I’ll Fund a Startup n00b But Here’s How Not to Look Like One

Years ago, I got invited by Steven Messer to join him and his co-founder (and brother-in-law) Tad Martin, two very successful NYC founders, out on a bike ride up the West Side Highway and up 9W over the Palisades. It’s a pretty standard route for hundreds of experienced road cyclists every weekend morning.

This is before I ever did a triathlon and before I ever even had a proper road bike. I had an aluminum commuter bike and I’m pretty sure I was wearing jean shorts at the time. I’m not going to argue whether or not jean shorts were ever in fashion, at that time or at any other time, but I’ll at least concede that they weren’t appropriate cycling gear for a 60mi ride with experienced riders.

But how was I to know? I didn’t have any friends that were into this kind of cycling at the time—and for whatever reason it’s something that people in their 20’s really don’t do that often. Maybe it’s because they’re not making enough money to fall down the rabbit hole of expensive carbon fiber road bikes and all the various gear that you can end up purchasing. Whatever the reason, I had no one who could warn me about how goofy I was about to look.

To my credit, I did actually keep up with those guys on the way up—but on the way back I just let them go ahead, leaving me to amble home, sweaty, sore and very uncomfortable (Read more...)