As startups scale beyond their early days, friction across the org isn’t just a possibility—it’s an inevitability.
This natural progression brings not only the obvious scaling challenges that founders already know to watch for, but also the more insidious issues that happen on the margins—like running teams slightly overstaffed or letting operational urgency slip by a few degrees, or diluting standards incrementally. These are the small compromises that can quietly undermine a company’s execution and culture.
This reversion to the mean is what Rippling COO Matt MacInnis calls organizational entropy, a force that manifests as startups scale and decisiveness peters out across the entire company.
“Everything in a business is about fighting entropy,” MacInnis says. “As an exec your mandate is to never lose sight of the feeling that ‘If I take my eyes off of a project, it'll slow down a little bit.’
Without the intensity that executives bring to each project, MacInnis says it will drift in terms of velocity or precision. “You have to remind yourself that there will always be constituents in your business for going just a little bit slower, or for spending just a little extra budget. Execs need to be the opposite—you need to be a constituent for the high bar.”
This type of vigilance, according to MacInnis, is exactly what separates the 99% of executives from the top 1%. “The difference between an effective executive and an executive who's more ho-hum is that the former fights entropy, holds the bar high, and tries to make things happen quickly, even though it's exhausting,” he says.
As more people enter the picture, they get further removed from the nuclear power source—the founder's drive and urgency. It becomes the duty of every exec to forestall this decrease in pace.
With MacInnis at the operational helm, Rippling has managed to spot and squash organizational drag before it takes hold, even amid astronomical growth. The company has seen 11x employee growth in the past four years—expanding from 100 team members and 2,500 customers when MacInnis joined in 2019 (shortly after Rippling had emerged from stealth) to just under 3,000 employees today, generating hundreds of millions in ARR and securing an eye-popping $11 billion valuation.
In this exclusive interview, MacInnis shares his unconventional playbook for fighting the constant pull of organizational entropy. His approach works on two levels: building organizational guardrails that keep standards from slipping, while developing the executive vigilance to spot the first signs of drift.
With advice that starts out on the milder side (like how to leverage impatience into velocity) to some hotter takes further up the Scoville scale (like his fundamental rejection of asking for advice), MacInnis pulls no punches when it comes to divulging all the practical wisdom in his repertoire.
But the lessons he shares will help any leader become more effective no matter where they sit in the org chart—whether you’re a founder, an exec or still climbing your way up the ladder. With that in mind, let’s begin.
Leveling up your organization
When a startup function shows early signs of drift, it's a signal that executives should start drilling down to the atomic level of their organization, examining every part of how work gets done.
This hands-on approach allows him to identify what Parker Conrad, Rippling's CEO, calls the “roving bottleneck.” “The roving bottleneck is the thing that's holding you back from the next unlock that grows you from two to 20,000 employees,” MacInnis says. “You focus on whatever's blocking your path forward. The minute you clear that obstacle, the next one becomes visible. It uncovers the next thing that's holding you back.”
To identify and eliminate these bottlenecks before they can slow an organization down, MacInnis has developed six core principles that separate exceptional leaders from the merely competent:
1. Keep your foot on the gas
“If you ever talk to somebody who's worked at Rippling, you'll hear lots of funny stories about how our CEO, Parker Conrad, personally approves every expense over $5,” MacInnis says. “He still runs payroll for the whole company.” While this might sound like founder micromanagement, consider that Rippling is an end-to-end payroll management platform. So the CEO approving an employee’s Uber ride isn’t about distrust. It’s about bringing founder-level intensity to every corner of the business, while also keeping a finger on the pulse of customers.
“There’s a company I know, a competitor even, with a pretty good payroll business that at a certain scale, switched to Workday for its payroll needs,” MacInnis says. “When they stopped using their own product, they lost the plot, because they outsourced the work of figuring out what’s useful to customers and staying abreast of the market. If your business is predicated on the very fine, nuanced things you believe about the market and a relentless pursuit of those things, somebody who's there from the beginning has to keep their hand on the yoke.”
If you stop being the most critical user of your product, you are toast. You take your foot off that gas by 5% or even less, you’re still toast.
If you’re thinking that this responsibility falls squarely under a founder’s jurisdiction, think again. Executives must maintain this founder-level “spend it like it’s yours” ethos too. “If you take your eyes off these things, you no longer have a founder mindset towards spending money, it becomes an employee mindset,” MacInnis says. “You’ve got to watch it like a hawk, or that stuff will slip away from you. And it’s very hard to pull it back.”
