Podcast Summary

Lenny’s Podcast: Product | Career | Growth

Episode: 10 Contrarian Leadership Truths Every Leader Needs to Hear
Guest: Matt MacInnis (Chief Product Officer, Rippling; former COO)
Host: Lenny Rachitsky
Date: December 28, 2025

Overview

This episode dives deep into ten contrarian leadership truths, presented by Matt MacInnis, Chief Product Officer (and longtime COO) of Rippling—a $16B+ SaaS powerhouse. MacInnis, known for his brutal honesty and pattern-breaking wisdom, shares frameworks, stories, and hard-earned principles on leadership, organizational design, product management, and the realities behind extraordinary company performance. The discussion offers actionable frameworks for executives, product leaders, and founders seeking to level up their teams and themselves.

Key Discussion Points and Insights

1. Extraordinary Results Demand Extraordinary Effort

• Relentless Pursuit:
  The best outcomes require not just hard work but sustained, exhausting effort—there is no comfort zone in high achievement.
  • “If you want to be in the 99th percentile in terms of outcomes, it’s going to be really difficult...if they ever find themselves in the comfort zone at work, they are definitely making a mistake.” — Matt, [05:03]
• No Relief in Winning:
  Even when things go well, the pressure to “press the gas” and keep going doesn’t stop. True success means no relaxing.
  • “There can be no relaxation of the organization… if you leave one, you’re just begging for the slightly more hungry competitor to come in and eat your lunch.” — Matt, [09:15]
• Morale Paradox:
  When teams are idle or over-resourced, morale dips and boredom sets in.
  • “When you do give your team space to just twiddle their thumbs, bad things start to happen. Morale actually dips. People get distracted.” — Lenny, [10:11]

2. Deliberate Understaffing as a Leadership Tool

• The Dangers of Overstaffing:
  Politics, wasted effort, and organizational “cruft” arise when too many resources are poured into a project.
  • “If you overstaff, you get politics… That is poison. It’s wasteful. It slows you down. It creates cruft.” — Matt, [10:44]
• Always Understaff, But Not Too Much:
  Understaffing keeps teams focused on the highest priorities, but requires wisdom to know when you’ve gone too far.
  • “The advice is: understaff, deliberately, always. And then the wisdom element is to know not to under-understaff.” — Matt, [11:41]
• Metaphor: Teams should always be “dehydrated”—wanting just a bit more—but not dying for it.

3. The Exhaustion Gap: Where Great Teams Win

• Good Teams Get Tired, Great Teams Win:
  The biggest separator is the willingness to keep going when others fatigue.
  • “Good teams get tired, and that’s when great teams kick the good team’s asses.” — Lenny, [12:52]
  • “You gotta run the engine in the red line at all times. Because the minute you let your guard down… the great teams are going to come in and kick the good team’s ass.” — Matt, [13:16]
• Nostalgia of Winning:
  Hard work only feels rewarding if it leads somewhere; victories make the pain worth it.
  • “If you are succeeding and winning, all of this is romantic in the end... If it doesn’t go anywhere, you don’t feel that.” — Lenny, [13:56]

4. You Learn More from Success than Failure

• Contrarian Take:
  Success is the true teacher, not failure—a reversal of Silicon Valley dogma.
  • “You don’t really learn from your mistakes. You learn from your successes… There’s more to glean from seeing how it’s done right.” — Matt, [14:23]
• Career Advice:
  Early-career PMs (and anyone learning) should join winning teams to accelerate their learning.

5. The COO-to-CPO Transition: Competing on the High-Order Bit

• Best Execs Bring Order to Chaos:
  Top leaders can jump into any function (even product) and create clarity, drive standards, and fix “injured birds.”
• Product: The “High Order Bit”:
  Product is the ultimate leverage point in a business; get this right and everything else (sales, marketing, finance) becomes easier.
  • “Now that I lead product, I’m like, oh, wow, this is the high order bit... If you get the product right, everything else gets easier.” — Matt, [40:18]
• Leading from First Principles:
  As a product outsider, MacInnis insists on breaking down advice into core principles, never blindly importing others’ solutions.

