The Real Money To Be Made Is In Sailing

Bobby White and his partner Laura have become quite well-known in these parts for their YouTube channel Sailing Doodles, the fourth most watch sailing vlog on YouTube.
But how did they become so popular, so fast?
Let’s start at the beginning. Bobby was born and raised in Dallas, Texas; a corporate pilot for two decades, he spent time overseas, including four years in Abuja, Nigeria, and another in Dubai but he had been back in Texas for five years flying Gulfstreams for a wealthy family to their vacation homes in the US and Caribbean when he suffered a stroke that ended his flying career.

One morning, in September 2015, Bobby woke up with a severe headache and took Ibuprofen, a blood thinner, not realizing he had a brain bleed going on. Picking up the phone to text his girlfriend at the time, Bobby realized he couldn’t read, so he knew something was very wrong, He was able to drive himself to an urgent-care facility, who rushed him to a hospital where he had a CAT scan and they realized he had suffered a Hemorrhagic stroke. He was soon put on a helicopter headed for a Dallas hospital that specializes in brain trauma. He spent eleven days in neuro ICU, undergoing three different procedures. The result was he lost his medical license to fly. By that time, Bobby figured he had flown 7,000 flight hours and approximately 2,000,000 nautical miles.

Bobby had to reteach himself how to read, and that took about two months. The first three months after post-stroke are extremely critical and patients need to be pro-active, otherwise they don’t recover much more after those first three months Bobby’s mother is a successful realtor, so he thought he would give that a whirl, but he lasted eight months. He hated it, “the most stressful job I ever had” he says.

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The Real Money To Be Made Is In Sailing

One day, Bobby was listening to the Sailing Podcast (no longer active) and Riley and Elayna from the Sailing Vagabonde were being interviewed (they had 100,000 YouTube subscribers at that time, now they have 570,000). Bobby had done some lake sailing and chartered boats in the Caribbean so he started following them. Bobby decided if the Sailing La Vagabonde folks could do it, so could he, so he sold everything he owned except for a few clothes and created Sailing Doodles, named after his two Labradoodles, Maverick and Goose.

He went to Houston and paid US$24,000 for a 37ft C & C (1984) and put another $4,000 into upgrading the boat. Within a month of buying her, he set sail with his friend Megan on Ruff Seas out of Galveston Bay and they sailed across the Gulf of Mexico in seven days to the Florida Keys. They then continued on through the Bahamas and into the US Virgin Islands.
“In hindsight, you don’t really know what you need in a cruising boat until you’ve gone cruising, Ruff Seas didn’t carry enough fuel or water, had a deep draft for its size — not suitable for the Bahamas — but it was a fast boat.”

Bobby’s goal with Sailing Doodles was just to offset expenses and the original plan was to sail around for a year and then sell the boat using the experience he had learned to get a job as crew on another boat.

He first met Laura, his Sailing Doodles partner, at a regatta in St Thomas in the US Virgin Islands. She was working there as a traveling nurse, and a mutual friend introduced them through Instagram. The irony being that Laura was an ICU nurse who took care of stroke patients; Laura was impressed that Bobby chose not to be sidelined by his injury, if anything it empowered him, so Laura decided to keep tabs on him.

Bobby sailed on Ruff Seas until June of 2017 when he left her in Puerto Rico as he took a job delivering a Lagoon 440 from St Maarten to Florida. He had his boat under contract to sell, and then the guy who was going to buy it backed out at the last minute. Hurricane Maria then ravaged Puerto Rico and damaged Ruff Seas, practically beyond repaid. Bobby ended up giving the boat away, as the mast was broken and she had considerable hull damage.


At this point Sailing Doodles was covering Bobby’s living expenses. He was posting once a week, and he was getting more and more comfortable with his sailing skills. But with Ruff Seas out of commission, Bobby didn’t have enough cash to buy another boat, so he thought about turning Sailing Doodles into a travel blog, and picked Thailand as his first destination.

He flew to Thailand in September of 2017, and one of his YouTube viewers said he should talk with Ron Patston of Gulf Charters. Bobby contacted Ron and asked if he could interview him and do a tour of his Island Spirit boat manufacturing company. The video received 50,000 views in the first days after it was posted, so an idea gestated; Gulf Charters had a boat sitting in Vancouver for three years that Ron was trying to get over to Thailand to put in his company’s charter fleet. Ron told Bobby the boat was his as long as he brought it to Ocean Marina by the end of August 2018.

