Truck Drivers: Beware the 1099! - Words of Caution

What follows is a social media conversation I had recently with a truck driver. He was seeking advice about signing up with a trucking company claiming they pay company drivers $100,000 per year (as 1099 income). It sounds great? 100k a year! You can live really well on that, right? But there's a little catch. 1099 statements mean you're being paid as an independant contractor, not an employee. Technically, there's a huge legal distiction between the two and not to be taken lightly.

I lost my patience knowing the guy had already made his mind up. I have not named him for obvious reasons.

HIM: I found a $100,000+ a year job as a company driver., but you are responsible for your own taxes you will be filing a 1099. Inbox me your information.

ME: Probably illegal. Find a reputable company if you're going to be an employee. This one, you'll get screwed.

HIM: how can you get screwed if they 1099 you I never heard of this before explain

ME: OK, John, I'll try. Any good road driver can make over 100k per year with a decent company these days. You said you can make 100k on a 1099. That means you will pay the full Social Security tax, both employer and employee portion,15% total. So you will pay 15k off that 100k knocking you down to 85k just to start. Then, say you want 2 weeks off for vacation. That cuts your gross income another 4k down to 81k. Now, you will need some health care insurance, oh that ain't looking good, figure on another 12k minimum. That knocks you back to 69k. What about some disability insurance in case something bad happens? Another 2k, down to 67k. And you haven't paid a dime yet in federal or state income tax. Now, what about road expenses, like meals, hotels, showers? I could think of more, but, please believe me, you will get screwed. I spent my life in trucking and I've seen so many get taken for a ride. Good luck. 

HIM: but this is standard and get an extra $600-$1000 a week should help with benefit. Correct me if I’m wrong plz

HIM: it’s call good business no one forcing anyone it’s a contract you have a right to hire a lawyer if you don’t understand the contract or you can sign the contract and get a lawyer to try to sue that company. This been around for a long time so I will say good luck with that.

ME: Yep, it's your life, go for it! I was just trying to warn you. And you were asking for advice. I knew I was wasting my time, but I tried. Carry on. Oh, and a couple things, since you'll be self-employed, don't forget to budget for a tax accountant/bookkeeper, minimum, a couple grand for a good one (That was quite a few years back, they're probably a lot more now). And you should put a lawyer on retainer, and those guys ain't cheap. And with that independant contractor status, you may now have some legal liability in case you get in a wreck. Better set up an LLC for that (more ongoing costs). Get a seperate business checking account to make it easier as you will have to file business tax returns as well as personal. More fees. DO NOT fall behind in your estimated income tax payments, as the IRS will come crashing down hard on you, I've seen what they can do. BTW, I was a driver for 38 years and also had a sideline income tax prep and bookkeeping service for many years, specializing in trucker service. You will quickly find a big fish (the government) and all sorts of little fish circling and taking chunks out of that 100K. Save this post and let me know how it's going in a couple years. Good luck.

I admit, I was short tempered with this guy, but I've seen it so many times. These trucking companies taking advantage of drivers that have no business experience, and most of them are not legal if a company assigns you equipment, tells you where to go. It is illegal to misclassify an employee as a 1099 independent contractor to avoid paying payroll taxes and benefits. 

If any of the following apply, you are an employee, not an independant Contractor.

• Company drivers: Drivers who use company-provided equipment, follow company-set schedules and routes, and are subject to the company's direction and control.
• Lack of investment: Drivers who do not have substantial capital investment in their own equipment and tools.
• Exclusivity: Drivers who are exclusively tied to one carrier with no ability to perform services for others.
• No control: Drivers who cannot decline loads and must adhere to specific instructions on how to do their job.

I've talked until blue in the face to some drivers that decided to try this, one in particular. He had a wife and young kids and was always near the top in earnings for us as he would do anything, take extra runs, work 6 days a week to make money. He didn't have an earning problem, he had a spending problem, if he had cash, he had a need to spend it. After a while, a small trucking company owner got in his ear, preaching that he could make $2 per mile working for him. "Just buy a used tractor and come to work for me". I couldn't talk him out of it, all he heard was $2 per mile and he was going. He eventually asked me to do his books and tax returns for him. He was in deep, so deep, it ruined his life. He ran hard for this guy, was never home. I talked to him once while he was on the road. He was running in 95 degree heat, his A/C had quit and he couldn't afford to fix it. He had trouble just paying for basic repairs to keep the truck on the road, let alone fixing the A/C. Finally, he went to the trucking company owner telling him he didn't know how much longer he could hold out. The owner told him, he could solve all his problems with a new tractor that got better fuel mileage! It didn't end well, it ended horribly.

There is not one driver, that I know personally, who successfully switched to be an independant contractor. Every one of them eventually went back to work as an employee, with most deeply in debt and paying off their previous obligations. That's not to say it can't be done, there are exceptions, but "why take the risk"? Many years ago my wife (the one I had at the time) asked me why I didn't buy a truck. That was my answer. Truck drivers have a difficult enough life, why add a whole bunch of stress to it, while working for less than a reputable company would pay?

