Questions to Ask When Starting a Trucking Company
Written for the driver who is thinking about going out on their own, and for anyone planning a first truck under a new company name. Part of the list is for you to answer at the kitchen table, and the rest goes to the people whose numbers decide whether the plan works: the insurance agent, the accountant, the factoring company and an owner who is a few years ahead of you. The groups follow the order the decisions come in, from the plan itself through authority, insurance, the truck, freight and cash to compliance and a second driver.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
The plan
Should I get my own operating authority, or lease on to an established carrier first?
Why ask it
Leased on, you run under another carrier's authority and usually its insurance in return for a share of each load. With your own authority the filings, the insurance bill and the hunt for freight are all yours. Leasing on for a year is a common way to learn the business side before the paperwork is yours, so ask a carrier you would lease to what share it keeps and what comes out of each settlement.
What kind of freight will I haul, and what trailer does that take?
Why ask it
Dry van, refrigerated, flatbed, tanker and hotshot work each come with a different truck, a different insurance quote and a different set of customers. Settle this before asking anyone for a price, because an agent or a lender cannot quote a business that has not picked its freight.
Will I run local, regional or long haul, and how many nights away can my household live with?
Why ask it
The radius changes the registrations you need, the truck you buy and what insurance costs, so it is a business question as much as a family one. Answer it with the people you live with in the room. An owner who is home less than was promised tends to hear about it in the first hard month.
How much money do I need in the bank before the first load, and how many months without income can I cover?
Why ask it
Write down the down payment, the insurance deposit, filing fees, plates, the first weeks of fuel and your household bills until the first invoices are paid. Then ask someone who started in the last few years what their figure was and which line they forgot. If the total is more than you have, a later start is cheaper than a loan taken in month three.
Have I driven long enough, in the right kind of work, for an insurer and a broker to take me on?
Why ask it
An insurer prices a new company largely on its driver, and some will not quote below a certain amount of recent experience. Brokers and shippers set their own minimums too, often on how old the authority is. Ask an agent how your license history reads to an underwriter before you spend anything else.
Will I drive the truck myself, or own the company and put a hired driver in it?
Why ask it
An owner who does not drive pays a driver's wage out of the same rate per mile, and has nobody to send when that driver quits or is off sick. Ask an agent how a new company with a hired driver is priced, since the quote will rest on that person's driving record. If you hold the license yourself, a first year in the seat also teaches you what the job asks of anyone you hire later.
Which legal structure should the company have, and what does that change about what I personally owe if it goes wrong?
Why ask it
Take this to an accountant and, if you can, an attorney where you live, since the options and their tax treatment differ by place. Ask what the structure protects and what it does not, and whether a truck loan or lease you sign for personally stays with you if the company closes.
Who does the booking, the paperwork and the books while I am behind the wheel?
Why ask it
A one-truck owner is the dispatcher, the safety department, the billing clerk and the driver. Put a name and a monthly cost beside each job, even if the name is yours and the time is ten at night in a truck stop. The jobs nobody is assigned are the ones that produce late invoices and missed filings.
If this does not work, what will I still owe, and what can I go back to?
Why ask it
List the truck note, anything you signed personally and the insurance you would have to cancel. Then check whether a company driving job would still be open to you. Knowing the cost of stopping makes it easier to stop in time, and it is the question a spouse will ask anyway.
What did the first year really look like for someone who has done this, and what would they change?
Why ask it
Find an owner whose authority is two or three years old, recent enough to remember and long enough to have survived. Ask for numbers: what insurance cost, how long until the first check, the worst month. One owner's year is a single case, so put the same questions to a second if you can.
Will I cross state lines or stay inside one state, and how does that change what I register for?
Why ask it
Staying in one state can mean a different rule book, written by that state, and it narrows the freight you can accept. Call the state agency that regulates carriers and describe your exact plan instead of guessing which side of the line you are on. Ask too whether a load that began in another state counts as interstate even if your truck never leaves home.
How long is it from filing for authority to the day I can legally take a load, and what am I paying for while I wait?
Why ask it
There is normally a waiting period, and insurance usually has to be on file before the authority goes active, so premiums and a truck payment can start weeks ahead of revenue. Ask the regulator or a compliance service for today's timeline. Then count those weeks into your startup money.
