Caracas Transportation, Inc.

Good luck with it. Hopefully they're all that sort of opportunity and more. I'd be surprised if they live up to your dream but I've been wrong before. I did a short "1099 company driver" stint for about a year when I got pushed out as an o/o until I could get the W2 job I really wanted. It was a stop gap.

It sucked and I was at a good company that was doing it legit. I had full control of the loads that went on the truck. Went home whenever I felt like it and back to work whenever I wanted. That was mostly dictated by needing money not living the dream or anything like that. The freight rates were terrible and they're the same or maybe worse now.

You'll spend a lot more time dwelling in the cab of that truck chasing a bunch of nothing freight trying to eek out a paycheck than you're thinking. I'd take a lousy job at some mega before I'd do that again.

 

Good luck! Remember, second chances have been given to drivers in the past. There will be companies that say no, focus on those willing to give you a second chance.

 

What will you do when the Chicagoland scam artists tell you to run illegal? They have been known to edit logs and tell drivers to make the delivery. Will you do that? If you don’t then they fire you and say goodbye to your last two weeks pay. Will you be able to afford to get home to Florida from wherever they leave you stranded?

 

I’m curious about your 6 years. We’re you making good money each year after taxes? If you don’t mind me asking how much after taxes? I’m assuming Chicagoland as location

 

I worked with a company outnof Memphis for 5 years and a ChicagoLand company for 1. Honestly, the money isn't that great after taxes. The problem is the consistency. All of those companies run only spot market freight. If the company is willing to haul cheap, and none of them are, then a driver can stay busy. Also, they plan loads that you'll be late for a lot so you become a work-in. All of which eats up time and stops you from creating some consistency. I remember getting a load out of Florida once. It delivered to Hunts Point in the Bronx. I got off loaded, but I ended up staying there for almost 3 days. Til they found something in Jersey. There are some good weeks but by enlarge, they're mediocre weeks. I've learned over the years is to find a company in which you can make steady money. One won't get rich driving, but you can make steady money. The formula, in my opinion is to find a reputable company that's small to medium sized, has newer and well maintained equipment, has customers, that way it's loads and money you can count on. You can make 1100 to 1300 take home after taxes with with a reputable W-2 company, but you'll make the same amount with a 1099 company before taxes....that's where they get you.

 

I hear you. I’m not really looking for something permanent which is why I’m considering a 1099 gig. I’ll be working a few months then take time off. Rinse and repeat throughout the year possibly. Is ask about Chicagoland because that’s where we’re thinking about moving to and I know there’s tons of trucking companies. I wouldn’t go OTR though. Just regional or local. I don’t have any experience in trucking and have been self employed for the past 18 years so my work history has been as a non W2 worker. At this point I’m just looking for some periodic work though.

 

Well if you don't have any experience, not even a 1099 company will hire you. I don't really understand..if you're not looking for something permanent, why choose a line of work that requires one to be fully invested?

 

I knew a man who did exactly what I’m wanting to do. He did that for several years. A driving job doesn’t require you to be fully invested if you don’t want it to.