I was on the Internet too much, reading about too many interesting apps. Some purported to save me money; others promised to simplify my life. By the time I stumbled upon FlightCar, a service that would allow me to park at the airport for free by renting my car to strangers, it was too late. I already knew too much.

At the time, I was planning a six-week trip to Washington, D.C., for a wedding and some good old live-at-home-with-mom time. While I was away, I imagined, FlightCar would rent my tiny, blue Ford Focus to a few strangers and hand me a check when I returned. Numbers began to rack up in my head like pictures of cherries on a slot machine. An ominous ladder beckoned me to climb.

“How can we help you?”

I leaned into my phone, nearly sweating. “Hi! I'm going to be gone for about a month and a half. How much do you think my car might be rented? Would you say, like, a couple weeks, or … ”

“ … Yeah.”

Ka-ching! One barely audible, very distracted answer: good enough for me.

As it turns out, FlightCar isn't in L.A. — just San Francisco and Boston. While the startup is planning an expansion here, its owners are stuck battling a suit filed by the San Francisco city attorney, demanding they follow the same regulations as conventional airport rentals. But hey, why should that stop me? I could just drive to San Francisco.

From there, I started to get even more ambitious. What other plucky startups could I callously exploit for my own entrepreneurial gain? Driving to San Francisco would cost around $60. To offset the expense, I'd heard of international students using Zimride, basically Airbnb for your car: You go on a road trip and rent out your passenger seats to the highest bidders.

A text document on my computer screen laid out a series of dizzying calculations: If I flew from SFO, rented with FlightCar, slept with AirBnB, set my Zimride fare to $35 a person and then crammed three people in the car, my ticket would be a whopping $212 cheaper than if I flew out of Los Angeles. Clearly, nothing could go wrong.

Then came the night before my departure. “What time are you leaving tomorrow?” a friend asked.

“I don't know. I'm still waiting for strangers to tell me.” Nobody had confirmed a single ride. Somehow, I began to worry.

I zoomed through the chic FlightCar website, obsessively looking for assurances. Instead I found that, since my car was older than 2008, I would make barely $50 from the service. This whole thing was destined to cost me, not help me. I tried to back out, but steep fares at LAX barred me in. I had made my bed, and now I had to drive to San Francisco to lie in it.

The morning of my trip, I made a couple frantic verbal agreements and, around noon, sped off to meet whatever passengers I'd been able to dupe into joining me.

Solomon was a UC Berkeley student headed back to school after a weekend home. A half-hour later we picked up Iris, who explained that she'd swapped out the name she'd been given in China for an American one inspired by her favorite Goo Goo Dolls song. I helped her load a heavy suitcase into my tiny trunk. “It's my birthday today!” she remarked. Suddenly I felt responsible for something.

What is it like driving eight hours with strangers? We were barely out of L.A. before Solomon fell asleep. Iris, conscious if directly behind me (it took me six hours to figure out what she looked like) seemed to abhor China. “Do not go to China … so boring.” The Asiaphile in me was crushed.

When we arrived, Solomon allowed me to charge my phone at the dorm front desk while Iris and I got birthday ice cream. Though I thought I'd never see these two again, I got a quick tour of Berkeley and now had a place to stay in Beijing. We felt like we'd emerged from the ashes — and accomplished something great together. (When you lack a car charger, everything is harrowing.)

My AirBnB couch, tucked inside an apartment in the luxurious Domain Oakland complex, was a good value at $35 a night, though my beautiful, tattooed hosts wanted out of the business. Apparently they'd had so much success hosting strangers in their home that they quit their “real” jobs, only to realize, just as I had, that ambition breeds alarming difficulty.

“So much laundry!” one of them yelled from the next room. I imagined her drowning in a quicksand of linens, the ladder that once beckoned her crumbling into bedsheets.

See also: I Live in My Office

Early the next morning, I arrived at the FlightCar parking lot in the quiet predawn dark. Floodlights illuminated the lot while a small office offered free water and coffee. The little operation felt like a relief tent at a refugee camp. I stepped into a slick black town car with another FlightCar patron, giving him a brotherly, knowing look just like, I imagine, any other secret society member might. Finally, things felt like they were on track.

In D.C. the days went by idyllically — I spent most of my time trying not to worry about my car. Every once in a while, though, I received an email letting me know it had been rented. I was proud but pictured my bumper scraping cement at every incline, the scene from Ferris Bueller's Day Off on repeat for a month and a half.

I'd already been feeling like a neglectful parent when I got the following message: “I regret to inform you that one of our renters experienced a flat tire in your vehicle. Everyone is OK. … He proceeded to keep driving, damaging the wheel.”

Oh good, everyone's OK. That's what I was worried about.

I returned to FlightCar's San Francisco lot in the harsh, sunny afternoon. Guys with clipboards were swarming around, swapping keys, making notes on the cars. Every employee seemed to exude the same energy as the company's teenage founders. They made sure my car got fixed, hooked me up with a new wheel, and gave me the $10-per-day price, plus an extra $10 here because they didn't get to wash the car, an extra $20 there because it wasn't ready in time. They kept throwing money at me.

To my surprise, the cherries aligned. My dream-world calculations were off by $112 but in the right direction. In the end, my journey netted me a new wheel, a few days of sightseeing, and $100 round-trip airfare to Washington, D.C.

Well, perhaps. My little car had 1,900 more miles on it than when I dropped it off. Those miles meant dollars — and I still had to drive back to L.A. “We tried to keep it to 900,” said the exuberant little clipboard guy, “but people really wanted this one.”

I looked at my dingy upholstery and the car's modest L.A. dents, a little confused. “Good gas mileage,” he explained.

Then I understood.

We're all trying to keep our expenses low: me, the other renters, even the startups. It's easy to save money by booking the cheapest fare, but we wanted something more: We wanted novel, challenging experiences.

That's what these companies provide, and it's what they're chasing after, too. Like me, startups like FlightCar, Zimride and AirBnB are attempting crazy schemes in the service of a simple idea. And based on my trip, I've learned that it's not easy to make things easier.

Which is why, personally, I'm rooting for FlightCar to make it to Los Angeles. Somehow I did.

Benjamin Caro (bencaro.com) is a filmmaker and health and travel writer from Washington, D.C. He loves L.A. but inexplicably wishes more things here were made out of bricks.

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