The Path to Becoming a Side Hustle Millionare

A very transparent look at the daily operations of my business and how I leverage my time, equipment, and resources. I've laid out and structured my business to offer so many overlapping services that I can target different niches and always stay busy, allowing for more cash flow with less overhead (the ultimate goal).
Dumpster Business, Storage units, Demolition, Landlording, Junk Removal, Hauling, etc.
Now, I am pushing each niche (each of which started as a kind of side hustle or side project) harder and harder.
This is my path to a blue-collar, side hustle millionaire. What's yours?

[@ProXPowerWashing]

Just found your channel man… I own a power washing biz. Made about 280k this year with just me and a part time guy. You’re motivating me to start documenting my day to day life.

[@danpowers1551]

where are you located im starting one in northern il

[@rollingops]

Keep grinding dude! Whatever you need to do to keep moving forward

[@A-TonHauling]

Great message! I am still trying to get my prices right when the transfer station owners charge a flat rate. There is alot of concrete and dirt work in my area and I may have to consider getting a cdl to handle the heavier hauling. Keep up the motivating content.

[@panagiotispanos2555]

Amazing work all round, I've been following up your journey my friend and I have to say that you are truly motivational and you give a great example with your videos for me to follow your path. I've been planning my side hustle little different in my head but nevertheless you are a great stepping stone. Best wishes!

[@motorcitycraftsman]

I love the variety and diversity of your services. I can relate to not being tied down to one specialty. Sometimes it seems inefficient, most of the time it feels right!

[@rollingops]

Yep, most days it works! Other days it does feel counter productive! I love efficiency and good flow

[@chargermopar]

It's great when you start up in a place that isn't insanely expensive and flooded with money yet the wages are super low. Any business you start has its challenges but if you provide a quality product to good customers success is very likely. My most profitable side hustle has been assembling hydraulic hoses. I am thinking of getting back into it because competition is low and demand is very high. Just need to get my Spanish speaking right.

[@rollingops]

Yes, location, location, location. A key factor in a lot of business.

[@dougbrawley6623]

Its awesome seeing you grow! Keep up the great work, you are very inspiring!

[@rollingops]

Thanks for watching, hope the videos help, even just a little!

[@BeefRocknmore]

You ROCK Dude! Biggest take-away is "learn to user leverage (loans / other people's money (not family)) and equity (stored value in real estate or other) !!! Loans are not taxed as income. And, yes, family/friends are the most likely to piss on your ideas. YOU CAN DO IT... most likely, if it does not work out, that is not the end of the damn world. When I was riding bulls, the phrase was "you gave it your try". Try meaning all you got, but also knowing when to bail.

[@rollingops]

Exactly! a great way to sum it all up! Appreciate you watching

[@kevinryan3241]

Love everything you’re doing keep up the hustle! 🤘😎🤘

[@rollingops]

Appreciate it man! Thanks for watching!

[@frankbalowski1074]

Kudos young man! You're kicking it good.

[@rollingops]

Appreciate you sir!

[@tsoffroad5834]

This mfer is making money! I love how all his "side hustles" compliment each other. First time i seen that. Subscribed to learn more. Keep grinding dude youre killing it. Id like to do the same in my area.

[@jayshoemaker2784]

Cool to see how you tie so much together

[@rollingops]

Thanks man!

[@BakerFitness14]

Loved my 2nd gen. Just starting leaking too many fluids to make it worth it for the business. Personal use now

[@rollingops]

Totally get that, I may be retiring mine as well! Either selling it, or backup of a backup

[@danielc3334]

love the content man, for the record my 22’ 3500 high output (Aisin trans) grenaded the transmission right off the lot with not quite 700 miles completely empty …still have it now seems good but ram trannys…

[@rollingops]

How in the worlddd. That's wild. We're on about 150k miles always hooked to a trailer too

[@danielc3334]

@@rollingops yea no clue apparently it is a common issue with the 22’s specifically

[@rollingops]

@@danielc3334 dang that's terrible

[@josuemiamire]

Open a commercial account with Oreilly auto parts brother, you’ll get better pricing on hydraulic lines, serpentine belts, radiators for your truck etc

[@aurian18]

If you flush the radiator and the issue comes back that's rust scale from the engine most likely. Flush it very well by running the vehicle with a hose attached to the top and allowing it to drain water from the bottom(remove coolant first and fill with water). Do this for about a half hour. Then fill with new coolant, run for 2 weeks and flush again. Then fill with coolant, run for 6 months, drain and fill with fresh coolant. You should be good for regular 2 year intervals after that. Run a 70% antifreeze ratio by doing 1-2 gallons of straight coolant and the rest in 50/50 mix. 70% is the best for overboiling if you overheat it and has the lowest freeze ratio, along with the best rust protection. However, it does not wick the heat away as water does. So it will run slightly warmer.

