My friend who works now as an engineer at Apple interviewed with Epic 6 years ago - he got a guidance from a fellow to make a few mistakes in test tasks to increase chance of getting a job offer, and it worked - he got the offer
https://www.healthit.gov/topic/certification-ehrs/certificat...
The only way a startup might be able to eventually replace Epic is to target a niche ambulatory care specialty first where meeting all the checklist requirements is less important than really nailing an optimal clinician workflow. Then gradually expand out from that foothold by adding the features that hospitals need.