Should I file everything myself or pay a service, and what exactly does their fee cover?
Why ask it
Most filings can be made directly with the agencies, and a service charges for doing them in the right order and catching mistakes. Ask for the government fees and the service's own fee on separate lines, and ask which filings come due again every year.
Which permits or tax accounts does my freight or my route add on top of the basics?
Why ask it
Hazardous materials, oversize loads, port and border work and a few individual states each bring their own credential, fee or mileage tax. Someone hauling the same freight on the same lanes can list them in five minutes. Finding out from a citation at a scale costs considerably more.
Will my new company be audited in its first year, and what will the auditor want to see?
Why ask it
In the United States a new carrier is treated as a new entrant and can expect a safety audit early on; elsewhere, ask the regulator how new operators are checked. Get the list of documents the audit covers and build those files from the first day. Rebuilding a year of records the week the letter arrives is hard work, and it tends to show.
Do I have to be in a drug and alcohol testing program when I am the only driver?
Why ask it
Ask how the rule applies to an owner who is also the driver, because a one-person company cannot randomly select itself. Where testing is required, the usual arrangement is to join a consortium that runs the pool for many small carriers. Find out the yearly cost and which papers prove you are enrolled.
Insurance
What will insurance cost in my first year under a new authority, and what is driving that number?
Why ask it
A company with no loss history is usually quoted well above an established carrier, and this is often the bill that surprises new owners most. Ask the agent which factors moved your quote: your record, your years of experience, where the truck is parked, the radius, the freight, the truck's value. Have the quote run on the exact truck you are considering before you sign for it.
Which coverages do I need, and what do brokers and shippers ask for beyond the legal minimum?
Why ask it
Expect to talk about primary liability, cargo, physical damage on the truck, coverage for when you are not under a load, and possibly general liability and trailer interchange. The legal minimum and what a broker's contract demands are two separate lists. Ask a broker you hope to work with for their carrier requirements and hand that page to the agent.
How many insurers will quote a new venture like mine, and can I see every quote you received?
Why ask it
Only some insurers write brand-new authorities, so an agent who works mostly with trucking will normally reach more of them than a general agency. Ask who was approached, who declined and why. One quote with no explanation is a reason to call a second agent.
How much of the premium is due up front, and what happens if a monthly payment is late?
Why ask it
A new carrier is often asked for a large first payment, with the rest financed at a cost. Ask what the financing adds over the year. Then ask how quickly a missed payment cancels the policy, and what a canceled policy does to your authority.
What does the policy exclude, by commodity, by distance or by who is driving?
Why ask it
Cargo policies in particular carry exclusions, and the freight you turn out to be offered may be on the list. Read them against your plan with the agent on the phone: theft from an unattended truck, a refrigeration unit that fails, high-value loads, a trailer you do not own. An exclusion you learn about at claim time can leave you paying the customer yourself.
If I have one claim in my first year, what happens to my rate and my chances of renewing?
Why ask it
Some insurers decline to renew a new carrier after a single loss, which sends you back to the market with a claim on your record. Ask which kinds of claim weigh heaviest at renewal. Ask as well how a small loss should be handled, because the policy has its own rules on what must be reported and when.
What would bring my premium down at the first renewal?
Why ask it
Get the answer as a list you can act on: clean inspections, no claims, a camera in the cab, a higher deductible, a year without a lapse. Agents differ on how much each one is worth with their insurers. Keep the list and bring it back at renewal with the evidence.
Which certificates will customers ask me for, and how quickly can you issue one?
Why ask it
Brokers and shippers ask for a certificate of insurance before the first load, sometimes with their own name on it, and a slow turnaround costs you the load. Ask whether you can request one online at night or on a weekend. A lot of freight is booked at exactly those hours.
What covers me if I am hurt and cannot drive for a few months?
Why ask it
A company driver hurt on the job is normally covered through the employer, and an owner has to arrange that personally. Which products exist, and whether you can or must carry workers' compensation on yourself, depends on where the company is based, so have the agent lay out the options with what each pays and for how long. Ask too whether any customer you hope to haul for wants proof of it.
Equipment
Should I buy new, buy used or lease the truck, and what does each cost me per month with everything counted?