[@jayhebert8775]

Great video. Thanks!

[@rollingops]

Glad you liked it! Thanks for watching

[@johnrolloffdumpsters]

We need to talk again. You're killing it

[@rollingops]

Ha I don't if I'm killin it, but I'm pushing my limits for sure haha

[@alexwest4362]

Bro you can’t beat a strong 2nd Gen. The market for those are unreal

[@rollingops]

Hard to get myself to ever get rid of it, she just keeps pullin

[@manuelmercado5465]

Awesome video thanks for the info!!

[@rollingops]

Glad ya like it!

[@sethhardin4351]

I only have 1 issue with your channel. We need more videos. 😂. I’ve watched all of them multiple times. Keep up the good work.

[@rollingops]

Working on it! I'll take that as a compliment!

[@archivaldoguzman8316]

Vertical integration is the way to go brother. Good job man you going big places I can see it.

[@rollingops]

Thanks mate! I sure hope you're right

[@gthree0239]

I swear…I have to say this is what I’ve wanted to do for so long. I feel like our brains work similarly. I have a million ideas and have never quite figured out how to incorporate everything together. Seems like you’re doing it well. My issue is that I have a great career (that eats up lots of time) and it’s very hard/impossible to give that up for a side hustle. I feel like I just need to take a leap and pursue at least one of my many ideas.

[@RNrob84]

I’m in the same boat as you.

[@greatestshowondirt]

What do you do for insurance on the rental equipment?

[@Peaceful_Reflections]

“Fortune sides with him who dares.” -Virgil

[@rollingops]

Agreed!

[@Bluekbizzel_gaming]

I've been mobile detailing on the side since last year with one of my homies and we do pretty good considering we still work a 9-5. I've been thinking about getting into junk removal...not sure if I should get a regular trailer and work my way up or get a dump trailer or a roll off. I have a 96 Silverado that is just sitting and not making me any money...I wish it was a diesel but its not so I guess I am limited on what type of trailer I can haul, but I can always start small and work my way up!!!

[@rollingops]

That's the way to think about it!

[@MrDpl096]

I have a dump trailer that I would like to start renting out. Any suggestions on the insurance I need to have?

[@cn9936]

Your channel is very motivational, I too started with a credit card and a vision years ago and started a bounce house company. Unfortunately that was closed in 2008. I have a great career now but want to start a side gig and like skid steers a lot. Id love to hear how to get started. Have you made videos on how you started with the skid? I also want to be a landlord so I need to make the down payment $$$. Thanks

[@rollingops]

Wow, I really appreciate that! I think I have a few videos explaining how I got my first skid, and the reasoning behind it! But they will be older videos, so don't judge me to hard! Great to hear you got a good job as well!

[@cn9936]

@@rollingops of course not! Thank you and keep on keeping on!

[@nickvickrey8692]

Love this long video, puts everything into one and shows how adaptable these businesses can be! I’m super interested to see the tax side of this. I know you said you use a CPA, but what all are you able to write off to bring down what you owe. And do you have a LLC or another holding company above that? Do you have an older video explaining all of it?

[@nickvickrey8692]

Also, where’d you store the dumpsters when first starting? Just in your yard or driveway and tried to keep most rented out, or did you pay for storage somewhere?

[@user-sm4lv3mx5n]

I'm a faily new subscriber love the channel 👍 what video talks about leveraging my existing property to buy additional properties? Keep the hustle brother.

