Personal endorsements are a very weird market, and they usually cost more time, money, and commitment to maintain than you get out of them. It's more like you're giving lots of volunteer time for your homies, and they're tipping you some gear for the help. Seek volunteer opportunities if free gear and status is really what you're after.
You don't need an endorsement to feel validated, everyone knows that the rawest skiers and skaters in the world are unsponsered.
But, if you really really want to be part of the action and collaborating with a bunch of brands and sponsers, host an event. Have a small rail jam, and make a website for it, and use a web form to ask for small cash contributions or product contributions for prizes and event permit fees. If you're not already an insider, sponsers won't want to sponser you, but they'll want to sponser an underground event that promotes their mission and engages people directly.
