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Simplifying Fleet Ownership with Shawn Williams, owner of Shostoppa Transport in Atlanta, Georgia

As one of the people who keeps America moving, Shawn Williams shares crucial lessons learned about filing taxes and purchasing his first truck. He offers bookkeeping and financial insights he was able to manage effortlessly using Learn how he did it now.

Marcus Cooksey: What do you see as pro’s and con’s between being a Company Driver versus an Owner Operator?

Shawn Williams: I compare being a Company Driver to a bicycle with training wheels. You got the Owner Operator on the bicycle (no training wheels).

MC: It’s almost like being on training wheels a little bit. That may not apply to everyone who wants to become their own boss, but when you become an Owner Operator you’re riding the bicycle. Shawn, can you break that down?

SW: When you’re a Company Driver, if anything goes wrong, the company lends a helping hand. So, if you have a breakdown, they’re gonna pay for your hotel. If your trailer or your tractor breaks down, they’re gonna help you. So basically, they’re going help you do everything that you need, so I’m going to compare that to a bike with training wheels: they’re helping you the whole way, the whole time.  As a Company Driver, you have no freedom, because you gotta go where they say. So, if it’s a blizzard or it’s raining hard and they say, “We need you to go to New York.” Then you gotta go to New York because it’s forced dispatch.

At some point when you want to venture out on your own, then you gotta take the training wheels off. At that point, you become an Owner Operator and you get out there. The difference between a Company Driver and being an Owner Operator. With the company: there’s no freedom. As an Owner Operator, you got freedom. With freedom, you’ve got more overhead.  You’ve got to pick. Do you want freedom and more overhead, or do you want no freedom and less overhead?

MC: For you, it sounds like you were ok with taking on that extra responsibility and that overhead, because eventually you became an Owner Operator. Why was that?

SW: I feel like any job you do, you should move up to the highest rank. So, for example if I was flipping burgers, eventually I need to go from flipping burgers to manager to running all the stores. I feel like I had reached my peak at the company. I did everything that I could do for the company. I was training. I was recovering trucks. I maxed out on the pay. When they said I could make six figures driving a truck.  At first I’m like, “Naw, that’s not possible.” But they kept saying, “Hey, go through these steps and become an Owner Operator.”

I told myself, “I don’t have anything to lose.” I’d rather try and fail, then not try to apply myself and fail. I decided to give this a shot. I knew I liked freedom. I wanted to be able to dictate what I do. If I want to lay in bed tomorrow and don’t go to work, I have the ability to do that. So that’s what made me become an Owner Operator: because I wanted the freedom and I wanted more money.

MC: Tell us some of the stuff you’ve had to learn, apart from just managing a truck. Now that you have a business entity, you’ve got income taxes to take care of, managing costs, filing taxes and possibly IFTA. So, the next thing you probably want to do is to move to authority and have even more

SW: I plan to have my authority within the next 6 months.

MC: That’s great. So, once you’ve conquered one challenge, you’re moving on to the next one. Tell us how you go about getting financing and managing all your accounts.

SW: At first, I was thinking bad. You see so much coming in all at one time. At first, I thought about not paying taxes, that’s the mentality. But long term that’s not what I want to do. Me personally, I’ve got an LLC. I file as an S-Corp, so I pay myself. Even though my business might make 3 Grand, I don’t pay myself 3 Grand. I pay myself a salary every week. So, I pay me, then I put the rest of the money toward the business. I started off using QuickBooks. QuickBooks was telling me this is how much to take out for taxes, this is how much you need to pay
when the quarterly comes up. I hate it. I’m like, I made all this money; I gotta pay these people all this money. But long term you have to do it, because if you don’t pay taxes and you try to go for funds to go for a truck, they say, “Let me see your business return.” They say, “Oh, you don’t have a business return? Then we’re not going to loan you money for this truck that costs 100 Grand.” That’s why I tell people the most important thing to do is pay your taxes, and you can go farther in your business. If you don’t pay the taxes, you have nothing to back you up.

MC: And to pay those taxes, you’ve actually got to keep up with Profit & Loss. You’ve got to show all your expenses. You’ve got to show that your business is profitable to get that loan. They ask for all that stuff: balance sheets, Profit & Loss statements – every time we go for working capital or a loan.