One driver told me he could write off meal expenses as an independant contractor, while employees couldn't. That is true, the income tax reduction reform in the first Trump term did away with the employee business expense deduction. While away from home overnight employee truckers could deduct $65 per day for meal expenses as an itemized deduction. It is important to consider that this was not a tax credit, but a deduction. And only those expenses that exceeded the first 2% of your adjusted gross income were deductible. If you compare this as an employee to your company paying half your social security payment (7.5%) as well as matching contributions that most make into your 401k of several thousands of dollars, paid time off, company contributions to your health care, disability and life insurance plans, it's not even remotely close to meal deduction savings.

A Canadian Trucker's Point of View

Karl Krebs is a Canadian trucker who "legally" trucks frequently in the USA:

Karl writes in referance to the link to the article below: "The author discusses the recent decline in the number of Canadians traveling to the United States through the Pembina ND crossing, suggesting that this decrease has been is a form of protest among Canadians. They express frustration over discussions about the potential annexation of Canada, stating could be further from the truth. This liberal-minded media outlet is guilty of falsely spreading fear. I refer ti them as "the false press" or rather than the "fear press."

Anyone who travels to the U.S. as frequently as I do understands the sense of freedom and exhilaration that comes with crossing the 49th parallel. It simply feels better—and is better—to be in the United States whenever possible. Donald Trump is not the issue; rather, we are facing a crisis of leadership in Canada that is prompting many Canadians to seek opportunities elsewhere. It may not be the U.S. right now, especially with the current state of our Canadian dollar, but as someone who spends a significant amount of time in the United States, I can assure you that it remains the best country, bar none. It saddens me to admit that this includes my own experience of living in Canada.

We were once a proud nation, but now we find ourselves feeling defeated. We are under a government that seems indifferent to our ability to thrive and proper in our own country. Currently, Pierre Poilievre is a prominent figure who aspires to be the Prime Minister , but he struggles to figure out how to win an election. This leaves us in a difficult position. I am reminded of the movie "Desperately Seeking Susan"; we are desperately seeking someone to lead this country toward a brighter future. However, I cannot clearly identify who that leader might be, as he has yet to emerge, and the party he would represent does not even exist.

This is just one man's opinion. Feel free to share your thoughts in the comments below."

The Road Not Taken

"No Name" CDL, Are you kidding me?

Imagine getting a Commercial Driver License from a state Department of Motor Vehicles and not giving your name? No Name. That's right, you can get a CDL in some states without a name on it! 25% of over 500 drivers in a Oklahoma check station 3 day blitz were illegal. No Name CDLs!!! My jaw dropped when I read this. State Patrol and DOT did a 3 day blitz at a check station just east of the Texas border. I never heard the term No Name CDL before. Are you kidding me? I told myself "this is fake bullshit." Then I checked it out, it's all over the Oklahoma news but so far ignored by major news media. This has to end! Get these illiterate steering wheel holders off the road and shut down the damn illegitimate trucking companies now! During my professional driving career, I lived in two states, Wisconsin and Utah. Having to be issued CDLs from each, I wonder what they would have said if I refused to give them my name? As the famous Vince Lombardi once asked "What the hell is going on out there?

Read it here, credit Americanwire News and Viveck Saxena:

Oklahoma partners with ICE, nabs 120 illegals with blank licenses from sanctuary states

Starlink on Standby - No More a Prisoner

It’s been almost a year now since we had Spectrum fiber internet installed. So far, we’ve been pretty well satisfied. We’ve had a couple short interruptions, but not very long, less than half an hour total. I do notice momentary interruptions where the signal cuts out for a few seconds and comes right back. Those are more frequent, but it’s never been an issue when streaming videos.

Previously, after a three year nightmare with CenturyLink/Brightspeed, we installed Starlink in 2023 and were extremely pleased with it. All was great except for the $120 per month cost. So, when they laid fiber in our neighborhood last year Spectrum offered us 1 Gig high speed internet for $70 per month, price guaranteed for one year. That year is almost up, so we’ll see how much they jack the rate up. I had left my Starlink equipment in place and paused service at no charge in case of Spectrum issues.

The last few weeks I’ve been getting notices from Starlink that they now offer standby service as an option on their plans for only $5 per month. (Since I first posted this, I have found out that Starlink has now discontinued the "Pause" option. Your choice now is to either cancel or go "Standby". Supposedly you can still cancel and resume your service at any time.) If you plug your equipment in, Starlink will be on and operational at very low speed 500 Kbps. That is enough to allow emergency messaging, software updates, and basic online functions. It also keeps your system updated.

Yesterday, I decided to give it a try and opened the app which I haven’t used since last year. It was easy to reactivate my equipment to standby and they took out about $3 for partial month going forward. Because the system had been paused and unplugged, it took about an hour to get all the system updates and the dish to orient itself to the satellites.

