It must be a fairly common scenario – You have an idea, you are lean or you have raised a small amount. At this point, you hire from your network, getting on people who are loyal, people who you like working with, people who are a good culture fit
You are OK with hiring generalists. You have time to groom them. You hope they will work hard and take us to the next level.

And they do! Then, thanks to their work your startup takes shape. You raise more money. You appreciate their work and praise them for what you expect of them – hard work & dedication & loyalty.
What you value the most is that they think of your company as their company. There is a strong sense of belonging & loyalty. This loyalty is what you value the most

With more money comes more pressure.Grow faster, make a better product, beat competition. It is like you suddenly graduated to the big leagues. Warm up is over. Shit gets real. This is war. Things get more difficult.
Founders get pushed. They push everyone else
Expectations become unrealistic. You expect things to be perfect. You expect to be on top of SEM. You expect conversion to be best in industry. You expect the product to be great. What was exalted as hard work earlier is mediocre now.

Now, as a founder you are left with 2 options. Maintain the status quo and live with mediocre performance ( since they are generalists. They can only be good. They can’t be great ) Or you start pushing them. Tell them what they are doing is not good enough. You tell them they are not good enough yet. That they must get better

This is where the men get separated from the kids.
The men take reality on their chin. They realize that they must get better for the company to win. They realize that the only thing that matters is winning. And do win we must have the best man at each critical position. They embrace this reality, worked harder than ever and if needed, concede that position to someone better. They do their best to level up and embrace the change. They keep the organizations’ best interest at heart. If they feel they are the best guy for the job, they work harder than ever and prove it. If they feel there is someone who can do it better, they embrace that change

The kids take it personally. They believe that the new-found criticism, pressure and unrealistic demands are unfair. They start feeling betrayed. They feel that the company that they treated as their own is turning their backs on them. They feel that all the hard work they out in is not appreciated. That they have been used and discarded. Instead of hearing “We need to get better at this”  they hear ” You are not good enough anymore”. They take it personally. Some of them become emotional about it. They sulk. They look hurt

And that is when you know that the startup has truly outgrown them