Why ask it
A new truck brings a warranty and a large payment, a used one a smaller payment and a repair risk, and a lease its own conditions at the end. Put payment, expected repairs, insurance on the truck's value and downtime in one column for each. The lowest monthly payment is often not the lowest monthly cost.
If I lease, who holds the lease, and what does it cost me to walk away?
Why ask it
A lease from a bank or dealer and a lease-purchase offered by the carrier you would haul for are different arrangements, and the second ties your truck to their freight. Read the end-of-term payment, the maintenance account and the exit terms, and have someone with no stake in the deal read them as well. Ask to speak to a driver who finished one.
What will a lender want from a company with no history, and what will the truck have cost by the last payment?
Why ask it
Expect questions about your own credit, your down payment and your years of driving, and expect to be asked to sign personally. Take the same truck to two lenders and compare the total paid over the whole term. A long term at a high rate can leave you owing more than the truck is worth for years.
What should be checked on a used truck before I buy it, and who should do the checking?
Why ask it
Use a shop that has nothing to do with the seller. Ask them about the engine's stored data, an oil analysis, the emissions system, the maintenance records, and tires and brakes, and ask what each finding would cost to put right. The inspection fee is small beside the first major repair on a truck nobody looked at.
How much should I put aside per mile for maintenance and tires, and which single repair would wipe that out?
Why ask it
Ask an owner running the same engine what they set aside and what their worst bill was. Move the money to a separate account every week, whether or not anything broke. The fund exists for the month when an emissions fault or an engine job lands on top of the usual bills.
What is my plan for a week with the truck in the shop?
Why ask it
The truck payment, the insurance and your household bills carry on while the revenue stops. Find out now which shops near your lanes will take you without a long wait, and whether a rental is realistic under your insurance. With one truck, a breakdown is the whole company off the road.
Should I own a trailer, rent one or pull other people's?
Why ask it
Owning adds a payment, insurance and maintenance, and lets you take freight that needs your own equipment. Power-only work, where you pull a customer's or a broker's trailer, lowers the startup bill and narrows the loads you can see. Ask how each choice changes your insurance, since pulling a trailer you do not own may need its own coverage.
Where will the truck and trailer be parked between loads, and am I allowed to keep them there?
Why ask it
Many towns, landlords and homeowner associations do not allow a commercial truck at a house or on the street, so check the local rule before you count on the driveway. A rented space in a yard is a monthly bill that belongs on the cost sheet. Give the insurance agent the real address, since where the truck is kept is one of the things a quote is built on.
Does my freight need a sleeper or a day cab, and which engine year and weight rating fit the places I will run?
Why ask it
A truck that is cheap to buy can be barred from where the freight is, because some states and ports restrict older engines, so check the rules for every place you plan to enter before you shop. The weight rating can decide which license class and which rule book apply; confirm that with the regulator before picking a lighter truck to stay under a threshold. An owner on the same lanes can tell you what they would spec differently next time.
Freight and cash
Where will my first ten loads come from?
Why ask it
The usual sources are load boards, freight brokers, a shipper you already know and larger carriers that hand off overflow. Many brokers will not use an authority until it has some age on it, so ask each one for their minimum and build the list of those who will. A plan that says only 'the load board' is a plan to take whatever is left.
Is there a shipper who would give a new carrier a chance, and what would they need to see first?
Why ask it
Direct freight generally pays better than brokered freight and takes far longer to win. Have the conversation before you file anything: a shipper may want a certificate of insurance, a clean safety record and references, and can tell you what their current carrier gets wrong. One steady customer on one lane changes every number on the page.
What should I look for in a broker's carrier agreement and rate confirmation before I sign?
Why ask it
The agreement sets the standing terms: days to pay, what is deducted for a late or damaged delivery, and whether you may pass the load to another carrier. The rate confirmation is the deal for one load, so check the rate, the stops, the appointment times, and what is paid for waiting at a dock and after how many hours. Anything agreed on the phone should be written into it before the truck moves.
What does it cost me to run one mile, counting the miles I drive empty?
Why ask it
Add the fixed bills for a month (truck, insurance, plates, permits, phone, software), divide by the miles you expect, then add fuel, maintenance, tires and a wage for yourself per mile. Empty miles earn nothing and cost the same, so the loaded ones have to carry them. Any rate under that figure is you paying to haul someone's freight.
