The Difference Between Getting Paid and Making Money

You don't get what you don't ask for

Making My First $13

I’d made well over $13 before 2008. In fact, I had a perfectly acceptable 9-5 job that paid me thousands of dollars per month (as many of you reading this probably do). But on one morning in 2008, I made $13 on my own. My own money that came from an idea I had and someone being willing to pay for it.

I’d made every single dollar, until 2008, in “normal” ways. I did chores as a kid and had an allowance (it was measly, but aren’t all allowances supposed to be that way?). I had a handful of “normal” jobs growing up:

  • I mowed lawns as an angsty teenager.
  • I worked at a “health-food grocery store” as a produce boy, and sometimes register boy when they weren’t afraid that a 15-year old kid would pocket money from the cash machine (quick aside for the younger readers: Cash was this thing we used to carry around in our pockets. It was like paper, but it had weird, made-up value. Oh, you know what cash is? Great, we’ll carry on!).
  • I sold pagers at a Verizon store.
  • I pumped gasoline at a gas station.
  • I worked as a summer camp counselor.
  • I had a whole bunch of part-time design jobs.

I share all of these jobs with you to point out that it was always a standard payment for services rendered. Normal jobs, if you will.

My first taste of entrepreneurial money

In 2008, I got my first taste of entrepreneurial money. That sweet, sweet nectar that I became addicted to and would continue to chase (and still do). My IWearYourShirt business had just launched to crickets (and they didn’t have money, those cheap-insect-jerks), and I started emailing friends and family to share the website with them. This was both in a moment of panic, but also because I had a thought: “If I don’t tell people about this idea, how in the world do I expect them to find it?”

Those few emails to friends and family weren’t sales pitches. They were just friendly hellos, accompanied by a request to check out or share this crazy t-shirt wearing scheme (err, business) I had come up with. Unbeknownst to me, a few of the email recipients took pity on me and deposited money into my PayPal account via the fancy buttons on the website link I’d sent them.

Brace yourself: After the first day of sending emails, I’d made $13.

I’ll give you a moment to pick yourself up off the floor. Are you okay? You are? Great. Things get a little bit more exciting from here.

In the coming weeks after sending those first emails, the money-making part of IWearYourShirt started to gain some traction. That $13 had increased to $500. Then $1,000. Then, after two and a half months of emails and tweets, I was looking at a PayPal balance containing over $6,000.

There’s a difference between making money and getting paid

I’m going to steal this wonderful sentiment from my girlfriend, Caroline. Mostly because she’s the better writer of the two of us, and because… joint household (see, babe? If I win, we both win!)

Anyone can get paid. Anyone can get a job. Anyone can exchange time for money. But it’s another ball of wax (why is it a ball of wax? who even has ever owned a ball of wax?) to make money.

When my IWearYourShirt business started making money, I noticed a shift in my thinking. Sure, I’d read about and seen other people who were making money from their ideas, but I had never done it. I had never had that experience.

That first $13 was like seeing the light. It opened my eyes to this idea that you literally can do anything and make money from it.

If getting paid to wear t-shirts isn’t proof of that, I don’t know what is. The feeling you get when someone gives you money for your thoughts is unlike any other. Many successful people, or at least experienced entrepreneurs, will tell you that the money itself pales in comparison to the transaction that happens. Someone is essentially voting for you, saying YES to you, with their dollars. If you haven’t felt this feeling before, I will warn you: Once you feel it, you won’t want to stop feeling it.

You don’t get what you don’t ask for

This little eight-word phrase has become a mantra for me. It works well in life, but it works especially well in business. Any time I have an idea and self doubt starts to creep in, I simply combat that self doubt with the broadsword of asking. It’s not a physical broadsword, although that would be really cool. But it is a weapon I keep in my arsenal.

Self doubt will say, “You’re an idiot! no one will pay for this! Hahahahaha, you’re also ugly!”
(We all know self-doubt is also a name-calling a-hole.)

My broadsword of asking will reply, “You may be right, self doubt, but we won’t know until we ask, right?”

Then self doubt retorts, “You’re still ugly!”

It’s silly, especially imagining self doubt and a broadsword arguing, but we all deal with it. We all have some version of these thoughts. But if I’ve learned one important thing since making my first $13, it’s this:


The asking gets easier over time. The rejection you receive from asking also gets easier over time, because you know you’ll have something more interesting to ask for again in the future.


This eight-word mantra, “You don’t get what you don’t ask for,” has popped up time and time again since that initial day in 2008. I continue to refer back to my broadsword of asking. I continue to make money, not only because I have ideas and execute them, but also because I’m unafraid of the consequences of asking.

Making money makes momentum

How about that for a sweet alliteration? It’s also the truth. If you can land ONE sale, you’ll feel a sense of empowerment that can fuel you to continue. But without that one sale, you can feel powerless.

So, is it that simple? You just have to make your first sale?

I’d say: YES.

Sure, you aren’t going to retire rich, pay off all your debt, and buy that gold-plated yacht you’ve been dreaming about with just one sale. But it will give you something you can’t manufacture: momentum. And with momentum, you can push through and more easily combat your thoughts of self-doubt.

If you’ve already made your first sale, awesome. Relish that. Enjoy it. Learn everything you can from it so you can make your next sale. And then your next. And then your next.

I hope you make way more than $13 from whatever you’re working on, but don’t lose sight of the fact that everyone starts with a version of this story. And everyone remembers their version, no matter if they go on to make $1,000 $100,000 or $100,000,000.

You just have to start.