“I used the same roadmap in creating Pink Diamond Yachts that I did creating Pink Limousine Service,” he said. “I started out with a concept, focused on the small details, and worked to provide an experience that was better than anyone else.”

His plan was simple with no shades of gray: He saw that there were dozens of limousine rental services in the Vancouver market using black and white colored vehicles. Even though he knew he was adding another similar service to the market, he also knew he could offer customers something different while standing out from the competition by painting his fleet hot pink.

“I literally went to Toys R Us, bought a Barbie doll, took the box to the paint shop and said, ‘paint it this color’,” he recalled.

With the help of a friend in the business giving him a crash course in the chauffeuring industry, Hoy launched the business in 2005 with a six-passenger limousine he bought from the Vancouver airport for $6,000.

Hoy drove the business forward for six years, his clientele ranging from locals and tourists to high-profile figures like Boy George, Sean Penn, and Pamela Anderson.

“It marketed itself,” he said. As the sole limousine service painting the streets of Vancouver pink, getting more eyes on his business was as easy as a Sunday drive. “If anyone who saw my fleet Googled “pink limousine” then my business would top the search results.”

The business shifted into higher gears at a steady rate, allowing him to upgrade to larger vehicles and purchase new vehicles. Unfortunately, the industry became saturated. Undercutting by his competitors, combined with rising operational costs like fuel and maintenance expenses, made it difficult for him to retain a healthy profit.

Hoy said he tossed away the keys to Pink Limousine in 2011 and used the sale of the company to fund his next venture… at sea.

Setting A Course For Something New

“Before the Pink Limousines, among other gigs, I was a part-time bartender for Vancouver Cruises,” he said. “During one of the cruises, the captain invited me into the wheelhouse to steer the vessel. With my hands around this big wheel, it’s hard to describe how it felt to be in control of a giant object carrying 400 people. Bartending was a job, not my career; getting behind the wheel of the ship is what sparked my interest.”

Still fondly holding the memory of his first time standing behind the wheel of a ship, Hoy decided to invest his money in his dream of becoming a commercial ship captain. He enrolled at BCIT when he was 26 and entered into a curriculum loaded with diverse coursework.

“To be a commercial ship captain, I need to have a degree in meteorology. I needed to become a paramedic. I had to go to the Justice Institute Fire Division and train alongside the Vancouver Fire Department,” he said.

From learning how to read paper charts to learning how to communicate in Morse Code, Hoy enjoyed studying in a modular environment that had him doing simulator training one month and chart work the next.

He also needed to get his certification as a marine engineer, a task he approached in a rather non traditional manner.

“I didn’t go to school for marine engineering; I was self-taught with help from a friend who was an engineer in the Navy,” he said.

Hoy boldly challenged the Transport Canada exams which included 50 multiple choice questions and an oral interview with a TC examiner that could last anywhere from 30 minutes to three hours depending on how much they wanted to test the applicant’s knowledge. This tough certification has a high failure rate, causing many applicants to take the test twice or more.

He passed it on his first try.

Hoy worked in nearly every sector of the industry, bouncing around from marine industrial construction, cargo ships, and ferries to private or chartered yachts and sunset dinner sailings with Vancouver Cruises among others.

Until the waves in his personal life sent him into a capsize.

Smooth Sailing On Rough & Risky Waters

“Two years ago at Christmas, I had a devastating break-up,” he said. “I ended up moving to the Caribbean for five months to put the pieces of myself back together.” Hoy’s sister and her husband owned an Italian restaurant on the shores of Anguilla. He hadn’t seen her in four years – and hadn’t even met his new brother-in-law – so he treated the trip as an opportunity to clear his head.

“I was wondering what to do with my life,” he recalled. “I had been working on and off for other people for a while and I wanted to work for myself again. That’s where Pink Diamond Yacht Charters came to be. Pink had been my brand for years and it treated me well, so I stuck with the name.”

There are a few key differences between Pink Limousine Service and Pink Diamond Yacht Charters. First, the thirteen yachts in his fleet, ranging in size from 42’- 88’, are not pink. The business is very much seasonal; while chauffeuring is a year-round business, Pink Diamond Yachts has to pay a full year of operating expenses with only six-months of revenue. Even starting the company in 2021 when Canada was still under significant COVID-19 restrictions, Hoy found success.

“We were the right size to operate during COVID,” he said. “There were limited activities you could do in a small group and ours was one of them.

Restrictions rarely impeded the business; it actually ended up being the perfect time to launch this business.”

Call it luck or call it fate, Hoy believes he’s always at the right place, at the right time, and knows the right people. He recently nabbed two of only nine moorage slips at the exclusive Westin Bayshore Hotel, which usually has a four-to-five year wait list. His optimism and positivity surely don’t hurt his odds either; whenever the chances he takes doesn’t pay off, he shakes it off.

“I go with the flow and things work out. I don’t push back; if something’s not going the way I want, I find another way to do it. I’m used to the stress at this point; I’m like the frog that’s been in the pot too long so the heat is different for me than someone else.”

Hoy is certainly the captain of his own destiny, cruising tourists and billionaires alike around Vancouver. Bold and lighthearted not unlike the color pink, Ryan Hoy is a vibrant example of what it means to be a Swagger Self-Made Man.

Pink Diamond Advice for Young Entrepreneurs

If you could go back and give your past self advice for running Pink Limousines, what would it be?

In the beginning, I definitely spent too much money on unnecessary marketing and ad campaigns for the limousine company. I realized that simply driving the vehicles around the city and handing out business cards to people who requested them was the most effective way to generate new business for my company. Once I noticed what a valuable marketing tool the vehicles themselves were, I installed huge hot pink decals of my logo, website and phone number on the tops of all the vehicles. You couldn’t see them from street level but they were visible from apartment buildings and office towers.

I got a lot of business this way and it cost me almost nothing. Do things differently than everyone else… Think outside the box!

Many of your crew members have decades more experience captaining ships than you do. What advice do you have for a young entrepreneur who works with more seasoned professionals?

Whether you work with someone from another generation or if you assume that they’re not “with the times”, you still need to listen carefully to their opinions and advice. A lot of what they have to say is applicable in one way or another. Remember, you can’t teach experience; you have to earn it. Also, everyone has an off day now and then. Any time I need to provide constructive criticism, I always do so delicately and with respect because, in many cases, my team is more experienced than myself.

The first time you stood behind a ship’s wheel, you knew you wanted to be a captain. When a young professional feels similar, strong emotions towards a new line of work, how can they tell the difference between the excitement of something new and the realization that it's their calling?

I think they’ll know deep down if it’s the right path for them. When I was in control of that ship, I knew right away that this is what I wanted to do. No question about it.

Do you have any funny stories about some of your high-profile clients that you can discreetly share?

I had a client book one of our largest and most expensive yachts for the day with some friends and a beautiful young lady friend of his. The following week, I saw the same client again, however, he was with a different woman who turned out to be his wife. She had booked the very same yacht one week later. As he was coming up the ramp, we recognized each other and I noticed the look of sheer terror and panic in his eyes. We had chatted for a while during the previous cruise so I’m sure he was thinking I would say nice to see you again or welcome back. Thinking on my toes, I said to him and his wife, “Hi, my name is Ryan and I’ll be your captain today”. After departure, he came upstairs to see me, handed me a very generous tip, and thanked me for my discretion. In this business, discretion is key. People are going to do what they’re going to do anyways but if you show them that they can trust you and rely on you, you will have a client for life.