Zigging vs. zagging: How HubSpot built a $30B company

The calories you spend on a decision should be proportional to the consequences of that decision, pure and simple.

I could become passively okay at management with some training, with some coaching. I don't want to spend any years of my life becoming passively okay at something.

Don't try to go learn something because you think it's worth learning. Find an actual problem that you care about and go try to solve it with that new thing.

Culture is a product, period, and every company builds two products, one is the product they build for their customers, and the other is a product they build for their team.

Just like you would never freeze the lines of code of a product, you would never freeze the lines of code of a culture. Culture should be iterated on just like you iterate on product.

"Bowling Pin" refers to Geoffrey Moore's go-to-market strategy of targeting one market segment first, then expanding to adjacent segments sequentially.

We are here for SMB. That's what we're doing. This is not a go-to market strategy. This is not like, 'Oh, we're going to conquer SMB first,' this is not Bowling Pin, this is not Geoffrey Moore.

You tend to be good at the things you enjoy. You tend to enjoy the things you're good at.

Some of the best startup advice I've heard is startups should focus on one thing and be really, really exceptionally world-class at that one thing. And one of our early zigs is we are going to do exactly the opposite of that.

Within a closed system, entropy increases over time. In the early stages of a company, you're essentially fighting to survive. In the second phase of a company, you're trying not to stagnate. But then the third stage is you're fighting complexity.

The one thing we wanted to be good at was solving for the actual customer problem that existed, and the customer problem that existed was not a dearth of tools, lots of great SEO blogging, everything, all the tools existed, but SMB specifically did not have the wherewithal to put all those pieces together.

Every time you say yes to something, by definition you're saying no to something else.