…to me, this looks flaky. Yes, Scott Adams (of-Dilbert-fame) is right in saying your best bet for success in life is being pretty good in several skills rather than trying to be the best ever in only one. So, a plan like this:

  1. Step one: become a decent entrepreneur
  2. Step two: become a decent MD
  3. Step three: ???
  4. Step four: profit!

might indeed be a good idea. However:

  • Medicine implies altruism. Entrepreneurship implies greed.
  • Programs want their residents to be 100% dedicated to medicine in general and the program in particular. Can you do that with a small business on the side?
  • Physicians in academia, i.e. those who conduct residency interviews, forgo 300k+ salaries so they could dedicate themselves to research and education. Are you sure telling them about your latest money-making scheme is a good idea?
  • As a resident, do you look at each patient as an opportunity to help them and learn from them, or to figure out how to build a business around them?

Residency programs exist to train physicians, not CEOs. Residency slots are already in short supply. Would program directors give a position to someone who is more likely to end up not practicing medicine at all?