Our guy on the field had zero hours, but then bought a new SR-22. Rumor had
it was that he did a lot of flying IFR without the rating, and he would
routinely fly over Lake Michigan in IMC in the single.

His take off routine was to rotate, pick up some speed, and then do a high g
pull-up. We called him "super pull up" on the field.

He then bought an SU-29, with absolutely no tailwheel time. He got signed
off in less than 7 hours as being good to go (yeah, right), and on his first
couple of flights he dropped it in from a height, requiring a new prop, and
major structural repairs.

To his credit, he took a lot more lessons, and appears to be flying a lot
more conservatively and safely since his experience.

Of course, some people never make a mistake, so this wouldn't apply to them.