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Ever shifting thoughts on earning money with a website.

It’s amazing how much you can struggle with this whole question of whether (and how) to make money from your website.

I seriously want to provide information and content that is genuinely useful. Where is the point where money gets in the way?

As a result, I’ve wrestled a lot with how I want to go forward with earning money from my website. What’s the best way? Advertising? Affiliates? Memberships? When does it get to be too much?

What is the best way to earn money from my work on this website?
What is the best way to earn money from my work on this website?

Because it can be too much

You can probably think of a website that fits this description. I can think of one that focused on a niche I’m interested in. There is a lot of good content. The guy who runs it is a recognized authority and well known in that particular niche.

And every single thing that I see posted, it’s clear the motivation is to get you to something that makes money for the site.

I see recommendations for things, things that I know enough about, and they’re things that I know aren’t really worth recommending, but they’re things that I know pay well on the affiliate market.

And to be honest, I don’t trust anything that I see there. I don’t feel like what I see is in my best interest, it’s all about what makes the most money. I might be wrong, I hope I’m wrong, but that’s the very strong impression I get.

I don’t want to be that guy.

Creating content without expectation

I made the decision when I started my sites that I wanted to provide useful information without expectation of anything in return.

I want to be able to say “I’m providing this for you. No strings attached.”

Just as importantly, I want my visitors to understand that. I don’t want them to feel like I am asking anything in return.

I think it ties into this thing about me that desires to be helpful. Part of it stems from my own lack of trust whenever I feel like there’s a hidden agenda. I want to offer the best advice because I truly believe it’s the best advice.

I don’t want someone coming away thinking it’s all about the money.

Balancing that with creating the ABILITY to provide that content.

My challenge is figuring out how to balance the desire to provide useful information with the desire to generate revenue from that content
My challenge is figuring out how to balance the desire to provide useful information with the desire to generate revenue from that content

When it comes to my one established website,, I have to be real here. When you put so much time into the website, there’s a point where you want to see a return.

And the thing is, I’d love to write more, to create more content. But there’s only so much time in the day. Some of that time has to be spent paying the bills. Eventually, the only way to do the more AND pay the bills is when the content can be the thing to pay the bills.

How do I do that without being that guy? That’s been my struggle.

Building, and building, until it’s ready to earn.

I decided early on to just focus on content for awhile. For a year, all I did was post content. I wrote as often as possible. I built a presence. I think I even established myself as an authority in my niche.

And I paid the bills out of my own pocket. The good news is, it hasn’t been THAT much, but it’s not without cost. That was okay, I was thankful to be able to do it. And I resisted the temptation to go for the quick buck.

That’s not to say that someone shouldn’t monetize sooner. It’s not even to say that was the best strategy with EntreCourier. I’m not sure I’ll be that patient with this particular blog or any others, to be totally honest.

At the same time, I’ve been highly influenced by some folks who preach patience. Build, build, build, be patient, create your audience, don’t hurry the process. I probably listen more to Gary Veynerchuk than anyone when it comes to podcasts, and he’s all about the long game.

And so I stayed patient.

And then, when it’s ready to earn…

More patience.

That part isn’t as easy. Once you’ve got a taste of potential, you want to double down, make it happen faster.

I’m not saying I HAVE that patience. Seriously, I want to create all the revenue streams. And I want them now.

And yet, the one revenue stream that has appeared almost out of nowhere is teaching me that the patient approach may still be the best.

Brainstorming on how to earn money.

I wanted to find all the revenue streams for my website
I wanted to find all the revenue streams for my website

This amazing thing started happening.

People were coming to my website.

I would post an article related to a topic of interest in the independent contractor/driver community, and Google would be nice to me, and I would have visitors.

Okay, so what can I do with this?

I have to say, maybe one of the best things to happen to me is that there IS a limit on time. I knew there were a lot of things I could do, but I still really only had time to work on content. Maybe at some point, I could take some time off and work on the other things?

Patience is still the key here. That’s a good lesson.

But… when it IS time to do something, what should I do?

During the winter, my wife and I were able to get away to our favorite vacation spot. Those couple of days were one of the best things to happen for me. It was just a time of retreat, prayer, and brainstorming.

And I started thinking, how can I create income from my website? Here were a few of the thoughts:

Affiliate marketing.

Affiliate marketing is a form of advertising, where you can link to products or services, and if people buy those products, you can earn a commission.

I started thinking through the kinds of things my audience would look for. There are financial products – book keeping, tax related, and commercial auto insurance. I could find products like delivery bags and phone holders. What about services and software that independent contractors can use?

I got on board right away with a couple of affiliates. Of course, there’s Amazon. I could recommend books. There are all sorts of bags people could buy. All sorts of things. And the pay…. is small. So far. This is a patience thing. I found a site that can put couriers in touch with commercial auto insurers. This site was one of my first revenue generators, although again, not a lot. But now I’m making enough money to at least pay for the monthly hosting costs.


There are all sorts of things you can dive into right away. Google Ad Sense. WordPress has their own ads. There are some ad networks that will start you out right away.

I read up a lot on advertising. I didn’t want to clutter up my site with some of the ads from some of the networks – they annoy the heck out of me on other sites, so I don’t want to do that here. And a lot of the entry level options? They pay like entry level options.

But I also knew that once my traffic reached a certain point, there were other options that paid quite nicely. I wasn’t there yet. But I was growing. I decided to wait.


This is similar to affiliate marketing, but there’s something unique about my particular niche. I write about delivery for gig economy websites like Grubhub, Doordash, and Uber Eats. Some of these companies will pay for referrals if someone signs up and delivers through your particular referral link.

