Plain interesting businesses · · 5 min read

From Homeless as a Teenager to $500k/Year Charter Business

From Homeless as a Teenager to $500k/Year Charter Business
Please, introduce yourself and your business.

Hey my name is Todd and I am a serial entrepreneur.  I currently own 3 businesses, but the one I'll be speaking on is my catamaran day-charter company.

How did you start your business? 

When we moved from NYC to Puerto Rico it was really about finding something that would work for both me and my partner.  She is a 100-ton master captain and was very successful in the day charter market in NYC.  I just like to start companies and grow them. 

So I started to see what was possible around the area and discovered a unique opportunity within the San Juan area.  So we did some studies and drafted our plan, raised some money, and started our operation.

How much revenue was your best year? (include margin if possible)

For this one, we are now officially on year 2.  We started last year and in Q1 did $45k in revenue on our one catamaran.  This year in Q1, we are over $125k in revenue.  Our margin is about 50%. We just added a new vessel in March, so we are expecting to increase our revenue another 60% in Q2. 

When did you notice traction when building your business? The “Oh S**t!” moment, what did that feel like?

So, the niche we saw was the lack of an option for a 'higher-end' sailing experience in the bay of San Juan.  While there were multiple options on smaller sailing boats, there really wasn't anything that gave people room to lounge, move around, or have a party. 

What really gave us that "yea, we were right" feeling was when we had a meeting with the Ritz Carlton Reserve on the island and they said right away "we have been looking for an option like this for 5 years" and instantly signed a deal with us.  They are still one of largest revenue sources.

What was your childhood like? Were you slinging candy on the playground?

I was always interested in selling things. If I could find a way to make money, I would do it.  To me the process of how to improve something and make it better was always a fascinating concept since I was 12. 

Where it got dicey was when I was going into my senior year of high-school and I got thrown out of my house because I didn't want to be a pastor, but really wanted to go into business. 

So I got to enjoy my senior year of high-school sleeping in a parking garage and bouncing around to some friends' houses, walking to school every day, then going to work as a bus-boy at TGI Friday's and cashier at Giant Food Markets. I struggled with homelessness off and on for almost 4 years.

What has been your best marketing marketing channel?

Concierge was our first target, and has been our best target.  Now this year we are expanding to search ads, which has provided some really good traction.  We have done ads now for 2 months and have seen roughly a 350% return on investment.

How many attempts at building something did you make before you found what you’re working on now? Did you always have an entrepreneurial drive?

This is my 5th business (the other 2 I currently have 6 and 7).  I have been fortunate that only 1 of them has truly failed. 

Two of them sold for a small profit and one of them we couldn't sell, but was closed down for other reasons.  In all of them there were many lessons learned and I have used them for each future business.

What is your biggest overhead expense?

It is easily labor, followed by debt expenses.

What’s the most important skill you’ve learned?

Patience, Patience, Patience.  Almost never do you get some giant accomplishment right away.  It's a game of small but steady steps.  So when you are a year in, 2 years in, etc take a moment to look back and acknowledge the giant step you did throughout the year.

What do you spend the majority of your time doing, in a given week? (I think a lot of people hear entrepreneurs “work,” but may not understand what that means on a day-to-day basis.

A lot of my day is handling client needs.  I am currently better systematizing this so that I can hire someone to take this portion over.  After that, I really troubleshoot everything. 

For example, after this, I'll be going to the one catamaran this evening to install new controls and control lines.  I'm doing this so my staff can watch, engage, and learn how to do this process. 

What do you know now that you wish you knew when first starting your business?

I'm lucky with this one.  I believe my years of starting and building businesses has led me to really getting a firm grasp of understanding a market.  Honestly nothing has taken me by much surprise. 

I think the only answer I could give here would be hiring a specialist to help me navigate Puerto Rico's government rules sooner, but even then it really wasn't that big of an issue.

The world of entrepreneurship can be misleading. Many people think it’s always easy and always glamorous. What’s a big problem you’ve faced as a business owner and what were the emotions behind it?

Entrepreneurship is not for everyone.  This I cannot stress enough.  My partner is learning this the hard way.  I think the biggest thing that hits people in general, and it's one I am always reminded of daily is...the buck stops with you.  There is no one else you can blame, it is ALWAYS your fault.  Client is upset because of how something was handled? 

Your fault.  Missed something on a government form? Your fault.  I can go on and on.  THIS is by far the biggest hurdle for people, whether they realize it or not.  You are to blame for everything and that can get insanely exhausting for anyone.   

But the opposite is not always true.  If everything goes right, it's the team that succeeds.  If an employee gets a rave review, it's their win and they should be rewarded.  

Failure is on you, success is on your team.  Whether you want to admit it or not, you work for them, you build them, you push them to higher heights...and they will make sure that your clients are happy and take care of your bottom line.

Many people don’t know where to start in the business world, they feel stuck. They may want to start a business to become their  own boss and create their hours. What is your best advice for someone who feels completely stuck?

Stop overthinking it.  Build it, sell it, test it.  Even if you have to start small, get creative and ask yourself "what is the easiest way to test and see if my product/service is desired".  Then do that.

To see everything Todd is up to, follow him here:

www.bluedoubloon.com

https://www.instagram.com/blue.doubloon/