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How it Started 

When I first thought of launching a boat business it was pretty random.  It sounded like a unique way to break away from the corporate-tech hold in San Francisco -- the opposite of a desk job.  I remember hiking the narrows in Zion National Park and thinking that I wanted to pursue a job where I could be outside and engaged with nature.  

I was working at the non profit Kiva.org leading their US program at the time and I got to work with a ton of entrepreneurs in the 5 years I was there.  I knew that starting a business was something I always wanted to do, so I started actively planning my next play.  

Lying on the couch in a quasi-therapy session I started pitching Julia (my now fiance) on business ideas.  There were a lot of bad ones and Julia was quick to shoot down every idea until I threw out the idea of becoming a boat captain.  She didn't shoot that one down -- so that's what I went with.  

I started to do my research by calling boat charter companies around the country.  Other charter captains liberally shared their advice, and the deeper I got the more hooked I became.  So I took the first step -- I bought a 12' jon boat to test the waters.

(that's my little blue boat, Kirby, there in front of all the white sail boats) 

I loved my 12 foot, flat bottomed, way too tiny boat.  It couldn't really handle the waters in the San Francisco Bay (if you went out with me you experienced that first hand).  It was almost laughable but I loved it.  It didn't take long before I was 100% locked on the idea.  I started by saving money, writing a business plan, and continuing to develop relationships with other boat captains.  

Memories & Connections 

San Francisco is a beautiful city, with access to so many amazing things. I loved my time there, but the intensity of tech and its influences on the city didn't always vibe with me.  I felt a lack of connection -- phones and apps and equity and money and more and more and more of that.  

When I was out on the boat people stopped checking their phones.  We had real conversations that were authentic.   There was a true sense of presence.  

It's the water... the ocean has a force that impacts us in a profound way.  It forces us out of the day to day mindset, it allows for reflection and perspective. This tiny boat created a unique outlet for me to connect with my friends.  Every boat trip turned into a memory that I cherished (shout out to all the OG homies who got to see it first hand!).   

I became obsessed with the concept of memories.  That was at the core of the business I wanted to start.  Creating authentic connections amongst friends and family -- and memories that would last forever.  That's the driving force for me -- my why.  

Starting the Business 

In January 2017 I finally made the jump.  Packed up my stuff and moved to San Diego on the pursuit of this crazy adventure (thanks for coming with me Julia).  

 

With some savings, a small loan (thanks mom and dad!), and a $27,000 campaign on Indiegogo.  I purchased my boat, got my captains license, and turned this into my full time job....

.....and the first year was super super hard.  The struggle was real.

 

I was lonely -- in a new city where I didn't know anyone, I was spending all my weekends and holidays focused on charters, and I didn't have a team of people to celebrate or commiserate with.  I was in way over my head -- when things on my boat broke I was lost and I didn't know where to turn.  I spent (and wasted) a ton of money on maintenance and marketing because it was all brand new to me.  The learning curve was steep and it was an intense mental and financial crash course into entrepreneurship.  My cash reserve was draining and I was about ready to quit.  

The silver lining was that I was getting traction and finding customers.  I got good at learning AdWords and ​I spent a ton of time optimizing my brand to get traction on different online platforms (e.g. making friends with the team at GetMyBoat).  I developed some good content and I was figuring out how to consistently deliver an amazing experience that people loved. 

Sonny to the Rescue 

Across the dock, was my friend Sonny, who ran his own fishing charter business.  We would hang out after a day of charters and shoot the shit.  It didn't take long for us to realize that we had a strong complimentary skill set. 

 

Sonny knew boats and was able to diagnose and fix problems super quickly and super cheaply which was something I was in desperate need of.  I was getting a lot of traction with marketing and was looking for another captain / boat to give my overflow to.  We were both really good with people. 

Sonny had come in and filled the two main gaps of my business.  I now had someone on my team that knew exactly what was up and I had a maintenance guy that could help with mechanical issues.  I had a guy I could throw business to and someone that would help me expand my brand.  Boom.  

Expanding the Network

Over time I naturally came into contact with other boat captains that had cool stuff going on.  I had a bunch of requests that I wasn't able to fulfill -- so I went out and partnered with boats that offered new, cool experiences that would compliment the existing fleet I had.  

For example, I used to only be able to cater to groups up to 12.  Now I've partnered with boats that can fit up to 40 people.  I didn't really have any realistic option of getting to Catalina or Ensanada for weekend trips but I partnered with a boat that regularly provides weekender packages and he has a big kitchen and a bunch of beds -- super tight!  I partnered with a one of a kind 55' sailing yacht that's truly a one of a kind experience.  

I've established a strong network and community here -- top notch people.  I want to provide a clean, safe, and fun experience every time -- and I've partnered with the best boats and captains in San Diego. I pride myself on having 150+ 5 star reviews (with zero reviews less than 5 stars).  

If you have any questions about my story or want to chat you can hit me up anytime at 619-629-5017 or justin@chillcharters.com.  I hope that I'll be able to hook you up with memories that will last forever. 

 

Jah Bless.