How Outlier is transforming freelance AI Trainer

Earning While Exploring: The Early Days

Zach grew up in Montreal, Canada, and after graduating from Herzing College with a degree in business, he jumped straight into the world of sales. He thrived there — helping companies grow revenue and lead high-performing teams. In early 2023, he took on a fully remote sales role at a startup, working directly with the co-founders to close deals and train their first sales team. It was fast-paced, hands-on, and a great learning experience.

But Zach had always been curious about the world. In 2024, he packed his bags and set out to explore Latin America, turning his remote job into an opportunity to live and work from places like Mexico, Colombia, and beyond. He kept crushing his sales goals, but also started to wonder: could there be a way to create even more flexibility and long-term freedom?

Discovering Outlier: A New Opportunity

Around mid-2024, Outlier reached out to Zach via LinkedIn. The opportunity sounded intriguing: train AI models, specifically in French, using his language and communication skills to help improve AI fluency and prompt responses.

He jumped in — and found the work unexpectedly fascinating. Curating training data, refining prompts, enhancing model accuracy — it was a completely different rhythm from sales, but it offered something he hadn’t felt in a while: creative autonomy. And better yet, it paid well.

For months, Zach balanced both roles: managing a startup’s sales engine by day, and training AI systems by night (or vice versa, depending on the time zone). He was earning consistently, traveling, and learning new skills across two completely different industries.

$42,000 Later: More Than Just Extra Income

Over the course of about a year, Zach earned over $42,000 USD from his freelance work with Outlier. But what mattered more than the number was the way he approached it.

Instead of absorbing the money into his monthly budget, Zach treated his freelance income as “opportunity capital.” He stored it in a high-interest savings account, untouched, while living off of his full-time salary. That separation gave him clarity. It wasn’t just money — it was a seed.

“I wasn’t just earning. I was building a foundation. Even if I didn’t know exactly what for, I wanted to be ready when the right idea came.”

From Freelancer to Airbnb Host

In early 2025, that idea became real. Zach used his freelance savings to purchase and launch his first Airbnb rental property.

He did everything himself — researching markets, handling logistics, furnishing the space, and crafting the perfect guest experience. It took patience, creativity, and risk — but it paid off.

Today, Zach’s Airbnb:

• Has over 50 five-star reviews
• Holds Superhost status
• Earns around $2,500 per month in passive income
• Is just the beginning — his second property launches soon

The transition was complete: Zach had gone from digital nomad with multiple jobs to business owner with sustainable, growing income.

From Gig Worker to Business Owner

Zach’s story is about more than making money online. It’s about rethinking how freelancers use their income.

Instead of burning out juggling gigs, he built a system that now pays him monthly — without having to trade his time for it. That’s the power of freelancing done right: using temporary work to create permanent freedom.

“I loved freelancing. But I didn’t want to do it forever. I wanted to use it to build something of my own. And now I have.”

The Shift: Trading Hours for Assets

Zach’s story is about more than just money — it’s about mindset. He stopped trading hours for dollars and started using his earnings to build something that pays him back, month after month.

And that’s the lesson for any freelancer: you don’t have to freelance forever.
You can build things that last. You can create systems. You can turn skill into ownership.

The Takeaway