← Back to all posts

The stage where most future courier business owners get stuck | Issue #5

by Roslyn Ellerbee
Mar 08, 2026
Connect

Hello Friend

Earlier this week I had a conversation with someone who wants to start a courier business.

Not just thinking about it casually.

They’re serious.

They’ve been researching the industry, watching videos, reading posts, downloading resources, and trying to understand how courier companies actually work.

Sound familiar?

If you’ve ever thought about starting a courier business, you’ve probably done the same thing.

You start exploring.

You look up how medical courier services operate. You start learning about contracts, deliveries, routes, pricing, and maybe even what type of vehicle you might need.

At first it’s exciting.

 

The opportunity feels real.

But then something interesting starts to happen.

The more you learn, the more questions start showing up.

How do you actually price deliveries?

Where do courier companies find clients?

Should you hire drivers first, or secure contracts first?

What software do courier companies use to manage deliveries?

Before long, you’re not just curious anymore.

You’re deep in research mode.

And here’s the thing I’ve noticed after being in this industry for more than a decade.

 

The Same Three Stages

Almost everyone who explores the courier industry goes through the same three stages before they actually start their business.

The first stage is curiosity.

The second stage is information overload.

And then there’s the third stage.

The stage where people either move forward… or stay stuck.

This is the moment where the idea of starting a courier business turns into something real.

Or it quietly stays an idea that never gets off the ground.

And the surprising part?

Many people don’t even realize when they’ve reached that point.

It feels like progress.

But sometimes it’s actually hesitation.

I see it happen all the time.

People spend months learning about the industry, but they never quite make the shift into building something of their own.

And honestly, I understand why.

Because when I started my business back in 2012, I had no idea I was stepping into the courier industry.

My original idea was simple.

I wanted to run errands for people visiting my hometown at the beach.

That was it.

 

No big logistics vision.

No long term courier strategy.

Just a small business idea.

But business has a funny way of evolving based on what people actually need.

Soon businesses started asking if we could deliver documents. Then prescriptions. Then medical items.

Before long, I found myself operating in the courier industry without even realizing it.

And over time, that small errand service grew into something much bigger.

Looking back now, I can clearly see the stages entrepreneurs go through when they start exploring this industry.

And I can also see where people tend to stall out.

It’s not because the opportunity isn’t real.

It’s because at some point, curiosity has to turn into action.

And that’s not always an easy shift to make.

 

If you want to read the rest of this story and learn the three stages most aspiring courier entrepreneurs go through before launching their business…

Subscribe to keep reading this post

Subscribe

Already have an account? Log in

Loading...
The Day a Contract Exposed Everything | Issue # 4
  Hello friend,  There’s a version of getting courier contracts that looks impressive. Predictable revenue.Recurring routes.Consistency.Leverage. And then there’s the version no one posts about.  If you’ve ever searched “how to get courier contracts,” what you’re probably imagining is stability. You’re imagining no more refreshing apps. No more hoping something pops up. No more guessing what ne...
Contracts Don’t Come From Apps | Issue #3
  Hello friend,  If you’re refreshing load boards in hopes of landing contracts, pause. Inside this week’s issue of From the Desk of Roslyn, I’m breaking down something most courier owners misunderstand: Direct clients don’t come from apps.They come from positioning. In this issue, I share: The real difference between gigs and contracts Where direct courier clients are actually located Wh...
The Hidden Cost of Running Everything Yourself | Issue #2
    Hello Friend, I want to talk to you like I would if we were sitting across from each other, no filter, no fluff. If your courier business feels tight…If you feel like you’re constantly checking your phone…If every day feels reactive instead of strategic… The problem usually isn’t your drivers.It’s not your clients.And it’s definitely not because you’re “still small.” The real issue is this...

From the Desk of Roslyn...

This weekly publication gives you a behind-the-scenes look at my life and business—both personal and professional. You’ll receive real-life lessons on leadership, systems, and growth, shared honestly from the CEO seat. No fluff. No recycled advice. Just real perspective to help you think, move, and lead differently as you build something that lasts. 👉🏽 Subscribe to get the insight most business owners learn too late—before it costs you time, money, or momentum.

Manifesting Greatness With Roslyn V. - 360° Business Coaching

© 2026 Coaching with Roslyn V.

Stay Connected


Join my mailing list to receive free weekly tips and insights!