10 Contrarian Leadership Truths Every Leader Needs to Hear

Matt MacInnis deliberately understaffs every project at Rippling. Not because he's cheap, but because constraint forces clarity. When everyone is constantly asking for more resources and teams are stretched thin enough to feel it, you eliminate the low-value work that fills available capacity. The trick is knowing when you've gone too far: when teams are asking for backup, new resources arrive. But until then, keeping people busy prevents distractions, low morale, and the creeping bureaucracy that kills velocity.

The contrarian insight here cuts against the entire Silicon Valley playbook. Extraordinary results demand extraordinary effort. Not grind-individuals-into-dust effort (people should take vacations and live their lives), but collective organizational intensity that never relaxes. You can't let up because slowing down creates room for competitors to take market share. This is the "high alpha, low beta" framework: you want high variance in returns (big wins) with low correlation to broader market movements (you're building something unique, not following the herd).

MacInnis calls it fighting entropy. As startups scale, friction becomes inevitable. Standards dilute incrementally. Operational urgency slips by a few degrees. These small compromises quietly undermine execution and culture. Rippling codifies this in their "go and see" leadership principle: leaders shouldn't live in the dashboard. When anecdotes disagree with data, you have a problem. You have to get down to the atomic level of the function you care about to gather context. Watch back a Gong call. See where the rep missed redirecting to your superpower. That signals a breakdown worth investigating.

The framework that built a $16 billion company isn't about having all the answers. It's about identifying the roving bottleneck (whatever is blocking your path from 2 to 20,000 employees), clearing that obstacle, and immediately spotting the next one. Parker Conrad still personally approves every expense over $5 and runs payroll for the whole company. Not because he's a control freak, but because using your own product at the atomic level keeps you honest about what actually works. This is how you spot entropy before it metastasizes.