Apr 25, 2024 · 1h 15m · in-depth
How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)
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In this interview, Rippling COO Matt MacInnis shares contrarian operational philosophies and frameworks for scaling high-growth startups, emphasizing the 'go and see' principle, first-principles problem-solving, and intentional understaffing. He demonstrates how elite leaders compress execution cycles, debug granular operational inputs, and cultivate high-accountability cultures to drive sustained velocity.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Brett holds 12.3% of the talking time here. How this is scored →
Brett as informed peer 4.2 Guest teaching 6.6 Guest disagreement 3.0 Brett pushing back 1.2
speaking balance: gold is Brett, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 59:42 MacInnis attacks conventional patterns and industry coaching
MacInnis aggressively asserts that 98 percent of coaching is vapid bloodsucking and that all market alpha comes solely from anti-patterns that reject standard playbook formulas.
Hardest push from Brett ▶ 59:33 Berson challenges MacInnis on embracing a woo-woo leadership bookBerson actively pushes back on MacInnis praising Conscious Business, noting that such touchy-feely leadership literature appears completely contradictory to MacInnis's anti-coaching philosophy.
Biggest teaching moment ▶ 13:56 MacInnis reframes the pace setter conceptMacInnis immediately shuts down Berson's characterization of executives as 'pace setters,' explaining why that framing is toxic and redirecting the concept to rigorous accountability.
Brett holds their own ▶ 6:20 Berson challenges the predetermined outcome theory with repeat foundersBerson counters MacInnis's fatalistic universe hypothesis by citing multi-time founders whose later companies succeed wildly while their earlier ventures failed.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Brett as informed peer | Guest teaching | Guest disagreement | Brett pushing back | Why |
|---|---|---|---|---|---|---|
| Episode Hook: Micro-Interest and Going to See | 0 | 0 | 1 | 0 | Introductory hook snippet followed by host housekeeping and introduction of Matt MacInnis. Host side scores remain zero for the scripted monologue portion. | |
| Complementary Leadership and Playing to Founder Strengths | 4 | 6 | 2 | 1 | Berson sets up the discussion on executive leadership; MacInnis explains his fatalistic philosophy on founder strengths and how a COO operates in the CEO's shadow. | |
| The Mindset Shift in Multi-Time Founders | 5 | 7 | 4 | 2 | Berson questions if multi-time founder success is just playing a random game; MacInnis rejects egomaniacal worry about looking like an asshole and argues winning founders shed self-doubt. | |
| Velocity as Competitive Advantage and Combating Entropy | 4 | 7 | 3 | 1 | MacInnis details why velocity combats entropy and how companies fail when leaders fail to continuously fight reversion to the mean. | |
| Intentional Understaffing and Upholding Rigorous Standards | 5 | 8 | 5 | 2 | MacInnis immediately pushes back on Berson's term 'pace setter', clarifying it as impatience and accountability, then outlines his deliberate understaffing strategy. | |
| Developing Executive Wisdom and Navigating Resource Allocation | 5 | 6 | 2 | 1 | MacInnis shares a vulnerable example of understaffing an operational team too aggressively, contrasting executive wisdom against raw experience. | |
| Eliminating Office Politics Through High-Urgency Workload | 4 | 7 | 3 | 1 | Berson probes internal vs external competition; MacInnis reframes corporate politics as an inevitable side effect of people not having enough urgent work to do. | |
| The Risks of Complacency: Dogfooding and Expense Rigor | 4 | 7 | 3 | 1 | MacInnis illustrates how letting go of internal dogfooding and strict expense oversight causes companies to lose the plot entirely. | |
| Why Founder Growth Comes from Reps Over Coaching | 5 | 7 | 5 | 2 | MacInnis criticizes executive coaching as 'bullshit', arguing that real CEO growth is driven by sheer batting practice and instinct refinement. | |
| The Pitfalls of Generic Advice Versus Shared Relevant Experience | 4 | 7 | 4 | 1 | MacInnis breaks down the 'Lucy five-cent advice booth' trap, arguing founders should ask for specific relevant experiences rather than abstract advice. | |
| First-Principles Decision Making and Coaching Up-and-Comers | 4 | 8 | 4 | 1 | MacInnis explains that high-level executive decisions are coin tosses and that outsourcing choices to boards strips founders of first-principles learning. | |
| The Tortured Fulfillment of High-Performance Builders | 5 | 6 | 2 | 1 | Berson asks if top founders are unhappy; MacInnis clarifies they are deeply fulfilled yet tortured by their intrinsic drive to build and win. | |
| Contrasting Clear Thinkers and First-Principles Thinkers | 5 | 7 | 3 | 2 | MacInnis creates a rigorous taxonomy contrasting clear thinkers against first-principles systems thinkers. | |
