The kid has money. Traveling to all these events isn't cheap. So I think it safe to assume he and/or his family are donors at some level. It doesn't take much of a donation to get a seat close to the front, far less than the cost of traveling to the event.
Parents in the US spend money on their kids' activities. This probably is equivalent to mid-level travel sports, selective musical organizations, and beauty pageants. It is almost certainly less expensive than traveling with horses.
Ten hours of driving each way and a budget hotel runs a couple of hundred dollars and provides a substantial operating radius...and that ain't much money for a lot of people.
Individual venture capital from parents to their son. Probably a lot less than a brand name university, with a lot more benefit in terms of network, personal brand, and skills.
once you get connected to people like he seems to be, he's probably getting rides with people and crashing at houses and other hotels too. hell do you know how many hippie bernie supporters are riding around in the 'mystery machine' living on $6 dollars a day.