The bike gang in front of the Pacific Ocean (from left: myself, Roman, Richard)

Starting a company is like riding a bike

Life lessons I learned riding a bicycle across the United States

I don’t mean that once you learn how to do it the first time, you never forget how it’s done. Maybe it is, I don’t know — that’s a question for another entrepreneur. But my experience of riding a bike is different than most peoples. A couple years ago I joined a college buddy of mine on a bicycle trip across the United States. As a couple of fresh-out-of-college-twenty-somethings, the thought of spending a few months traveling across the country on a bicycle was the most enthralling experience we could think up. In the months leading up to securing my diploma and hitting the road, this adventure was all I could think about. I kept imagining the complete freedom and the awe-inspiring adventure that was ahead of us, and I couldn’t wait to hit the road. As I would soon discover, our trip was an incredible and formative experience, but it was far from easy. And our first day was downright terrifying.

Had my friend, Richard and I been experts on bicycle maintenance and competitive cyclists, our lives might have been a little easier. As it turns out, we were neither of those things. As Richard and I stared out over the Chesapeake Bay on the morning of the first day of our trip, we were both less than mediocre bicycle mechanics and not in terribly good shape — far from the spandex wearing, competitive cyclists that would usually embark on a trip like this. (Richard’s entire training regimen had consisted of an 8-mile round trip to Bojangles a couple days before our trip). Nevertheless we dipped our back tires in the Atlantic Ocean and took off, Richard on a hand-me-down mountain bike with fat, 2-inch wide tires and myself on an old 12-speed road bike from the 1980’s.

We had a beautiful morning riding along the coast, hitting up the historic town of Williamsburg on the way, and making it about 40 miles inland before disaster struck. It was late in the afternoon on the first day, when Richard’s back tire burst, and we found ourselves immobilized on the side of the road. (Hint: If you plan on riding a bicycle across a continent, it’s definitely in your best interest to learn how to fix a flat tire). Not having followed this advice ourselves, we would just have to figure it out then and there. After a couple minutes of finagling, Richard discovered that he had accidently bought the wrong size tube for his tire. The only spare tube that we had would simply not work. We were stuck on a backcountry road in the middle of nowhere and about 10 miles away from the closest campground.

So we decided to hitchhike. The closest bicycle shop was located in Richmond, Virginia, about 30 miles away. We ditched the bikes in some brush on the side of the road and waited about 45 minutes before we were able to score a ride into town. It started to rain as we rode in the back of a pickup truck and headed into downtown Richmond. After getting dropped off, we rushed to the bike shop to get a new tube (as well as some quick lessons on how to actually replace the tube), and made plans to get back to the bikes. After hopping on and off of a couple buses, and getting yelled at by an impatient bus driver, we called a taxi.

It was just getting dark as we got back to the bikes. We rolled the bikes out of the bushes, fixed the back tire, and hit the road. At this point it was pretty clear that this trip wasn’t going to be easy — but hey, at least it wasn’t boring.

With 10 easy miles to go, and having just overcome the stress of hitchhiking, we rolled down the road in no particular hurry. As I tried to put the stress of the last couple hours behind me, my mind started to wander. I started to think about the giant meal we would fix for ourselves once we got to the campsite, and the simple pleasure of taking a shower after spending all day in the hot August sun.

We were about a mile down the road when Richard’s tire blew. Again. Our first day definitely wasn’t turning out as planned. Not to worry though, we had made sure to buy a spare at the bike shop to avoid any future disasters. Having gone through the motions just 10 minutes before, he quickly made the repair we started back at it again.

The carefree journey through the Virginian backcountry that I had imagined earlier that morning wasn’t matching up very well with reality. Nevertheless we kept going. I made up my mind early on that no matter how tough it got, I wasn’t going to quit. We were making it to California.

It wasn’t 5 minutes later when I heard some angry yelling over my shoulder. I turned around, and Richards tire had gone flat. Again! We would figure out a couple days later that there was a problem with the lining on the rim of his back wheel that was causing all of these flats. But in that moment we had no idea what was going on, and we were in trouble. We didn’t have any more spare tubes to repair his flat and we were still about 8 miles away from the campsite. We were on a country road in the middle of nowhere, surrounded by trees, and it was now completely dark. We were starving, thirsty, and tired, and we had no idea what to do.

After spending a few minutes deciding on a plan of action, with more anger and frustration being generated than good ideas, our luck finally changed. A nice local guy in a pickup truck passed by and asked if we were alright. After a quick explanation of our situation he offered to give us a ride. We loaded up the bikes and rode over to the campground, having narrowly escaped disaster. I distinctly remember going to bed that night, staring up at my tent, and wondering how on earth we were going to make it to California if we barely made it through the first day. I felt like we were completely unprepared to accomplish the feat we had set out upon. I had no idea how tough this journey would be when I had started just 12 hours earlier.

As fate would have it, we did make it to California. About 3 months later we rolled over the Golden Gate Bridge and into San Francisco. We even did a little extra and spent some time riding down the Californian coast, going through Big Sur and Half Moon Bay.

At times, starting a company is like that first day of our long bicycle journey. It will challenge you more than ever. It’s tougher than you ever thought it would be when you started. It will require you to be immensely resourceful — like building makeshift bike parts out of a tree branch resourceful (that’s another story). But at the end of the day it’s an incredibly rewarding experience, and it’s a journey that’s worth taking.