2. Wield impatience
Startups are an exercise in patience. Fundraising can be a slog. It can take years to get to product-market fit. Sales cycles are long when moving upmarket, the list goes on. But the best executives know when and how to inject a healthy dose of tempo into their teams. “Every successful outcome is led by an executive who is deeply impatient,” MacInnis says.
To set the record straight, MacInnis does not characterize the role of an impatient exec to be a pacesetter. “To me, pace-setting means, ‘I'll do it faster than you can do it. Now you have to catch up to me,’” he says. “That’s a negative dynamic with a team member. Impatience is about accountability. It's about challenging assumptions and asking somebody why something can't be done faster, sooner, or better.” (This focus on organizational speed echoes advice from another First Round Review favorite on making speed a habit.)
Tiny markets and a poor team will kill a company. But slow velocity is the most lethal.
To put your foot on the gas, MacInnis shares three examples he uses at Rippling:
- Challenge set deadlines. “If a team says they're going to do X by next Friday, you should reflexively be asking, ‘How about this Friday?’” he says. “If a team lead says ‘We're going to do A, then B, then C,’ execs should be following up with questions like: How about doing A, B and C right now? Why don’t you start B and C today? Why are you waiting to finish A before you start B and C?’”
- Be upfront about what you’re asking. If what you're asking is outside of the norm, you have to be transparent with people. For example, if a deadline is encroaching, and you’re asking for work to be done outside of a typical 9 to 5, MacInnis is firm that execs can’t dance around that. “If they wanted in on the startup adventure, then that’s what they’re in for,” he says. “As a leader, that’s something you have to be comfortable with saying out loud.”
- Accelerate your rate of learning. “A good product with a good team will still get outrun by competition if they never find the right formula before time runs out,” MacInnis says. “The more tests you run in a given period, no matter the function, the more likely you are to find something that works.”
This hard-driving approach might seem daunting—especially if you’re newer to the exec seat. But that’s no excuse to skirt the hard conversations. “If it’s your first time around, the thinking goes something like, ‘I know I need to push these guys hard to get the right product into the hands of the customer as soon as possible, but what if they quit? What if I look like a jerk? By your third leadership role, you realize that people might quit and some folks will not like your style, and that is okay,” says MacInnis.
“What if I look like an asshole?” is a fundamentally egomaniacal question and a terrible question for a leader to ask. The right question to ask is: “What is it going to take to win?”
3. Hold the bar up to the sky
“If you want to do something right, you have to do it yourself,” is how the old adage goes, but the reality is that no executive can play hero ball to propel a startup at scale. To successfully reinforce this idea of combatting entropy, this excellence mindset must be engrained across the whole organization.
On a tactical level, here’s what raising and holding the bar up high can look like:
- Nixing candidates at the finish line even when it’s super painful. “Not only because they were the wrong people for the job, but also to remind people that the standard has to be super high,” MacInnis says.
- Rejecting an additional headcount request for a team. “Because as the exec, you know that if someone else were making that decision, they might not have the fortitude to do so, and would let that team drift toward looser constraints,” he says.
- Rooting out negativity and victimhood. “Negativity, to me, really means victimhood, and it’s contagious,” MacInnis says. “When you sit down to play a game of poker and you’re dealt a bad hand, you don’t just fold. You play the game, and sometimes you win with a crappy hand. The minute you permit negativity into your culture, you’re permitting victims to grab the microphone and own the narrative. They’ll say your company was dealt a bad hand, so we shouldn’t continue to play with vigor.”
Perhaps this is why Rippling is notorious for hiring former founders (MacInnis is one of 150 former founders on the team, by his count). “When it comes to holding people to a standard or finding rare talent who’s hungry to win and terrified of losing, those are two sides of the same coin. They have to go together,” MacInnis says. “The entropy that trickles in comes from the fact that at every company, you’ll have people there just to get the job done. You have to be strategic about where you work those people into the company in its early days and how many of them you tolerate,” he says.
You're not going to fill every seat in your company with the best people—it's just not possible. But if you demand a high bar, you fill way more of those seats up than is reasonable to expect. It’s about always applying pressure in that direction.
Maintaining high standards isn't just about saying no to mediocrity—it's about making structural decisions that force excellence to emerge.
4. Understaff on purpose
Chasing a perfect equilibrium of work on a team is a fool’s errand according to MacInnis. Which is why the first thing he asks himself before he staffs a project is: Is it better to be slightly overstaffed or understaffed? “For us, we've found it's always better to be slightly understaffed.”
