top of page

This Looks Weird

In my five years at Kiva I met with and spoke to a ton of entrepreneurs. As I knew this business was on the horizon, I became even more tuned into the trends of their stories and advice. There was always one common theme -- their success lied in their ability to keep going -- in their ability to overcome obstacles -- in their ability to not give up.

Easy enough. There will be obstacles, I will overcome those obstacles, I will not give up and I will keep going.

As with so many things -- it's drastically different in theory than in practice. Understanding it in theory was easy. Understanding it in practice is hard. Really hard.

Let's take the last week for example:

I ran my numbers. I burned through $5,000 in March. More than twice what I had budgeted for. I need to get customers! Still waiting for my federal background check. Can't submit my paperwork to the Coast Guard until I have that. Once I do have all of that, it'll be another 4-12 weeks (that range seems ridiculous to me) for the Coast Guard to approve my credentials and send me my Captain's License. Doh! I invited a guy out to do drone photography on my boat. It didn't work and we crashed the drone which ended up slashing my seat cushion. That's another $250. Shit. This is a money drain! I need customers ASAP. Do I break the rules? Maybe go start marketing? No. Stay patient. But I'm running out of money! Too many random expenditures! No -- if I break the rules it'll all be over for me. But the chances of getting caught are slim to none! I should do it the right way. MVP this thing! Wait! Can't forget about these other million things over here that I'm getting distracted from! What do I prioritize -- so many things!

A snapshot into my mind. I feel like this guy:

It's not one obstacle here and there.

These are weird obstacles that are nuanced and complicated. They have different implications. They are stacked on each other, they can compound one another, yet they are separate and distinct. I'm seeing each of these for the first time and having to prioritize and figure it out. Seemingly, each one is more expensive and time consuming than I want. They pop up randomly and every week is a new series of challenges. The reality is that these hurdles are constant and manifest in all kinds of situations.

What's the hurdle I'm working on now? Managing my mind.


I went out on the boat for 5 hours yesterday, alone. I was able to catch up with a few close friends. It was super hot out. I took a cat nap while anchored in the little cove off Shelter Island. I went out into the open ocean. The Mexican islands off the coast were in clear sight. Again -- it was legit hot out and I was shirtless (hot, right?). I was jamming to music and having the time of my life. In that moment I was truly present and filled with conviction.

It's all good. This is why I'm doing this.

Patience in the macro. Hustle in the micro. Take time to enjoy it. Learn as much as possible and embrace the risk and the challenges I'm facing.

Easier said than done. I'm doing my best to get it done.

bottom of page