What are some differences/similarities to shooting sport in the mountains vs urban streets?
There are a lot of differences between shooting in the mountains versus shooting in the streets, but luckily for me, I grew up shooting skateboarding, so I’m quite comfortable with both.
In the streets, at times you have much more time to set up a shot and think more about placing artificial lighting to create dramatic effects.
On the other hand, in the case of shooting photos that will attract issues with the police or security guards you're going to want to set up your lighting plan ahead of time, metering everything offsite, so all you will need to do is drop the lights into place and shoot.
Or like in this case (the photo of Drew jumping gap) you will need to choose the right time of day to shoot all natural light. If that is not a possibility, then you will have to choose an angle depending on light. In the mountains, you're solely relying on what Mother Nature gives you. You're likely working with natural light, so choosing a location and time of day will be more crucial.
How did you shoot the street spots? (lighting, settings etc)
This particular shoot was a more run and gun style of shoot, so I would work around the existing light. Some locations and obstacles worked really well and others bombed.
On a normal day I would have either brought a few lights to help or shot things at a different time of day.
What’s the hardest part of shooting with a pro athlete?
There are three things that come to mind working with a professional athlete.
One, they are professional, so you likely won’t have their talent to blame when you make mistakes.
Two, because they are pro, your subject will likely have a large bag of tricks and will be able to preform the proper trick that looks better from the angle you choose to shoot from.
And three, one of the more difficult things manage as a photographer, likely they will be trying something so difficult that it becomes a “one and done” shoot. This means they will do it once, stick it and leave. So that means you have once chance to get the shot.
For me, shooting a one and done photo adds so much stress to the shoot.