Plenty of startups aim to stay lean. But MacInnis’ reasoning behind this approach has less to do with growth as it does company culture. “One of the most sinister side effects of overstaffing is politics,” MacInnis says. “When you have too many people, they won't have enough ultra-high-priority work to do. They'll start working on things that are of a slightly lower priority, which, of course, the executive is not barking at them about or pushing hard on because it's not the most important thing on their list.”
This is the turning point where things go sour, according to MacInnis. “People start to get a little more relaxed,” he says. “The more you relax, the more room there is in your head to start asking questions about if you’re safe, how you’re doing, etc. When there's less interaction with senior people, employees often lose confidence and default to team-based decisions rather than trusting their own instincts.”
The cure to company politics is not to lecture people about being apolitical, it's to make sure the team has too much to do to even worry about it.
But no matter the size, scale or industry of the organization, politics in the workplace is still bound to surface, and Rippling is no exception. Which is precisely why understaffing is MacInnis’ preferred method to underscore that everyone is contributing to high-priority work. “People feel it and they’ll complain about resourcing. It’s worth it, though,” says MacInnis.
A team of five that ought to be seven performs much better than a team of nine or 10 that ought to be seven.
If you are looking to replicate a similar mentality in your own company, the key to making this work at scale is consistency. “Executives need to deliberately oversteer in the direction they want, even to the point of it being a little crazy,” he says. “Fighting entropy is a tug of war. On the other end of the rope is the army of folks who are inadvertently pulling in the opposite direction. It’s the role of the exec to pull the rope toward the impossible standard.”
5. Engineer your inputs (not your outputs)
Fighting entropy at scale requires more than just maintaining velocity—it demands knowing exactly where your organization’s pressure points are located. This brings us back to the injured bird metaphor: How do you diagnose which function has a clipped wing? For MacInnis, the answer lies in understanding the fundamental relationship between inputs and outputs at every level of the business.
He tees this up by using a particularly tantalizing example: corporate finance. “Think of a company the size of Apple,” he says. “There's such a diversity of activities happening, from creative design and engineering and sales and operations, yet somehow corporate finance reliably every quarter draws it down to a single floating point number—free cash flow. I find that completely magical.”
This principle of distilling inputs down to outputs, he argues, applies at every level of an organization, for example:
- A marketing team's various activities (the inputs) drive toward qualified opportunities (the output).
- An engineering team's processes and decisions (the inputs) lead to shipped products (the output).
“As an executive, you're constantly thinking about inputs as a means by which to achieve desired outputs,” MacInnis says. “Where people mess up is by over-rotating on the outputs. As a soccer coach, it’s easy enough to scream at your team about the specific score on the board when you’re losing. But what’s more effective is screaming about the plays they need to run.”
It's a subtle but powerful shift in your executive mindset. Instead of gathering around dashboards to scrutinize outputs, MacInnis advocates for an almost obsessive focus on the inputs you can control. And no input has more leverage than taking your star players and giving them the power to call the next play.
“It's extraordinarily rare, but there are people who love their work and get out of bed in the morning fired up by it,” MacInnis says. “That person is your star player, and you don't get too many of those to work with.”
If and when you do find those people, MacInnis says to load them up with responsibility in excess of what you think they would be capable of on paper.
One of the keys to scaling a business successfully is to focus on potential acumen, hunger and impatience. These are the telltale signs that someone needs to be given extraordinary scope.
6. Find the right mix of first principles and clear thinkers
When it comes to problem-solving, the most effective orgs have a healthy mix of two kinds of people on the team: clear thinkers and first principles thinkers.
- A clear thinker is someone who thinks through every angle of a problem. “They can assemble the full model of a concept in their head, so by the time you ask them questions about it, they've got an answer. When you pressure test that answer, they’ve thought through those things too,” says MacInnis.
- First principles thinkers are the folks who do less testing and more reasoning. “These are the people that break things down into constituent parts and think about the dynamics of the system from its atomic level,” he says.
While both are useful in different situations, MacInnis doesn’t sugarcoat his view on the types of folks who play each role. “Clear thinkers don’t have to be smart, they just have to be experienced and have lots of at-bats on a given topic,” he says. “First principles thinkers, on the other hand, have to be able to hold a lot in their head. They’ve got to be able to make sound predictions based on limited information, which means they are also good systems thinkers.”
