This is not news to be concerned about. However, I appreciate that someone went to the trouble of collecting and presenting this data.

Why does this matter? You're bound to sell the stock of the company you own eventually, right? If this happened 10 years from now, people would make a big deal of this. If it happened 50 years from now, same thing.

It's only a couple million worth - hardly significant.

Honestly is square worth 14bn? why would he be selling hear end if he doesn't think it will be worth more next year?

The valuation of Square in the future is possibly not the only factor. Dorsey could be leaving the company, seeking liquidity, relinquishing control of the company or making another investment that has a better expected return. Also, he could be diversifying as he likely still holds a lot of shares. He seems like a smart guy and there are rational reasons an investor would divest a company with a positive forward outlook.

His trades are only a small data point to consider when valuing square. Whether it is worth 14b or not has little to do with him selling 150k shares without additional information.

He's probably selling to diversify. It looks like he's selling based on a 10b5-1 plan, i.e. he's selling on a predetermined plan.

These small sales are routine.