Once it was done, I switched my phone to Starlink to see how it worked. I was able to go on email and Facebook and while it was slow, it worked and was usable. So now, if Spectrum goes out I can switch in a few seconds and still be online. And if I decide to go back to full service Starlink, I can switch my plan with the app in a few seconds, go downstairs and switch the router from the Spectrum modem to the Starlink and should be good to go! Note: On the Gen II Starlinks you need an adapter to bypass the internal Starlink router. You can order one from Starlink for $17. But that makes it SO easy to switch as you don’t have to connect each individual device over again.

Update 8/21/25: I received the adapter from Starlink today, went downstairs and plugged it in. I then went to my phone and switched over, Starlink did a quick reboot and update and it's working fine.

No more a prisoner of ANY internet service provider. And that's great relief after the insane, customer abusing Brightspeed days! And, I would have no hesitation to switch back to Starlink if Spectrum starts gouging us customers.

How I Switched to Starlink for a Net Increase of Only $24 Per Month

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My (One Week) Project Car

In 1969, after blowing reverse gear in the transmission and junking the first car I bought, I was in the same predicament as before. I had a motorcycle for transportation, but when needing a car due to weather, I had to borrow one of my parents' cars. And, I knew winter in Wisconsin was coming pretty quickly. I had a part time job after school at a Clark gas station, so riding the school bus was not going to enable me to get to work on time.

 

Within a month or two a guy at work told me he knew somebody with a car (1953 Dodge) that was free to take away. Well, the words car and free rang in my ears as I perked right up. I asked him if it ran and he said yes, all it needed was the brakes fixed. So we went over to his house to take a look. It was a kind of ugly brown and kind of beat up but the body was in OK shape. I didn’t care what it looked like and I said if it runs, I’ll take it. He said “OK it’s yours for a dollar to make it a legal sale” and asked how I was going to get it home. I replied that I’ll drive it and get it there and he signed off on the title while I gave him a dollar. I also didn’t tell him I was only 16 and underage to legally buy a car.

After getting a ride back to his house, I got the keys and jumped in. It had a straight 6 motor and 3 on the tree manual transmission. It started up and I drove it slowly home and when having to stop would leave it in gear and turn the engine off. The hand parking brake didn’t work or I would have tried using that. It’s funny how hearing the word “free” kind of caused me to neglect looking very carefully at the car. I noticed as I was poking along Silver Spring Dr. at a few miles per hour a blue haze behind me from burning oil coming through the tail pipe. Getting back home I parked it in the driveway and started to look the car over a bit more, finding two tires nearly bald. Opening the hood there was smoke and fumes caused from oil getting on the exhaust manifold. Looking underneath there were some wet spots on the motor from oil leaks already dripping on the asphalt. Not exactly a chick magnet. I had to keep telling myself “it was free”.

Well, then dad gets home from work. “What’s that car sitting out there?", he asked. I told him and said I got it for free, all it needs is the brakes fixed. He asked “How did you get it here with no brakes?” I told him how. My dad could be a man of few words, especially with me. I remember these, “Get that thing out of the driveway!". He was not happy and I went out and parked it on the street in front of the house.

So, there it sat for about a week. I imagine dad went out and looked the car over after I went to work, but he didn’t say anything or tell me. I was still young and knew nothing about fixing cars. Although I was reading every Hot Rod and Car & Driver magazine I could get my hands on, I had no idea of brake systems and how they work. As I started to realize that I may have made a foolish decision, I kept a low profile around the house, made myself scarce and stayed quiet.

The following Saturday, my dad came in and asked “What are you going to do with that car?” I told him I wasn’t quite sure and he said “Don’t you think that the reason the car was free was because it isn’t worth fixing?” I said “Yes, I suppose so.” He then said “Then get the car title and start heading down to the junkyard and I’ll come pick you up". And, that was the second trip for me to Larry’s junkyard in Butler, with many more to come! I wasn't having very good luck buying cars.

A day or two later mom came up to me and said she was going to stop driving for the time being. She was pregnant with her last child, my sister Karin, and was content to just stay home and didn’t have a need to go anywhere. Altough, knowing mom, I knew she was sacrificing her freedom for my benefit. So, I took over the 1957 Chrysler New Yorker after that and my car shopping was over for a while. And I was a happy guy! That car had a 392 hemi motor and could easily bury the 120 mph speedometer needle!

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More of my classic car stories:

Classic Car Stories:1970 Pontiac GTO - Dick Hands me the Keys!
Classic Car Stories: My Buddy's 1968 Plymouth GTX
Classic Car Stories: My Hemi Chrysler
Classic Car Stories: My 1965 Buick GS400
Classic Car Stories: Mopar Man to Chevrolet
Classic Car Stories: My Second Corvette
Classic Car Stories: My First Corvette
Classic Car Stories: My 1993 Camaro Z28
Classic car Stories: My Three Camaros - One Good, One Bad and One Great!
Classic Car Stories: Mom's 1961 Plymouth Valiant