What are loads like mine paying per mile right now on the lanes I want to run?
Why ask it
Watch a load board for a few weeks and ask two or three owner-operators what they are booking, since posted rates and booked rates differ. Rates move with the season and the wider freight market. If today's rate sits below your cost per mile, the plan has failed on paper, which is the cheap place for it to fail.
How long will brokers and shippers take to pay, and how do I buy fuel until they do?
Why ask it
Payment terms commonly run to weeks, while fuel is bought every day and the truck note comes monthly. Count the weeks from your first load to your first cleared payment and price the fuel, insurance and living costs inside them. That total is your working capital, and it is separate from what the truck costs.
Should I factor my invoices, and what does the agreement really cost?
Why ask it
A factoring company pays you most of an invoice within a day or so and collects from the broker itself, for a fee. Ask each one for the fee per invoice, whether you repay if the customer never pays, how much is held in reserve, any monthly minimum, the contract length and the cost of leaving. Read the termination clause twice, because some agreements renew on their own.
How do I check that a broker will pay before I accept the load?
Why ask it
A factoring company or a load board can usually show a broker's credit rating and how many days it takes to pay. Look the broker up in the regulator's records and call back on the number listed there, since load fraud often borrows a real company's name with different contact details. A rate that looks too good on a lane you know deserves that extra call.
What will fuel cost me per mile, and what brings it down?
Why ask it
Work it out from the miles per gallon the truck gets with a loaded trailer, and expect that to be lower than the figure in a sales listing. Ask other owners which fuel card discounts are worth having and whether a fuel surcharge is built into the rates you are offered. Speed and idling are the two parts you control from the seat.
Do I need a dispatch service, or should I book my own loads?
Why ask it
A dispatch service finds and negotiates freight for a percentage of each load or a flat fee. Ask what else that covers, whether you approve every load, and whose name is on the paperwork with the broker. Booking your own for the first months is slower, and it teaches you what your lanes pay before you hand that job to anyone.
How much do I pay myself, and what share of every payment goes aside for taxes?
Why ask it
An accountant with other trucking clients can give you a percentage to move into a separate account the day money lands. Ask as well how meals and nights away are treated where you file, and when tax payments fall due during the year. Money in the business account is not all yours yet, and the first tax bill catches owners who spent it as if it were.
What will I do in a month when freight is slow or rates fall?
Why ask it
Freight has seasons and the market has down years. Decide ahead of time how many weeks of fixed costs you hold in reserve and at what rate you would park the truck instead of running at a loss. Ask an owner how they got through their worst quarter, and what they wish they had kept in the bank.
Compliance and hiring
Which records do I have to keep, for how long, and where will they live?
Why ask it
The list normally covers a qualification file on every driver, including you, plus hours logs, inspection reports, maintenance records, testing records and trip and fuel records. Ask the regulator's guidance or a compliance consultant for the retention period on each. Pick one place for them, paper or cloud, before the first load.
How will I track miles and fuel by state for the fuel tax return?
Why ask it
If you cross state or provincial lines you will probably report miles driven and fuel bought in each jurisdiction on a regular schedule. Ask whether your logging device or a mileage app produces that report, and keep every fuel receipt. Find out who files it, you or a service, and what a late return costs.
Which electronic logging device do I need, and is there an exemption that fits my operation?
Why ask it
Ask the regulator whether your kind of operation must use one, since short-haul work is sometimes treated differently. Where the regulator publishes a list of accepted devices, check that yours is on it before you buy. Compare the monthly fee, the contract length and whether it also produces the mileage reports you will need at tax time.
What does a roadside inspection cover, and how do the results follow my company afterward?
Why ask it
Inspection results and violations build a record that insurers and brokers read before they deal with you. Ask a compliance consultant or an experienced owner how the scoring works where you run and how to look up your own. Learn how to dispute an error too, because a wrong entry counts against you until someone challenges it.
What should my books show me every week?
Why ask it
Have the accountant or bookkeeper set up the accounts for trucking, so that you can see revenue per mile, cost per mile, loaded against empty miles and unpaid invoices by age. Looking once a week is a short job. Owners who only see the numbers at tax time find out a lane was losing money nine months after they could have dropped it.
What would have to be true before I add a second truck or a second driver?
