12/6/24
I started Chill Charters with this. Goodbye and thank you.
Today was the day to deliver Chill Charters to her peaceful deathbed.
It started with annual bookkeeping day. Line by line, tracking every penny that moved through my bank account, credit card statement, and venmo accounts in 2024. After seven years I’ve developed a slow, steady, stoned, and INTENSELY focused approach to bookkeeping.
The truth is, I really enjoy the bookkeeping function.
And I’ve gotten better and better at it over the years. In 2024 we had 312 transactions and $385,000 in total money movement, with an average transaction of $915. It’s a delicate dance of “be as close to 100% accurate as possible” because one mistake is expensive. Over the past seven years, we’ve seen a couple thousand transactions and a couple million in money movement. I would guess that over that span I’m at 96.9% accuracy on bookkeeping.
It’s a skill that I take pride in.
These are the truths that few others see. These are the skills you develop in secret. Entrepreneurship is full of secret dens of skill building.
And these skills translate in weird ways. Freakishly organized bookkeeping has had a major influence on my email inbox at Wefunder. And in how I track my personal finances. And probably contributes to having a squeaky clean kitchen, my first task of every day.
This is the nuanced beauty of entreprenurship. It’s shaped who I am, inside and outside of work.
I’m going to miss it. And I’m also glad to move on.
The truth is that Chill Charters became about pragmatic money. It’s a cash cow. And it doesn’t require a huge amount of time or effort. You’d be stupid to not do it.
At least for a while.
2019-2022 were insane years. I didn’t do anything proactive and we were seeing huge growth every year. It was too easy, and it was bringing in meaningful profit. It truly was a sick side hustle.
But then in 2023 revenue dropped 50%. And then in 2024 revenue dropped another 50%. Why? GetMyBoat and Boatsetter dried up.
They were the lifeline. If GetMyBoat and Boatsetter was hot — Chill Charters was hot. If they dried up — Chill Charters dies. They dried up.
Demand in San Diego wasn’t there, and supply exploded. I had dozens of competitors that came in hustling. I was going to have to hustle.
I dipped my toes in the water. I invested in a new website and spent $15k in an agency to help drive revenue. But I learned a very important lesson, and I learned it quickly.
“Results depend on how much effort and time you put into it.”
“You can’t delegate to an agency and be hands off.”
“If this was going to work, you have to lead the charge.”
The honest answer was that I didn’t want to put in the time and effort. Passive hustle or bust. Bust.
Because Chill Charters became about money. It lacked meaning. Money without meaning is a stupid thing to put time and effort into. The juice was not worth the squeeze.
My love for boats imploded quickly (“origin story”). Progressively, boats inspired negative emotions. My love for boats was dissolved as quickly as I developed my love for them. A truth bomb.
And there’s immense pride and joy. I do not write this with a heavy heart. I write this inspired and grateful and with shameless authenticity. Chill Charters changed me, and I believe those changes were intensely positive. I learned so much.
I hold onto hundreds of memories that I shared with everyone important to me in life. In my eyes, everyone I care about has a connection to the story of Chill Charters. Mission accomplished.
Last weekend I took Julia on a cruise around San Diego Bay. I left with a happiness that I haven’t felt in a long time. I’m going out again this afternoon with my dad, and I’m looking forward to it. I’m giving myself a window of opportunity to fall in love with it again. A “circle of life” moment — a curiosity similar to what I had in 2016. The gift of her death.
Beautiful.