He illustrates this with a quick example:
- “Say you are trying to predict how customers will react to a product launch,” he says. “While a clear thinker might methodically gather evidence through focus groups and historical data analysis, a first principles thinker can think through all the components happening under the hood—who the champions are, who the buyers are, what motivates them, and how they make decisions—without needing to test their approach.”
As for where to place these different types of thinkers, MacInnis recommends ushering first principles folks to issues without clear precedent while reserving your clear thinkers for projects with more well-tread paths—just like he does at Rippling.
“One of the challenges of marketing a product like ours is that you've got to be able to talk about why every application that runs on the Rippling platform is better than any standalone SaaS app,” says MacInnis. “It’s why we built out our GTM team with first principles thinkers, because marketing a product like Rippling was something that required a totally novel approach. There's no established rule book for how to market a compound startup with a lot of disparate products. Sure, there's Microsoft and Oracle, but those are companies that solved this problem decades and decades ago, so we had to go at it from scratch. That’s where first principles folks are your best bet.”
MacInnis also notes that just because clear and first principles thinkers are different doesn’t mean they can’t work together. In fact, he sees collaboration between the two as key to successfully scaling an org.
Clear thinkers come to the table with relevant experience and an ability to describe the way things are. First principles thinkers use that as a springboard to come up with novel solutions.
Striking the right balance between the two also helps neutralize any negative side effects. “First principles thinkers tend to over-engineer things,” says MacInnis. “There are only so many times you have to solve a problem and come up with a novel solution to something. That’s why it’s also important to have your clear thinkers—the folks who know how to implement things and turn the screws when the timing’s right.”
Leveling up your personal leadership acumen
As a startup emerges from its cocoon into a full-fledged company, one that goes from 30 people to 3000 people, the margin for executive error becomes razor-thin. As a result, the decisions leaders make here will have the most outsized impact on their company’s next stage of growth. MacInnis doles out specific techniques execs can apply to carefully tune both their personal leadership acuity and their decision-making chops.
7. Increase your decision-making at-bats
First, MacInnis strongly urges execs to let go of the myth of perfection: “You will never get it exactly right, and this applies to virtually any decision you can think of,” he says.
The question isn't whether you'll get it wrong, but in which direction you'd rather be wrong. Instead of seeking perfection, MacInnis advocates for maximizing decision-making reps. He shares a concrete example of how this idea crystallized for him.
“There was a time where Rippling decided to bring an operational process in-house that we had previously outsourced to a third party,” he says. “The team working on making that happen came to me with a proposal for what it would take to staff this up and asked for seven heads. The problem was we had already finished our annual planning. We just squeezed every ounce of fat out of the plan. Adding seven heads now would be crazy.”
He decided to go with his gut and, leaning on the understaffing philosophy that fuels Rippling, asked them to try it out with only two people. “Guess what? It came crashing down on me,” he says. “We really did need seven people, and that was my mistake. As an executive, I made a poor decision in judging between that and the other 20 headcount requests I received where I said no.”
As an executive, think of yourself as an LLM. With every decision you make, you are constantly training yourself with inputs.
It was a swing and a miss for MacInnis, but the more decision at-bats an executive gets, the more likely he is to spot the next curve ball when he’s at the plate. “To me, I don’t place as much value on an executive’s experience as I do their wisdom. The difference for me is that wisdom lies in intuition. It’s being able to detect subtle, but important, differences of cases where you have to make these kinds of resource decisions, or judgment calls,” he says.
“You can only get that wisdom with batting practice. To bring it back to the operational example, now I know that next time I need to look more closely at the capacity planning and do a better job of probing each team’s assumptions on the plan.”
8. Identify your injured bird
At Rippling, all the functional leaders have a running joke: “Who is MacInnis's injured bird?”
It's not a question about ornithology. They are referring to his surgeon-like approach to executive attention.
While most startup executives spread themselves thin—jumping between financial forecasts, hiring plans, and product roadmap decisions—MacInnis operates with the precision of a skilled physician: identifying his most critical patient, bringing them to the operating table, and giving them his undivided attention until he's solved the underlying problem.
“If there's any one secret to ‘effectiveness,’ it's that great executives do one thing at a time and they do the high-priority things first,” MacInnis says.
At Rippling, this philosophy is codified in one of their nine leadership principles: go and see. “It means leaders shouldn’t live in the dashboard,” MacInnis says. “When the anecdotes disagree with the data, you've got a problem. You have to go and see for yourself, which means getting straight down to the atomic level of the function you're interested in to gather context.”
I’m not a micromanager, I’m microinterested.