6. The Alpha/Beta Organizational Framework

• Alpha = Outperformance, Beta = Volatility:
  Borrowed from finance, alpha is the drive for unique results; beta is variability (unpredictability).
• Process Lowers Beta (Stability), But Can Suppress Alpha (Creativity):
  A leader must judiciously apply process to suppress volatility where needed, without killing creative upside.
  • “Processes in a business exist for the sole purpose of lowering beta… but they suppress alpha.” — Matt, [26:10]
• High-Alpha People/Projects:
  Room for “Dennis Rodmans” (brilliant but challenging), but only in the right context.

7. The Power of Cultural “Memes”—and the Pickle

• Creating Vessels for Ideas:
  Internal memes, language, or branded frameworks drive cultural change and memory.
• Rippling’s ‘Pickle’:
  The “Product Quality List” (PQL) is purposely dubbed “Pickle” to make the quality process memorable and unique.
  • “If you want to bring about cultural change… you gotta create an entity, a vessel for meaning, and then fill that vessel with your meaning.” — Matt, [29:01]

8. Hiring Frameworks: Spotak and More

• Spotak:
  Candidates are evaluated as Smart, Passionate, Optimistic, Tenacious, Adaptable, and Kind. Decoding intuition with a framework improves hiring judgment.
• Relentless Expectations:
  Use grueling, technical case studies in PM interviews—not to seek perfect answers, but to see how far someone gets, how they handle ambiguity, and their humility in the face of challenge.

9. Product-Market Fit: Don’t Lie to Yourself

• You Absolutely Know It When You Have It:
  Lying to yourself or your team is dangerous.
  • “If you don’t absolutely know it, you don’t have it.” — Matt, [43:01]
• VC Advice Is Incentivized:
  The “never quit” trope is often VC-friendly, not founder-friendly.
  • “Silicon Valley’s ‘never quit’ is complete venture capital bullshit… you should quit, reset the clock… Product market fit, when it arrives, is insane, and you should pursue it.” — Matt, [45:11]

10. Feedback and Escalation: The Selfishness of Withholding

• Constructive Escalation:
  Withholding feedback is selfish; high-performance teams make feedback and escalation routine.
  • “The most selfish thing you can do is withhold feedback… you’re optimizing for your own comfort.” — Matt, [71:48]
• Escalations Are a Gift:
  Problems brought to leadership are opportunities to improve both the immediate issue and the supporting system.
  • “There’s no greater gift to me as a product executive than receiving an escalation from a customer.” — Matt, [73:00]

11. The Power Law, Entropy, and Compounding in Business

• Power Law Outcomes:
  10x effort yields 100x outcomes—mediocrity is not rewarded linearly.
  • “People think the world plays on a more linear relationship… that is absolutely not the case… you have to relentlessly inject energy at every single step of the game.” — Matt, [61:00]
• Entropy Fights Organization:
  Decay and comfort creep in naturally; leaders must inject energy constantly to maintain performance.

12. Rippling’s Traction and the Future of SaaS

• Most People Underestimate Rippling:
  It’s not just an HR/payroll company—it’s building a composable, all-in-one business software platform with deep data integration, underlying everything with a “people primitive.”
• SaaS in the Age of AI: Bundling Returns:
  Companies without rich, first-party data (i.e. point solutions) are at existential risk in the AI age.
  • “Point solutions don’t have enough data in the age of AI to be useful. If you’re a point solution, you’re in hard water…” — Matt, [78:18]

13. Leveraging AI as an Executive Thought Partner

• AI for Communication and Language:
  Tools like ChatGPT and Gemini help refine the articulation of ideas (“20% of the stuff it comes out with…hits the nail on the head”), but are less useful as originators of ideas. [84:36]

