Painful, Embarrassing Shit I’ve Done Trying To Make Money Online

by / ⠀Entrepreneurship Startup Advice / October 28, 2013

When I began writing at Rich20Something, I felt like a small child lost in the woods.

First, let’s get something straight: A lot of other bloggers or writers will tell you “Oh, I hardly even considered making money off my blog. Why, it happened practically by accident!” That’s bullshit. It doesn’t happen by accident.

And I knew from day one that I wanted to figure out a way to make money with Rich20Something by sharing the things I’d learned launching my other businesses. I just had no idea HOW to actually do this.

I saw a lot of these sketchy, over-the-top, narcissistic personalities online and it made me think of what directors used to tell me when I was acting in stage work:

“When you’re on stage, you have to be BIGGER so that even the back row can see you.”

So I saw all these over the top personalities supposedly making money and I thought THAT was who I would have to become in order to make a name for myself — and then one day…maybe I could make money online.

So for months, I tried a bunch of shit to attract attention. Now, I’m going to reveal some of the painful, embarrassing shit I attempted.

WARNING: All of these ideas are horrible. They make me want to set the treadmill to infinity and do the endless walk of shame. After reading them over again, I’m reconsidering religion.

(This is an actual screencap of my first video.…)

  • I tried putting up a bunch of Google Adwords campaigns to a corny landing page that looked like a 2004 advertisement for OxyClean. Google suspended my account.

  • I tried writing posts every single day and using Hootsuite to spam my friends and family on Twitter/Facebook. It was a marvelous failure.

  • I even tired…gulp…ok…I hired a professional ventriloquists to make a video for me to announce a web event. Yes. You read that correctly. Don’t believe me?

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Puppets? Pants? WTF was I smoking?

  • Bonus fuckup not related to Rich20Something: I once lied to a web design client to get a project and told them that my team and I were ex-Google coders. Then when I got the job, I scrambled to find people who could help me do it. It didn’t work. I had to pay back everything. Umm…readers, never do that. Dumb x infinity.

Can you tell I was in gifted classes in high school?

Looking back, It seems pretty obvious that these approaches would be complete, total flops…but nothing is really obvious when you’re IN THE MOMENT — and you’re trying to copy what it appears other people are doing

How many of us are in the moment – trying to figure things out in our business and personal lives on a day-to-day basis?

Raise your hand if one of these strikes a chord with you:

  • You’re just looking for a way….ANY WAY to make an idea of yours work.

  • You find yourself quietly contemplating the meaning of life, saying things like: “WHAT THE FUCK IS THE SECRET TO MAKING MONEY?”

I feel you.

In my case, I was dying to know what the “secret sauce” was that all these other bloggers had (and I clearly didn’t).

They certainly weren’t better looking than me.

Then, one day, LIGHTNING STUCK. I had an “a ha” moment.

See — all this time, I’d be coming at this blog from a selfish P.O.V.

 How can DANIEL make money?

 How can DANIEL get noticed, get attention, get flocks of adoring female fans to send him semi-nude selfies?

I made it all about me. Me, ME, ME.

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I started looking at the blogs of other people I admired who were making money — but also being themselves. People like Ramit Sethi, James Clear and Derek Halpern.

I smacked my head so hard, it’s still hurting…and in an instant, I finally realized the two components that make ANY business — whether it’s a product or a service…or even a blog — successful:

  • Authenticity

  • Offering your audience a genuine solution to their problems

So now, it was time to do a little soul searching and take an inventory. I started asking myself probing questions.

First: Authenticity

How could I really connect with my audience?

  • How can I reach them in  a way that makes them feel  a genuine connection to me?

  • How can I be the most honest version of myself.

I started writing posts that just expressed my feelings, hoping that people would relate. Not mushy, woo-woo, “The Secret” stuff. I began to write real, truthful pieces in the form of open letters.

These resonated. They stood out from the pack because people could tell there was no agenda. It was just me talking…and if they liked what I had to say…they could read more of my blog. That’s it. This type of genuine concern for others built my community faster than any other “tactic” I’d tried in the past. Imagine that.

Next: Offering my audience genuine solution to their problems

Now that I had peoples’ attention, what could I actually help them with?

  • The biggest mistake you can make here as a beginner is thinking that your experience has no value. It always has value.

  • You can always teach somebody something. You always have something to give.

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So I started teaching — and I got great responses

Now, after some time I’d learned how to offer REAL, TANGIBLE value to readers — and it was a very simple transition to turning readers into clients and the blog into a business.

I started learning what people wanted by learning what people wanted via survey. I listened to what they were feeling and created something to help them.

 A few months later, I created a simple, program called the Tribal Accelerator where I help entrepreneurs one-on-one to take concrete action on their goals, stop messing around, and finally launch their start ups.

Now, I’d leveraged a legitimate business from my blog.

In my first 6 months of business, I made about 16,000 in sales from Rich20Something.

Now, it’s your turn.

  •  What do you want to know about my failures? My successes?
  • What specific questions do you have about how I run my businesses?

You can ask me about marketing, product creation, finances. Anything you can think of. Nothing is off limits.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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