5 Lessons From My Failure With Passive Income

It’s always been a dream of mine to have some sort of online business that can allow me to live life on my terms which is why I got started in the space in the first place.

I used to watch this show called The Big Idea with Donny Deutsch back in the day. I loved listening to the stories of your average person doing something cool that enabled them to transform their lives by creating greater wealth and freedom through entrepreneurship.

I was deeply envious of these people because I was working 14 hour days at PricewaterhouseCoopers, doing financial consulting work.

Maybe, just maybe in 10 years time I could become a partner making a million dollars a year. But for what? To spend my life working away in a cubicle?

Nothing wrong with work and most people don’t work hard enough to achieve their dreams in retrospect (more on this later) – but I did not want to spend my life like that. I wanted freedom, travel, adventure and to escape Connecticut.

I dreamed of making money from an online endeavor I could do anywhere. So I quit my job to free up my time so I could make something happen online and I failed:

Failed? Yea I f*&king failed

I built a lot of websites, created a lot of mediocre content and employed foolish link building schemes to rank my sites. I felt like I was on a treadmill.

About 5 months in I had no income to show for my work and was working constantly.

What’s the point I thought?

This is not working! I’m not lucky!

I don’t have that magic touch like other people online who make it seem so easy! Like Ben Deen who amassed 200,000 subscribers in his first year of vlogging on YouTube, or other bloggers who got to 10k subscribers in a year and were able to make a job replacing income from their online work.


I was 5 months in and and sitting pretty at 10-20 visitors a day for each of my sites give or take. I was really annoyed and upset because I was not getting anywhere.

So then I just quit my online projects. I decided I’m not wasting any more of my time on this and needed a break. My girlfriend at the time was an exchange student from Thailand and she was going back there so I decided to go with her. Once I got to Thailand I loved it and wanted to stay so I stayed.

The idea of going back to Connecticut to find a boring job in a cubicle had ZERO appeal.

To stay in Thailand, I need the proper visa which I obtained from working as an English teacher. I also needed money as my websites were only making pennies a day.

Then something cool happened.

I started making $2 a day from Adsense, then $5 a day then $10 and growing. Wow, $300 passively from the work I previously did. Then I started making affiliate commissions:

For the next year I worked as a low paid English teacher while at the same time making a pretty substantial side income from my own business. I also did NO work on any of my websites (huge mistake – well kind of – I wanted to enjoy life and enjoy this new part of the world. All my life has been work, work, work work. Military, school, job. No travel, no parties, no fun).

Life was so, so good. I was not rich, but where other teachers we’re constantly broke on their $1,100 a month teacher salary and had to do extra classes just to make money to live and travel, I was making a nice $2,800 a month working 16-18 hours as an English teacher in a country where I was only spending $800 a month to live.

I had money and time to travel and it’s what I wanted and did. It was a nice reprieve from my life at PriceWaterhouseCoopers in Connecticut.

Until things came crashing down of course.

Remember? I told you I failed.

You thought this hero’s journey was over didn’t you?

Google had a few updates and penalized ALL of my website because of (and this is just an assumption) all the forum spam links I did. You see, I was copying the links that Pat Flynn was getting for his niche site duel site over at SecurityGuardTrainingHQ.com.

Publicly he was saying one thing but in reality he built A LOT of silly links. I don’t mean to call him out or anything, but it’s the reality of the situation. I don’t know if he personally did it or if he hired someone.

It’s those low quality links that I used for ALL my sites that did me in I think.

Life went from being great, to being one of my lowest points. You have no idea how it feels to get what you want, to experience what it’s like to have that sort of freedom to then have it taken all away in a day.

Which lead me to make a choice. Give up, or try again.

I had no choice but to start over, the main thing I needed to learn how to do was to simply build better websites and promote them in a totally honest and legit ways. No shortcuts.

I studied other websites, bought courses, listened to podcasts and read up on SEO content. I became a man possessed and I only incorporated concepts that would keep me on the right side of any search penalty.

I also, *shock* started trading my time for money by doing freelancing and living abroad. Building new websites and doing what I needed to. The result?  I now have websites that make me money (including this blog!) and I freelance. This combination is a bit more adult than the childish dream I had as a 20 year old at PWC of making money passively from a bunch of websites.

I’m obviously going to keep working on my passive business income obviously, but it’s great having a skill I can leverage to make thousands of dollars a month.

The truth is, you always have to work unless you’re rich. The next question is, how do you want to spend your time? Even though freelance is not passive, doing SEO audits, making WordPress websites and doing UX reviews is pretty profitable and not too time consuming. It frees up enough of my time to focus on more long term projects.

Anyways, here are my 5 lessons learned from my passive income failure

1 – If you don’t sacrifice for what you want, what you want becomes the sacrifice

I got this line from Sam Ovens, it’s great and spot on. I learned this the hard way. I should have worked on my websites, but instead I choose to have fun.

I honestly don’t regret this decision as I really enjoyed my life for the first time in a long time. But I still learned that in order to get to where you want to be, you need to sacrifice aspects of your time, attention and relationships in order to get there.

You have a choice, you want to build a business and an income or you want to have fun, drink beer, sleep with girls (or guys – most of my readers are men)?

You can’t have it all.

Women are lead to believe they can have a career, a family and that they don’t need no man. Lies.

But men are feed the same BS, just a different narrative of living this carefree amazing lifestyle where you make all this money, travel, have cool toys and you don’t work that hard.

It’s also BS.

2 – Be an expert for your FIRST venture

For your first website, blog and associated products and services, be the expert. Now, as a veteran of online marketing I could simply find a partner to jump into an industry I know nothing about. Like using FB ads to sell courses on weight loss to people living in Germany for example. I don’t speak German and I could care less about weight loss. But my marketing skill combined with an expert we could get something to work.

But for your FIRST thing, pick the thing you know deeply about and care about. At the very least, pick something you like and can provide results.

My first venture was a dating blog. My goal was to make money from advertising and commissions on dating products. I had no business giving dating advice as a 26 year old who only had 3 girlfriends his entire life. Not surprising why it failed. Oh, and it was called super awesome dating. So dumb, so, so dumb.

3 – Focus

This is not some feel good personal development crap. I really mean it. Your ability to focus and work is what will get you results.

What can you do?

Delete Facebook from your phone.

Stop playing video games too you loser.

“But, but but I’ll just play a little.”

NO. Stop it.

Beers with friends? No. not when you’re not there yet with your income.

Stop having your phone near you when you work too.

Stop being a weirdo checking the same 5 apps every 15 minutes.

4 – It takes a long time and consistency

You can enjoy life after you’ve built systems. These systems take time, day in and day out. Passive income and business income does not happen fast unless you’re willing to leverage paid advertising. If you’re not willing to do that, then you’re in for the long haul.

I’m not saying paid advertising is the way to go either. The evolution of most online is to sell products and services to free traffic and to then leverage paid traffic once you have a proof of concept.

5 – Passive income is a lie

Passive income needs to die. It should be called business income because a business is built upon various systems that deliver value. These systems run on their own without your input, however they are never totally hands off (unless you don’t care if they fall apart).

Did you know that I do an SEO audit once a month for my websites? That I comb though the content and combine posts? Check broken links? Check open rates for email sequences and better optimize open rates? That I dive into my YouTube analytics to learn how to make better videos?

Do any of these things sound passive to you?

Passive income is a lie.


Stop focusing on the many things that simulate forward progress and instead focus on the few things you do THAT ARE forward progress.

Till next time,


Find your edge, enjoy life.

What?! No Bribe? No Free Something?

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