How to Lose Over $1 Million in 10 Years

And How I'll Make Much More in the Future

Updated: September 15, 2016

I’ve been running my own businesses and building my own sites since 2003. In Internet years, I am 145.

When I was 23 (2003) I had the idea that I would be a millionaire by age 30. That time has come and passed and I definitely didn’t achieve millionaire status.

However, I’ve seen a number of my friends and colleagues become millionaires or close to it over that time. They weren’t smarter, more talented, taller (not sure what that has to do with it), or could eat more hot dogs. They just did one thing that I never did.

They stayed consistent.

In this post, I want to highlight all of the awesome things that have happened to me in the past 10+ years that has caused me to lose out on over a million dollars. I’m writing this post because if you are just getting started on your thing now I want you to understand that you need to stick with it.

It’s much too easy to read about the successes of others and believe they got there instantly because often that is how they present things, but that is rarely the case. All they did is stick with things longer than anyone else and eventually it paid off.

So let’s take a trip down memory lane to see how many times I screwed things up.


This was my first major hit. It was a blog about web design and it was awesome. I would write almost every single day and built up a nice sized tribe. I would not hesitate to say at the time it was one of the top 20 blogs on the web about web design.

I made a lot of mistakes with it.

  1. I never thought about how to monetize my tribe. I didn’t create any products. I didn’t do any courses. I didn’t do anything but sell ad space which was a huge pain in the ass.
  2. I didn’t gather emails. Nowadays you know that right when you start a site you need to collect emails, but back then it didn’t seem as important. Instead, you wanted subscribers to your RSS feeds.

Eventually, I burned myself out talking about web design as I believed I hit every single topic a person could talk about. I failed to read the pulse of my audience to see what they wanted to read and instead only focused on the things that I liked. Instead of creating value I started to create a site where the content was meh.

I ended up selling the site for $5,000. 3 years of hard work, tons of backlinks, over 100 pieces of content (some more valuable than others) and I sold it for $5,000 because I was tired of it.

Now things are different. Every time I launch a site I have a monetization plan in place that doesn’t involve ads and also a plan on how I am going to communicate with my tribe. I make sure to continuously check around to see what type of topics people might be interested in and ensure that everything that gets published has some sort of value attached to it.

CSS Vault

When CSS was starting to get big I created a web gallery that focused on beautiful designs created solely in CSS. The site became pretty popular amassing hundreds of thousands of pageviews a month. I didn’t monetize it at all because I just liked to find awesome looking sites.

Of course, I also had zero business sense back then as well so I didn’t bother researching the different revenue paths I could take. One day someone emailed me offering to buy the site for $20,000. I didn’t hesitate and sold it right away.

I was happy with $20,000. I’d never seen that much money in my life and the site wasn’t that hard to create. I thought I made easy money, but I valued the wrong thing. I valued the effort it took to build and maintain the site, while the buyer valued the tribe/audience that was attached to it.

Two years later they sold the site for $100,000 to HostGator.

I punched a wall.


My very first company was a blog network called 9rules. It was an idea that I came up with in the shower and by today’s terms it might seem overly simplistic, but back then it was awesome. In 2003, blogs that weren’t about cats were still pretty new. 9rules members were composed of some of the best bloggers on the web.

I can’t tell you how many people talk about how they wanted to be a member of 9rules. It was just that cool. It was great.

At its peak, it had over 300 of the best blogs as members. Now imagine you had access to 300 of the best blogs on the web, millions of readers a month, and doing nothing with it.

That’s right, we did nothing or I should say that I did nothing. I ran the ship so I take full responsibility for everything. You see back then, for whatever reason, I was hesitant about making money. There were a number of ways to go about, but I always wanted to keep things pure. I would like to say I was risk adverse, but more likely I was just a big chicken shit.

Instead of taking the Tribe I had built up and figuring out how to get them to pay for even more great value, I did nothing and let things slowly die.

I remember one of my business partners at the time constantly suggested we start an ad network and sell ads across the sites. With the best sites on the web, selling ads across them shouldn’t have been that hard, but I was hesitant due to the programming involved. Not too long later, BuySellAds launched and took over the blog advertising scene.

They made millions while I made nothing.

Eventually, we sold 9rules for way, way, waaaaay less than what people think we sold it for. I squandered a huge opportunity because I let apathy kick in due to the fact I wasn’t happy with the results that were being produced.

Damn I’m Cute

I created a celebrity gossip blog because I liked looking at pictures of celebrities. In 2 months I got the site to over 400,000 pageviews a month.

In 2 months.

I’ve never been able to repeat that success again.

However, the same story prevails. I didn’t think about better ways to monetize besides ads and I quickly grew tired of trying to write for it. I sold it for $10,000.