This type of diligence can take many forms, but execs must do whatever it takes to understand the ground truth of what’s really happening, which could mean:
- Reading through customer support tickets
- Watching sales call recordings
- Dissecting customer interactions with the brand website
“By watching back a Gong call of a sales engagement, an exec can say ‘Hey, I noted in this call, when the customer said X, the rep did not redirect back to the superpower we have that would solve the problem,” MacInnis says. That’s a signal that should kick off a chain reaction of curiosity for any high-impact exec.
“It implies that the rep doesn’t understand what our superpower is, which in turn, implies that a bunch of reps don’t understand what our superpower is. Which implies that our training sucks, which implies that the product marketing organization has failed, which implies that we’re screwed,” says MacInnis. “You’re packaging this all up as a hypothesis and serving it to your department heads, and asking them what they think.”
It then becomes the functional team’s job to disprove that hypothesis. Most of the time, MacInnis says, they can quickly point to the incorrect assumptions. “But if they can’t, then we work together to figure out if my hypothesis is true or false. We’ll write it down and go through the motions over the course of weeks, trying to debug the system. But it always starts with ‘go and see.’”
When should executives know it’s time to hang up their scrubs and step out of the operating room? By closely monitoring the vital signs. “We haven't solved the problem until we've seen the output metrics begin to turn in the direction that we want them to,” MacInnis says. “We keep fiddling with the system until our output metrics start moving in the right direction.”
9. ‘Chew the cud’ yourself
One of the biggest lessons MacInnis learned as a founder (and that he credits with making him a far better COO), is that executives are never going to feel wholly comfortable with their game plans. “The hardest questions are always going to bubble up onto my plate, so if there was an easy or obvious answer, it would’ve been done below me,” he says. “By definition, execs get all the nuclear stuff.”
Yet, when faced with any sort of complex, or high-stakes decision, MacInnis has observed a dangerous outsourcing tendency in the C-Suite: Folks often seek out advice from trusted sources, falsely believing it will lead them to the “right” answer.
In his experience, leaning heavily on advice (even from a reliable confidant) can have two pernicious effects:
- Hazard #1: It alleviates the need to think from first principles. “The hazard of accepting advice is that it can let execs off the hook for thinking about the problem, but it's their job to synthesize and then come up with solutions that apply,” he says. “The point of going to college is not to walk into a classroom and have someone just give you the answer key to the problem set, you actually need to go and do it yourself.”
- Hazard #2: It reinforces the idea that there's a “right” answer. “When you take advice and fully base your decision on it, you have this false sense of confidence in your answer because you got it from some trusted source,” MacInnis says.
Rather than looking to someone else to provide the answer key or validate a decision, embrace a mindset of decisiveness over perfection.
“The high blast radius questions are inherently ambiguous, so you’re never going to have confidence in your decision. You could spin your wheels for days and weeks on Option A and B, if you’re lucky enough to even have options,” he says. “What you eventually learn is: 1) You’re going to have to learn to live with that discomfort and 2) It’s about how quickly you choose an option and learn from it, rather than whether or not you choose the right one.”
If both options A and B suck, pick one and go. Don't waste time dwelling on if you should put seven people on the operations team or two. Pick one and learn.
Let’s say there are two highly qualified candidates for a senior leadership position.
"Candidate A has some strengths, Candidate B has different ones, so to help decide, the exec team brings them both in front of their board, asks them to interview these two people and come back with an opinion,” MacInnis says. “Which candidate do you think ended up getting hired? The one that the board favored of course.”
Not only did the hiring committee miss out on an important decision-making at-bat, but they might have just made a worse choice. “Your board only has one percent of the context that you do to work at your company every day. They also carry their own personal histories and biases,” he says. “But the hiring manager is ultimately accountable for the outcome of the decision. That is really dangerous because by outsourcing this decision, you now have a false sense of confidence in this candidate.”
As an executive, you can’t give others the grass, have them chew the cud, and give you the milk. You've got to do the work yourself.
Dig for context, not advice
If you absolutely must seek outside counsel to resolve an issue (he shares an example below from Rippling), make sure the person you are going to has the appropriate experience to be a proper sounding board.
“If the person you’re taking advice from doesn’t have any relevant experience, their advice is bogus,” says MacInnis. “Everyone looks at things in different ways, so always ask them about their context first.”
He uses this approach every time—including a conversation with former Twitter board member Peter Currie. “When I was assembling our board and needed some guidance, I called him up and asked, ‘What’s the best board you ever served on?’” MacInnis says. “A question like that has nothing to do with Rippling, but it was a chance to see what roles he’d played, where he’d been successful and where he might be able to help.”