SW: I find the same. You’ve gotta show you’re making something. My first truck I had, I was leasing that truck. Then I saved up enough money to buy me a truck. I had an accountant help me with things like Profit & Loss and all the sheets showing what I made. Six figures looked good, until you see that Profit &  Loss. Your Profit & Loss reveals the true numbers. You can make 100 grand and 30 grand went to fuel.

MC: The only way to see that is by capturing that on a regular basis. Shawn is one of our very active users. What do you see is different by using

SW: I’ve been using about six months now. It’s a quicker way to keep up with all your expenses on the road. For example, I know every day I go to the truck stop, I’m going to get bottles of water, get some type of hot food to go down the road. Before I was introduced to, I was having to save the receipts, trying to take pictures and try to do everything to keep up to get back to my accountant. Now, since I got introduced to, now all I gotta do is get the food, snap a quick picture and boom! It’s uploaded, maybe in 3 or 4 minutes, then just throw the receipt away.” At nighttime, I check in with DUKE. I like how it organizes everything for me. If it’s food receipts, it’s
going to be listed under food. If it’s mechanical, it’s going to be listed under mechanic expense. It’s real user-friendly and it makes my process with taxes and those things a lot easier.

MC: Do you also upload settlements to DUKE?

SW: I like that too. When I upload my settlement, it shows me what I made for that week, what I made that month and what I’ve made that year. I like that it keeps up with everything without having a second person asking me, “Hey, Where’s this? Hey, I need this” to get the bookkeeping calculations done. I have DUKE upload my settlement, upload my mechanic receipts – it shows me: this month, this is how much you made; this week, you took this much loss. It organizes everything for me without me doing the math on my own.

MC: So, you don’t have to type in anything. You just take a picture, it uploads and automatically categorizes your document and then processes the settlements. The app categorizes your fuel, income and all the different expenses automatically.

SW: On my settlement, let’s say I spent $500 on fuel every week for the month. When I go to look at my monthly expenses, it’ll show all the fuel I used for the month and all my settlements for the month; it organizes everything for you.

MC: I always tell guys, when they say, “I made a lot of money but I’m gonna have to pay taxes on it.”

You know, a lot of that stuff is tax deductible. There’s a per diem tax deduction that the government provides as an allowance for food this year. The goal is to reduce your taxable income by keeping up with your receipts. Fuel, for example is recorded as Cost of Goods Sold. You can ultimately reduce
what you’re being taxed on in the beginning by keeping good records.

We always hear that rich people don’t pay taxes because they know how to take advantage of all the loopholes. In the trucking industry, we’ve gotta learn how to take advantage of those too.Shawn, thank you for taking the time to share your experience with us. What message would you like to leave others in the trucking industry with?

SW: Whatever you do in trucking, go to the highest level you can go. Some people are like me: I was stuck being a Company Driver. There might be time where you say, hey, I need more money. I need more freedom.

Once you get your own truck, pay your taxes. That’s the main thing. Pay your taxes. And if you can start your own fleet and hire employees, I feel like the more employees, you can get, the more money you can make. So, one person can make an average of 100 Grand. You got three or four employees, you can make 400 Grand. So I say, have a plan, stick to it.

The good thing about being an Owner Operator is the freedom and money. The bad part is you gotta pay for everything. The month of March, I took a loss of 5 Grand, because my truck was in the shop. So that’s the bad part about it, but long as you stay up to date on your truck, you shouldn’t have no problems.

MC: And when you’re a business owner using DUKE, you can see profit models. You can actually start forecasting what your income will be and even factor in some of those unforeseen occurrences based on trends in the financials; use of financial trends is how a lot of businesses operate. When I worked for a Fortune 500 company, we always knew that there were going to be supply issues we knew there were going to be customer slow pay issues, and that would be factored in based on trends from the previous year. I think that’s a cool thing DUKE can do for you as well.

Special thanks to user Shawn Williams, owner of Shostoppa Transport in Atlanta, Georgia, for his openness in talking trucking from the Owner Operator’s perspective. We salute you for showing people how to be more successful in the transportation business.

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