$10k/mo On The Side — Sharing What You Already Know

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Hugo Ortega

If you’ve ever thought about traveling the world while getting paid (and mingling with the rich and famous on the side), Hugo Ortega’s side hustle story may appeal to you.

After spending 9 years working as a yacht crew member and captain, traveling to over 60 countries, the former engineer decided to turn his niche career experience into a fast-growing online course business—Superyacht Sunday School.

Now, it has grown into a full-time business earning $10K/month.

(Sign up for Hugo’s free superyacht training here!)

Tune into Episode 602 of The Side Hustle Show to learn how to:

  • build your audience with free valuable content
  • turn followers into email subscribers
  • boost sales through live virtual trainings and webinars
  • monetize your expertise with courses, one-on-one mentoring, and memberships


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A Stumble into Yachting

Hugo didn’t grow up dreaming of working on boats. In fact, he admitted he couldn’t even swim when he first discovered the yachting industry.

It happened by chance while he was backpacking through Southeast Asia and met someone working as a yacht crew member. The more he learned about the job and lifestyle, the more appealing it became—especially the opportunity to get paid to travel the world.

As Hugo shared, “It’s really common for people to have envy towards your job and ask you, ‘How did you get into it?'” He was constantly fielding these kinds of questions from others interested in breaking into yachting.

Hugo thought nothing of it at first. He’d explain the basics of getting started, certifications needed, tips on finding jobs, etc. But then he started to notice a trend of people attempting to work online and leverage their existing skills and knowledge.

That’s when the light bulb went on for Hugo. He thought, “Maybe there’s something I can do on the side.”

Starting Small as a Service Provider

In late 2022, Hugo began putting together some basic resources to help aspiring yacht crew members. This included PDF guides on how to create an effective CV/resume, a list of top crew recruitment agencies, and checklists outlining the steps to get started.

To get things going, Hugo turned to Facebook groups related to yachting and began engaging with the community, answering common questions, and adding value wherever he could.

Anytime someone asked a common question, Hugo made sure to answer it thoroughly. At the end, he’d say something like “If you want more resources on this topic, I’ve got a great guide here,” and include a link to opt-in to his email list. He also uses the software ManyChat to automate his audience engagement.

This was the “free upfront, paid content later” type of funnel. By offering valuable free content, Hugo could gain trust, expand his email list, and prepare for future paid offers.

Pretty soon Hugo had his first $299 sale for a basic package that included a 1-hour phone consultation and those same PDF guides he had offered as opt-in incentives. It was a simple proof of concept, but it showed there was real revenue potential.

Building the Signature Course Offering

Bit by bit, the email list began to grow. He uses a visual email builder called Flodesk for a more expensive/luxurious feel, as he claims.

He then constantly paid attention to which lead magnets were getting the most downloads, which content resonated best through open rates, and what people’s most burning questions were.

The current main offering from Super Yacht Sunday School is priced at either $997 for full upfront payment, or $99 per month for 12 months.

But as Hugo explained, “But if you go through the webinar sequence and funnel, that’s when I offer it pretty much at a 50% discount.” So students can get the full course for either $499 upfront or $99 per month for 6 months only.

Using a limited-time discount required Hugo to adopt some new software to handle the “open/close cart” expiration timing. That’s where the Deadline Funnel tool came into play to enforce that scarcity.

The tool that really helped open the revenue floodgates? Switching from a pre-recorded evergreen webinar to live weekly training sessions.

Hugo said this single shift doubled his webinar conversion rates. Now, instead of people watching a pre-recorded pitch at their leisure, they had to show up at a designated date and time for Hugo’s real-time training session.

By adding some artificial scarcity and demand, it created better shows, more engagement, and ultimately more course sales.

Short-Form Videos for Marketing

Hugo cited cheap or free marketing strategies as critical to his exponential revenue growth in 2024. That includes organic traffic through short-form videos on Instagram and TikTok.

The videos follow a similar pattern of catchy one-line hooks followed by simple cuts of life on a superyacht.

