Ok so my father has been running a hill climb TT for the past 4 years, to raise funds for Habitat for Humanities, and it has grown each year. This year they had 50% more riders than last year and 100% more women than the previous year (still only 8 women).
Winners of each sex got $200 and a King (or Queen) of the Monutain Jacket.
Looking at the times IMO the top guys are flying (IMO no doubt some racer is going to say they can do it faster), with the winning male having an avg speed of 16.67 MPH on the 5 mile climb, and the female at 10.57 (thin female field).
So the question is how can he take this to the next level? How far in advance should he advertise?