You might think that isn’t bad for a couple months work and if viewed that way, it isn’t. However, I could’ve easily gotten it to millions of pageviews a month and sold it for over a million dollars if I just stuck with it. I base that selling price off of the prices other celebrity blogs were going for back then.

My mistake was thinking that something that I liked doing, looking at celeb pictures, could translate into something that I liked doing as a job. It’s no fun finding celebrity pictures every single day, editing them, and then uploading them to your server. It takes the fun out of everything.


After a while, I had the itch to write about web design again so I started another blog. Actually, this was more of a community with a blog attached to it. At the time, most web design blogs were nothing but list articles. I wanted to take a different approach and bring opinion back to the web design niche.

In its first month the site got over 100,000 pageviews and for the next 10 months, it never dropped below that figure.

But guess what I didn’t do?

Collect emails. Now you might be thinking that collecting emails is dumb, but it’s hands down the best way to build your tribe. You really being to understand who your greatest ambassadors are and also get great insight into your audience.

But I wasn’t collecting email addresses.

I also had no idea how I was going to monetize the site. I figured it was going to be with ads, but that meant I had to spend time as a salesman trying to convince companies to advertise on my site.

I rocked with content creation and sucked at everything else you need to create a successful site.

Unlike the other sites, this one didn’t disappear. In fact, it changed into Makers Cabin 3 years after its creation. However, I had another popular site in a popular niche and failed to utilize the audience that I had.

Instead of continuously building on top of the foundation that was strong, I continued to knock it down and start all over.

Failed at the Basics

As you can see, none of the sites or blogs that I created were mind-blowingly complicated. In fact, they were things that I think anyone could do. While I always seem to do a great job of content creation, I failed miserably at a ton of other things.

Growing My Tribe with Intent

Each site was predicated on the fact that I believed if I created awesome content, people would come back and that holds true for some people. However, there is so much stuff vying for our attention today, you need a way to constantly remind people that you exist.

This could be via social media or your mailing list. Preferably you are utilizing both and growing your tribe with intent. I never did such a thing and it costs me big. Each and every time I started something new I was starting from scratch. It would’ve been wise to collect email addresses from the beginning and with each new venture, I could bring some of that audience with me.

Instead, I had to constantly remind people who I am, what I’ve done, and what I am doing now. That gets tiresome after a while.

What I do now is to make sure that I have some type of email list setup. Some are more complicated than others, but at the very least it just takes a couple of seconds to create a free MailChimp account, create a form, and throw it on your site. The first 2,000 subscribers are free so you should be good to go for a while.

I don’t try too hard to push my audience towards my social media accounts because you really never know who is active on what. On the About page I explain how I treat each network that Obstacle.co is on and I leave it up to you to decide if it’s worth it. This isn’t because I place little value on social media. I think social media is huge, but I don’t think it’s a good way to keep a captive audience if you are a blog unless you reach critical mass.

It’s a great way to get your brand out there and to let people get to know you, but don’t spend most of your time trying to get likes or followers because you never know what is going to happen with those platforms. Your email list is yours and yours alone.

Promoting Content

I did a terrible job of this. My promotion plan for the majority of my content was to simply post a link on Twitter and then move on. We all know how easy it is to miss something on Twitter so just posting something once wasn’t going to get me very far.

I also never took the time to build relationships with thought leaders in my niche, which would have helped me get even more promotion. I stupidly went with the if you build it, they will come approach which severely limited the growth of my sites.

Derek Halpern suggests that you spend 80% of your time promoting your content. While I think 80% is a bit much, if you find that you aren’t spending at least 40% of your time promoting your content or growing your brand, then you will find that you are handicapping yourself.

And I know promoting yourself is hard. I have a hard time doing it because it means that I am telling people that I believe they should take time out of their day to read what I wrote. I don’t want to waste anybody’s time and the thought of doing so makes me feel ill.

Promoting your content over and over and over again is putting yourself out there like you probably never did before.

And it’s needed.

Don’t wait till you think you are a great writer because odds are you will never think like that. Don’t wait till you think a post is perfect because that will never happen either.

Just look at your content and think of the person you are targeting and say out loud the value they will get out of reading it. If you can point something out that a person will gain from reading your content then you should go on and promote it.

Being Consistent

I do things in spurts. I get really excited about something, work really hard on it, and then fade away. I don’t know if I burn myself out or if I am terrible at seeing the big picture. Either way, I never took the steps to help me be consistent.

When you first begin to blog, writing consistently can be pretty easy because you have a ton of ideas. As time goes on you will find that it gets a bit harder to blog consistently. To counter this, you should work on setting up an editorial calendar.

This doesn’t have to be anything complex. It can simply be a spreadsheet with the following fields:

  • Post title
  • Post status
  • Published date

That’s it.

