Kriti Mehrotra
Despite being someone who is deeply devoted to his family and his job, Greg Whittier found himself struggling with setting boundaries to ensure he actually has time for things he is passionate about. Known as Red Beard owing to the way he has built a life on a boat, the maritime maintenance man had dreams of setting up his own business, but was procrastinating with the paperwork when we first met him. That’s where the Fab Five came into the picture, to help him recognize that there is always time for things he is ambitious about and loves if he just recognizes that his dreams are not selfish at all.
Greg Whittier is a Self-Taught Maritime Professional
It was back around the mid-2000s when Greg Whittier came to Washington, DC, as a young 20-something-year-old with dreams of leading a life full of adventure, joy, and spontaneity. Therefore, when he found the love of his life in Aubrey Andre and realized she shared a similar outlook on life, they began building towards a future that served both of them. They struggled to find a home owing to financial constraints, though, which is when the latter suggested that maybe they should just live aboard a boat as it would be cheaper and more fun. Greg loved the idea, resulting in them making the S/V Tenalach their home.
Greg and Aubrey took only a few sailing lessons before they moved aboard their 2-bed, 2-bath boat, after which the former began learning everything there is to know about it. Little did either of them know that he would eventually become the go-to maritime maintenance man for the entire dock and earn the nickname Red Beard owing to his newfound life as a sailor. We say newfound because he was previously a manager at a local restaurant. Then, he served as a nurse for a while before trying to establish a career in the IT industry, only to later shift gears and evolve into a bartender. However, things changed when Greg and Aubrey welcomed their daughter Rue into the world because the father realized that he wanted to be able to spend time with his family.
Greg couldn’t do that if he was working till 4 am closing time every day, so he earned his license and joined a local contracting/maintenance company. Unfortunately, over the past few years, despite his devotion to his family, their love for cooking together, and the unwavering love they shared, he couldn’t make enough time for them. That’s because he had issues switching off because he remained on call all the time, and he didn’t know how to say no. Moreover, it led him to procrastinate his dreams of establishing his own business, Red Beard Marina Maintenance, so as to ensure he could juggle every aspect of his life before retiring for good by the age of 50. He had logged enough hours to earn his Captain’s license and had the tools to start his company, but he continued to procrastinate on the paperwork for it because the desire to do and be something more felt selfish to him.
Greg Whittier is Gradually Working Towards His Dreams
At 40, Greg continues to live aboard his boat with the two people he loves most in the world: his loving wife and lacrosse coach, Aubrey, and their 8-year-old daughter, Rue. We should mention that the couple tied the knot for the first time on August 15, 2015, in a beautiful ceremony in Washington, DC, before having two more weddings – one in Vegas and one in a bowling alley in Pennsylvania. Since then, they have led a happy, healthy life aboard their beloved boat, which they have poured even more love into after Jeremiah transformed it into a truly functional, safe space for them all. Their garden is thriving too, enabling them to continue thriving as vegans.
On an individual level, while Greg continues to cuss like a sailor and serve as a maritime maintenance professional, he has been taking better care of himself and has learned to separate work from family time. “I’ve been much better about setting boundaries and being more intentional with how I spend my time,” Greg told Netflix’s Tudum in a candid January 2026 interview. He added that saying no to his nautical neighbors when he needed a break was difficult at first because of how grateful he was to them for helping him get to where he is, but he learned to do so because he knew it was important. As for his Red Beard Marina Maintenance business, he has earned his Captain’s license and filed for an LLC, but “it’s in progress and moving forward.” So now, his focus is on renovating the family sailboat even more so that it satisfies all their needs. “We did add a new dodger, which has been a solid improvement.”
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