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

**Matt MacInnis** (0:00)
It is really important to me that we feel that we've deliberately understaffed every project at the company. If you overstaff, you get politics, you get people working on things that are further down the priority list than necessary. That is poison. It's wasteful, it slows you down, it creates cruft.

**Lenny Rachitsky** (0:15)
You've been a long time COO at Rippling. Recently, you moved into CPO, Chief Product Officer at Rippling, something you talk a lot about, is that extraordinary results require extraordinary efforts.

**Matt MacInnis** (0:26)
If you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult. You got to sort of remind people that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. It's supposed to be really freaking exhausting.

**Lenny Rachitsky** (0:40)
You're a big fan of escalating issues.

**Matt MacInnis** (0:41)
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.

**Lenny Rachitsky** (0:53)
So many people have teams that are not functioning incredibly well.

**Matt MacInnis** (0:56)
Teams will always optimize for local comfort over company outcomes. 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. That is fucking dangerous. As an executive, as a leader, your job is to preserve that intensity at its highest possible level.

**Lenny Rachitsky** (1:22)
You've had a couple really interesting experiences with your own startup.

**Matt MacInnis** (1:25)
We talk in Silicon Valley about never quit, but that is complete absolute venture capital bullshit.

**Lenny Rachitsky** (1:33)
Today, my guest is Matt MacInnis, Chief Product Officer and formerly long-time Chief Operating Officer at Rippling. If you don't know much about Rippling, it's a massively successful business, last valued at over $16 billion. They have over 5,000 employees, and Matt has been instrumental to that success. He's also got a really rare combination of brutal honesty, a ton of experience building a very complex and very successful business, and being able to clearly articulate what he has learned really well. Matt shared a lot of insights and advice that I have not heard anyone else on this podcast share, and I left this conversation feeling that every leader needs to hear his advice. A huge thank you to Albert Strashim and Sunil Raman for suggesting topics and questions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And, if you become an annual subscriber of my newsletter, you get a year free of 19 incredible products. An entire year of lovable, replete, bold, gamma, innate and linear, devin, post-hawks, superhuman, dscript, whisperflow, perplexity, warp, granola, magic patterns, raycast, chapier d, mobbing, and striped atlas. Head on over to lennysnewsletter.com and click product pass. With that, I bring you Matt MacInnis after a short word from our sponsors.

**SPEAKER_3** (2:48)
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**Lenny Rachitsky** (3:18)
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