interesting is that until somebody does that, it's hard for them to really get how impactful that is on them. Yeah, I mean, it is, for them. For a lot of people, charity and giving back is often just a, hey, we're hosting this black tie, we've got a table, can you write a check for two thousand bucks? And I'm going to have fun for an evening. That last 15 minutes, that's not a deep, meaningful memory that you're creating, in the way that you'll often experience when you're really rolling up your sleeves and making a difference. And so there's something very real there. And to your point, wealth gives you the freedom to be able to do that, whereas it's really hard for most people to carve out the time and the money before that, because you're just so stretched in every direction. Yeah, and I think that is one consistent theme with the vast majority of the people we partnered with: time and some capital to do those kinds of things, time being an important one. And just the financial freedom, even if they had money before, this is an exponentially larger chunk. So there's just a sigh of, okay, all's okay, and I can go do these things. Yeah. And I think that security, which happens for different people with different amounts, and often I find that having a defined financial plan can also be an important part of that. Because without that, people may have a lot of money in the bank, but they're writing such big checks all the time that they still fear whether they're going to be okay, even if the normal person would be like, oh my God, if I had that amount of money, that'd be a dream.
A financial plan, and knowing what enough is
Well, it is. Given the business you're in, it is fascinating, the number of people, and most of them have created some good personal wealth, but this is just kind of a note when they get the big liquidity event. Most of them, until they have this big liquidity event, don't have a very sophisticated investment advisor or approach. And so this is the time they take the opportunity to say, okay, this is different, I need to go make sure I have a good view of what I should be doing here. Yeah, and it's surprising, you'd be surprised how many people, even after that, don't have it. Because while they're going through it, the fear is, I don't want to create a plan that assumes the egg hatches. I don't want to jinx it. So it's very interesting watching that process and being part of it, helping people, like, no, look, you really need to have a plan, so you know, and that'll help you on your exit. Like, hey, you thought you needed to get 30, you really only need 20. So while you're arguing around 25, fine, argue a little bit, but realize you're winning. And it's an interesting perspective: no matter how much you have, there's always a temptation to want more. And so having some non-financial grounding in what's enough, I think, also helps you feel and appreciate the true wealth that you actually have, if that makes sense. Yeah. It is interesting, you just jogged my memory on something: the number of business owners we encounter who have a target number they want to get to that's not necessarily even related to the value of the business. They have a target. And sometimes they're like, I'm not going below the target, even if the value of the business doesn't get them to the target. So we don't really know how to deal with that when we're trying to help them think through the situation. I've seen deals fall apart over that very thing. And often it's because that person doesn't understand that what they need is well below this mental number. Their fear is, I'm not going to have enough, and they've somehow set a number in their head, and that may or may not relate to reality for them. But it's there, so you've got to deal with it.
Why respect beats control
So, look, I think it's really interesting. You have a very unique model, Mark. And for all that our industry focuses on the financial-capital side, I think it's human capital that really drives the world. Obviously we need financial capital, and you combine it together to do even greater things. But I commend the courage you have, and I say courage because I think most venture-capital investors would be scared out of their minds doing what you do. Most people can't wrap their heads around it. And at the same time, I know that a lot of owners will walk away and say, I'm never going to deal with another venture company again, because they didn't like the feeling of being micromanaged or controlled, or the kind of outcomes that felt that way to them. And maybe that even led to them feeling more disconnected, because they weren't actually in control anymore. Whereas in your model, they are. They've got a lot of equity and they're formally in control. They have to drive. And I think it's a really beautiful and very rare model, because it gives that entrepreneur the space to continue to be the builder and the leader. Even in scenarios where they step aside, because maybe, to your point, they're getting in their own way, and the answer is, let's get a professional executive in here, it's their choosing. That's right. And their light bulb finally turning on to that, and doing that in collaboration with you, as opposed to just waking up to an email one day informing them. Yeah, right. We're extremely collaborative. And you talked about human capital, the people we hire in our firm; we like them to be very smart, but they need to be very focused and respect the party on the other side. That's been really important to us. Even if we think we could help improve a business, we have extraordinary respect for what the founders have created. Yeah. And the temptation for a lot of people is, well, if we just control them with this clause and this part of this agreement, and this ownership, these rights and these procedures, if we control them, we'll be protected. But I've seen too many situations where that didn't work out that way. And even though it may be scarier for people to follow in your footsteps and take the approach that you do, I think it's more realistic. You want somebody to have a good working relationship with you because they want to, not because they're forced to. And the goodwill that comes out of that, I feel, is just immeasurably bigger than whatever you can squeeze out of somebody by force. So good on you, but I recognize it takes courage, and such a unique model. You're the first guy I've talked to that really embraces it in the way that you do. So keep up the good work, and great having you on the show today. Thank you for making time, and I look forward to staying in touch. Yeah, thanks for inviting me. I really appreciate it.
