Some rides are perfect.Other rides are just good fodder for stories.A few years ago, I received a friendly email typed up from an enthusiastic 16 year old high schooler from San Francisco, interested in pursuing acceptance to Middlebury. Along with that, he was toying with the aggressive pursuit of a fledgling cycling career despite the winters Vermont has to offer. He seemed smart, he was already 3+ years ahead of me into his cycling career, and if I'm not mistaken he had already medalled at the world championships. Ladies and gentlemen, Zeke Mostov.Over the years he's graduated from the polite, nerdiness of a 16 year old, and turns out he shreds the bike. Bonus: he's a cool kid and good riding partner. I'm allowed to say kid because now three years later, he's now all of 19 years old. Being that he's currently home in the Bay area this semester, we've met up now and again to pedal our bicycles, chat life, and reminisce about rural Vermont.Fast forward to the more recent past, I set out yesterday without any real ride plan. Zeke drove to Marin and since I have zero structure in my bike riding these days, Zeke got to dictate the ride. We met up and he unfurled his very specific training for the day featuring "one to four hours with no real structure". Love it. Complimentary to that, he asked that we try riding new roads. Here's a kid who's lived in San Francisco and has been riding for probably a decade now looking to me, who's lived in Mill Valley for a full two weeks, for new roads.Strangely enough I could oblige. Mount Tam is literally in my backyard and after a few sinuous miles of pavement, we hit the trailhead and started our off road adventure. The road, err, trail snakes skyward eventually peaking out the saddle just beneath Mount Tam's East Peak via the Railroad Grade.However, we didn't quite make it to the summit. I was aboard the burly Cannondale Synapse and Zeke was on his... time trial bike. The Synapse is designed for this sort of ridiculousness. Zeke's time trial bike, umm, not so much, but where's the sense of adventure taking a time trial bike exclusively on pavement?! Don't forget, you can't spell pavement without pavé. Meanwhile, I'm running super sweet Zipp 30c tires which can shred this sort of terrain. But given that the only tube I could find was designed for 18/23c tubes... let's just say oops.Suffice it to say that my first flat was probably deserved after conking a rock at top speed. A speedy and scenic tube change and we were back up and running. It was around this point that Zeke pointed out, "Man, I hope we don't get another flat. I forgot my tubes in the car." Literally one single pedal stroke -- and one more sharp rock later -- I suffered a second flat.So I'm screwed, he's screwed if he gets his first flat. Thankfully I'm in my super comfy Giro shoes and extra convenient aero walkable Speedplay cleats, because right now I'm about to go for a long, craggy walk. I send Zeke on his merry way, because you're damned if you do and damned if you don't. I can't fix anything from here on out and he's up a creek if he gets a flat. After a quick powwow, it's decided that he'll ride down 20 minutes, then climb 30 minutes back to me to fetch and deliver his tube which as I've discussed is in his car.Five minutes later, I received the dubious text, "Yay I just flatted. I'm going to ride the flat to my car". I told him to go home, I'm a adult, I can survive the rest of this adventure.Turns out, people on Mount Tam are friendly, so after throwing my hitchhiking thumb into the air, it wasn't more than three cars that had passed, and conveniently, the first pickup truck that went by, when one stopped and the spandex clad Ted King hopped in. To the nearest bike shop, please!What's the moral of this story? Beats me. Maybe ride with the right size tubes, because if you think for an INSTANT that this will dissuade me from going offroad, you're crazy.