Some examples:

  • “This is how much money you can make working as a yacht crew.”
  • “Here’s how much a superyacht captain makes per year.”

His best performing video with over 1 million views and counting is a short clip of Hugo on a yacht posing in different crew positions with text displaying those jobs’ earning potential.


How much do yacht crew actaully make? #salery #howmuch #crewtraining #superyachts #fyp #yachties #belowdeck #industry #luxury

♬ Summer day – TimTaj

Short videos under 15 seconds seem to be the sweet spot for engagement and views according to Hugo. The videos are designed to attract eyeballs to his free lead magnets and eventually to his paid training offers.

On the SEO front, Hugo has started expanding into long-form blog content as well. This involves taking some of his popular Instagram posts and spinning them into deeper “how-to” style articles to build his website’s authority and search rankings.

Of course, these blog posts include opt-in offers and calls to action to join Hugo’s email list and get more free training from him.

And as an advanced tactic, Hugo has started experimenting with paid Facebook ads, specifically targeting members of big yachting enthusiast groups on Facebook.

He uses a tool called LeadEnforce that can combine the audiences of up to 10 separate Facebook groups into a custom list to upload to Facebook for ad targeting.

Though he admits these are still cold audiences compared to his existing email list and followers, Hugo says he’s acquiring new leads through Facebook ads for $1-$1.25 each, which seems promising so far.

User-Generated Content, Influencers, and Continuity Programs

Beyond his organic and paid marketing efforts, Hugo has found ways to leverage other people’s audiences and influence too.

For one, he’s been working to build partnerships with cast members of the popular TV show Below Deck featuring real-life superyacht crews and owners.

Below Deck

The goal is to have these influencers co-host trainings and events to cross-promote and tap into their large followings on social media (which can exceed 1 million fans in some cases).

Hugo is also starting to source user-generated content from his successful students to build social proof and case studies. The plan is to leverage these stories and transformations in an upcoming podcast currently in the works.

Another new frontier for Super Yacht Sunday School is creating paid continuity/membership programs to serve existing industry professionals.

Currently in a testing phase with a small group paying $59 per month, Hugo envisions building out more advanced crew training and development resources on an ongoing basis.

The tech tool he’s using for the community and course aspects of this premium membership is Hearbeat.chat.

Beyond just helping people get their first yacht crew job, this program would serve as a lead nurturing channel to continue advancing their skills and knowledge over time.

Branching into Other Revenue Streams

The online education piece was just the start for Hugo. Given his extensive industry expertise and connections, it was a natural pivot to also offer staffing and recruitment services for yacht owners.

Through some nice positioning and branding, Hugo started getting inquiries from yacht owners looking for crew. And as he explained, “Every time you place crew onto a yacht, as long as they stay at least 3 months, you get 1 month’s salary paid out also to you.”

Now Hugo has another income stream by placing his own students on crews after certifying them through his training programs.

Unforgettable Experiences as Yacht Crew

One of the perks of working in yachting is getting to meet ultra-wealthy individuals and occasional celebrities like Jon Bon Jovi, George Lucas, and Pharrell. Though the “star factor” wears off as it becomes your everyday life and work environment.

Hugo claims that celebrities are actually more down-to-earth than you’d expect when on vacation.

He also had his share of wild experiences like getting caught in powerful storms during Atlantic crossings where the entire boat felt like it was going to capsize.

The luxury yachting world is full of surprises, but owners can simply postpone trips if conditions look too risky since they have the flexibility that cargo ships don’t.

What’s Next for Hugo?

Looking into the future, Hugo sees other opportunities to further modernize and innovate in the yachting industry through tech products and services:

“I feel like there’s a lot of antiquated practices, even with recruiting, where it’s just people emailing each other and saving PDFs,” Hugo said. “I want to automate and show that a small online entrepreneur can really take this by storm and make it better.”

Sounds like there’s potential for Hugo to develop some sort of “Upwork for yacht crews” style recruitment platform or marketplace.

Hugo’s #1 Tip for Side Hustle Nation

“Just don’t give up.”

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

Usually Hustling, Occasionally Social

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