Tee up I Feel Fine by the Beatles.
This song always gives me a smile, it's a melting pot of emotions.
On one hand it's an awesome song. Very light, very fun. For that reason it was the song I started all charters with. The kickoff to the Chill Charters experience. To this day, I wouldn't pick any other song to represent the vibe of Chill Charters. It's the song you want to listen to on a boat with friends. It set the mood in a wonderful way.
On the other hand, I WAS NOT FINE. As I reflect back on the two years running Chill Charters full time, it was by far the most challenging time period in my life emotionally. I felt I was breaking down. I had no confidence. I felt lost.
So whenever this song would come on -- it would be this weird mix of -- this is the perfect vibe -- and -- I DON'T Feel Fine.
Chill Charters
It's funny how memories and storytelling works. You capture these snapshot moments and string them together. The story of Chill Charters feels like a picture book. Inflection points over years. Hindsight makes this easier, as I can pinpoint those momentum or directional moments -- frequently having no idea what was happening in the moment -- but their significance shows with time and perspective.
This story is still evolving today. There's been a big development in the works since I started my sabbatical and it's starting to show some real promise. My confidence in Chill Charters is at an all time high. I'm very proud of how the story has developed. With each year, the success of Chill Charters grows. With each year it gets easier, things flow, stress goes down, and I can more easily figure it all out. Each year my relationship with Chill Charters evolves, and the story evolves. It's dope.
And a massive nod to my best homie and business partner Sonny. This story would be very different without Sonny. Without Sonny, Chill Charters would have died in 2017. Sonny saved my business.
And business is so much more fun with a great partner. Finding a great business partner is extremely hard, and involves a healthy dose of luck. Sonny was a drop of luck that blossomed into a friendship and partnership I'll appreciate for the rest of my life. Mad love to the homie.
::
Chill Charters started in the Narrows of Zion. It was a Wednesday. I got a notification on my phone at 11:50 for our weekly team meeting. I told myself -- I need to do something in nature -- I can't work in an office in front of a computer every day. I need to try something different.
I think I would have always wondered "What If" if I didn't try to break away from the day to day office life after that experience.
I think I have a more mature perspective of this concept now, which is to have a job that allows for a lot of time flexibility (better results = more flexibility). That flexibility allows for more free time to be in nature.
I have a fond memory sitting in my apartment in San Francisco, it was as if I was talking to a shrink. Julia is sitting in a chair, as I lay on the couch pondering life.
"What does a job in nature look like? What about selling corn on the beach?"
Julia was not amused by many of my ideas.
In her words, this couch therapy session led her to (justifiably) question things with us. "Who am I dating?!?!"
"What if I became a boat captain?" - Me
"That could work" - Julia
Alrighty -- let's start there.
I think maybe I should have taken a bit more time in the brainstorming process, but as soon as Julia didn't immediately shoot down the boat idea, I started down the wormhole, and it was a very addictive wormhole. Maybe it was just meant to be.
I jumped on Craigslist and found a boat partnership for $1,000, and that week I became a part owner of a sailboat in Fort Mason. The terms of the engagement were that he would take me out sailing three times a month. I also got a marina access card to hang out on the boat.
I loved being out on the boat, but the dynamics of sailing were complex. I didn't appreciate the craft of all the ropes and knots and "work". I just wanted to chill. I ended up spending a ton of time chilling at the boat when it was docked at the marina. There was a Safeway across the street and I was spending most of my afternoons getting a 6 pack and drinking beers with a friend until sunset. I didn't even need to go out on the water. Being on the boat was all I needed for fun.
This was a really good call. Super small buy in, tease it out, see if I like it, see how I engage with it. My interest in the concept was exploding, which led me further down the wormhole.
On a random Saturday in April 2016, I was camping at Kirby Cove (the coolest campground), while very high on acid, sitting on the beach with the homies. A very tiny boat pulls up onto the beach. I think to myself "I could probably afford a boat like that".
