Matt MacInnis

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.

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.

Every company succeeds on the foundations of the idiosyncrasies of the founder. The idiosyncrasies of the founder. Rippling succeeds for almost the polar opposite reasons that Notion succeeds, but in both cases, the companies succeed on the idiosyncrasies of the founder.

The market is immutable, no amount of tweeting, LinkedIn posting, advertising is going to change whether the market wants your product. It might raise awareness about your product, but it's not going to change whether somebody wants it.

You don't really learn from your mistakes, you learn from your successes. Of course, I learned and grew a ton during that time, but in now what I think is six or seven years at Rippling, I've learned so much more because I've seen success.

There's no greater gift to me as a product executive than receiving an escalation from a customer. Escalations are a gift, and it's like, if you're a listener right now on this podcast and you are a Rippling customer and you have shit that you think we should know, the fact that I might already know it is not a reason for you to withhold the gift of your feedback.

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 fricking exhausting.

Product market fit is a sort of thing where you absolutely know it when you see it, and therefore if you don't absolutely know it, you don't have it.

Don't ask people for advice, ask people for relevant experience. If you ask them for advice, they will always give it, but if you ask them for relevant experience, they rarely have any to offer, and if they don't have any to offer, then don't ask for their advice.

Point solutions don't have enough data in the age of AI to be useful. You got to be able to provide the AI with a lot of context about a lot of data so it can do things. It can do joins. It can do correlations.

We talk in Silicon Valley about never quit, but that is complete absolute venture capital bullshit. The incentive of venture capitalist is to put money into your company and milk you dry. They never get their money back. There is no way for them to take that investment back.

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.

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.

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.

If you want to create a moment that sticks in people's brains and sort of becomes a zeitgeist or something that they latch onto, you got to create an entity, a vessel for meaning, and then you got to fill that vessel with your meaning.

The only antidote to entropy, the only antidote to decay in a system is energy. You got to inject energy. Your job as an executive, as a leader, is to fight that entropy tooth and nail every single day.