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Delivery Boi by Caleb Smith

Delivery Boi

by Caleb Smith

March 22nd 2019

I’m sitting a coffee shop in Kansas City Missouri.

Today is my birthday and although 29 isn’t necessarily a year that should be noted as special compared to other years, for me it is.

For two reasons,

One I’m sitting across from Bambi Bloodlust roller/in-line skater extraordinaire, and she is smiling at me as we scroll through the collection of photos that we have amassed these past few months,

And two, I am here, happy, healthy, alive and thriving and I have some how magically managed to get to this point by skating my buns off for the last few months. (in addition to the last 25 years.)

Before Rollerblade® reached out to me in January I had already made the conscious decision that I was going to fully embrace my passion for skating and figure out a way to support my life through it.

Having Rollerblade® ask me what I wanted to accomplish this year was interesting. My heart and mind skyrocketed at the thought of a sponsorship, after all isn’t that every 12 year olds dream? So I immediately listed of as many of the crazy nearly impossible tasks I’ve been thinking I wanted to prove possible. 12 century skates, a skate-mission trip to Nigeria, RAGBRAI, BRAG, STP, I wanted to do everything and prove myself worthy of Rollerblade®’s recognition.

But how do I do these things, or more importantly how do I afford these things?

There’s no way to work a regular job and ask for all this time off. I’ve been asking bosses the same question for years, “hey boss, may I take this week off to go skate around the world…” and my bosses would 99% of the time say no. Often they couldn’t see the value in what I was pursuing. So I was stuck in this cycle of working to pay my bills to stay alive to work to pay my bills.

How do I change the world when I’m stuck in the same pattern with the same restrictions keeping me from going out to truly and fully share my passion?

So I pulled that old fashioned move of relocating to a bigger city (Chicago…) to see what possibilities I might open up. (And obviously to be closer to Bambi)

The first thing I did when I arrived was reach out the the in-line community there in hopes of being directed towards some work, and some money….

A few skaters/ avid cyclist said “try delivery work”…

This idea sounded just crazy enough that it might work.

So I signed up for post-mates food courier service and every other app I could find that might potentially allow me to make money and stay alive, and best of all spend more time doing what I love most in-line skating.

The first few days, weeks even were extremely disheartening and I almost gave up. 

I was going out to skate in single digit temperatures with icy, snowy, salty, slushy roads. I was on constant alert of the infamous Chicago traffic and the always looming thoughts of being smashed by a reckless driver, probably on their phone… I faced the cold temperatures amplified by the wind wiping off of Lake Michigan, sometimes feeling like a knife that would cut through me and stop me dead in my tracks.

Lesson 1 - layers, layers, layers...

It took me a week to realize I needed to construct something better to protect my face and neck, so I finally crafted the mask I had been contemplating for months. 

Bambi helped me brand it with my favorite word “STRANGE” which so accurately describes me.

I quickly learned to carry a small can of wd-40 to fight the constant barrage of salt and water that destroyed my wheels and bearings.

I was barely making any money but I was spending entire days rolling around downtown on my RB80’s, sometimes 3 hours sometimes 8 hours, however long my body could manage to fight the cold and fatigue. 

I often would find myself laughing out loud when I thought about people asking me how I was doing this or how I trained… This was it, training at its finest I thought. Every 20 minutes sprinting 2-4 miles in hopes of making a few bucks..

The one thing that really kept me going was the response I received nearly every time I delivered a meal.

“Woah! You’re on skates!”

I noticed that there is an innate reaction in every single person, skates and skating make people smile, but why? 

I thought about this a lot, why are people drawn to skates? 

Why am I drawn to skating? 

I mean obviously I love it, obviously I think it’s cool, I’ve meet my friends and traveled to amazing places and experienced so many beautiful things.

But deep down, what about skating is so magical?

So January goes by with an assortment of hard learned lessons. February I started to adapt, to change myself and my skating to better suit my goals.

Rollerblade put me on a set of 3 x 110 hydrogen pro wheels, which I don’t want to sound biased but they have the best urethane composition I have ever rolled on in my life. Period. The speed and control they gave me were unmatched and this made the entire “delivery-boi pursuit” 1000 times more achievable.