[@rollingops]

Welcome aboard! Oh man, there are a few I have talked about the subject. But I don't know if there is a very specific video about it. This one is old, so don't make fun of me. But it likely gets talked about in this a bit. kzbin.info/www/bejne/a6bGo5SOgKeUkJIsi=nn1n21LweDpr-Atk

[@kbrown706]

Take your fan shroud off and you’ll see oil all on the sides and a nice clean circle spot in the middle

[@rollingops]

100% what it is. I've washed her out a few times. Helps for a little bit and then goes back to it. Also relocated the oil bottle to the rear, so it would stop spray on the radiator

[@DTRhoads21]

When you first started did you pay for your equipment in cash or did you finance? How would you recommend starting for someone wanting to get into the business?

[@rollingops]

I bought my first setup with a 0% interest credit card for 18 months. Paid it off, the. Did it again because I paid it in under 8 months. Not that I recommend it, because it's not a strategy for everyone! Just what I did.

[@kylegrimm]

Delegate and elevate.

[@rollingops]

To the moon

[@kylegrimm]

I say this as I’m literally spending 3 full days working on gravel which I should be delegating to someone way more experienced than me 🤦🏻‍♂️

[@rollingops]

I mean, you're not wrong! But I bet you're saving way more than you would have paid for the job. There were a lot of aspects to that project that you probably were still working through in your head.

[@lawnrebel]

First. 🔥

[@rollingops]

Heyyyy!

[@lonestarcollectiblezcom2602]

Hey Clayton, with the demand getting stronger for your Kubota's, do you think down the road it would make sense to have about 3 skid's and 3 excavators? Enjoy the channel and your video's, keep hustling! Thanks, Brian

[@rollingops]

Yes, absolutely. If the demand goes that way I will absolutely do that. But I want to make sure to hyper focus on the most profitable thing. And at the moment, that is dumpsters.

[@rollingops]

I really need to do more demos with my equipment to get some real value out of the two pieces I have right now

[@larrytanks3844]

would you say having the skid steer has boosted your business? i have 7 dumpsters and live in a town where the closest equipment rental place is like 20 miles away. i think i could do really good renting one or two

[@rollingops]

It has definitely started to pick up for me. And having it for our own junk removal and demolition side business has been amazing in value. The Renting out is icing on the cake!

[@larrytanks3844]

@@rollingops awesome! keep up the great work boss

[@rollingops]

@@larrytanks3844 appreciate it!

[@camerondawley8221]

What kind of insurance do I need for renting out my equipment/dumpsters?

[@rollingops]

Comercial hauling, and liability. Rental insurance is a special one for equipment. Only a few companies offer it

[@brendanstearns6717]

Did you have to get any permits to do the junk removal/hauling. I have thought seriously about starting a junk removal business in my area (also in Illinois but farther south) but I am curious about all the permits I would have to get.

[@rollingops]

Not needed in my area

[@brendanstearns6717]

@@rollingops that’s sweet I’ll have to see if my county has any local permits I would have to get but thank you for the response! Ever since I have been considering it your videos have been a big influence and inspiration!

[@taywest7287]

Turo rentals I also flip pallets

[@rollingops]

Nice!

[@justinrogers8096]

How do you get around cities having deals with waste removal services to only allow their services in the city?

[@rollingops]

Luckily I don't have that problem where I am. I have heard of it though. I'm not sure how it's even legal to restrict the public to using only one company. Screams monopoly to me. But apparently, it happens.

[@poweredbyford87]

I know this is an old comment now, but maybe could start a general junk removal business and be choosy about who you market to and accept as customers to stay in the demographic you want?

[@jasonmerlino3903]

We use an old dumpster for a burn dumpster.

[@rollingops]

Might need to do the same, once one is beyond saving! Good idea

[@kylegrimm]

Caleb talks way too much. On a serious note: I’d really like to hear him talk more about his business

[@rollingops]

You and me both, Caleb's not one to give away secrets, though!

