Uber Diaries: Uber For Rich People.

Pickup: Portland International Airport.

The guy had airport ID and a "crew"tag on his bag, so I imagined he worked for an airline, but I didn't recognize the logo on his shirt.

"We need to pick up my friend at the Atlantic terminal before we head out to the hotel."

The Atlantic terminal is the place where private or charter planes land. It's not the sort of place a "normal" person would normally go to, and certainly not a place where there would be many Uber pickups. But it turns out, I knew exactly where the Atlantic terminal was because it's where the Timbers landed after winning the MLS Western Division championship last winter.

We pick up the second passenger and are on our way to Beaverton. One person is from Denver, while the other is from California's central coast. It seems like they may not have seen each other for a couple of weeks and they spend part of the ride catching up.

Once that was done, I had some questions about their work. What sort of charter flights do they work on?

"It's a service where you can call up and get a plane to take you where you want to go. It's kind of like Uber for rich people."

I ask how much like Uber it really is. How long do you have to wait between calling for an airplane and taking off?

"It depends on a few things, mostly the level of service you choose, Normally you'll have to wait about one day, but if you've put enough money into this, you can get a plane in a couple of hours sometimes."

The guy from Denver chimes in:

"For us, we get at least two hours notice before we need to take off. So we know we've got this thing going out of Hillsboro and down to California, and we'll probably be in San Diego and Orange County this week, but that could all change."

As I listen, this all sounds very attractive to me. I kind of like the idea of getting a phone call and hopping on a plane to a destination you didn't know at the start of the day. It's like of like driving Uber, where you never know where you'll be in the next hour, but with even bigger distances.

The rest of the ride was spent talking about different sorts of planes, the insane security the Secret Service requires when the President travels, and, of course. the Faroe Islands. Because how can you have an Uber ride without talking about the Faroe Islands.

I like these guys a lot, and as I drop them off, I wish I could chat with them more, and maybe I'll pick them up for another ride one day. But there's pretty much no chance I'll ever meet them at their work. The "private jet on demand" world will probably never be within my financial reach.

As they take their bags out of the back of the vehicle, I offer them each a firm handshake and say, "Thanks for using Uber for poor people."

Drop off: DoubleTree Beaverton.

Uber Diaries: Federal Pen

Pickup: Portland International Airport

As I pull up to the curb, the app sends me a text message saying I should be looking for “a tall Asian man in a Zoo York sweatshirt.” I don’t usually get messages like this. The only time this happens is when a parent has sent me to pick up their kid at a middle school activity (this happens more often than you’d think).

So I sit at the curb and eventually I see the guy. He’s wearing a Zoo York hoodie, sweatpants, and sandals with socks. He has no luggage. I imagine he’s dropped off a friend or works at the airport or something.

“I need to go to Sheridan,” he says.

“The Sheraton by the airport?” I reply.

“No, Sheridan, Oregon.”

“I think there’s a Sheraton downtown. Let me look that up.”

“Sheridan, Oregon.”

“Oh, the town. There’s a town called Sheraton?”

Eventually we work it out and I see that the town, which I’ve never been to or heard of before, is about 75 miles south of the airport.

“I’m turning myself in at the federal prison in Sheridan.”

He explains that he can’t have anything with him when it surrenders, so he doesn’t have his cell phone with him. His wife was the one who set up the ride. As he’s explaining this, a message comes up on my phone:

“Sorry, I shouldn’t be doing this but can u tell my husband I love him very much always and forever so sorry again.”

The drive to Sheridan is about 90 minutes. During the long drive, he tells me about his daughter who’s 10 and the mortgage business he used to run in Central California. It was in that business where the troubles began.

I didn’t ask exactly what he did, but it had something to do with the go-go days of the mortgage bubble when, as he put it, “something was legal, and then one day it’s illegal.”

He says he’s been sentenced to 40 months, but he has 47 months of credit, so there’s a chance they’ll just turn him around and send him right back home. But maybe not. The process seems a little like changing colleges, he’s not sure what credits will transfer or how long it will take the feds to figure everything out. His attorney says it could take 13 weeks before everything is straightened out. So he doesn’t really know what’s going to happen. He just knows he has to show up to prison. Today.

I joke, “So if you’ve been sentenced to 40 months, and you’ve got 47 months credit, you should get some sort of voucher that you can redeem later. It’s like you could go out and commit a crime that would usually get you six months for and you’ve already got the credit.”

Amazingly, he laughs at this.

We get about 10 miles from Sheridan and he says, “I’m told this is the nicest prison camp in the federal system.”

He’ll be in a minimum security prison camp and spend most of his day working on various projects, maybe landscaping, maybe highway cleanup, that sort of thing. At his camp, there will be no fences, no walls, no razor wire. But if you walk off, you end up in the real prison, serving real hard time.

At a nearby town, we stop at a bank. He came with money because he thought he would need it. But upon landing, he learned he can’t bring anything inside with except ID and the clothes on his back, maybe a wallet. So he deposits the money and we drive the last few miles to the prison.

It’s been rainy in Oregon these last few months, but as we pull up to the prison, the sun has come out and it’s a gorgeous late morning. The facility has the minimum security prison camp, and a proper prison, with the fences and the razor wire… I’m guessing medium security.

I don’t know which way to turn towards. That’s when I see the lawn sign that points towards the regular looking prison and says, “Self Surrender.”

I pull into the parking lot and hand the guy my phone. I tell him to go outside the car for some privacy and call his wife. I can’t help but empathize with the guy. We’re about the same age, have kids about the same age, probably about the same socioeconomic status. If I really got myself in trouble and ended up in prison, I imagine this is what it would look like.

 I try not to listen to his phone call, but I hear him tell his wife he loves her and that he’s made a bunch of videos for his daughter on the phone he’s left at home.

When he’s done, he opens the car door, hands me my phone, and thanks me for the call. Then he puts two pens and small note pads down on the passenger seat.

“I can’t bring these inside, so you can just have them.”

They’re now on our kitchen counter. My wife uses them to make shopping lists for me. My daughter scribbles on them, making the lists illegible.

He stands in the parking lot for a moment and is about ready to walk towards the door. Just then, a van pulls up and three guys with shotguns get out. The back door of the van opens and a man in an orange jumpsuit gets out. His legs are chained together and he’s making the slow, shuffling walk towards the door as the guys with shotguns watch.

My passenger decides to stay in the parking lot a few moments longer. I put the car in “drive” and head back to Portland.

Drop off: Sheridan Federal Correctional Institution.