[Blogging Handbook] Introduction

We’re going to go on a journey. Don’t worry, it’s going to be worthwhile.

If you want to make money with a blog then reading this story will set you up completely to do that.

True story.


Let’s begin.


In 2015, I had no job.

I was doing some freelancing but that was it.

My wife and I had just moved to Colorado from LA so she didn’t have a job.

In fact, she gave up her successful dog walking business so we could move. I still have a lot of making up to do for that.

The freelancing was okay but it was barely making ends meet. It wasn’t that I couldn’t get work. It’s that I didn’t want work.

I quit working for others because I hated the idea.

Freelancing, however, felt like another job where I was just exchanging time for money and I hated that.

If I really wanted that then I’d just get another job where the paychecks were steady.

But I couldn’t go back to that life. I had tried it enough times to know that I was miserable then.

It just wasn’t for me so this is the route that I took.

I figured that eventually I’d come up with some amazing business idea, build it, make money with it, and then sell it to retire.

That would remove me from this freelancing stuff.

My Brother

Around the same time, my brother had recently graduated with a Master’s degree in Sports Administration. He got a job as an assistant coach and hated it.

He was lost.

So being the big brother that I am I told him that he could move to Colorado with us and I would teach him some things.

To be honest, I had no idea what I was going to teach him. I figured I knew how to code so I would teach him how to code.

After that? I had absolutely no plan.

So when he arrived he started to learn how to code.

At this point I’ve brought two people to Colorado in what felt like the world’s smallest town with nothing to do.

I kept on doing freelance work and my wife…well, she was left to stress about money.

Stressing about money is never fun. Especially, when you see the people you love doing it.

You can only say, “don’t worry, it’s going to be okay” so many times before a person snaps.

I think my wife was getting close to that and I have to admit, that stressed me out a lot.

Thankfully, my wife had a bit of a release of the stress by going to the gym.

Because my wife and brother both enjoyed fitness, they would go to the gym in the morning and workout.

I don’t know what about that inspired me but I remember one day I got them together and I told them that we were going to start a blog about health and fitness.

Because I’m a persuasive kind of guy they went along with it.

So we started a blog. We called it Thrive/Strive.

(Some quick background, yes, even earlier than what we are talking about now, I had started my first blog in 2003 and started a blog network in 2004. I sold everything off and got a job eventually so it’s not like blogging was new to me.)

But because I felt like I had more time on my hands than I did I decided to start another blog. This one would document my blog journey and I called it Obstacle.co.

Launching the Blogs

On June 1st we launched both of the blogs to great fanfare.

Nah, I’m just joking.

Absolutely nobody besides us gave a shit. That’s how it is for everyone.

I don’t know what was going through my mind but I envisioned that somehow, some way a lot of people were going to come to the site and we were going to make a lot of money.

Money so my brother didn’t have to find another job.

Money so my wife didn’t have to worry.

Money so I could stop freelancing.

Blogging was going to be our path to freedom.

Unfortunately, nothing happened in that first week.

In fact, you can check out the numbers here.

234 pageviews but I can guarantee that at least 170 of them were from us.

There is nothing wrong with getting no numbers in the first week. It’s to be expected and my wife and brother seemed okay with it.

They didn’t expect miracles so they put their heads down and continued to write.

Everyday I would check the analytics and everyday I would see the same results.

Basically nothing.

It’s okay, these things take time I continued to remind myself.

After a month I figured we would start to see traffic going up.


Those damn Pinterest bloggers.

Because my wife loved Pinterest she would always show me cool things that she liked on it. When I decided we should start a blog I went right to Pinterest to look for inspiration.

Somehow I landed in the blogging Pinterest circle and I discovered that lots of people were making money with blogs!

It was inspiring. Everyone told you how much they made and how they did it.

If they could do it then I certainly could!

As I was writing about blogging I continued to read these bloggers and I would get so excited to see their results.

Then I would look at the numbers for our health blog and get disappointed.

At the 60-day mark nothing had really changed. I could start to sense the disappointment in both my wife and brother.

What was the point of doing this if nothing was going to happen?

More importantly, why should they believe me anymore if this was the path that I was going to lead them down?

I’m generally an optimistic person because that’s just the best way to live life, but I have to admit that even I was starting to get a little discouraged.

Thankfully, my blog about blogging was picking up and I was making enough money with freelancing (booooo! hissssssss!) to cover things.

But that’s not what I wanted.

I wanted this health blog to work.

I wanted to share the excitement between the three of us.

And that wasn’t happening.

At the 90-day mark, I was banging my head against the wall. Why was nothing working? I thought we were creating amazing content.

We were pinning it and being consistent with everything.

The pace of the writing from my wife and brother was slowing down because honestly, what was the point if no traffic was coming?

I didn’t blame them.

Nobody likes to work without seeing some type of reward.

Especially after 90 days.

So here I am. This guy who supposedly is smart and convinced two people he loves to follow him into the gates of blog hell with the promise of riches at the end.

But we were still in blog hell.

I honestly didn’t know what to tell them. I was embarrassed. I was ashamed.

Let me tell you how hard it is to hide from two other people in a two-bedroom apartment.

It’s really hard.

In fact, some might say it’s impossible.

We would go and walk the dogs and I would joke about life and keep the discussion away from the blog because what was the point in talking about it?

You can only encourage someone about a thing for so long before they start to catch onto the fact that it isn’t happening.

90 days.


But that 91st day?

That is my most favorite day ever when I think about this online business journey that I’ve been on.

Here, let me show you what happened.