Transcript edited for readability from the video. Machine-transcribed; may contain minor errors.
Key Takeaways
A written companion to the episode, written for those who prefer to read.
Most investors would find the arrangement unthinkable. A firm puts its capital into a company, takes a controlling stake, sixty or seventy percent of the equity, and then, having paid for control, hands the board back to the founder. It keeps the economics and gives away the steering wheel. Ask a room full of private equity professionals to do the same, and most of them, as Stefan Whitwell puts it, would be scared out of their minds. Mark Sullivan does it on purpose. He has built a firm on the conviction that it is not only the more humane way to invest but the more realistic one.
Sullivan is a co-founder of Lineage Capital, a Boston firm that partners with owner-managers of established, lower-middle-market businesses, the kind that have been around ten, twenty, thirty years, what he affectionately calls mom and pop mainstream America. These are not venture bets on unproven ideas. They are seasoned companies with real cash flows and, at their center, a founder or family who built the thing and still cares about it. Lineage offers those owners something the rest of the market rarely does: significant liquidity, a chance to take real money off the table, without asking them to surrender command of what they created. Even when Lineage holds the majority of the equity, the owner keeps control of the board.
The model only works because of what sits underneath it. Whitwell, who traces his own fascination with human capital back to a lesson from Michael Milken, is struck by how completely Sullivan's approach turns on the person rather than the paper. Because Lineage deliberately gives up the contractual control that most investors treat as protection, it has to understand its partners before the money moves, not after. Their motivations, what matters to them inside the business and outside it, become the real due diligence. Understanding what is important to a person in and outside the business, Sullivan says, is foundational to everything the firm does. The bet is not on a spreadsheet. It is on a human being.
A bet on the person
What makes the bet defensible, Sullivan explains, is that the model quietly screens for the right people. Because Lineage requires owners to keep a meaningful stake, typically thirty or forty percent, the only founders who sign up are the ones who still believe in the business and think they can move it forward. A person looking to cash out entirely and walk away simply does not fit. The structure does the sorting. What is left is a partner who has kept skin in the game by choice, which is exactly the person Lineage wants beside it.
The question after the money
Whitwell raises the question that haunts every liquidity event, one that had surfaced in an earlier conversation with a venture capitalist on this same show. The only thing guaranteed in building a business, that investor had said, is that you will run into hard times. Before the money, the reason to push through them is obvious: you have to make it work. After a transformational payday, a quieter and more corrosive question can creep in when trouble hits. Why am I still doing this? I have money in the bank. Why am I putting up with this? Sullivan is handing founders precisely the kind of wealth that could trigger that drift, so Whitwell asks how he manages the risk that a newly rich partner simply loses the will to fight.
The answer surprised even Sullivan. For the most part, he says, the owners work harder after the liquidity than they did before, and the reason is not the money; it is the partnership. They do not want to let their partner down, and in years of doing this, Lineage has never watched a founder pocket the check and throw in the towel. Some of the businesses go sideways for a stretch, as businesses do, and still no one has walked away. Either we are good at picking partners, Sullivan offers with some humility, or partners are good at picking us. Money, which so often dissolves motivation, turns out to bind it more tightly when it arrives inside a relationship a person does not want to disappoint.
Where the friction lives
That does not mean the road is smooth. The friction, when it comes, tends to arrive from an unexpected direction: the very traits that made a founder successful can be the ones that keep the company from reaching its next level. The classic flashpoint is the first serious professional hire. Why do I need a CFO, an owner will ask, I have never had one. If Lineage and the founder choose well together, the objection evaporates within months, replaced by a rueful admission: what was I thinking, why did I not always have a CFO. Choose badly, and the owner has all the evidence he needs that the whole exercise was a waste. Loyalty adds its own complication. Founders are fiercely loyal to the people who came up with them, and Sullivan admires that, but sometimes the person a founder is loyal to cannot make the climb to the next stage, and that is where the hardest conversations live.
A multiplier, not a magic wand
The conversation turns, as most now do, to artificial intelligence, and here Sullivan is refreshingly unromantic. He describes a board meeting held only days earlier. Three months before, one of Lineage's companies had done essentially nothing with AI. Now, unprompted, every functional area stood up and explained how it was using the tools to sharpen analysis, clean data, and speed up routine work like bank reconciliations. The company had gone, in his words, from zero to sixty. And yet he refuses to oversell it. The business is a children's publisher, and its market does not want content generated by a machine, so the humans there guard the actual creative work carefully. Across his portfolio, AI has improved productivity and the speed of decent analysis. It has not, he insists, revolutionized a single company, and he is not sure it ever will.