So here I am, March…

I landed a job for a local bicycle courier company in St. Louis Missouri called foodpedaler.

I filled out an application online and they reached out immediately. They were surprised and interested in the concept and possibilities of an in-line skater vs. the traditional method of cycling.

They agreed to take a chance on me so I relocated again, which isn’t hard due to the fact that I can fit all of my worldly possessions into a backpack and go at a moments notice.

So suddenly I’m spending my days in downtown St. Louis.

My days have become the most beautiful reciepe, that goes as follows.

I wake up, make coffee and do yoga. Cook my breakfast and pack a lunch. From there it’s a beautiful 3 mile commute on a raised “rails to trails” style bike path that leads directly from where I’m staying to the metro link rail. Each morning I spend the 3 miles listening to the news or giving thoughts to how I would like my day to unfold. The STL metrolink train takes me right into the heart of downtown in just under 20 minutes, enough time to read a few pages and write in my journal about my prior days adventures. From the train stop in downtown I walk two blocks to T-Rex – a modern innovative co-working space for entrepreneurs and startups looking to change the world. Which for me is the perfect environment to spend my time when I’m not delivering and plan out my 2019 world goals.

 Plus there is always free coffee,


My boss Alex is obviously a cyclist and a bright-eyed computer wiz marketer who seems to invest himself in too many projects to count. It’s been nice to spend my free time talking to him about skating and worldly ambitions.

And finally the delivering…

11-3 Monday through Saturday I’m delivering food to hungry STL downtown patrons. 

I put my RB’s on in the building lobby, sling my large red courier backpack over my shoulder. Honestly my bag has so quickly morphed into a piece of me and my life it’s crazy. I’ve developed a relationship between me, my skates, my pack, and my body allowing me to navigate crazy terrain, anticipate and execute maneuvers through the tiniest of gaps to jumping over walls and obstacles that might normally inhibit a bike or a car. 

I have only a 3 mile radius in downtown to navigate. I’m outside observing people, the skyline, the art, the whole world is just there moving and I’m moving through it on my skates. 

I’m constantly meeting new people, always again with the reactions to my skates, to me as this character I’ve become lately, or more likely always have been.

I spend a lot of downtime honing my skills in Kiener plaza, a newly renovated park that sits in the middle of downtown with a perfect view of the arch, surrounded by art and people walking past, I am an unchained skater dancing around to the beat of my own drum, and the beats inside my helmet. (Often lofi-hip hop) 

I’ve had truly so much time on my skates lately that I’m always in a state of falling in love with this beautiful world and the freedom my Rollerblade® in-line skates give me.

Oh, and that’s it, I finally found out what it is people smile about when they see me roll up with their delivery, or when they watch me spin and roll endlessly in circles around the city streets and parks,


They see the freedom skating brings to me.

It’s so clear when you realize it, freedom is what so many of us are seeking, freedom from our jobs the keep us glued to a screen or a chair, freedom from the stress of life, freedom from the same old routines that we often allow to permanently keep us in our habits and crippling patterns. 

Skating brings me freedom, and even better it is teaching me how to share that freedom with others. 

So… being an in-line delivery boi for the time being is pretty pleasant, I’m making enough money to feed myself and provide myself with the basic necessities of life.

 I’m learning to truly value that things I have, no longer craving and consuming to feel better and more fulfilled, 

And my heart is re-aligning with the goal of sharing my passion and this dose of freedom skating breaths into life.

When Rollerblade® asked me what I wanted to do with my year and with their support I would have never guessed I would be delivering chicken panini to tech-workers and police officers. I wouldn’t have guessed I’d be spending hours a day talking with strangers about skating, causing kids to gasp with excitement when this in-line skating crazy man jumps over a park bench going at Mach 10 speeds. I wouldn’t have guessed that being a sponsored skater would be more than impressive athletic feats and dangerous stunts.

Being a skater is just about being a skater, through any and every form, no matter where you are, what you’re doing, or what your skill level is, skating is skating, and sharing the love you find in it.

Peace, love, & good vibes,

- Kaleboston






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