College Dropout and His Million Dollar Delivery Business

Hey dumpster fam! Taking a break from the usual junk hauling to bring you something totally different today. I'm hitting the road for a ride-along with my little brother, Caleb.
Now, this kid's a total badass. At just 21-years-old (and a college dropout, no less!), he built his own package delivery business from the ground up.
Let me tell you, the world of package delivery is a whole different beast than the dumpster business! Overhead costs are through the roof - way more than anything I deal with in the junk hauling world.
But Caleb isn't afraid of a challenge. He's already managing a fleet of 15 trucks and a team of 15 employees, and that number's only going up!
We're gonna be diving into the daily grind of package delivery, seeing the pressure firsthand, and maybe even learning a thing or two about taking risks and building something from scratch.
This was a wild ride, folks, with a lot of lessons learned. Trust me, you won't want to miss it!

[@need4speed98]

"I fought the wall and the wall won" exact quote of some song, I'm sure of it. Least he didn't get hurt, hitting solid objects is never fun

[@alanhawkins9478]

Exact misquote. Song is "I Fought the Law, and the Law Won"...........

[@BeefRocknmore]

Carts! Had one when I was in my teens. SO much fun. You guys rock! Of course Caleb is fast. That stache adds 10 HP.

[@darwindropmazda]

Great video! Im a ups driver and definitely knows what he goes thru 👍🏾

[@rollingops]

Some might say the job comes with a lot of.....baggage.

[@darwindropmazda]

@@rollingops I’m just glad we are company employed and don’t have to do that contract stuff.

[@grrrr6999]

When I was in Reno they forced a 10 route minimum on ownership. You could do it with the rigs (feeder) there though it was a main hub. Hopefully your bro gets to a point where he can hire a supervisor. The contractor I knew, I would usually run into at the country club twice a week playing golf.

[@kylehamm7287]

Best vid to date. Was great seeing a day in a life of your brother capped off with carting. I just hope my 2 boys have a bit of the ambition that you guys share

[@rollingops]

We pulled this together on a whim, but it was fun one to make!

[@localguy9416]

Love your videos. It was great to see your brother's perspective on his fedex business.

[@rollingops]

Glad you liked jt man! It was a fun one to make

[@autotec20]

I think I have seen most if not all of your spots that's one of the better ones you can tell you love your brother and for those of us with siblings who are also our closest of friends, it makes for a nice life😬

[@andrewmusholt9327]

This reminds me of my old job as a process server (serving court papers) - when your route was in town, you make bank. When your routes were out in the boonies, delivering to random houses/towns ....you'd burn so much money, and tear up your car from all the gravel roads, and not make much to cover it.

[@chucksterock]

Love the karting. I've run a superkart the last 15 or so years. Stupid fun!

[@rollingops]

Absolutely!

[@AdamRapier]

The whole “must be nice” or “daddy’s money” comments always get me when I see them. Really the only “privilege” (sarcasm on the privilege) you guys have is being smart with your money to have the capital to start businesses. Most people either weren’t taught that skill or willing to learn it. Keep hustling and let the haters drive the algorithm to help the channel grow more.

[@rollingops]

Appreciate it man! We're both just grinding it out and taking risks. That's the formula in my opinion

[@lisawilson4551]

I love my delivery guys and gals, I just can’t believe what they grow through each day. When they come here, they always have a smile on because I have never ending parcels. I think I have an automatic beacon to my house. Lol but I have a big yard to turn around. We always have it ploughed out for them at least three cars, wide boys and girls don’t back out onto the street. Turn around and be safe. See you tomorrow.. It takes a lot to keep business like this going. You’re doing a great job hang in there.😀👍❤️❤️❤️

[@rollingops]

Drivers definitely rember customers like you and appreciate you! I promise

[@Lifes_Apprentice]

Starting and running a business is hard...It sounds great until you are there

[@kmcclarney]

Love the video. Im curious how yall both got the entrepreneurial bug in ya? Has your family always been self employed?

[@rollingops]

Our dad was a police officer, and our mother was a teacher. It really starts with us. Honestly, as I sit here, I can't think of an aunt or uncle either who runs their own business.

