From the Trenches

I am irrationally obsessed with the climb. The entrepreneur’s journey. The underdog. The grind. The comeback story. The struggle. Eric Thomas. Basically every rapper ever. The “take my last $5,000 to Vegas to make payroll to save my company and turn it into FedEx.” When Eminem gets on stage and rips the final rap battle.

It’s beyond obsession. I won’t even fill out March Madness brackets because in almost every case I’m rooting for the lower seed.

I can’t get enough of it. And that’s why we’re here. There are plenty of great stories recounting tales of the climb, but they’re almost always told after the fact.

The post-success story is never the same as the story from the trenches.

I have a story to tell, and the most fascinating part of this story is that it hasn’t happened yet. It’s happening right now. As we speak. A mix between the Never Ending Story and the Truman Show. It’s unfolding as we’re reading this, and we have no idea how it’s going to end.

I’m grinding behind the scenes on this healthcare product that I think can radically improve the health of our country. Or maybe just help a few dozen people become more self-aware. Who knows. We haven’t gotten to that chapter yet.

I’m helping another guy launch the startup he’s been dreaming about for years. Maybe it’ll be the next Seamless or maybe it won’t even get a single order. It’s too early to tell.

I’m working with another entrepreneur who thinks he’s going to bring humanity back into corporations. How fucking cool is that? He’s been grinding on this for 7 years. He’s starting to see some massive traction, and the business is about to take off. Or it’ll fizzle out into the nothingness of the startup graveyard. I hope it works. The world needs this.

I’m having intense conversations with my cofounder about the future. What if none of this works? What if we’re just wasting our time? When do we throw in the towel? These are all intriguing questions. He’s the most talented developer I know, and he and I have a lot more building to do together. I have to make sure we move past these very rational fears and stay in alignment.

I’m writing this at 1am on a Friday night of a holiday weekend after I was at the office past 1am the night before because that’s just what needs to be done.

I’m now living in a 3 bedroom apartment where I rent out the other two bedrooms on Airbnb to keep my personal burn rate at a minimum. Cash flow is king. Speaking of cash flow.

I’m also now the proud owner of $50,000 of personal debt. Didn’t see that one coming. This is the third time I’ve gone all in starting companies and chasing opportunities. Third time’s the charm, right?

This is my story.

The view from the trenches is so full of the unknown, and that’s why I love it. I’m going to document every step of the way. I’m giving you a front row seat to the action. Maybe the audience is just my future self five years from now, my grandchildren decades from now, fans who want to yell at Bastian and Truman or other people who love the climb as much as I do. Whoever it is, buckle up, because you’re in for one hell of a show.

It’s time to grind. Well, sleep first. Then grind.