Bobby jumped on the boat on October 27, 2017, it was a 50ft Beneteau called White Squall and it had just had an extensive refit. Laura had decided to join his journey five days before. Bobby left Comox on Vancouver Island on October 29th and picked up Laura in Bellingham, Washington, on November 2nd. Laura had become burnt out after doing relief work in the Caribbean after the hurricane season (the couple hadn’t seen each other since they first met in April though Bobby invited her to sail a few times). Laura had been nursing in Alaska but left to learn to sail and find a job in the Caribbean.

The original idea was that Laura was going to be Sailing Doodles crew for two months and then she would start nursing in Florida. Apparently, she had been looking for a guy who wanted to sail for a decade. Laura’s original leg of the journey was from Bellingham to Coos Bay Oregon, but she quickly became hooked and decided she wanted in for the long haul.

Sailing Doodles opened up the crossing to their viewers, they rented out cabins to them and they could sail with them for a set rate per night, which included their meals but they were expected to do night shifts and help with chores on the boat. This extra cash help cover things like marina fees. The most they had on board at one time was three other crew. When they first started cruising down the west coast of the US not many people wanted to join them, but once they got to La Paz, Mexico, interest picked up.

They did “Meet & Greets” along the way with fans and their subscribers would bring food, batteries, movies and hard drives, anything they thought would make their trip more comfortable and set them up for success.

The Real Money To Be Made Is In Sailing Terms

The stayed in Mexico for three months, Bobby’s dogs stayed with them during that time as they waited out the cyclone season. They set sail from Cabo St Lucas in Mexico for Hiva Oa in the Marquesas in French Polynesia on March 17, 2018, doing 2700nm in 17 days, with good wind almost all the way.

They spent a month traveling through French Polynesia and Gulf Charters helped them plan their route. They moved on to Tuamotu, Bora Bora, Niue, Tonga and then Fiji, where they spent a month. Bobby figures they spent a third of their journey at sea. After sailing to Vanuatu, they had a hard eight-day journey to Papua, New Guinea, with rough seas and rough wind all the way, the crossing was rougher than their 17-day sail from Mexico to Hiva Oa. Next, they sailed through the Strait of Torrez off the coast of northern Australia. They then spent a month traveling through Indonesia entering at Saumlaki in the south east and leaving at Belitung in the northwest. Their sailing schedule hinged on weather windows, so they did miss chances to explore many beautiful destinations.

Their Pacific crossing was relatively incident free when it came to boat maintenance. Their throttle cable broke in French Polynesia, so Ron sent them a new one. Things started to get tricky once they left Bali though, just as two Gulf charter students had jumped on board. Their autopilot failed and then their starter quit on the motor going into Singapore, so they sailed very slowly in pitch black across the Singapore Straits where Ron met them at One Degree 15 marina with a new autopilot and helped fix their motor. Ron then sailed back with them and another Gulf Charters student through Malaysia and into Ocean Marina. They arrived at August 31st at 1:45pm, making their deadline and they flew home on September 8th.
Their viewers, depending on their PATREON sponsorship, could track Sailing Doodles live through their Garmin tracker and even send them text messages, so people were giving them everything from cooking recipes to weather forecasts. Laura compared their followers to family, who wanted to help in any way they could to make sure they had a safe & successful delivery.

The Real Money To Be Made Is In Sailing Time

Thad Eacret was their longest crew mate as he was with them for a week in Mexico and stayed with them for almost three months all the way to Fiji. They only had problems with one crew mate, who sailed with them for 17 days from the US into Mexico.

Despite all their wonderful experiences and adventures there is one irony that lingers, most people go on this type of journey to get away from the trappings and technology of modern society. But Sailing Doodles was dependent on modern technology to fund their journey and it wasn’t easy, in the Marquesas, it took Bobby 17 hours to upload a video.

And the journey was hard work, not just the navigation, boat maintenance and dealing with the weather conditions but documenting the journey. For every hour of footage Bobby would shoot only two minutes of it would make it to the vlog and Bobby could spend up to six hours a day editing footage and then God knows how many hours trying to upload episodes, depending on their Internet connection. They did an episode on Sailing Doodles called “the business of vlogging” to give their subscribers an idea what they were up against.
Bobby and Laura have made quite a journey since they started as they now have 25 million views with an average of 100,000 views per video. They have the fourth most subscribers of any sailing vlog on YouTube.
Bobby can be reached via This email address is being protected from spambots. You need JavaScript enabled to view it. and you can follow Laura on her Instagram account @SailingDoodles.