[@kmcclarney]

@rollingops that's awesome.! I own a medical repair business that I started. I was lucky where I saw my dad owning businesses all my life and that gave me the entrepreneurial bug. So I think it is even cooler you two have gone at this on yalls own drive. I'm looking forward to seeing more of your business adventure

[@2Peachcobler]

Since he only has one semester left, I think he oughta go back and complete that semester so he has his degree otherwise the money he put towards all the other semesters is lost. Also, why is it FedEx mail UPS also, prime why do they not knock on the doors anymore. I hate it when packages are delivered, but I don’t know they’re delivered because nobody knocked on the door to let me know they were delivered. porch pirates or so active in my area so I really would wish they would knock. On his rule route I guess they don’t really have to worry about that as much.

[@kylegrimm]

Next you need to show how talented your brother is on the drums

[@rollingops]

Absolutely

[@chargermopar]

Around here if a road is not paved you cannot go more than 15 miles an hour or you will destroy your vehicle. With all of that dust it can't be good breathing it all in. I can imagine the debt he's having to service. The go kart track we had is now a condo complex. I need to get my Attex six wheeler back into action someday!

[@BentIronBins]

Hmm loose money on that route sounds like the perfect route for me don’t want to wreck my perfect record. 🥺

[@travisB58]

Did you create your own plans for the roll off truck on the metal needed or did you find something online with plans for it?

[@rollingops]

I just based all my measurements off my existing trailer system. Copied that but made it longer and beefed it up a little

[@user-sm4lv3mx5n]

Went carting for the first time my boys are hooked. I'm sure it will cost me some money 😮

[@rollingops]

Open your wallet!

[@Not_sure5]

Is he allowed to have a winch on the FedEx truck? Seems like it would pay for itself. Also, love the checkers or wreckers attitude towards racing 😂

[@rollingops]

He has a winch setup on his jeep! It has def paid for itself

[@Not_sure5]

@rollingops I figured he could put it on the trucks and they can pull themselves out. Save a bunch of time.

[@joshmcaloon6998]

@@Not_sure5 people that drive little delivery trucks typically aren’t smart

[@joshmcaloon6998]

Only the owner will care

[@Not_sure5]

@joshmcaloon6998 Dude is the owner. I see what you're saying though. But options are to wait hours in the cold, or suck it up and pull some cable.

[@andrewmusholt9327]

Super nerd question: is the device he's holding at 16:20 a Zebra TC77?

[@jake22-1]

At least you guys don't live in the Northeast. Illinois in that place called Chicago. Highest crime rate. No guns go figure.

[@ronkegley6591]

You need to pur a mic in him. Can barely hear your brother.

[@hornedgod2873]

Your brother is thin Shane Gillis? Lol

[@rollingops]

Bruhhhh, I'm weezing 😄🤣

[@grrrr6999]

Ask your bro about the complaint fine.

[@rollingops]

The what?

[@grrrr6999]

@@rollingops fedex used to fine the contractor if they got a complaint about $200. I seen a lot of crazy crap with that company although I never worked for them.

[@BigBushFarms]

First

[@sparksmcgee6641]

Just had that video of you whining about getting caught running a commercial staging yard in a residential zone distric on a person at risks home that didnt understand what was going on. Have you manned up and started following the law or are you still bragging about making money while not following the law? Do you have commercial insurance on your truck? Do you have commercial insurance on youre trailers? Do you have insurance for equipment rental? Let me guess you still have a "liability policy", fake million dollar policy that covers nothing.

[@rollingops]

Uhhhhhh I pay an insane amount of insurance. Actually, and always have. Probably one of my largest expenses unfortunately. DOT numbers and crossing state lines kinda make it necessary. So, to keep those numbers, I'm required to have a million dollar policy just from that. Not including insurance for my truck and trailers, which are also insured commercialy, yes. I won't get into all the numbers, but I pay thousands per month, for all my liability, equipment and employee coverage. That video I made a couple of years ago got an insane amount of attention I never expected. I never said I was right for what I did, only that I didn't like how the city handled it. Especially because they never could cite what was being done illegally, and that they made it my grandfather's problem instead of addressing my company directly. Again, I never said I was correct for it, I just felt there was a quicker and easier solution. There hasn't been a can at the property or any other residential property since. I'm sorry that video was the first impression you got of my channel and my business. I'm in no way perfect, but I try to do my best to follow every law. So maybe I "manned up" I guess that's your call.

[@JackofHaulTrades]

Day in the life videos are the best kind of videos! 🫡

[@rollingops]

Glad you like em!