What he keeps returning to is that the tool rewards effort and punishes laziness. AI, he says, is a fabulous multiplier, and a multiplier works in both directions. Feed it careless input and it will produce confident, spectacular mistakes and make you look like a fool. Put real thought and sweat into the front end and the result can be genuinely powerful. Whitwell recognizes the pattern from his own work: the outputs that astonished him were always the ones he had labored over, not the ones he had tried to shortcut with a single lazy prompt. Sullivan reaches for martial arts, a shared interest, to make the point. Be lazy on the front end of anything and you will pay for it on the back end. He has seen it even in hiring, where a flood of cover letters were plainly written by AI with no thought behind them, and Lineage simply passed on those candidates, strong resumes and all. The machine changes the leverage; it does not remove the requirement to do the work.
What the money did and did not
Whitwell has spent his career watching what happens to people on the far side of a windfall, and he asks Sullivan the question at the heart of this book: where does money help more than people expect, and where does it fail to solve anything at all. Sullivan's answer is almost comically undramatic. He makes a habit of asking the owners he backs what they plan to do with the money, the beach house they have been dreaming of, whatever it is, and the striking thing is how few of them actually change their lives. One man traded a twelve-hundred-square-foot house for a forty-five-hundred-square-foot one and promptly wished he had the small one back; the new place was all upkeep. A couple of owners started foundations they were genuinely excited about. One threw himself into his state's school funding, not to write a check but to help administrators manage their cash more intelligently than they ever had. Maybe, Sullivan says with a shrug, we are dealing in the boring crowd. It is a telling admission from a man who makes people rich for a living: the money, by itself, rearranges very little.
Health, wealth, and purpose
What does move people, both men agree, is purpose, and it tends to be discovered late. Whitwell has long believed that true wealth is lived at the intersection of health, wealth, and purpose, and that the years of building a business leave little room for the third. One of the quiet gifts of financial freedom is the time to finally go looking for it. Sullivan has watched the return on that search, and he calls it off the charts. When an owner gives to something they care about, not to win a contract or a connection or a visible board seat, but simply to make a difference, whether through money or sweat or both, the impact on them is larger than anything they anticipated. The contrast he draws is sharp: the black-tie gala where you write a check and enjoy a pleasant evening that fades in fifteen minutes, set against the deep and lasting memory of rolling up your sleeves for a cause. The difference, he notes, is nearly impossible to explain to someone until they have felt it.
The consistent thread across the owners Lineage has backed is not a bigger house or a faster car. It is time, and enough capital to spend that time on what matters. Even for owners who were already comfortable, the big liquidity event supplies something a smaller cushion never quite did, a kind of exhale that Sullivan describes simply as a sigh of relief that all is okay, and now a person can go do these things. Whitwell names it security, and observes that it arrives at wildly different numbers for different people. What consistently helps a person actually feel it, he adds, is a defined financial plan. Without one, people can hold a fortune and still write every check in fear.
The number in their head
That fear has a shape, and Sullivan sees it constantly: a target number lodged in an owner's mind that bears no necessary relationship to what the business is worth, or to what the owner actually needs. Some will refuse to sell below the number even when the company cannot justify it, and Whitwell has watched entire deals collapse on that single point. The tragedy, as he sees it, is that the figure is usually far above what the person truly requires to be free. The math says they have already won; the number in their head will not let them believe it. Stranger still is the resistance to planning at all. Owners often will not build a financial plan before a sale because, as Sullivan puts it, they do not want to assume the egg will hatch. They fear jinxing the very outcome the plan would help them secure. The work, for both men, is to coax a person toward a non-financial grounding in what is enough, because only then can they appreciate the wealth they already hold.
The goodwill you cannot squeeze
In the end the conversation returns to where it began, to control, and to the courage required to let it go. The instinct of most investors, Sullivan acknowledges, is to build a fortress of clauses and rights and procedures, to believe that if they can just constrain the founder tightly enough, they will be protected. He has seen too many of those arrangements curdle. Owners who feel micromanaged and boxed in disengage, and some walk away vowing never to take institutional money again, precisely because the control stripped away the one thing that made them great. Lineage's wager is the opposite. Give the founder the equity, the board, and the genuine authority to build, and you get a partner who works with you because they want to, not because a contract forces them. The goodwill that comes from that, Whitwell observes, is immeasurably larger than anything a person could squeeze out by force. Sullivan's version is quieter: even when Lineage is sure it could improve a business, it holds what he calls extraordinary respect for what the founders have created, and it hires people who are not just smart but disciplined enough to respect the party on the other side of the table.
It is, in its way, an answer to the question this book keeps asking. Sullivan has made a career out of proving that the surest returns, in business and in life, come not from the capital you control but from the people you trust and the purpose you serve. The money is real and it matters; it buys the house, the time, the exhale, the freedom to give. But it was never the point, and the owners who thrive are the ones who work that out, ideally before the sale rather than after. Once a person has taken the money off the table, the question that remains is the one Lineage asks its partners on the way in, and the one Whitwell asks his clients every day. What do you want it to make possible?