Fighting Entropy to Preserve Organizational Intensity for Extraordinary Results

Lenny's Podcast: Product | Career | Growth · December 28, 2025 · Listen to Original Episode →

Original Title:

TL;DR

Extraordinary results demand extraordinary efforts, requiring leaders to preserve organizational intensity and fight entropy to maintain a competitive edge in dynamic markets.
Deliberately understaffing projects prevents politics and ensures focus on high-priority tasks, avoiding the waste and slowdown caused by overstaffing.
Learning from success is more informative than learning from mistakes, making it crucial for career growth to join and contribute to winning teams.
The "high alpha, low beta" framework guides hiring and process design, prioritizing high-impact individuals and reliable systems where appropriate to balance innovation and stability.
Founders should quit startups earlier than venture capital often suggests, as prolonged efforts without product-market fit are rarely rewarded and consume valuable time.
The market is immutable; startups must discover the right product-market fit like a drug binding to receptors, rather than attempting to market their way to success.
Leaders must actively fight organizational entropy by modeling intensity, demanding feedback, and escalating issues to maintain high performance and prevent decay.

Deep Dive

Extraordinary results demand extraordinary effort, but an organization's ability to sustain this intensity is directly challenged by entropy and the natural human tendency to optimize for comfort. Matt MacInnis, Chief Product Officer at Rippling, argues that effective leadership requires actively combating this decay by preserving and mirroring the founder's initial intensity, which is critical for achieving outsized outcomes in competitive markets. This relentless energy, when aligned with genuine product-market fit, becomes a powerful engine for growth, distinguishing successful companies from those that falter.

The core of MacInnis's leadership philosophy centers on fighting entropy, the inevitable slide toward disorder. He posits that while individual employees may need breaks, the collective team must maintain a high level of intensity to avoid creating openings for competitors. This is particularly crucial in dynamic markets where any perceived weakness will be exploited. MacInnis contrasts this with the common misconception of learning from mistakes, arguing that significant learning and growth primarily stem from experiencing success. He advocates joining winning teams as a strategy for accelerating personal development, as observing and replicating success offers more tangible insights than analyzing failures.

MacInnis also emphasizes the importance of deliberate understaffing as a means to maintain focus and prevent the dilution of effort on lower-priority tasks. This approach, while seemingly counterintuitive, aims to keep teams "dehydrated" for resources, ensuring that every project is critically resourced and aligned with top priorities. He introduces frameworks like "high alpha, low beta" to guide decision-making, distinguishing between areas requiring creative risk-taking (alpha) and those needing reliable execution (beta). Processes are tools to lower beta, but must be applied judiciously to avoid suppressing alpha. The "pickle," a product quality checklist, exemplifies this by imposing standards without stifling innovation.

Furthermore, MacInnis challenges the Silicon Valley mantra of "never quit," arguing that recognizing when to pivot or cease efforts is crucial for entrepreneurial success. He contends that the venture capital incentive structure often perpetuates this "try until you die" mentality, which serves the VC's need for continued investment rather than the founder's best interests. True product-market fit, when achieved, is an unmistakable and exhilarating state, and founders should be liberated to pursue it with a clean slate rather than prolonging efforts that demonstrably lack market traction.

Ultimately, MacInnis believes that success in competitive markets, especially in the age of AI, hinges on owning first-party data and building integrated platforms. Point solutions, whether in traditional SaaS or AI, struggle due to insufficient data context, leading to consolidation or failure. Rippling's strategy of unifying business processes under a common data graph allows for the development of powerful AI capabilities that leverage this rich data, positioning it for sustained growth. This intensity, coupled with a clear understanding of market dynamics and a willingness to fight entropy, forms the foundation for achieving extraordinary outcomes.

Action Items

Audit team structure: For 3-5 projects, assess if deliberate understaffing is creating necessary urgency or causing burnout.
Implement "Pickle" checklist: Define 5-10 critical quality standards for new product releases to systematically reduce beta (volatility).
Track "high alpha" individuals: For 3-5 key roles, identify individuals exhibiting high initiative and impact, and ensure their energy is preserved.
Develop feedback escalation process: For 10-15 critical customer touchpoints, ensure clear paths for feedback to reach executive leadership.
Measure intensity drop-off: For 2-3 management layers below the founder, quantify and address any significant decrease in energy and focus.

Key Quotes

"if you want to accomplish something truly extraordinary if you want to be in the 99th percentile in terms of outcomes it's going to be really difficult like it's going to be really uncomfortable and you've got to sort of remind people of that that if they ever find themselves in the comfort zone at work they are definitely making a mistake like they have definitely screwed up somehow"

Matt MacInnis argues that achieving exceptional results requires embracing discomfort and avoiding complacency. He emphasizes that finding oneself in a "comfort zone" at work is a sign of underperformance or a mistake, suggesting that true progress demands pushing boundaries and facing challenges.