That Sunday I went on Craigslist and found a boat being sold in Sausalito for $800.
I called the marina and they had a slip for me.
I drove to Sausalito with $800 and got myself my first boat. I named her Kirby.
Another sick power play. Another nod to good decisions with LSD.
On my maiden voyage from Sausalito to the Marina in SF the engine pooped out and I couldn't get it to work. I was floating without power in the middle of San Francisco Bay. I literally crashed into Alcatraz. I had to get towed into my new slip by the guy who sold me the boat. Awkward.
The next day I had to get myself a new motor, so I went to the boat store and purchased a new 35hp motor for $3,500. My little boat experiment just quadrupled in cost. But I was a man on a mission and at this point I was so excited that nothing was stopping me.
I get the new motor on my boat, and it causes my boat to heavily tilt in the water. I soon learned that my boat was rated for a max 10hp motor. The motor I purchased was way too heavy. No return policy, it was a used motor as soon as that bitch left the store.
Problem solving time.
Home Depot. Cinderblocks. I bought a ton of cinderblocks and put them in the front of my boat. Tilt problem solved.
If there was ever foreshadowing, this was it. I didn't know what the fuck I was doing and it showed. It was okay for a piece of shit $800 boat, but this same cycle repeated itself when I bought the big important business boat, and that's where serious problems came into play.
Despite the motor weight, cinderblocks, and lack of experience, it was smooth sailing for the next year. I loved that boat.
Multiple times a week I was going out with friends. It was sketch. It wasn't super safe. But it was so much fun. I felt so incredibly connected to the experience. I would motor under the GG Bridge and then float back with the current. A 90 minute excursion. Pure bliss. Lots of peaky afternoons. I was thriving.
I loved how disconnected people were with their jobs / emails / phones when they were on the boat. It was living in the moment. And at that time, being in tech in SF, the career / job / work energy was heavy. A true breath of fresh air to be out on the boat living in the moment. It was a drug.
I only have good memories of boats from that year in SF. If you want a true snapshot of what this all meant to me, check out the Chill Charters Indiegogo page. So idealistic and beautiful really.
Chill Charters spoiled my love of boats. Today I hate boats. I have a "for fun" boat right now that I haven't seen in 6 months. It's just like business and money and pride at this point. No joy or love for boats or being on the water in San Diego. Sad but honest. It was very much true for me that turning a passion into a business can spoil the passion.
The idea of starting my own boat charter business became an obsession. I started interviewing other boat charter captains. I started taking savings more seriously. I started writing a business plan. I was telling anyone and everyone about my grand aspirations. I was locked in. It was happening.
The planning period was roughly a year. What I recommend to all startup founders, go talk to other founders doing the same thing. Founders are generally very open, available, and willing to talk. They have insights, nuances, subtle hints of advice and wisdom that will help you in the planning. If I were starting a business today I would take this part of the planning far more seriously.
I moved to San Diego and the first 6 months of Chill Charters were planning. I needed to buy a boat, get my "ducks in a row", and get my captains license . A MIXED BAG.
I purchased my boat because it had a "brand new" motor installed. It was installed by some dudes who owned a car shop. They didn't know what they were doing. Everything else was old, rotten, and broken. But I didn't know any better. New motor seemed to be all that was needed for Kirby. But the bigger the boat, the more shit that can break. Very different with a 30 foot boat. Shit was breaking right out the gates. Big miss.
I really wish I would have paid a consultant to help me buy a boat. A boat guy who knew what they were doing. I suggest that to anyone I talk to who's considering buying a boat (after giving them the advice to not buy a boat). Sonny would have been able to see through all that bullshit. I'm very lucky to have Sonny now. We've purchased multiple boats together and he has a great eye for what's important and what's not important. He also found my truck. Dude is a baller. He will join the story soon.
