Saving pennies and spending dollars

[Cordell M.]

I hear others talk of 'saving pennies and spending dollars' when starting out, trying to do too much themselves, etc.  I see the meaning in terms of say hiring someone to hang/finish drywall who gets it done faster, better and turns the unit around more quickly vs doing it oneself and not having to pay a contractor, but paying oneself $4.50/hr and having a finished job that looks south of awesome.  

What are other concrete examples of saving pennies to spend dollars and better ways to do things?

Thank-you for your time!