"the purest form of ambition and most intense source of energy in the business is the founder ceo every next concentric circle of management beyond the founder ceo has the potential to be an order of magnitude drop off in intensity and that is fucking dangerous"

Matt MacInnis highlights the critical role of sustained intensity, originating from the founder CEO, in driving business success. He warns that a significant decrease in this intensity with each subsequent layer of management is dangerous, potentially leading to a dysfunctional organization.

"processes in a business exist for the sole purpose of lowering beta processes are for decreasing volatility in the output of the system the downside of a process is that it suppresses alpha and you have to be super super careful and judicious in the application of process in the product team to know that you're lowering beta in the places where you want to do that without suppressing alpha in the places where you need it"

Matt MacInnis explains that processes are designed to reduce volatility (beta) but can also stifle innovation and outsized performance (alpha). He advises leaders to be highly selective in implementing processes, ensuring they enhance reliability without hindering creativity and exceptional results.

"you don't really learn from your mistakes you learn from your successes and i it's like you do of course and he would admit you you learn a bit from mistakes but i do think that this is sort of feel good bullshit that you know like well you know you didn't succeed but you know at least you learned something"

Matt MacInnis challenges the common notion that learning primarily comes from mistakes. He suggests that learning from successes provides more valuable insights, implying that the idea of learning from failure is often an overused, feel-good platitude with limited practical substance.

"the market is immutable no amount of tweeting linkedin posting advertising is going to change whether the market wants your product it's not it might raise awareness about your product but it's not going to change whether somebody wants it then you take a different mindset you have to view your startup as running an experiment in the universe to see what you get in return for that"

Matt MacInnis posits that market demand for a product is unchangeable by marketing efforts alone. He advises founders to view their startup as an experiment to discover market fit, rather than trying to force market acceptance through promotional activities.

"fundamentally the most selfish thing you can do is withhold feedback from someone when you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable well you're optimizing for your own comfort and it's fundamentally selfish"

Matt MacInnis asserts that withholding feedback that could help someone improve, solely to avoid personal discomfort, is an act of selfishness. He argues that high-performance teams require open feedback, and prioritizing one's own comfort over another's growth is detrimental to team dynamics.

Resources

External Resources

Books

"Pale Blue Dot: A Vision of the Human Future in Space" - Mentioned as a book that profoundly impacted the speaker's perspective on life and work.
"Conscious Business: How to Build Value Through Values" by Fred Kofman - Recommended as a user manual for human beings, particularly for leaders and managers, offering gold for those new to leadership roles.
"Thinking in Systems" by Donella H. Meadows - Recommended as a framework for understanding how systems work, applicable to all aspects of life.
"The Effective Executive: The Definitive Guide to Getting the Right Things Done" - Recommended for its simple, enduring advice on leading teams effectively.

Videos & Documentaries

"Wall-E" - Mentioned for its prescient depiction of robots similar to the Matic robots discussed.
"Heated Rivalry" (HBO Max) - Mentioned as a recent TV series enjoyed by the speaker, described as smutty but delightful.

Articles & Papers

"New banking records prove Deel paid thief who stole trade secrets from Rippling" (Rippling Blog) - Referenced in the context of business practices and competitive dynamics.
"SPOTAK: The Six Traits I Look for When I’m Hiring" (Yahoo Finance) - Mentioned as an interview framework adopted by the speaker.
"Brian Chesky’s contrarian approach" (Lenny's Newsletter) - Referenced in relation to leadership and business strategy.

Tools & Software

Google Gemini - Mentioned as an AI assistant and a tool for building apps through vibe coding.
Datadog - Mentioned as a platform for product managers and engineers, including its Eppo feature flagging and experimentation capabilities.
GoFundMe Giving Funds - Mentioned as a donor-advised fund product for year-end giving.
Fellow coffee maker - Described as a favorite product with a slick interface and high-quality coffee output.
Matic robots - Mentioned as house-cleaning robots similar to those depicted in "Wall-E."
ChatGPT - Mentioned as a tool used for refining articulation of ideas and as a thought partner.
Claude - Mentioned as an AI tool, potentially better at writing and language than others.

People

Matt MacInnis - Chief Product Officer and former COO at Rippling, the guest on the podcast.
Dan Gill - Chief Product Officer at Carvana, credited with the phrase "extraordinary results demand extraordinary efforts."
Steve Jobs - Mentioned as a former CEO of Apple under whom the speaker learned about relentless product development.
Parker Conrad - CEO of Rippling, discussed in relation to leadership and decision-making.
Sunil Raman - Suggested topics and questions for the conversation.
Albert Strachum - Suggested topics and questions for the conversation.
Brian Schreier - Mentioned as a Sequoia partner who recommended "Conscious Business."
Ivan - Founder of Notion, discussed in relation to the company's success and persistence.
Geoff Lewis - Mentioned in relation to investing.
Mike Vernal - Mentioned on X.
Sarah Guo - Mentioned on X and as a co-host of the "No Priors" podcast.
Dennis Rodman - Mentioned as an example of a high-alpha, low-beta personality.
Derek Lee - Founder of Macro, an invested company that is now out of business.
Ned Rokson - Founder of Debrief, an invested company that is now out of business.
David Hertz - Founder of Verb Data, an invested company that is now out of business.
Carl Sagan - Author of "Pale Blue Dot," mentioned for his profound impact on the speaker's perspective.

