Why Upwork Is the Sleeper Long of 2025
When ChatGPT and all these LLMs started hitting the market hard, a lot of people (myself included) thought Upwork and Fiverr were toast.
I figured—who needs to hire a freelancer when you’ve got an AI that can design logos, write blog posts, and build websites in seconds?
But something funny happened. It turns out all these AI tools didn’t kill freelance platforms—they amplified them.
Let me explain.
For years, people like me have had ideas bouncing around in our heads. Maybe it's a new business concept, a browser extension, a tool, whatever. But more often than not, that’s where it ended. The idea stayed stuck up there because I couldn’t visualize the design or break down the steps. I’d get excited, hit a wall, and move on to the next half-baked idea.
Now? It’s different.
LLMs like ChatGPT finally give idealists like me the missing piece. I can work through my thoughts, ask questions, flesh it out, and in a matter of minutes, I’ve got a rough concept. From there, I pop into Upwork.
They’ve even made that easier too. You can literally type something like “I want to hire a designer to mock up a dashboard for a trading tool” in 150 characters and their AI bot spins up a job post for you. You hit publish, and boom—freelancers start applying within minutes.
I used to maybe hire on Upwork once or twice a year. Now? I’ve hired people more times in the past few months than the last five years combined.
I've spun up 4 or 5 different businesses. A couple are looking promising, others won’t make it. But that’s the point—ChatGPT made the front-end brainstorming faster, and Upwork gave me the backend horsepower to actually build something.
You can see this shift in Upwork’s latest earnings call too. Demand is coming back. More builders are hiring. The platform is sticky again.
This is why I believe Upwork is the biggest sleeper long of 2025.
The LLM boom isn’t their death sentence—it’s their revival.
$UPWK's closing price of today is $17.35. See you in a year!
*This is not financial advice, no shit right?
📩 Enter your email so we can catch up in a year on how this turned out!
PS: Join 100,000+ traders who start their mornings with this FREE, must-read newsletter.