My ducks in a row involved the LLC, taxes, and all the legal setup for a new business. At the time I was trying to be super frugal. I went to the local law school to have them help me get my LLC incorporation. I tried doing it myself with LegalZoom and TurboTax. Ended up being a total shit show.
I really wish I would have also paid someone to do this part of the business for me. That would have made my life so much easier. To this day, the entirety of the legal "ducks in a row" pieces to my business are all over the board. I don't know what's happening and it's a shit show. It's going to be a big investment of time and money to untangle the whole thing and actually go legit -- which is that thing on my to do list that I'm dreading. It would have been so much easier and worth every penny to pay someone who knew what they were doing to do all the legal / tax / "ducks in a row" work. That'd be my first investment if I started a new business. Don't cheap out on that stuff. Don't try and do it yourself. Hire someone.
Getting my captain's license was pretty chill. I have fond memories of those two weeks. I stuck out like a sore thumb. In a room with 20 salty boat guys, and I'm fresh out of tech with virtually zero boat experience. "Talking shop" was a disaster for me.
“Oh, knots, huh? Alright! Welp, see ya later!”
The best part about captains school was the school part. I was always good at school, always had good grades, knew how, when, and where to cut corners and still get As. These salty boat guys were not good at school, and my guess is that many of them were boat guys for that reason.
The mapping exercises were a big part of the curriculum. We'd have these 3'x3' maps of Chesapeake Bay and have questions like, you wanna go from this point to this point with current and wind of this strength and direction. Then you'd physically map it and answer questions along the way. Now this type of stuff has no relevance in practice. You have technology that gives you all this stuff and more. It's completely pointless. The boat guys hated it. I loved it.
Tee up Una Mattina by Ludovico Einaudi.
I crushed mapping excercises to this song. It was like a scene out of a Beautiful Mind as I worked my way through the mazes of Chesspeake Bay. Piano music blasting, I am slaying.
Everyone hated me. I had no business being there. I loved it.
One minor (major) detail I overlooked in getting my captain's license -- you needed 365 "eligible" days at sea to qualify for a captains license. I had a grand total of one eligible day. The day I drove my boat from Oceanside to San Diego Bay -- a very fun and memorable day -- I hired a captain to come with me because I was scared shitless. I ended up lying and forging 364 eligible days and I'm thankful it all worked out.
You also needed a clean drug test. I quit smoking weed for three weeks. Passed the drug test. Then celebrated by getting very high. Then I realized I had taken my drug test at a facility that was not recognized by the Coast Guard. Then quit for five days. Bought myself some take home drug tests. Passed. Then went to a recognized facility. Passed.
Slowly but surely. On my way to the promise land.
Marching to the beat of my own drum. No regrets.
I was official. Had my captains license in hand. The legal stuff was more or less okay at that moment. I had a boat, which mostly worked. Good enough to start booking some charters. I spun my wheels on the marketing front. I tried a bunch of stuff. The vast majority of that stuff didn't work. Some stuff did work.
Before I go into a laundry list of random wins and losses I did on the marketing front, there was really only a need for three things. A basic website. Good photos. LOTS of reviews. That's it. Website and photos are a checklist thing. You do it once and you do it well. Then you just focus 100% of your time on reviews. Hindsight is 20/20 and I don't regret anything I did to try and earn business, but if I had exclusively focused on reviews I would have gotten to the promised land with less emotional bruises.
The decision to join Business Networking International (BNI) was the decision that got me the closest I've ever come to killing myself. The basic premise was showing up every Wednesday at 7 AM to network with a bunch of losers committed to cycling referrals and business within the group. It's good in theory, but in practice it was soul sucking. BNI killed my spirit. I almost quit Chill Charters because of how much I hated BNI. It actually accounted for a decent number of charters early on, but I was surrounded by people I hated. This isn't what being an entrepreneur looked like to me. I wasn't willing to accept that. I did BNI for maybe 4 months and it was the worst marketing thing I did -- mostly because of the impact on my spirit.
