How these 3 entrepreneurs made their first dollar online (and you can too)


It’s fairly easy to see how entrepreneurs make their money today: whether it’s through affiliate marketing or YouTube, their business models are often in plain sight. But what about how those same entrepreneurs made their first dollar online? How do we discover that?

As it turns out, the easiest way is to ask them, which is why Ladders asked three entrepreneurs to step into the archives and share how they made their first buck on the web.

In 10 words or less, how did you earn your first dollar online?

I got paid to surf the web in 1999.

Explain your first online venture in greater detail.

In 1999, my computer tech friend told me that I could get paid to surf the web. “No way!” I thought to myself. So I checked out this company, AllAdvantage, and signed up. AllAdvantage paid you to surf the web and shared revenue from the ads that you viewed.

This business model was cutting-edge in 1999. After weeks of web surfing, I received an actual check in the mail for $20 or so. I thought it was great. Then the company went bust. There were no advertisers to sign up to promote when the dot-com bubble happened in 2000. But what an experience!

What are you working on now?

Today, I’m a content creator for multiple brands I own and operate.

What’s the connection between the first dollar you made online and your current business?

I was a high school kid and was a part of a revenue-sharing deal. I didn’t know that term then — I only knew I was getting paid to surf the web — but that concept is still one of the ways I generate income today. Anytime you’re a part of an affiliate program (eg. the YouTube Partner Program), you get paid a percentage of the revenue for your activity. In 1999, I made money viewing ads, and in 2021 I create content that helps provide value and drive sales.

In 10 words or less, how did you earn your first dollar online?

Freelance copywriting.

Explain your first online venture in greater detail.

During my junior year in college, I went on a month-long study abroad trip to India. It was my first time traveling abroad, and after such an incredible experience, I knew I couldn’t stay in my university town. There were too many experiences out there for me.

I had no idea how I was going to make it work or what I was doing, but I stumbled across freelance copywriting and decided it was something I could do as someone who always had a knack for writing and sales.

From there, I did what any millennial trying to make it online does these days: I slapped “Freelance Copywriter” in my Instagram bio and started building my brand online. I transferred the remainder of my university courses online, packed my bags, and moved to Spain on my own.

I was pretty good at the whole Instagram marketing thing, fortunately, and quickly landed my first ever client, a $1,600 monthly retainer (who had no clue they were my first client). I managed to build a strong presence on Instagram, dominated all of the relevant copywriting and content writer hashtags, and developed an interesting enough blog to draw people in. It worked.

I operated with Beyoncé-level confidence and it paid off ten-fold. Anytime I received inquiries, I always went for new projects, even if I had no clue what I was doing. I figured everything out as I went along, learning the skills I needed along the way.

I got my start as a freelance copywriter and became highly sought after for those skills, but my hunger for knowledge led to me picking up many more skills, which is how I operate as a strategist and consultant today.

What are you working on now?

Today, I am a content marketing consultant to B2B SaaS companies, specializing in sales platforms and the tools that integrate with them.

What’s the connection between the first dollar you made online and your current business?

Copywriting and content writing introduced me to content marketing, which led to me gaining new skills in search engine optimization, public relations, and content strategy. Now, I consult with some of the fastest-growing B2B SaaS companies.

In 10 words or less, how did you earn your first dollar online?

I sold exercise gear on Amazon.

Explain your first online venture in greater detail.

After doing some research on private labeling, I dove into the world of creating, designing and building my own branded products. I worked with overseas manufacturers to create exercise accessories and grew a bestselling product line on Amazon.

What are you working on now?

Today, I run a consultancy for small businesses.

What’s the connection between the first dollar you made online and your current business?

My product line on Amazon eventually failed because competitors replicated my exact product and began competing on price. I learned the value of creating a unique selling proposition while trademarking and protecting the brand (and asset) you’re building for the long term.

My private label products also showed me the importance of building a powerful brand and a loyal customer base. Today, I help small businesses do the same thing.

In business as in life, there’s no perfect way to get started: the key is to throw a lot at the wall and see what sticks. These three entrepreneurs are perfect examples. Their early income streams did not stand the test of time, but the lessons they pulled from them did.

My story, of course, is largely the same. Today, I make money writing about investment newsletters and trading platforms, but it wasn’t always this way.

I got my start just like many others: finding and filling a gap in the market. In my case, it was buying iPhone cases on eBay and selling them on Etsy, textbook marketplace arbitrage. The lessons I learned from that experience have helped me to build a global team and recognize new market opportunities today.

Everyone starts from a different place, which is part of what makes the journey so exciting. Perhaps the grandest allure, though, is that you also don’t quite know where you’re going to end up in your career. And that, in the end, is a beautiful thing.

You May Also Like