A small communication breakdown is enough for everyone to be working on slightly different things. And then you loose focus.

One of the biggest advantages that start ups have is execution speed and you have to have this relentless operating rhythm.

You want an idea that turns into a monopoly. But you can't get a monopoly, in a big market right away; too much competition for that.

For most of the early hires you make in a startup, experience doesn't matter very much, and you should go for aptitude.

As the company grows and about this 25 or so employee size, your main job shifts from building a great product to building a great company.

Most of the best hires that I've made in my entire life have never done that thing before.

You don't need to make the structure complicated, in fact you shouldn't. All you need is for every employee to know who their manager is.