This is a great idea - thank you for starting this thread! I recently started a position in TVK.
One *potential* (still to be proven, keep an eye on) suggestion is Savneet Singh at PAR. He is a big Buffett fan: https://medium.com/@Savneet/building-the-berkshire-hathaway-of-software-4ec6a1b25e26. Essentially, he has sought to create the dominant unified end-to-end technology stack for restaurants (mostly QSR). PAR has executed a number of acquisitions (MENU, Punchh, and most recently Stuzo and TASK) to broaden its offering and extend its reach. If he can scale ARR and get the company in a better position on cutting costs and improving profitability, this could be a real winner.
So far, this has not yet translated into much value for shareholders, so definitely too early to call him a "successful" outsider, but I'm increasingly thinking this space will be a "winner take most" market and that PAR is positioning itself well for that.