From that simple spreadsheet, you will be able to see out into the future. You will never stress about coming up with another blog post idea and you can actually plan ahead. If your goal is to publish 3 new posts a week, then why not build up a backlog of posts so you can get ahead of the game?

Imagine having all of next month’s post already done and being automatically published when the time comes. Setting up a calendar and automating systems allows you to look consistent to your tribe without always having to be consistent behind the scenes.

So why is consistency important? Why ISN’T consistency important is a better question, but I’ll answer it for you because that’s why you pay me the big bucks.

  1. Helps build audience expectation. The first time someone visits your site they don’t care how often you write for your blog. As your tribe begins to grow they have an expectation to see awesome content X amount of times per month or year. That is a good thing since it keeps your brand on the forefront of their mind. Once you stop being consistent your brand begins to fade.
  2. Google loves fresh content. By no means should you try to write every single day, but Google loves fresh content because it means the site is being constantly updated. Google doesn’t want to show their users content from 10 years ago, they want stuff that is current and relevant.
  3. Your blog is a business. If you work a 9-5 job then you understand that you need to show up to get paid. Same goes with your blog. You need to show up to build your tribe and make money. You can’t make it an on and off type of thing.

Figure out what schedule you can do with your blog and stick with it. Be careful of overachieving and thinking that you will write every single day when you have a million other things to do. If you only plan on publishing once a week then stick to it. If you happen to get two articles out in one week then good for you, but don’t deviate from your schedule.

Make it a habit and after some time, you will see how your blog grows.

Plan a Monetization Strategy

It’s way too easy to start a blog and think that you will figure out how to monetize it later (if that’s the goal) or that you will just slap ads on the site when the time comes.

You don’t want to do this.

Have a plan in place right from the offset. This doesn’t mean you need to stick with the plan, but you do have to have an idea of which direction you are going.

For example, let’s say I plan on selling e-courses (which I do) and that one of the courses I have tentatively planned is around SEO. Then that means I can write a number of SEO-based posts to gauge the interest of my audience and set up a sales funnel to lead them towards the course.

When you have no monetization strategy in place you just write random stuff with no plan of action. Having a plan allows you to think about the different ways you are going to grow your audience and can help set your content strategy as well.

Again, you don’t need to know exactly what you are going to do, but it’s a lot better to tell yourself that you are going to sell ebooks than it is to not have anything at all.

If you aren’t sure about the ways you can monetize a blog I have a nice writeup that goes into detail about the topic.

Plan for the Long Haul

Building a successful blog, or any business, takes time and a lot of effort. You need to make sure you are ready for the long haul and this isn’t something that is going to last a month or two. It’s way too easy to get caught up in the initial euphoria and mistake that as a passion for what you are doing.

There will be times where you don’t want to write and think about taking a month off. This works if you already have an established audience, but doesn’t work so well when you are starting off. It just means you have to start from scratch all over again.

There will be times you question whether you want to write about your specific niche anymore. This might mean you start to mix things up, but I’d advise you either completely switch niches or just wait things out to see if you really want to write about something else.

There will be times at the beginning when nobody is coming to your site and nobody is paying for a thing. Very rarely do people see instant success from scratch. These things take time and effort and if you aren’t willing to put the work in, then your time would be better spent elsewhere.

You Never Know What’s Coming

Blogging and producing great value for people can open up huge opportunities. You don’t know what lies ahead of you, but if you are consistent and continue to promote your value good things will happen. I made the mistake of not completely understanding the opportunities that I had and failed to take advantage of them and paid the price.

You might be thinking that I haven’t lost money I never had and I guess you might be right, but I don’t see it like that. I see my own mistakes causing me to miss out on the things that I’ve wanted.

It’s very easy to get in your own way. As I say, you are your greatest obstacle.

No matter who is reading this you have the potential to do well with your site. You just have to understand what it takes to make it successful, follow your plan, and then send me a check for $10,000 since this post is the one that inspired you to greatness.

Did you know that there are exactly 13,783 steps to building a successful blog?

I'm just playing, I have no idea how many steps there are but believe me there are a lot.

In fact, one of the biggest reasons why many bloggers don't even get off the ground is because they suffer from analysis paralysis.

The other ones simply don't know what the next step is supposed to be.

That's why I created the 12-Day Blogging Bootcamp.

The idea behind it is that once you see the big picture of everything that you need to build a successful blog, it will become much easier to take the next step.

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These are the things that I do over and over and over again with my blogs, not just my how to make money blog. All of them.

  • Personal Finance
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My knowledge is coming from a place of diversity with the different blogs that I run so when I say you're going to learn things you won't find elsewhere, I mean it.

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You don’t get what you don’t ask for so I’m asking you to take a second to share How to Lose Over $1 Million in 10 Years with your audience. They respect great content.

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How to Lose Over $1 Million in 10 Years

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