| Applying First-Principles Thinking to Novel Go-to-Market Strategy | 4 | 7 | 3 | 1 | MacInnis uses Rippling's product marketing team restructure to explain why novel compound products require first-principles thinkers rather than traditional domain veterans. | |
| Assessing First-Principles Thinking in Interviews and Balancing Execution | 4 | 6 | 2 | 1 | MacInnis describes using deep iterative questioning in interviews to probe whether a candidate can break down a system to its atomic components. | |
| Company Culture and the SPOTAK Executive Hiring Framework | 4 | 7 | 3 | 1 | MacInnis details the SPOTAK hiring rubric and how he detects negativity and lack of tenacity during executive interviews. | |
| Fighting Victimhood and Embracing 'Conscious Business' Anti-Patterns | 5 | 8 | 5 | 2 | Berson notes the irony of MacInnis recommending Conscious Business; MacInnis passionately explains that all outsized alpha comes from finding true anti-patterns. | |
| Managing Inputs to Influence Corporate Outputs | 4 | 7 | 2 | 1 | MacInnis explains how corporate finance distills complexity to free cash flow and why executives must manage inputs instead of yelling at teams about outputs. | |
| The 'Go and See' Principle and Fixing the Roving Bottleneck | 4 | 8 | 3 | 1 | MacInnis outlines Rippling's 'go and see' principle and how he engages deeply with priority 'injured birds' to debug operational bottlenecks. | |
| Balancing Intense Accountability with Core Human Kindness | 4 | 6 | 1 | 1 | MacInnis reflects on self-acceptance, combining accountability with kindness, and marveling at the creative energy of contemporary Silicon Valley. |
Statements from this episode (33)
MacInnis: Successful CEOs blindly apply instincts without worrying about downsides
“One thing that's really clear about successful CEOs is that they don't ever really worry about the downside of their strengths. Like they just go almost blindly, just like at the business, applying their instincts.”
MacInnis: Rippling CEO Parker Conrad lacks empathy when delivering directives
“One area where my CEO Parker spikes is like, he's very direct, does not pull any punches. He almost, you might even say lacks empathy when it comes to delivering a directive or difficult information to somebody.”
MacInnis: Effective second-in-commands enable CEOs to act with impunity
“The CEO job, the most successful CEOs act with impunity in the work environment in a way that number one, a good CEO doesn't really think about it. And number two, a good second in command does think about that and enable it.”
MacInnis: Anyone starting a company is definitionally narcissistic about failure odds
“Everybody who starts a company is almost definitionally narcissistic and sort of believes that they are not subject to the statistics.”
MacInnis: Repeat founders prioritize product and hard driving over peripheral worries
“The third time you start the company, you're like, fuck that. Like that doesn't matter. What matters is I got to get the right product into the hands of the customer immediately. And I've got to test it in market and I've got to focus on sales and win rates. A…”
MacInnis: Asking 'Do I look like an asshole?' is egomaniacal for founders
“What if I look like an asshole is a fundamentally egomaniacal question. It's a terrible question to ask. The right question to ask is what's it going to take to win?”
MacInnis: Every successful outcome is led by a deeply impatient founder
“Every successful outcome is led by a founder who is deeply impatient, really impatient.”
MacInnis: Rippling employs 2,800 people and maintains massive revenue growth
“Everything I do today in my job at Rippling, we're, you know, 2800 employees. We're still growing at, you know, a massive growth rate on a very large base of revenue.”
MacInnis: Top executives actively fight organizational entropy
“The difference between a really effective executive and an executive that's more ho-hum, I think, is that the more effective executive Fights the entropy, like, holds the bar high. Tries to make things happen more quickly, even though it's exhausting.”
MacInnis: All teams at Rippling are deliberately kept understaffed
“All of our teams at Rippling are pretty deliberately understaffed and people feel it and they'll complain about resourcing, but like at the end of the day, a team of five that ought to be seven is way better than a team of nine or 10 that ought to be seven.”
MacInnis: Executives must oversteer toward tighter constraints to fight entropy
“I find that executives need to deliberately oversteer in the direction they want, even to the point of it being a little crazy, but it's because they are the sole tension on the line of tighter constraints, higher bars, harder, you know, harder standards versu…”
MacInnis: The cure for company politics is keeping teams overloaded with work
“The cure to politics is not to lecture people about being apolitical. It's to make sure the team has too much to do.”
MacInnis: Parker Conrad approves every Rippling expense over $5
“Parker still approves every expense over five dollars personally. He still runs payroll for the whole company globally in our product.”
