I’ve been lucky to have been part of building, advising, or investing in
40+ tech companies in the past 10 years. Some $100M+ wins. Some, complete
losses. Most end up in the middle. 

One of my main observations is that there are certain companies where
growth seems to come easily, like guiding a boulder down hill. These
companies grow despite having organizational chaos, not executing the
“best” growth practices, and missing low hanging fruit. I refer to these
companies as Smooth Sailers - a little effort for lots of speed.

In other companies, growth feels much harder. It feels like pushing a
boulder up hill. Despite executing the best growth practices, picking the
low hanging fruit, and having a great team, they struggle to grow. I refer
to these companies as Tugboats - a lot of effort for little speed.