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A Month of Marketing

Before anything -- I wanted to send another huge thank you to everyone who contributed to my crowdfunding campaign that ended exactly one month ago. That experience was nuts and I'm very thankful.

I'm going to spend the next hour barfing out all the random stuff that I've learned in my first month of proactive, on the ground marketing. It's probably going to be long and have little structure -- an accurate reflection of what my weeks look like right now.

Getting Content

I've done a lot of free boat rides for photography in an effort to drive content. One big learning is that more content isn't super helpful. Having the right content is important -- so now when I go out to collect content I have a very specific idea of the specific photo I need (a close up of my boat well positioned under the San Diego skyline --see below) or the specific type of people I need to get content of (families and kids). This will help as I start to test online marketing and create specifically tailored collateral. I realized I had over 100 photos but not one that was *the photo* -- so I went out and got it -- and I'm super stoked. One thing on my to-do list is to ensure that this is the first photo people see in all my online profiles (updating all that stuff is annoying!)

Get My Boat

Last week I was lucky to get a connection to someone at Get My Boat -- an online marketplace where people can rent boats. I worked with their team to optimize my listing with the right message, photos, and overall offering. I copied a bunch of stuff I liked from other listings and tried to really go above and beyond to position myself competitively. In less than a week I've already landed three charters and have two pending. It was a huge break -- I'm very excited about building the business through this channel.

There's 4 other platforms that do boat rentals but I haven't gotten one request yet. I'm building relationships at these companies and trying to leverage my listing so it's front of mind for the right people at those companies. It'll be interesting to see what % of business these marketplaces create for me.

My Favorite Story

Last week I went out to the tourist part of town and set up my big banner and tried to hustle down tourists. That was round three for me and it was wildly unsuccessful. Not only did it not work but I absolutely hated it. Approaching random people and selling on the spot is not my jam.

I hired someone on craigslist who came out to help me do it. The real reason was that I wanted to be held accountable to testing it out and actually execute. The universe handed me a total character who I've really loved working with. He pushed me to keep going when I was really over it....and then something magical happened...

Last Thursday, we walked past the ticket booth at the Hornblower (the mega-tourist boat tour of the bay) and I walked up to a family that was in line and asked if I could chat with them. They ended up ditching the Hornblower and paid me $350 for a private charter with their family. It was a huge win. It ignited something in me -- stealing business from "Goliath" has a lot of meaning. I'm going to keep doing that.

Craig is my dude and he's going to teach me the concierge game (one that most boat charter captains have had trouble cracking). I'm thankful that we crossed paths.

Google AdWords and Facebook Ads

I've been incredibly intimidated to jump into google/facebook advertising. I'm terrified I'm going to lose tons of money because I don't know what I'm doing. Luckily I know a couple people who are really really good at this stuff and I'm going to lean on them to show me the ropes. Tonight I'm meeting with a girl who is going to sit with me and and start some experiments -- that's going to be a big focus for me in the next couple months and I'm excited to see how to best leverage online marketing to drive business. This will be the most interesting thing to reflect on in a months time.

If I figure out this online thing I think it's going to be a massive win -- coupling the offline and online acquisition channels will give me a massive leg up on my competition.


I'm proud to announce that Craigslist has been my biggest driver of business. As a die hard fan of Craigslist I'm thankful for the free channel that brings the best of the best (craigslisters) as customers. Funny enough -- my craigslist customers have been some of my favorite.

Yelp and Trip Advisor

I've had about 25 people write reviews over the past couple of weeks but Yelp and Trip Advisor are consistently rejecting my reviews. It's incredibly frustrating because they are legitimate reviews (I'm not hitting up random friends). It's annoying but they make the rules and I play by them.

Everyone in this industry says they lean on Trip Advisor (I've heard as high as 80% of the revenue coming in) -- I badly want to leverage this to help me gain exposure but it's a slow game and it's going to take time. A review on Trip Advisor is my primary call to action for every successful charter.


I've met and started to build relationships with a number of small private BnB's around San Diego. I have my flyers there and have tried to start building the trust/relationship with the owners. It hasn't brought any business though -- not totally sure if this is going to be a good channel for me.

Offline Networking

I've invested a lot of time in this network called BNI (Business Networking International). They meet Tuesdays from 6:30-8:30 AM and it's a very tight operation. They take referrals super seriously and force ~5 hours a week of active networking, 1:1's, and homework. It's a very big time investment but I think it's going to give me a good ROI. They live by the idea of "givers gain" -- the more you give the more you get. At a high level (life level) this is a philosophy I 100% subscribe to. It's a good community.

I've also joined two spinoff networking groups with the same structure and style of BNI -- thats a much more passive commitment. We show up twice a month and talk business, connections, and opportunities. The networking that involved building relationships is something I'm good at and enjoy so this has been a nice way to stay productive.


With all this networking I've had so many ideas and thought partnership from random people. My list of ideas -- people to reach out to, platforms to get on, places to check out, ways to find customers -- is incredibly long right now. Having "too much" is a comfortable place for me -- 5 years of that at Kiva -- the days go by quick because you're always running. It's a good problem to have.

Need to be more strategic in how I spend my time which makes me very happy. I get to say no to certain ideas (yay!). As I start to see what's working I'm trying to carve out time to double down -- but still want to try new things -- and always want to be meeting people. I'm happy about it.


When I go 3, 4,5....days without business it starts to really grind on me. I start to feel the stress come up on day 3 and grow linearly until I book another charter and that's like the re-set button. It's stupid but it's how I actually feel.

I don't mind working the long hours and weekends -- I thought that would bother me more than it has. When I get those charters and when I'm making money and seeing the business in action it's incredibly motivating.

Yesterday I met with both a life coach and a business coach (through the BNI group). It forced me to take a step back and reflect and really helped me put all my worries in check. I need to be more explicit in forward in carving out time to take a step back. I think that's a very good investment and I'm going to start working that into my schedule more proactively.


I've taken big losses over the past 6 months. Looking at the money drain every month has been the most stressful thing -- it's painful.

I've had to be ruthless in cutting my personal costs which sucks but it's a short term sacrifice for a long term goal. A good challenge and learning which is the silver lining.

I'm really hoping that this whole money-stress-thing can be slowly phased out. It's the thing I dislike the most. July is looking like it could be a break even month -- which is a huge deal for me. To plug up the money drain -- or even tighten it a little bit -- is a big deal psychologically.

What's Next?

My 30th birthday is one month from yesterday (August 18th). My primary goal super early on (like 2015) up was to have this up and running by my 30th birthday -- and as I look at what I have at this moment I'm proud.

This has been a good week. I've booked over 10 charters in the past week. I'm hoping that I can keep a steady flow of business and shoot for a more consistent stream of charters coming in.

The way to get there is to keep going -- every day. Pushing myself outside of my comfort zone, try new strategies, doubling down on stuff that works, meeting more and more people, building my online profiles, getting the right content.....and about a million other things I have on my to-do list.

Will give another update in a month or so. Love yall homies.

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