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Enter the EntreCourier

What’s a guy who is passionate about older adult ministries doing writing about delivering food for gig economy apps like Grubhub, Uber Eats, Doordash, etc.?

IF that lead question confuses you or you read my post talking about starting up Paradigm Squared, let me help out a bit. That’s what I write about on my website at

These are two extremely different topics. How could they possibly fit together?

It all started with quitting my job as business manager for a nonprofit

I was working as business manager for a local nonprofit. I loved the place, I loved what they did, I loved the people there. So I quit.

I quit my job to pursue the things I was passionate about

If you read the earlier post you might be noticing a pattern. I went to school to study for a career that didn’t exist. I take a job that I enjoyed doing for people I like, and I quit. What’s up with that???

As I started formulating the things I wanted to do around older adult ministry, it became clear that 9 to 5 wasn’t going to give me the flexibility to do those things. I had joined the organization to help them along when they needed help, and they now had some others who could step in, so it was the right time to step away.

To pay the bills, I picked up some delivery gigs. I started delivering with Uber Eats, then picked up Grubhub, Doordash and eventually Postmates.

And it was… not that bad. In fact I kind of enjoyed it.

Here’s the crazy part: Once I started thinking like a business owner and treating my deliveries as though they are a business (these companies hire us as independent contractors, so technically we ARE businesses) my earnings started shooting up. I was actually earning more than I had as a business manager, with a lot less stress and a lot more freedom.

Noticing the employee syndrome

I started noticing a lot of people acting and thinking like employees while doing this work. The thing is, when a company hires you as an independent contractor, they’re taking a pass on all the protections that an employee should have. There’s no minimum wage, no guarantee, no insurance, no expense reimbursement. None of it. You’re completely on your own. Too many contractors are taken advantage of in this environment, where they think they have to obey the company’s every whim. Those companies gave up the right to control your work when they use contractors.

I thought I could help.

I started as a platform to teach contractors the business side of gig economy delivery work. It was something I could use to inform couriers of their rights. I could show them best practices. I could teach them how money works and how to tell what their real profits were. Here was an opportunity to show people how to stay out of tax trouble and prepare for upcoming costs. I could encourage them to be the boss.

A Training Ground for Paradigm2

I started the site, and actually pulled it down at one point. I worried that the effort I was putting into EntreCourier would distract me from building Paradigm.

It’s probably a legitimate concern. More than a year later, to be honest, I still wonder how much that’s the case.

At the same time, as I’m putting together my ideas for Paradigm, I kept thinking EntreCourier is where I could practice. It was a sort of low hanging fruit to help me get a feel for content creation. I heard about how consistent content creation could make a huge difference, and I knew all the different things I wanted to say.

So on July 1, 2019 I made a commitment. I decided to commit to 31 days straight of content. I created a series that I called the 31 Day Courier MBA (Master of Business Attitude). To go along with that series, I launched a podcast and set up a weekly newsletter. I was going to find out what consistent and (what I felt to be) quality content could really do.

And I found out it works

It didn’t happen right away. In July I had 2,079 page views on my site. I was thrilled when a podcast episode got 20 listens.

And then August had 1,941 page views. I wasn’t growing, I was shrinking. But I kept at it.

September jumped to 6,453 page views. October down to 4300. December: 8800. January 14,500. It was growing. In May and so far in June I’ve averaged more page views per day than I had in the entire month of July.

Along the way Google found me. And I think the content was consistent and it focused on the business of delivering for Grubhub, Doordash, Postmates, and Uber Eats to the point that I think I’m started to be recognized as an authority site when it comes to those platforms. I probably did some things right and probably got very lucky on some other things. But along the way, the growth has been steady.

The growth has been almost overwhelming. The last six months, each month has had at least 50% more page views than the month before. This month (June, 2020) things will level out a little (though I think a lot of that is because there were some extraordinary circumstances behind the last couple of months of growth). The newsletter is growing slowly, and the podcast is also pretty slow. But it’s growing.

To the point where I think I’m ready to turn a corner…