[@blaynebriceno]

What makes it a goos area for a dumpster rental business ? What are some things to look for so you have some peace of mind that it could do well? thank you

[@rollingops]

Compare competitors. See what they charge vs landfill prices. Would indicate something. If there is no "small competitors" find out why. Price, ordinances, exclusive contract, or just simply no one has taken on the big guys yet? Check if your population could keep you busy. 30,000 people minimum is what i would I'd suggest, if you want to eventually be full time. Lots of things to consider. And of course your overhead costs vs profit potential

[@blaynebriceno]

@@rollingops thank you very much. I have a diesel truck.. selling my 5th wheel camper for 20k. So I’ll have the money to grab the dump trailer and bin. There are about 5-7 small dumpster business in my area. I am split between 2 counties, ( on the edge) 140k in one and 60k in the other. Lots of construction going on as I currently work as a gas pipeline inspector I see all the building. Landfill dump is super cheap 20-30$ a ton here.

[@rollingops]

@@blaynebriceno best advice I can give. Don't price yourself cheaper. Price differently. Provide value. And don't undercut. That only hurts you and the industry as a whole

[@blaynebriceno]

@@rollingops yes I did watch your video about that topic. I appreciate your insight and helpfulness

[@loganebey1501]

I have to ask how many dumpsters do you have and how many did you get to before you hired help

[@rollingops]

I started with 1 Dumpster. Basically run 12 dumpsters now (seems low), but we do short term rentals, so we can rent one single dumpster 3 times a week. I needed help in the summertime, when I had a 10 dumpster inventory last year. Because we average 40-50 dumpsters a month off of only having 12. That doesn't include the ones we use for demos or junk removal either. We honestly need about 4 more. Because I've had to turn several people away in the last few weeks. I anticipate the heat of the summer to be out of control this year compared to my last. Marketing, Branding, and more marketing

[@loganebey1501]

@@rollingops Ok yeah I started march 22 and I’m now at 30 managing but barely i just don’t want to hire someone to not keep them busy

[@jazlawncare7126]

Hi there how can I get a hold of you I just ordered my first two dumpsters and 14 foot trailer with 8 k axles it’s a MAXX D got all the info you have provided. Would like to see if you can guide me in the right direction

[@MountainManservices]

Hiring is so key

[@seancasey2444]

Looks like anyone can bust into the storage place with no fence around it .

[@rollingops]

Work in progress! Stay tuned

[@zart3374]

What is your main job? Main job is the sidehustles?

[@tjjohn9992]

looks like you need more team.

[@rollingops]

Getting to that point

[@user-pj3rd5tp1u]

hey Dude you have to teach some jump classes

[@rollingops]

Haha did I jump in this video? 😅

[@user-pj3rd5tp1u]

@@rollingops just messing with dude ,your content is awesome

[@MountainManservices]

Second

[@rollingops]

If you're not first, you're last!

[@nephewsque6751]

Thanks for the ride alone... you brother didn't seem to happy at all 😢

[@rollingops]

Nah, that's Caleb's happy face 😄

[@choricrudo]

Blow out the radiator with some compressed air

[@rollingops]

I have a few times, think fins are just too far gone

[@adanr150]

Is your truck manual?

[@adanr150]

What year? I got 2002 it’s a beast

[@rollingops]

Nope, only downside to it. But my auto has been a tank. I don't believe it is stock

[@danpowers1551]

do you own rentals

[@rollingops]

Yes

[@patrickswagger]

Are You The Millionaire yet?

[@rollingops]

If you look at all my assets, cash flow and equity on paper, yea I guess my net worth would just make it. But it's not quite the way I want to see it. I'd like to clear a million in networths just based on equity. And this path so far is leading me there

[@patrickswagger]

@@rollingops I hope you become a billionaire, my man, living the American dream. Good luck and America first if you can.

[@rollingops]

@patrickswagger that's a wild goal if I was ever to go that route. I appreciate the encouragement man!

[@andrewmusholt9327]

9:47......timelapse p*rn. If you recorded that for the entire property I'd watch that ^.-

[@rollingops]

I have to give credit to @kyle.grimm on that one!

[@vilmafuahingano4805]

Caleb does not look happy 😂

[@rollingops]

Trust me, that's Caleb's happy face 😄

[@MountainManservices]

But not crack heads

[@rollingops]

Crack heads do really good for about an hr lol

[@GaryM42069]

I work for a big rental company , I drive a tractor trailer for them. I was thinking of doing something like this. Do you own the machines you deliver? Can you make money by sub contracting deliveries and pick ups for sunbelt/UR/Cooper

[@rollingops]

I do own the machines! But I like your idea as well, that is definitelysomething I should look into