Plenty of airline pilots participate in extreme sports. IMO that probably makes them better pilots in a pinch, as opposed to say a career-changing accountant who's never had to perform while fearing for his own life and limb.

But this sort of activity may not be something you would want to highlight or dwell on at an interview. If this is a private business activity, well they don't ask about that on applications. They only ask about previous W2 employers, although for any period where you were not in school or employed with a W2 they will want some verification of self employment, or whatever activity you doing at the time.

Sounds like you'll probably need to explain it as a period of self-employment.

If it comes up at an interview I think you could gloss it over by going immediately into the BUSINESS aspects of what you're doing, with details about marketing, ROI, those kinds of things. Make their eyes glaze over, don't make their eyes go wide with shock. They have no problem hiring self-employed go-getters who are responsible enough to develop and run a legal business.

Now if they goggle your name and find a bunch of videos...you had better hope that your demeanor and language in the videos is fairly respectable.

I think you'll be fine at almost any regional, and would eventually be able to get hired at a majors...after the tickets are ancient history. Also might want to consider a regional which has flow to AA, that would hopefully bypass the major airline interview process.

It is important in your circumstances that you keep your nose very clean from here on out.