Craigslist. If a website could be your friend, Craigslist would be my best friend. The joy of a free listing on Craigslist and having those charters roll in. EASY MONEY. Let's go. I actually got my first charter from Craigslist. It was a family and they just wanted to hug the coastline and wave to people. They had the time of their life, a very memorable moment from the early days.
Hanging out on the sidewalk in Seaport Village (the main tourist strip in San Diego) with a huge banner. I was handing out flyers and playing The Beatles. I got a grand total of zero charters after two days of testing that one out. NO THANK YOU! That was brutal on the spirit too. Never doing anything like that ever again.
I worked really hard to get a ton of Trip Advisor reviews. Trip Advisor is great for SEO and brought about a decent number of new trips. If I were to put any extra effort into marketing now (I don't need to and that feels good) it would be 100% focused on engagement with existing clients to drive repeat business and reviews on Trip Advisor and Google. That's the best and highest leverage tactic for organic growth.
AirBnb experiences -- garbage. I actually got a ton of charters from Airbnb experiences, but I had to drop my price to an extreme level (making $135 out the door on a 90 minute sunset cruise was barely cutting it, even when I was desperate). Worst part about Airbnb experiences though -- boring clients, a bunch of couples on a budget. It's like getting kicked in the nuts three times. You lower your price to get business, and the business you get is boring couples, then you don't get tipped. HAWT - gar-bage.
GetMyBoat -- the Airbnb of Boats. Thanks to a very fortuitous mutual friend (shout out Mike Cusenza, my guy) I became buddies with the COO of GetMyBoat ( shout out to Brian, my guy). I became their poster child for the first couple years as we were both building (now we're both chilling). To this day, GetMyBoat has accounted for over 70% of the 1,100 charters I've done (repeat clients being the other ~30%).
Once GetMyBoat started crushing bookings, I killed all marketing activity and went all in with GetMyBoat. GetMyBoat was my golden ticket.
Good listing. Good photos. Good placement. Lots of reviews. Business drives business. Cash money. The key was time efficiency. All my time was spent responding to inquiries. No prospecting, just intake. No more wheel spinning. A complete game changer.
In that first season I wasn't crushing it -- but I was getting trips and things were starting to click on the marketing front. I had charters every weekend and I was making money.
But my boat was breaking -- all the time. I was a few months into the business, after two years of planning and preparation. I had ~3 breakdowns mid charter that required a tow. I had to cancel ~5 charters because the boat wouldn't start. I had another ~5 charters that I barely made it through with issues happening mid charter. It was taking a serious toll on me. I remember moments where I had panic attacks, I remember crying, I remember being at the brink of throwing in the towel. Completely deflating.
My boat was a piece of shit. I had no knack for how to fix stuff when it broke. I was getting burned constantly by mechanics (a good boat mechanic is very hard to find). It was a different issue every week.
I had never felt that level of hopelessness. I didn't think it was something I could overcome. It just felt like it was an inevitable death, this was going to kill Chill Charters. To date, that was the hardest challenge I've faced professionally. My dreams crashing down around me. Feeling helpless on how to prevent it.
One random day in August 2017 Sonny and I pulled into our slips at our marina at the same time. His boat was covered in blood from a full day of fishing. My boat had 6 hot girls on a bachelorette party cruise. Good conversation starters, on both ends.
He wanted to know how he could get in on these bachelorette charters.
I wanted to know how to fix my boat.
Well how about I put your boat on my website? I'll book you bachelorette parties.
And in exchange you fix my boat when it breaks.
Cofounder was what I needed. I had a knack for branding and marketing and computers. Sonny knew boats. That was my golden ticket. You do boats, I'll get trips. We'll build it together. Pretty dope that I got a best friend out of it too.
From my perspective, the rest is history. Five years and six boats later, we're cruising. That was the inflection point. This is the moment that Chill Charters went from inevitable failure to success. One key person at the right time can make a big difference.