MacInnis: A top SMB payroll rival lost its edge by adopting Workday
“This company, you know, is pretty well known, and they've got a good SMB payroll business going, but like, at a certain scale, they switched to Workday. When they switched to Workday, they stopped using their own product, and when they stopped using their own …”
MacInnis: CEOs who embrace coaching perform worse as executives
“I'm friends with many CEOs who I've, you know, met over the years of having been one and then doing this job, and the folks who are really into the coaching and really into the touchy-feely stuff for themselves on the balance just have not performed as well as…”
MacInnis: High-performing executive teams rely on autonomous blind passes
“Like the hallmark of good executive collaboration is sort of seeing lots of 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, but you kind of know they're there, and they take…”
MacInnis: Founders should ask for relevant experience rather than advice
“If you ask someone for relevant experience, then if they have some first advantage is that like you get to integrate their experience into your context, as opposed to trying to give them a bunch of context so that they can chew the cud for you and give you the…”
MacInnis: Most executive decisions are coin tosses
“Like, the vast majority of executive decisions are coin tosses.”
MacInnis: Hiring managers should never ask others who to hire
“Hiring managers should not ask someone else who they should hire. They should simply ask for objective inputs to the decision, and then they can make the decision themselves.”
MacInnis: Elite founders are energized by work but tortured by fear of failure
“I think they're fucking filled with happiness and enjoyment and energy and also tortured by the fear of failure and by whatever demons drive them or whatever passion drives them. Like there's this awesome Jekyll and Hyde yin yang You know, dynamic to what it's…”
MacInnis: Clear thinkers rely on experience rather than high intelligence
“Clear thinkers don't have to be that smart. They just have to be experienced, or they have to have lots of at-bats on a given topic until they've rounded out their understanding of a system. They might not understand why something is the way it is, but they da…”
MacInnis: Product marketing rarely demands deep first-principles thinking
“If you look into the ocean of product marketers, it's kind of like shopping at Ross. It is not a job that demands a lot of really deep first principles thought from people in the job.”
MacInnis: Rippling avoided hiring traditional product marketers for GTM
“And so in our case, in building out what we call a go to market management team, because we didn't even want to use the term product marketing. We didn't want to go shopping in that pool for talent. We were able to be focused on hiring people who were demonstr…”
MacInnis: Peter Thiel's first-principles thinking enables him to spot trends early
“There's a guy who's just a stunning first principles thinker, and you just engage him in a conversation on the dynamics of the market or how some technology is going to play out, or you ask him to explain, like he has this concept of the three types of innovat…”
MacInnis: Too much first-principles thinking causes over-engineering and stalls execution
“Oh my God, yes, you can have too many first principles thinkers because they have a tendency to over-engineer things. Not so much about having too many first principles thinkers as it is having too many people doing first principles thought. There's only so ma…”
MacInnis: Executive interviews evaluate behavioral metadata rather than subject-matter content
“The interview is the metadata. I don't care what topic we're talking about. I'm studying the way you think. I'm studying how you communicate. I'm studying how you respond to challenges and pressure.”
MacInnis: All alpha and outperformance comes from anti-patterns
“All alpha, all outperformance relative to the index comes from anti-patterns. Patterns are the things people do over and over again... None of it is predictive of success. It's the anti-pattern.”
MacInnis: 98% of coaching is vapid blood sucking by poor operators
“Coaching is stupid. Most of it is just vapid blood sucking on the part of people who weren't very good operators and decided to make a career charging people by the hour to tell them how to be good operators. That's like 98% of the market.”
MacInnis: Rippling runs weekly 10-person reading clubs for Conscious Business
“When you get everyone in a room, and we do this at Rippling, we have Conscious Business Reading Club. Each of these chapters gets one Hour per week in a group of 10 people, and we talk about them.”
MacInnis: Managers Fail by Fixating on Outputs Instead of Inspecting Inputs
“As an executive, you're constantly thinking about inputs as a means by which to achieve desired outputs. Where I think a lot of people mess up is that they over rotate on talking about the outputs. Just operationally speaking, no soccer coach ever gets up in f…”
MacInnis: Leaders must inspect raw atomic details when anecdotes contradict data
“One of our nine leadership principles at Rippling is that Rippling leaders go and see. And what go and see means is that you don't live in the dashboard. And in particular, like when the anecdotes disagree with the data, you got a problem. You go and see, whic…”
MacInnis: Company scaling is a continuous process of resolving roving bottlenecks
“The roving bottleneck is the thing that's holding you up from achieving the next unlock from two to 20,000 employees. You're currently working on the thing you think is most holding you back from achieving what you want to achieve. And the minute you solve it …”