I don't think it's a hugely slanderous or inaccurate thing to say that pro skateboarders are on average fairly poorly educated. It's kinda the nature of the profession: if you waited to start your pro career until after you got a college degree you're going to have missed some of your best years as a skater. Dudes like Ocean & Suciu are super rare.
Despite all the talk about working class resentment blah blah, the main factor that determined how people voted in this last election was education level. And race, of course.
Put simply: if you're white, the less educated you are, the more likely it is you voted for Trump. So, I'd assume there are probably lots of pros with Trump sympathies.
But I'd also bet that 90 percent of pro skaters did not vote at all.
I understand where you are coming from, but I think your analysis of the situation is a bit off.
First, you forget a key break between Clinton and Trump "supporters" was age. Young people were more likely to vote for Clinton.
Second, we have to remember that the majority of the skateboard industry is based in California and the demographic characteristics that define the country may be different from the demographics that define CA. Voters in Michigan are probably a bit different than voters in California, a state where only 31% of the population voted for Trump. The number is even lower in most of the counties that house the skate industry. Only 9% of SF County voted for Trump, 21% of LA County voted for Trump, and 38% in SD County (
http://www.nytimes.com/elections/results/california-president-clinton-trump) . So even if we are going to base our hypothesis on who is likely to be a Trump or Clinton supporter on broad demographic data, maybe we should look at where the skaters live first. Also, it is important to remember broad demographic info can't tell us about specific individuals within that data.
Third, the notion that most pro skaters are conservative because they are white and don't have much education seems rather unlikely. Skaters are often a group individuals who wrap themselves in an existential identity and probably aren't lining up to vote Trump. (Outside of Street League) the art/bohemian based philosophy of skateboarding doesn't really overlap well with Trump's neo-conservative authoritarianism. The fact that liberals
tend to seek out novelty and uncertainty and are more willing to accept risk aligns well with skateboarding (
http://www.smithsonianmag.com/science-nature/study-predicts-political-beliefs-with-83-percent-accuracy-17536124/#GOHuXvzlH2Hu708J.99 ). Moreover, skateboarding's image doesn't often align well with religion, business, ultra-pro police values, etc. And, skateboarding's heavy emphasis on travel in skateboarding probably also reduces xenophobia and fear of immigrants. Not to mention that skaters often aren't likely to say, "No to drugs" and Trump's attorney general nominee is super anti-marijuana.
Fourth, skateboarding, a winner in global free trade market, appears to be struggling under the current conditions where we pay some poor Chinese or Mexican guy to make our shit for basically nothing. I'd imagine most of the dudes in the industry are terrified of the idea of having to bring manufacturing back to the US or losing their international markets if this neo-nationalist movement expands across the globe (looking at you France/Le Pen). Without heavy automation like Adidas has done with their new German shoe factories (no employees needed), the companies would need to raise prices or cut their margins. Something, that they probably don't want to do considering skateboarding seems to be struggling pretty hard as it is. The dude who owns BBS had a whole story in CNN about how the huge tax breaks Obama offered wouldn't off set the cost of manufacturing in the States compared to Mexico (
http://money.cnn.com/2012/02/03/smallbusiness/us_manufacturing/).
Finally, despite my belief that most skaters would lean towards democratic values, I'd agree that most are probably apolitical. Other than dudes like Walker Ryan, I don't see many really giving a shit about anything other than the present and the immediate world around them.
P.S. I'm not sure how much I back the crowd sourcing of information for private gain.