Organizations & Institutions

Rippling - A unified workforce management platform, the company where the guest works.
Google Gemini - Mentioned as a sponsor and an AI product.
Datadog - Mentioned as a sponsor and a platform for product teams.
GoFundMe - Mentioned as the platform behind GoFundMe Giving Funds.
Lenny's Newsletter - The platform hosting the podcast and associated content.
Carvana - Mentioned as a company with a Chief Product Officer who coined a key phrase.
Apple - Mentioned in relation to the speaker's experience working there.
Pro Football Focus (PFF) - Mentioned as a data source for player grading in a previous context.
Inkling - The speaker's previous company, which was sold to a private equity firm.
Sequoia - A venture capital firm, mentioned in relation to Brian Schreier.
Genentech - Mentioned as an example of a company focused on drug discovery and receptor binding.
Microsoft - Mentioned as an example of a company that started with a core product and expanded.
Workday - Described as a company with terrible software, despite its success, and a competitor in the business software space.
OpenAI - Mentioned as a "shovel provider" in the AI landscape.
Conviction - An investment firm focused on AI, recommended by the speaker.
No Priors - A podcast recommended by the speaker, co-hosted by Sarah Guo and Ilad.
HBO Max - The platform where "Heated Rivalry" is available.
Crave - A platform where "Heated Rivalry" is available.
Fellow - A company and a Rippling customer, maker of the speaker's favorite coffee maker.

Websites & Online Resources

ai.dev - URL provided for Google Gemini.
datadoghq.com/lenny - URL provided for Datadog.
gofundme.com/lenny - URL provided for GoFundMe Giving Funds.
lennysnewsletter.com - URL for Lenny's Newsletter.
x.com/stanine - Matt MacInnis's X (formerly Twitter) handle.
linkedin.com/in/macinnis - Matt MacInnis's LinkedIn profile.
rippling.com - Rippling's website.
linkedin.com/in/sunilraman - Sunil Raman's LinkedIn profile.
linkedin.com/in/dangill - Dan Gill's LinkedIn profile.
carvana.com - Carvana's website.
lennysnewsletter.com/p/brian-cheskys-contrarian-approach - Article on Brian Chesky's approach.
linkedin.com/in/parkerconrad - Parker Conrad's LinkedIn profile.
inkling.com - Inkling's website.
linkedin.com/in/akothari - Akshay Kothari's LinkedIn profile.
notion.com - Notion's website.
en.wikipedia.org/wiki/Conway%27s_law - Wikipedia page for Conway's Law.
seekingalpha.com - Website mentioned in relation to financial outperformance.
dennisrodman.com - Dennis Rodman's website.
slackmojis.com/emojis/456-dancing_pickle - Link related to a Slack emoji.
en.wikipedia.org/wiki/Pickle_Rick - Wikipedia page for Pickle Rick.
finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html - Article on the SPOTAK hiring framework.
linkedin.com/in/geofflewis1 - Geoff Lewis's LinkedIn profile.
en.wikipedia.org/wiki/TriNet_Zenefits - Wikipedia page for Zenefits.
rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling - Rippling blog post.
workday.com - Workday's website.
maticrobots.com - Matic Robots' website.
imdb.com/title/tt0910970 - IMDb page for Wall-E.
conviction.com - Conviction's website.
x.com/mvernal - Mike Vernal's X handle.
x.com/saranormous - Sarah Guo's X handle.
linktr.ee/nopriors - Linktree for No Priors.
gemini.google.com - Gemini's website.
chatgpt.com - ChatGPT's website.
claude.ai - Claude's website.
linkedin.com/in/bryanschreier - Bryan Schreier's LinkedIn profile.
hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c - HBO Max link for "Heated Rivalry."
fellowproducts.com/products/aiden-precision-coffee-maker - Link to the Fellow coffee maker.
amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595 - Amazon link for "Pale Blue Dot."
amazon.com/Conscious-Business-Build-through-Values/dp/1622032020 - Amazon link for "Conscious Business."
amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557 - Amazon link for "Thinking in Systems."
amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459 - Amazon link for "The Effective Executive."
penname.co - Website for production and marketing services.
podcast@lennyrachitsky.com - Email for podcast sponsorship inquiries.
www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language - Lenny's Newsletter URL with tracking parameters.

Podcasts & Audio

Lenny's Podcast: Product | Career | Growth - The podcast featuring the discussion.
No Priors - A podcast recommended by the speaker, focusing on AI.

Other Resources

High alpha, low beta framework - A framework for evaluating people, processes, and products based on outperformance and volatility.
PQL framework - Mentioned in relation to product management.
Conway's Law - A principle stating that organizations design systems that mirror their communication structure.
Pickle (Product Quality List) - An internal framework at Rippling for product quality standards.
SPOTAC - An acronym for a