From a snow shipping service to name generators, here’s how one man from Boston makes a buck on the internet

I started developing my own websites when I was 14, in 2002. Without even realizing it, I was taking small steps building my first business. What started as a hobby, evolved into a cash generating website.

The product itself was fun to develop. I coded it in html and learned the most basic <?php switch statements ?>.

After a little while, my php skills evolved and I built one of the first “Pimp Name Generators”

The product was decently funny, my friends and I came up with about a fifty ridiculous ones. Luckily I don’t even remember one… but what really made the website stick out was an early social sharing mechanism.

When a user copied their name and pasted it into their AIM profile, it added a link to “Get your own pimp name” right below it.

O.G. K-factor

0–2 million visitors / month!

Essentially the same tactic Zynga skyrocketed Farmville in 2009.

Two years later, I ended up selling my very first business:PimpedMedia.comfor $10,000 to Eric Borgos — the founder of Bored.com.

I was 16!

“Started from the bottom now we here” — Drake

In the 12 years after the sale of my first business, I’ve ended up launching just shy of a dozen businesses with varying degrees of success.

Each one was unique in their own esoteric ways. All of them at one point had potential to make money, and timing is everything.

Here’s a somewhat chronological list of the various MVPs I’ve launched over the years:

• An AIM buddy icon network
• A college humor competitor, CampusBreak.com (sold in 2007)
• A T-shirt company: RMX Clothes (failed)
• Multiple online text-based role playing games: PimpinGame & Ghetoo
• A domain holding business: Arrowed.com, Clumzy.com, Unjam.com
• A flash gaming network: DailyFlashGames.com
• A paint party business with my wife (growing)
• A market where Gaming Publishers license games: Game Brokerage(failed)
• A snow shipping company: Ship Snow, Yo! (growing)
• A foliage shipping company: Ship Foliage (growing)
• A Donald Trump Emoji App: Trumpoji (on the verge of collapse)

Most of these businesses were side projects.

I’ve been building my career in parallel since 2008, where I tripled Bored.com annual revenues from $600k to $1.8m (user+monetization growth), lead a team to execute a roll-up strategy acquiring high traffic gaming websites, and now work as a Product Manager, Ad Ops at GSN Games monetizing 2MM DAU.

In 2014 I left Bored.com to focus full time on Game Brokerage — which I built slowly as a side project over 3 years and would go on to invest 13 months and my life savings into. It was my big swing, which eventually turned into a big whiff. Big trees fall hard. I’ll save the full story for another time…

Looking back at Game Brokerage: I should have pivoted quicker, spent less time building the product, and more time brokering games and up-sell services (monetization, advertising, and analytics).

It was painful realizing that this business had failed, and that I had run out of working capital (and personal liquidity).

Hindsight is 20/20 — I know exactly where I failed. I invested too much. Too much time, too much money, too much emotion.

Over engineered the frontend, backend, both, twice. What if I changed this, would I increase the number of sign ups? Remove this field. Add this feature.

And In the end, I became too obsessed with the product and making everything perfect — when all I needed all along was to objectively look at the data and start something new.

I closed Game Brokerage in January 2015.

I launched Ship Snow, Yo! on February 6th, 2015.

I love Micro entrepreneurship.

Why? Minimize downside, maximize upside.

Launch a lot of different businesses — horizontally and vertically across different categories and platforms.

If you need help on refining your business ideas, Paul Graham wrote an excellent essay on “How to Find a Startup Idea”. I found this particular quote insightful in narrowing focus:

You can either build something a large number of people want a small amount, or something a small number of people want a large amount. Choose the latter.

Zeroing in on something a small number of people want a lot, or should I say, need — should be prioritized.

Secondly: Prove your business — product or service — has a market fit. Nothing new here, I know — but, establish that your business can attract paying customers or advertisers. This is fundamentally why you’re starting a business. Cash is King despite what Russ Hanneman says on Silicon Valley:

It’s not about how much you earn. It’s about what you’re worth. And who’s worth the most? Companies that lose money. Pintrest, Snapchat, no revenue. Amazon has lost money for every fucking quarter for the last 20 fucking years and that Jeff Bezos is the king.

Amazon is an outlier, and you obviously can’t bank on being an outlier yourself.

In other words, plant seeds and cultivate your own success. Try new things. Explore different markets.

Eventually you’ll grow an evergreen business.