Chill Charters became stronger with each charter. Fast forward 6 years and 1,000+ charters -- I'm now an established and reputable player in San Diego, purely based on a combination of consistency and longevity. That's a competitive advantage in itself. I've done 1,000 charters so I'm more trustworthy in the eyes of the world (unfairly, but in my favor).
The execution of a boat charter became boring pretty quickly. Too repetitive for me. I enjoyed the mix of people I got to interact with, but the same boat - party - cruise - chill - cycle lost its appeal. My love of boats was dying quickly.
The next inflection point came when I started booking charters, but not running them. Sonny's boat started to book more regularly, and I would take a small % of the revenue. It was easy money. "Who else wants charters?" I started lining up boats and at one point had 10 boats that I was marketing through GetMyBoat.
I would take a percentage of the revenue of anything I booked.
Leverage. The money:time ratio was incredible.
95% of the time of running a boat charter business was getting to the boat, getting it ready, running the trip, cleaning up, and getting home.
If you take that out of the equation you save yourself 95% of the time of running a boat charter business.
Well shit -- if my time just dropped from 100% to 5%, I have options with my time.
I was stoked to go get back into the tech grind (weird, but honest).
Distance makes the heart grow fonder.
A familiar and recurring topic.
Sonny was a stroke of luck, a gift from the universe. And I was creative and savvy in figuring out my role in the mix. The mark of an entrepreneur. To this day, this was the move I'm most proud of. This made Chill Charters a long term play.
When I started at Wefunder I was struggling to manage the boat business and the new job. Jonny told me I needed to prioritize Wefunder and figure it out. Sometimes the best advice is direct and simple. That was the advice I needed.
All these boat listings became incredibly complex and hard to orchestrate. Everyone had their own system, and I was trying to cater to everyone. It was a bitch to manage so the next move was to simplify.
My way or the highway. I laid down the hammer.
I ended up splitting from the vast majority of the people I was working with, but became incredibly time efficient. I went all in with the folks who rocked with my system. Sonny and I had it down.
I had one consistent process and system. Everyone working with me subscribed. Tighten the screws. Time efficiency and leverage.
I had GetMyBoat and repeat clients making up the entirety of my business.
I had one uniform process / system for booking charters and everyone was on the same page.
Rinse and repeat. Efficiency was the name of the game.
Over a few seasons, I had worked Chill Charters to a place where I could manage everything with this schedule:
Monday -- one hour, finances, payouts, weekend inquires and confirmations
Tuesday - Friday -- 15 minutes/day responding to inquires and sending confirmations
Cake.
This made Chill Charters very easy to sustain. This process took a few years to develop, but it was through a series of small tweaks and micro-efficiencies that I could get it to the streamlined operation I needed. That gave me the ability to go fully into other interests (primarily Wefunder).
By this point the love had been sucked out, but I had a nice cash cow that paid incredibly well given the time I put into it. Certainly not the idealistic outcome from the original vision of Chill Charters but a good outcome. I built something I'm super proud of.
The final chapter in the saga is one that's developed very recently. On the brink of my three month sabbatical I was fully out on Chill Charters. It's late in the season -- my intention was to end the season early, and focus on the book for the three month stretch. Pick it back up next season. No bookings, no business, no worries.
Earlier this year we hired Mark to be the captain of our pontoon boat. We've had to cycle through a number of captains over the years. More bad captains than good ones. A laundry list of issues and bullshit we've had to figure out. Boat people are a tricky bunch.
Mark was different. The best captain we've ever had, by far. He checks all the boxes.
What to do when you find someone like that? Reel em in. Make them family. I offered co-founder status to Mark.
His role in the mix -- do all the bookings from GetMyBoat and line up all the charters. So far so good, he's crushing it.
I had delegated out my final piece.
And we're all feasting.
Now I get to guide the ship, lead the troops, make sure everyone's on the same page. The fun macro vision leadership guy. That's the role everyone really wants to ultimately get to, right?
I'm excited for the future.