The Time I Bet $1000 To Prove I Could Make $10,000

Corey Koehler
3 min readFeb 13, 2024

It was bowling night circa the mid-2000s.

I made a bet that would teach me a big lesson.

At the time, my tolerance of the cubicle life was waning, and I was dabbling in ways to make money on the side.

The side hustle at the time was in Network Marketing (MLM).

I was all in.

Dollar signs in my eyes and swiggin’ the Kool-Ade I had it all figured out.

$10,000 per month easy.

I was so confident that one night, I bet a friend of mine $1000 that I would be making $10,000 per month within a few months.

But guess what…

I lost that bet.

And it really, REALLY sucked.

I was depressed for weeks and constantly reminded of that feeling every time I had to make a payment to my friend — which took many, many months.

Why I Lost

With hindsight being 20/20, I was in the wrong business… for me.

Network Marketing and MLM just weren’t my cup of tea. I never felt comfortable, and never really believed in the stuff I was selling. And if you don’t believe in anything you’re doing, people can smell it on you, and they stay away.

Add to that the fact that for this MLM in particular, I was selling travel.

What’s funny is I traveled maybe a handful of times in my entire life.

Why the hell did I think I was going to be able to sell something I didn’t even use myself?


Lose And Learn

Even though I lost that bet, there were some good life lessons that came out of it.

First, for the first time ever, I felt confident enough to bet on myself (No matter how misguided it was at the time).

Second, I discovered Pay Per Click Marketing.

I learned how to run Google Ads (or AdWords as it was called at the time) to promote my business. It was work, but they didn’t like it, and it wasn’t allowed.

Fast forward to today, and that Google Ads knowledge has made me comfortably over $10K per month for the past 5 years running.

Third, and most important, I kept going.

I kept learning, experimenting, and failing. I learned to identify opportunities, and the wins started coming slowly but surely.

Belief was the key.

Once I believed, I started seeing opportunities; I could see them everywhere.

Whether you think you can or think you can’t, you’re right. — Henry Ford

Maybe this MLM stuff didn’t work for me, but being my own boss, mailbox money, freedom, and remote work was.

And I knew in my guts that there was something out there that would work.

My Latest Bet

I’m betting that there are a lot more people, like me, who are willing to bet on themselves.

They just need a little push.

So, if any part of you feels you need something different from what you’re doing in your 9–5, find an opportunity and get to work.

Even if it ends up being the wrong opportunity, betting on yourself is the safest bet you’ll ever make. Because you’re going to learn new skills, you’re going to grow, and you’re going to gain confidence.

If you need a starting point, here’s one.

Go check out part one of a series I’m writing on how to use your personal stories to discover ways to make some money (and maybe even a new career like I did).

Tap here to read part one.

You’ll also see how this story blueprint is helping me future-proof myself — and how you can too.

See you over there.

Before you go…

Wanna see something cool? I just learned this. Tap and hold the clap button and see what happens. (Cool huh?)

Don’t be a stranger. Share your thoughts below and follow for more on music, marketing, and the future of work whatnot.

Introduce yourself. Join my newsletter to receive my Gen Xer’s email mixtape on music, marketing, and mastering the future of work — I promise you, there’s no other newsletter like it. Join us here.



Corey Koehler

Google Ads Guy | Entrepreneur | Music and NFL Geek | 80s Kid Sharing adventures in music, marketing & early unretirement.