I knew a lot of people who were active on other channels such as Youtube and Instagram who were utilizing this a lot. I knew this could be a fantastic source of revenue. However, I wanted to do it right.

More patience.

Paid content and membership sites.

There’s a common practice among websites that provide information for their readers: You can get some content for free, but the REAL GOOD STUFF you have to pay for. Join a mastermind or become a member, and you get the best of the information.

I could see some things where that would really come in handy. What could I offer that is special that people would pay for?

I think this can be a useful way to do things. I’ve paid some folks for information on their sites and to me, it’s been worth that money. But, to be honest, I struggle with whether this is right for me.

I go back to wanting to provide content with no expectation in return. I don’t want someone to come to my site, get some good info, but then feel pressured into plunking down money to get the real information. Not that I’m ruling that out, but again, if I do it, I want to do it right.



Much of my audience will deliver for one particular delivery site, and sometimes they’ll get shirts or delivery bags with the company logo slapped all over it.

But what about someone like me, who discovered the best way to work is to deliver for more than one company? That’s part of the advice I put forth. Are there better options?

Maybe I could provide them. I read up on a lot of people flipping merchandise or creating products to sell on Amazon or other sites. They gave advice to build up a social media or website presence around their product, become an expert in the field to draw people to the products.

I’ve already done all that. Can I utilize that to sell my own products?

Trying to put it all together.

Okay, so what do I do with all these ideas?

I started putting together some thoughts on how I could develop these streams. What steps do I need to take? Which ones should I prioritize?

Honestly, it kind of created some stress for me. I think because there’s still that hesitance in the back of my mind. I think mainly, I didn’t want the content creation to be distracted by the monetization strategies. And there was that time thing.

I put a little bit of affiliate marketing into place. I started brainstorming ideas on the membership idea. That could be really good.

And then as soon as my traffic hit the right levels to qualify for one of the better advertising programs, I applied.

But the rest was going to have to wait. I still need to pay the bills, and I don’t want to shut down the content to do the other things.


A big surprise, and an epiphany

I got the wonderful news: I was approved for the advertising program.

I thought I could make some reasonable money. A few hundred dollars a month maybe, to get started. I could build on that.

I did not expect the results I would be getting. I wrote more about that here, but… the money that I started earning immediately was a game changer.

Now, it’s not money I’ll get right away. The money I earn right now (July) will get paid to me in October. That’ll be my first REAL revenue (okay, a nice boost in September for the last few days of June).

It was enough of a surprise that it really shifted around a lot of my thinking. In fact, I started thinking about the one thing that is really working, and honestly, it’s the thing that reinforces what I was thinking in the first place:

Provide great content, provide it consistently, and help people out who are looking for help.

And be patient.

Return on my time investment.

I went out and bought some delivery bags, put my own logo on them. I bought some shirts. I listed them, and I’ve sold a few.

I make about $4 apiece when I sell a bag. It’s a lot more than I get if someone buys a bag off my Amazon affiliate link.

I could probably really ramp that up. I could put a lot of promotion into it, maybe buy some ads…

… and sell a few more.

I’ll still continue to provide the merchandise, but I think that’s more of a branding thing than a revenue thing. I realized that for all the effort that I could put into the merchandise, if I put that effort into my content, building my audience, and adding to the number of people coming to my site, I’d make a LOT more for the time.


I thought about all the things I could do to add to the affiliate income. More effort, and a few more dollars here and there.

Again, if my attention is put more into content, there’s a far greater return that way.

More patience.

And then the light went on

A light went on in my head about how to handle some of the monetization opportunities with EntreCourier
A light went on in my head about how to handle some of the monetization opportunities with EntreCourier

Last night, I was re-listening to Gary Veynerchuk’s audio book Crush It.


Play the long game.

And I started thinking through where I wanted to go next. The advertising is great, but do I want to rely solely on that stream of income? What should I do next.

I thought about the membership thing. One of the things I have been thinking about is creating an email course, something like “31 Days to a More Profitable Delivery Business.” I could create a community with that, add some live Q&A, track everyone’s progress.

And the light went off. Is it possible I could earn more by not charging?

What if I just made it accessible to anyone. I could remain consistent to that ideal of not expecting anything in return. Keep providing all my information at no cost.

But in doing so, I’m bringing more traffic in. I’m creating more content. That’s going to help the advertising revenue.

And I’m building a community. I’m walking people through steps they can take to up their game in the gig economy. And sometimes, that’ll mean looking into some products. I can point the way (affiliate revenue) or sell it (merchandise revenue) or I can give them ideas of where they can find other options – no expectations for anything in return.

Jab, jab, jab, right hook (go read Gary’s book by that name, it’ll make sense).

And that’s where I am right now.

There’s more to be thought out. More to be worked out. And that’s okay.

This isn’t a sprint.

And that’s what this site is for – to just show my journey as I work it out.

I think the beauty right now of the whole advertising revenue thing is, if that’s remaining consistent, then by October, I can scale back on the delivery work I do. That’s how I’m paying the bills right now. By October, there’s real money starting to hit the bank.

I’ll still deliver some. As much as anything, to keep current on what’s going on so my content remains relevant. But now it can be my side hustle. And at that point, I can be full time on my content.

More time to develop the revenue at EntreCourier. And even more important, more time to start pouring into Paradigm Squared.

Are you earning revenue from your website?

What’s working for you?

I think we all have different philosophies around how we want to do things. Some of the things I decided I want to wait on might be fantastic opportunities for you.

What are your struggles when you determine how to make your money? Let me know down below!