A man with a ponytale sits at the computer, the text reads "How I made my first dollar on the internet'

A dollar buys you nothing.

Well… a dollar can buy you some things… in fact there’s a whole menu of choices at your nearest Taco Bell.

But I think we can all agree that a dollar isn’t really anything to write home about.

Whether it’s a lot of money or not… I have to say that making my first dollar online felt like a real accomplishment.

How did I do it?

In late January I wrote a post about “how you make money on the internet’. In it I sketched out my plan to finally turn this site from a time consuming hobby into something that resembled a business (or so I hoped).

Step one was to earn my first dollar.

First dollar on the internet - From Rags to Reasonable

One dollar. That’s not hard, right?

You might think that the distance between 0 and 1 is just … 1. But that’s real math, and has nothing to do with the mental difference between making no income, and making some income. The difference between 0 and 1 is an impossible chasm.

It wasn’t hard to find something that I thought I could sell for a dollar. I had put together a debt workbook for some of the workshops I run … and figured that was worth at least a dollar!

But how do I take a physical object that I made and transfer it to someone else over the internet after taking their money…?

Action is worth more than the ‘perfect solution’

At a conference last fall I heard a line that’s really stuck with me…

“If you’re 75% sure that you’ve got the right answer… just do it. Sometimes the right decision is that one you make RIGHT NOW.”

So if you’re wondering how I ended up choosing the service GUMROAD  to sell my workbook, the answer will most likely be unsatisfying.

I had heard of it. It ended up being insanely easy to use. And it cut down on the excuses my brain was trying to throw at me:

“Is this the best way? Whoa, those fees look a little high… you should just keep looking to see if there’s something better… you don’t want to look dumb, do you?”

The act of making my first dollar was much more a mental exercise than a real financial plan. I didn’t give much thought to scalability or market positioning…

I thought about how to change my mental stance about this site. I thought about how to finally admit publicly that I wanted to make money, to make a business… and how I wanted to offer something that I hoped people who find useful (or at least useful enough to spend a dollar on).

The cost of making money:

Gumroad charges a 5% processing fee, which seemed totally fair to me… especially at that point.. the point at which I didn’t even know where to begin. They were offering to do all the heavy lifting by providing safe, secure transactions as well as hosting for my workbook.

The thing that nailed me, though (at least in terms of my ‘1 dollar offer’), is that they also charged 25 cents a transaction.

So for every dollar that I ‘made’ … I was actually only taking home 70 cents.


The 25 cent transaction fee will hurt less when the price of something I’m selling is higher, since it’s not a percentage, but it stung a bit to realize that even when my first sale came through (it was from my girlfriend… she’s very sweet) I hadn’t yet made it to my very humble goal.

The final numbers:

In the flagging days of January, I did manage to sell a few copies of my workbook. The first few that went out were to family and friends (which is always so appreciated, and also… a little bitter sweet).

The real joy was when subscribers and strangers bought in (and then sent very nice comments about how it was worth more than a dollar… which it will be soon… so if you want the DEBT DOLLAR DEAL… buy now!!…. And if you’re reading this later… sorry you missed it).

So in four days (the four final days of January) this is how it turned out:

  • Copies sold: 17 workbooks
  • Total fees:  5.1 dollars
  • Profit: 11.9 dollars

I don’t know what I expected, so I can’t tell you if I feel great about that, or disappointed. All I know is that I successfully made my first dollar on the internet…

and that’s pretty damn cool.

Don’t miss next month’s instalment to see how I managed in February when I try to double the stakes…. TWO dollars. Doesn’t seem hard… but I still don’t know how I’m going to do it (and February is already half over… yikes). 

First dollar on the internet - From Rags to Reasonable