The flight from Austin to Guadalajara was uneventful. The Uber ride from the airport to our Airbnb was not.

After we landed and collected our bags in the Guadalajara airport, I called the Uber. As the driver loaded our bags into the car, his face tensed. Under his breath, he muttered, “Pretend we’re friends.”

Before I could ask him what he meant, a cop from the Guardia Civil sidled up to the car. The Guardia Civil, a federal law enforcement agency in Mexico, is known for enforcing customs and airport rules with an authoritative presence. As we sat in the backseat, another officer joined, and they asked the driver for his license and registration.

This is when the stakes became clear: Ubers are banned from the airport. Apparently, the airport and taxi companies don’t want competition cutting into their profits, so Uber pickups are strictly forbidden. The driver knew it, the police knew it, and yet he decided to push back. Hard.

“This is unconstitutional!” he declared, pulling out documents from his glove box like a lawyer on a procedural. He claimed to be in law school and waved papers around to support his argument. But the officers weren’t impressed. Their expressions barely changed as they listened to him rant about personal sovereignty and rights. Their patience, however, was wearing thin.

The standoff escalated. Officers trickled in one by one, until four of them stood around the car, arms folded, faces inscrutable. A police cruiser pulled in front to block us, in case the driver tried to make a run for it. At this point, Sarah and I were in the backseat, trying to figure out the driver’s endgame.

One officer turned to me and asked, “Is this guy your friend?” Following the driver’s instructions, I nodded. “Yes.”

Another officer then asked, “Do you speak Spanish?”

Dear reader, I do speak Spanish. But in that moment, I decided it was best not to. The last thing I wanted was to be dragged deeper into this standoff. “No,” I replied.

Luckily, this redirected the officers’ focus back to the driver, who had by now opened a live-streaming app to document the encounter. Every few minutes, he’d announce, “My rights are being violated,” while filming the officers. That’s when I realized his strategy: he was filibustering—stalling in the hope that something more pressing would pull the officers away.

After an eternity, one officer finally turned to us again. She typed something into Google Translate and handed over her phone: “We will escort you to a taxi stand and cover the fare as a courtesy.”

Forty-five minutes after we’d gotten into the Uber, I wasn’t about to argue. We got out of the car, and the officer personally escorted us to the taxi stand. She spent another ten minutes making sure the taxi driver understood: Do not charge them. She even typed it into Google Translate again for us: “NO MONEY.”

The taxi ride was smooth. I chatted with the driver about restaurants and life in Guadalajara, relieved that things were finally calming down.

When we arrived at our destination and started unloading our bags, the taxi driver turned to me. “So, how do you want to pay?”

Of course he did.

I replied firmly, “No estamos pagando! We’re not paying. The police said the ride was covered.”

He wasn’t having it. “How do you want to pay?” he repeated. What followed was a five-minute argument in the middle of the street. I’d just endured a constitutional law debate for nearly an hour—I wasn’t about to back down now.

The driver called his boss, who insisted I was supposed to pay despite what the Guardia Civil had said. He was pissed. But I stood my ground, and eventually, the driver gave up. He took out his phone to snap a photo of us—I guess they have a wall of shame for non-paying customers back at the dispatch.

That’s when I knew everything would be fine. I gave my biggest eff-you smile and we walked away.

What I experienced is a perfect example of what entrepreneurs face every day: pick your battles. I’m sure I didn’t handle this situation perfectly. I’m not certain feigning ignorance of Spanish was a great move. My pushback against the taxi driver wasn’t exactly a model of rhetorical brilliance. But that’s the beauty of these moments—you don’t need to play a perfect game. You just need to give some thought to when you’ll get pushed and when you’ll push back. Remember that the next time entrenched interests start pressing down on you.​

Thanks to early readers: Charlie Becker

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P.S. I wrote today’s story using the SITO (“Speech In, Text Out”) approach to AI. Here’s a how-to guide if you want to use AI for better written storytelling.