Just a question for people in the Masters age category. Is it possible for someone to turn Pro at this age group. More less anyone in the 36+ age range.
Pro as in to drop everything and train and race bikes full time. I know some people pulled it off such as Ned Overhand, but that is rare. But a question is this possible and if so is there a good population of masters who done it? thanks

I can't address your main question, but just want to point out that Ned Overend turned pro (I think) in the mid-80s, not recently.

Technically it's possible because basically anyone can just drop everything and ride/race full time. Whether it's responsible or not, whether the rider can actually make a living wage, those are different questions. In fact many lower level pros nowadays don't make a living wage. They might get paid, to meet minimum pay requirements, but then pay the team various fees and such, effectively reducing their actual wage. This is why you see lower level pros have "regular" jobs in addition to their racing one. In women's racing it's worse, it's basically out in the open ("so and so is our sprinter and she's a doctor when she's not training").

The guy that won the pro RR and pro Crit last year is a chiropractor? He was 34 or so when he won his titles, won against ProTour type riders in the RR, won against mainly domestic pros in the crit.
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Ned Overend became a mtb pro. Back in that same era there was a road rider that turned pro, his name escapes me, but he was a diesel type climber rider. Rode for Coors Light. Mike Englemann. There was a guy Chip something that would take out a pro license mainly because he wanted to do Corestaes/Philly, but he wasn't on a team because he was basically sponsoring himself.

A rider with a lot of talent, they can do well, pro or not. Do you need to be a pro? A lot (most/all?) of these older guys don't think it's worth it. They work their regular jobs and get their racing fix in regular Masters and P12 races. These include some pretty good ex-pros out in SoCal, for example.

All the pro racers who made it past 40 started much earlier. And were mutants.

I did my first pro race at 49. I had offers to ride with local P1/2 teams in my late 40's. Free bike, kit, and some travel money. Help the kids out.

Can you get to that level at 36? Absolutely. I started at 44 and am no genetic freak.

As CDR noted though, "paying the bills" as a full time cyclist depends on your bills. At 36, you might be able to squeak by with 3 roommates eating a lot of ramen. Same at 22. Difference is most teams are going to go with the 22 year old looking at a possible upside. Aside from physical development it takes a lot of years just to learn the sport. Most teams figure 1 out of 20 make it to a decent level. Why invest in a guy who will be over the hill when they peak?

There may be one mutant out there who can take the sport up at 36 and crush the world. One in a billion though.