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Steven started letsworkremotely in 2017. They detail the beginnings of their company in their Starter Story interview: 
Q: How did you get started on letsworkremotely?
This sounds terrible and I mostly accredit that to being a 19-year-old college kid, but I was bored and wanted a challenge.
Most of my summer at the time was wasted on video games, carbonation, and junk food. I wanted to do something that challenged me, be a good learning experience and hopefully make some money. After deleting all my games off my computer and phone, I fired up Google and got sucked into the wild world of making money online.
> Not all of your competitors are bad, everyone is just trying to make it out there in a competitive world. Instead of trying to steal value from each other, see if you can find ways to create value together. At the end of the day, it’s always about the community and your customers.
Some of the stuff I found was really interesting but generally, they fell into three categories: blogs, online stores, and online services. Most of them usually are a mix of two or three of those categories. Blogs are content and knowledge centers including YouTube channels, streaming or even an Instagram page.
They’ll likely make most of their money by gaining loyal followers that buy affiliate products you recommend/sponsor because you’re an influencer to them. Online stores sell products (software and physical) where you make yourself or resell from a supplier or dropshipping. Online services generally mean freelancing or employment where you trade your time and talent for money.
Being 19 at the time, my expertise and credibility are very close to 0. I wasn’t a guru or nearly entertaining enough to maintain a blog. Products seemed to take too long to develop and could easily be replicated. Freelancing sounded cool, but I really wanted to build something. However, freelancing was something I did in the past and I really enjoyed working with clients to solve problems, the autonomy and working from home. That’s when I really started to explore the world of remote working, freelancing and digital nomadism.
What I found out from my exploration was that there were two very distinct types of remote workers: those who actually work remotely and those who post pictures of their laptops and “work remotely” on the beach. The latter are usually “gurus” who sell you the idea of a lifestyle, make you pay hundreds or thousands of dollars so you can “work from home” and make 6 figures while you vacation in Sri Lanka.
Now I’m not saying that it’s not possible to do just that, but the reality of it is that for most people, that’s not what remote working is all about. There’s still plenty of real companies that are hiring great remote talent with all its other benefits. If you don’t believe me that remote work isn’t just about traveling to sandy beaches, then check out Buffer’s State of Remote Work 2018 Report. Or you can try bringing your laptop to the beach, it is NOT fun or productive.
Anyways, I researched the competitive landscape and there are two big categories: freelancing and employment. Freelancing is what most people end up associating with remote work. Platforms like Upwork, Freelance and to some extent Fivver have been great at helping those interested in freelancing make a career out of it. Despite how great freelancing can be, there are many downsides people don’t consider.
Most people don’t realize how much work it takes to land a client, chasing them down to pay you, unstable income flows and covering your own expenses. Doing the work is the easy part. Like the romanticized view of remote work, this lifestyle is not for everyone despite what your Instagram feed might say.
That’s why I ended up focusing on the latter, where the market has not been explored as much but is a growing category in the remote working world. Companies are beginning to build their workforce on a remote-first basis of implementing remote work as part of their culture.
Still, there are many implicit problems with traditional remote job boards that aren’t freelance focused. Many of them make remote job seekers pay a monthly fee to access the jobs, which I think is pretty ridiculous. That’s why the first promise I made to the groups was to make it free for job seekers. Another big problem is that most resumes get sent to the void and people have no idea who to reach if there are questions. letsworkremotely was born to create the best remote community to help connect the remote talent to remote opportunities from anywhere in the world.