14. Balancing Intensity with Perspective

• Intensity as a Feature, Not a Flaw:
  High-energy environments are the birthplace of innovation and achievement.
• But Remember: It’s Just a Game:
  The perspective of cosmic insignificance (Carl Sagan’s “Pale Blue Dot”) infuses work with necessary levity.
  • “Never forget that it’s just a sport and that none of it matters is super important as a counterpoint to the intensity we talked about.” — Matt, [88:58]

Notable Quotes & Timestamps

• “If you want to accomplish something truly extraordinary…it’s going to be really uncomfortable. If you ever find yourself in the comfort zone at work, you are definitely making a mistake.” — Matt, [05:03]
• “Overstaffing is poison. It’s wasteful. It slows you down. It creates cruft.” — Matt, [10:44]
• “Good teams get tired, and that’s when great teams kick the good team’s asses.” — Lenny (quoting Sunil), [12:52]
• “You don’t really learn from your mistakes. You learn from your successes.” — Matt, [14:23]
• “Processes exist for the sole purpose of lowering beta…The downside is they suppress alpha.” — Matt, [28:00]
• “The most selfish thing you can do is withhold feedback from someone.” — Matt, [71:48]
• “If you’re not winning, then the exhaustion isn’t fun; if you are winning, it’s what you remember most.” — Lenny, [13:56]
• “Chill doesn’t accomplish shit. Be intense. Be good, be respectful, Be intense. Don’t be chill.” — Matt, [69:20]
• “Never forget that it’s just a sport and none of it matters… but it’s an absolutely beautiful and amazing phenomenon that we get to be alive doing this right now.” — Matt, [88:34]
• Advice for founders: “Don’t ask people for advice. Ask people for relevant experience.” — Matt, [49:37]

Timestamps for Important Segments

• Extraordinary Efforts & Understaffing: [00:00] – [13:56]
• Success as Teacher, Join Winning Teams: [14:23] – [16:35]
• COO to CPO Transition: [17:07] – [22:46]
• Product Org Frameworks (Alpha/Beta, Pickle): [25:44] – [33:34]
• Hiring Frameworks (Spotak): [34:25] – [37:03]
• Product Market Fit & When to Quit: [42:34] – [53:00]
• Power Law, Entropy, and Company Energy: [60:58] – [70:08]
• AI and the Future of SaaS: [77:48] – [83:59]
• Executive Use of AI: [84:36]
• Intensity vs. Perspective: [86:34] – [89:00]

Memorable Moments

• The origin of the “Pickle” (Product Quality List) and its impact on internal culture.
• The debunking of “never quit” as dangerous VC propaganda.
• The high-alpha/low-beta hiring metaphor (“there’s room for one Dennis Rodman”).
• Candid advice to founders: Quit if you don’t have product-market fit by year four.
• Comparative breakdowns of why Notion and Rippling succeeded—both due to founder idiosyncrasies but for opposite reasons.
• The insistence on public, unbuffered intensity as an executive’s role in scaling organizations.

Recommended Resources (from Matt’s Lightning Round)

• Books:

  • Conscious Business by Fred Kaufman — “Absolute fucking gold” for leaders, used in team book clubs at Rippling.
  • Thinking in Systems by Donella Meadows — The best introduction to systems thinking.
  • The Effective Executive by Peter Drucker — Timeless advice on leadership and effectiveness.

• Products:

  • Fellow Coffee Maker — “Slick interface, high quality coffee... I have one in the office, one at home, and one in the garage.” — Matt, [92:06]

• TV:

  • Heated Rivalry (HBO/Max) — “Smutty but delightful”; praised for normed LGBTQ+ representation.

Final Thought

“Play the sport, play it with everything you’ve got, but never forget that it’s just a sport and none of it matters… is super important as a counterpoint to the intensity that we talked about.”
— Matt MacInnis, [88:48]

How to Contact Matt

• Twitter: @easytay9
• Email: [MacInnis’s last name]@rippling.com

For those building, leading, and aspiring to world-class teams, this episode delivers a dose of sobering reality, energizing frameworks, and practical wisdom you won’t hear anywhere else.