Painful, Embarrassing Shit I've Done Trying To Make Money Online : Under30CEO Painful, Embarrassing Shit I've Done Trying To Make Money Online : Under30CEO
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Painful, Embarrassing Shit I’ve Done Trying To Make Money Online

| October 28, 2013 | 14 Comments

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.

  • I tried putting naked women in my videos to get more clicks (yes, I did think this would work so shut the hell up)

(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. It was their way of letting me know how good my content was…

  • 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?

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 we 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.


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.

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.

Leave any question in the comments below with your questions and I’ll answer it.

BTW: If you want to learn inside info on freelancing, building your own online business and conquering the biggest startup hurdles, you have to join my tribe — I share private things there with my readers that I’ll never post anywhere online. Sometimes my emails are so ridiculous, my mom freaks out and calls me.

About the Author: Daniel DiPiazza

Daniel DiPiazza teaches young people how to stop doing shit that they hate and break free of 9 to 5 boredom by starting their own businesses at his blog

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  • Marisol

    This is a great one Daniel! I strongly believe that being yourself will give you more rewards than anything!

  • Econ At Uni

    Great post Daniel! I even spent a good 15 minutes reading the Elance guide you linked to early on.

    My question for you is how to best monetise a website I set up in 2009. I worked hard to get into the University of my choice and when asked for my tips, I decided to start writing them on a blog so that no one missed out.

    I would now like to monetise (at least to cover costs) and am experimenting with Amazon Associates and also creating my own products.

    However, engagement overall is low (perhaps because students use it for 2-3 months during their studies and then move on) and as a result sales aren’t as high as hoped.

    If I share the address, would you be be able to share your tips? They will probably be obvious for you once you see the site.

  • cate moore

    The authenticity piece is critical, Daniel. I agree with you whole-heartedly. In a time when anyone can claim anything about who they are and what they do, people must trust you are authentic/the real deal. Recently, I decided to close a business that I put my heart. soul, and ridiculous amounts of money into…and before I rake myself over the coals too much, I have to look at all that was done extremely well.

    It’s important to be honest about how much work and drive and mental strength it takes to be successful. The failures are equally as important as the successes – in fact, I think most of us learn much more from the painful stuff than through easy stuff. They test and challenge us and refine what we are made of…!

    I love the candour and honestly with which you write. Great post!

  • Daniel DiPiazza

    Thanks, Marisol! Can you think of a time where it would have been tempting to lie about yourself — but you told the truth, and it paid off BIG time?

  • Daniel DiPiazza

    Sure! What’s the site address?

  • Daniel DiPiazza

    Thanks, Cate! You’re 100% right. I think ESPECIALLY on the internet, people want to put up this facade about how easy it is “AND IF YOU FOLLOW ME, YOU CAN DO IT TOO!” I think it’s worth it to listen and learn from other people – but there really is no way around hard work.

    Since you closed down the business, what are you doing now?

  • Jenna Hawkins

    Thanks for this post! Amusing, yet insightful. I’m starting up an online business (as a student with limited funds)… how would you recommend I develop a website? Paying for a pro developer is VERY expensive, white-label sites are expensive in the long run, and I can’t code it myself… any ideas?

  • cate moore

    Building my own brand. Not wanting to be like everyone else. Offering valuable content. It’ a process, as you know. Speaking about the stuff nobody wants to talk about…that sort of thing! Loving every minute of it. :)

  • Barbara Mckinney

    Successful blogging provides solution to the problem of their valued customers.The fact that there are a lot of competitors out there,providing your readers with relevant information will make you stand out from the crowd.

  • Pingback: Painful, Embarrassing Shit I’ve Done Trying To Make Money Online |

  • Daniel DiPiazza

    Hey @barbaramckinney:disqus , thanks for reading! You’re totally right about providing a solution. What are your favorite blogs to read, besides Under30CEO and Ruch20Something, of course?


  • Daniel DiPiazza

    Hey @a3a13e9f9807ae494dceb984382560f8:disqus. Thanks for reading! Why not just start a simple WordPress?

  • Barbara Mckinney already know the answer :)

  • Frédéric Paul

    Thanks for this post! Amusing,

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