MacInnis uses these types of openers to search for what he calls “gold nugget” examples. “Sure, you might bounce a few ideas off of them, but before you give them your situation, you really want to hear about their relevant experience and do the integration yourself.”
Especially when you’re in the CEO or founder’s seat, honing your judgment for what differentiates good from great can be a problem-solving superpower.
Plain advice is the easy, cheap option that will always get you the garbage. You’ve got to figure out how to sort through it for the tiny nuggets of gold that can actually be helpful to your situation.
10. Smooth over where your CEO spikes
It's rare to hear a startup leader channel deterministic philosophy, but MacInnis has spent considerable time wrestling with fate. “If you talk to me long enough, I’m bound to bring up that your company’s outcome is predetermined by the universe,” MacInnis says. “As an executive, you’re just showing up to run the experiment and find out what that outcome may be.”
This philosophy goes all the way to the tip-top of the org chart. “The CEO job is inherently idiosyncratic,” he says. “It's specific to the market you're in. It's specific to the team you have. It's specific to the moment in time. It’s specific to the scale of your company. The third-time founder is far more equipped to play the game better because they've shed the misgivings about acting on their instincts, while first-time founders are shrouded in self-doubt.”
If you're the CEO, show up and be yourself from day one. Apply your strengths as they naturally come to you. Don't question whether they're adequate. Trying to be somebody you're not is the only surefire way to lose.
Where a COO can be most effective in this dynamic, is to pick up any balls that the CEO inevitably drops while charging up the court. “It's not actually the job of the CEO to refine his or her strengths, it's about knowing the strengths of the counterpoint executive who's going to take that thing that you're not good at and run with it independently,” he says.
Think Steph Curry’s signature no-look behind-the-back passes. “The hallmark of good executive collaboration is spotting blind passes where you just toss the ball generally in the direction of the executive who you didn’t even look over to see was there, and they take it, and they run with it, and they execute on it,” says MacInnis.
MacInnis and Rippling’s CEO, Parker Conrad, have mastered these blind tosses. The two met at Harvard the very first week of freshman year and have remained close friends ever since. “He really has witnessed the arc of my life. When you have friendships like that, they have context for you that is so deep and so personal that their advice actually becomes useful.” (Yes, this is the one exception to his steadfast rule on advice.)
In the five years that they’ve been side-by-side at Rippling, they have developed a highly complementary working relationship. “One area where Parker spikes is his directness. He does not pull any punches,” MacInnis says. “There's a downside to that, especially when delivering a directive or giving feedback to somebody.”
But ultimately, MacInnis says this doesn’t matter, as long as the COO recognizes these snags, and is prepared to step in to mitigate them. “It's about learning how to apply your strengths in the right context,” MacInnis says. “I’m more of an empath. I can get people to understand difficult things without creating upset. As COO, I’m content to go to work every day and apply my strengths to areas where we would otherwise be falling down. It’s a hand-in-glove relationship.”
Above all: Kindness matters
A simple acronym MacInnis keeps on hand when looking for folks to fill Rippling with is SPOTAK—smart, passionate, optimistic, tenacious, adaptable and kind—with a particular emphasis on kind. While being a successful leader at a scaling org can at times feel ruthless, MacInnis stresses the importance of kindness in every interaction.
“Every day, almost 3,000 people choose to get out of bed and put their limited energy into our company,” he says. “All of these people could go get jobs somewhere else, but they choose to come and do it at Rippling. That gives me a sense of purpose in my life, but it also serves as a reminder that if you don’t treat people with respect, they can go somewhere else.”
The long and short of it: It’s bad business to be unkind to people. “You can be tough on people, and you should be tough on people,” says MacInnis. “You should demand the very best of them. You should make them uncomfortable. You should hold them accountable. You should even ruthlessly weed out those who are unethical or not right for your culture. But, above all, you should never forget to respect your fellow human.”
Running a company is a lot like coaching a sports team. The reps in the gym, the at-bats, the drills, or whatever athletic metaphor you’d like to substitute, are a collection of individual moments leading up to that ultimate feeling of gratification on game day (even if the day-to-day practice feels strenuous).
“Sure, there are days I don’t want to go to work,” he says. “But work has always been the natural thing that I can't not do. It’s catnip, and that’s something that a lot of the most successful founders and execs share—they're filled with enjoyment and energy, but they’re also tortured by the fear of failure and by whatever demons drive them to keep working.”