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  1. Lenny's Podcast: Product | Career | Growth
  2. 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth · Dec 28, 2025

Rippling's CPO Matt McGinnis on why extraordinary results require intensity, understaffing deliberately, and knowing when to quit.

Rippling's CPO Deliberately Understaffs Projects to Eliminate Politics and Waste

Intentionally assigning fewer people to a project than seems necessary forces extreme focus on the highest priorities. Overstaffing is "poison" because it breeds politics, encourages work on non-essential tasks, and creates cruft that slows the entire company down.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

Great Companies Are Built on the Founder's Idiosyncrasies, Not Replicable Formulas

Success stories like Notion's cannot be replicated because they are a direct result of their founder's unique personality and 'narrative violations.' Great companies succeed based on the specific, unrepeatable idiosyncrasies of their founders. The key is to embrace these unique traits, not follow a generic playbook.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

Treat Customer Escalations as a Precious 'Gift' for Improving Foundational Systems

Don't view customer escalations as a nuisance; they are a valuable gift. Each one provides a critical opportunity to find and fix not just a specific bug, but the underlying process failure that allowed it to happen. Leaders should actively encourage customers to escalate issues directly to them.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

Managers Must Mirror CEO Intensity, Not Buffer Teams from It, to Combat Entropy

The founder CEO is a business's purest energy source. Each subsequent management layer risks an order-of-magnitude drop-off in that intensity. A leader's job is not to shield their team from this pressure ('be a shit umbrella'), but to mirror and preserve it to fight against organizational entropy.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

To Achieve 99th Percentile Outcomes, Your Team Must Feel Constantly Uncomfortable

Achieving extraordinary results requires extraordinary, often exhausting, effort. If your team ever finds themselves in their comfort zone at work, they are making a mistake. This high-intensity environment is easier to maintain when the company is clearly winning, providing leadership with "air cover" to demand more.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

Withholding Feedback Isn't Kind, It's Selfish Optimization for Your Own Comfort

The most selfish thing a leader can do is withhold feedback because giving it would be uncomfortable. In that moment, you are optimizing for your own comfort at the expense of your colleague's growth. High-performance teams require radical candor, which is fundamentally an unselfish act.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

Name Key Internal Processes (like Rippling's 'Pickle') to Create Shared Culture

To drive cultural change and ensure adoption of a new process, give it a memorable, idiosyncratic name. Rippling calls its Product Quality List the 'Pickle' (PQL). This creates a 'vessel for meaning' that becomes part of the daily lexicon, making the process stick in a way a generic name wouldn't.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

Bundled Platforms Will Win in the AI Era; Point Solutions Lack Sufficient Data

Point-solution SaaS products are at a massive disadvantage in the age of AI because they lack the broad, integrated dataset needed to power effective features. Bundled platforms that 'own the mine' of data are best positioned to win, as AI can perform magic when it has access to a rich, semantic data layer.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

The Mantra 'Learn From Failure' is Overrated; True Growth Comes From Studying Success

Contrary to the popular trope, you learn far more from success than from failure. It's more informative to see how things are done right than to analyze what went wrong. To accelerate your career, you should prioritize joining a winning team to observe and internalize successful patterns.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

Silicon Valley's 'Never Quit' Mantra Serves VCs, Not Founders Who Should Quit Sooner

The persistent "never quit" advice is "venture capital bullshit." Since VCs can't recoup their investment, their only rational move is to encourage founders to keep trying against all odds. For founders, it's often better to quit, reset the cap table, and start fresh rather than waste years on a failing venture.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

Use Financial Concepts 'Alpha' and 'Beta' to Decide When to Apply Business Processes

Frame process management like a portfolio. Processes exist solely to lower 'beta' (volatility and unpredictability). The tradeoff is they also suppress 'alpha' (creativity and outperformance). The key is applying rigid processes where you need low beta (e.g., payroll) while allowing freedom where you need high alpha (e.g., new product discovery).

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago

Your Market Has Fixed 'Drug Receptors'; You Can't Market New Ones into Existence

Treat your startup like a drug discovery experiment. A market's needs are like biological 'binding receptors'—they either exist or they don't. Marketing can raise awareness of your 'drug' (product), but it can't convince the body to grow new receptors. If you lack product-market fit, don't try to market your way out of it.

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) thumbnail

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

Lenny's Podcast: Product | Career | Growth·2 months ago