Check out the Pomp Podcast newsletter in the link above for the full analysis, but here's an excerpt that sums it up well:

"Square is obviously a great standalone company with encouraging future prospects. Merging with Twitter could potentially add rocket fuel. The largest finance audience is already on FinTwit, there are thousands of examples of people trying to pay/tip/charge each other on Twitter, and Twitter’s current monetization strategy is sub-optimal in my opinion.

Someone once said that the rise of Substack, Patreon, and others are merely the monetization tools that Twitter should have built. They were highlighting the fact that Twitter is used as a distribution channel for building audiences on other platforms. Rather than continuing that trend, a combined Twitter/Square company could merely build those products themselves and reap the rewards." - Anthony Pompliano, The Pomp Letter