This week, we’re sharing an article based on our most popular podcast episode of 2024.
Everything in Business is About Fighting Entropy — Here’s How Rippling Does It
At Rippling, all the functional leaders have a running joke: “Who is MacInnis's injured bird?”
It's not a question about ornithology. They are referring to COO Matt MacInnis’ surgeon-like approach to executive attention.
While most startup executives spread themselves thin—jumping between financial forecasts, hiring plans, and product roadmap decisions—MacInnis operates with the precision of a skilled physician: identifying his most critical patient, bringing them to the operating table, and giving them his undivided attention until he's solved the underlying problem.
“Everything in a business is about fighting entropy,” MacInnis says. “Everything I do today in my job at Rippling—where we have a massive growth rate on top of a very large base of revenue—all day is to fight entropy. It’s the feeling that if I take my eyes off of a project, it'll slow down a little bit. Without the intensity that I bring to each of these projects, it will drift in terms of velocity or precision.”
As a former founder, MacInnis spent nine years building Inkling and leading the company as CEO through its acquisition. These days, he’s focused on scaling Rippling into a full-service workplace management platform, a role he stepped into early on in the company’s lifecycle. And as more people enter the picture, entropy is a force that becomes every team member’s responsibility to combat—but senior execs are most acutely responsible.
In this exclusive interview, MacInnis shares his unconventional playbook for how startup executives can become more deft at both diagnostics and treatment. His advice is two-fold: tactics for making the organization better and strategies for making you a better exec.
With advice that starts out on the milder side (like how to leverage impatience into velocity) to some hotter takes further up the Scoville scale (like his fundamental rejection of asking for advice), MacInnis pulls no punches when it comes to divulging all the practical wisdom in his repertoire. The podcast interview with MacInnis was our most downloaded episode of 2024 for a reason.
The lessons he shares will help any leader become more effective no matter where they sit in the org chart—whether you’re a founder, an exec or still climbing your way up the ladder.
Thanks, as always, for reading and sharing!
-The Review Editors
Recommended resources:
-Is great operations the sneaky undertow that sinks multi-product bets? Shreyas Doshi makes the case.
-You can now watch this TedNext talk from Molly Graham, one of our favorites here on the Review, about why winners forget the corporate ladder and focus on taking risks.