Why ask it
A fair test is three things at once: freight you are turning down on a regular basis, a reserve that covers the second truck's first months, and a cost per mile taken from your own records over a full year. One strong month is not that. Put the conditions in writing now, while nobody is offering you a truck.
If I hire a driver, are they an employee or a contractor, and what does each cost me in full?
Why ask it
How a driver is classified is decided by rules that differ by place and are enforced, so ask an accountant and an attorney where you operate instead of copying another fleet. Have them total the cost beyond pay: payroll taxes, injury coverage, insurance and the time you spend managing. Run that total through your cost per mile before you make an offer.
Who will my insurer accept as a second driver, and what does adding one do to the premium?
Why ask it
Insurers approve each driver by name and can refuse one for too little experience or a mark on the record. Get the agent's criteria before you advertise the job, so you do not interview people you cannot put in the truck. Ask for the premium change as a figure in writing.
What do I have to have on file before another person drives under my authority?
Why ask it
Hiring a driver makes you the carrier responsible for checking them. Ask the regulator or a compliance service for the checklist, which usually runs through an application, license and record checks, past employers, a medical certificate and a pre-employment test. Do it in full for a friend or relative as well, because an auditor will not make that distinction.
How to work through these before you buy a truck
Practical guidance for the conversation itself
Who gets which questions
The ones only you can answer
The plan group is yours: the freight, the radius, the money you can afford to lose, who does the paperwork. Write the answers down before you call anyone. An agent or a lender gives better figures to someone who can say what they will haul, how far, and in which truck.
The insurance agent
Take the Insurance group to an agent who writes trucking every day, and take it early. Bring your license history, the freight, the radius and the truck you have in mind, and ask for the quote in writing. The same details given to a second agent make the two quotes comparable.
The accountant and the factoring company
The accountant gets the structure, owner pay, tax set-asides and the employee question. The factoring company gets the payment questions, and the same ones should go to two or three of them. Ask each for a sample agreement before any call, so the time on the phone goes to the clauses.
An owner a few years ahead of you
Someone with their own authority can answer most of Equipment and Freight and cash from memory, with real figures. Offer to buy lunch and ask what the first six months cost them. Drivers who chose to lease on to a carrier or stay with a fleet are worth hearing too, on why they decided against this.
The order that saves money
Quotes before the truck
Insurance and financing quotes cost nothing and can change the whole plan. Collect them while you still have a paycheck. A truck bought first turns every later answer into something you have to accept.
Cost per mile before any rate
Build the cost per mile on one sheet from the quotes you collected, and only then look at what your lanes pay. Doing it the other way round invites you to shrink the costs until the rate works.
Freight conversations before authority
Talk to brokers about their minimums, and to any shipper you know, while you are still employed. You will learn how old an authority has to be before they will load it, which tells you how long the lean stretch after activation may last.
File when the reserve is in the bank
Filing starts a clock: insurance bills, plates and an audit somewhere ahead. Start it when the startup figure from the first group is saved, or borrowed on terms you understand, and not because a truck came up for sale.
Building the cost-per-mile sheet
Fixed costs by the month
List what you pay whether the truck moves or not: truck and trailer payments, insurance, plates and permits, parking, phone, logging device, load board, accounting. Use the written quotes, not round guesses. Divide the total by the miles you expect in a month.
Running costs by the mile
Fuel, maintenance, tires and tolls rise with every mile. For fuel, take the mileage per gallon that an owner with the same engine reports under load. For maintenance, take the set-aside you settled on in the Equipment group.
The miles that pay
Be conservative about miles. Count the weeks you will take off, the days in the shop and the empty miles to reach each load, then divide the costs by what is left and not by what the truck could do in a perfect month.
Your own wage
Add what a company would pay you to drive the same miles. If the business only works when the driver is free, it is a job that pays less than the one you left, with a loan attached.
Where new carriers get caught
Running under cost to stay busy
A moving truck feels like progress. Loads below your cost per mile drain the reserve faster than a parked truck does, because fuel and wear are added to the fixed bills. Know your floor before the broker calls.
Signing the factoring contract unread
The fee is the part everyone compares. The term, the automatic renewal, the minimum volume and the charge for leaving are where the regret usually is. Ask what it would take to end the agreement a year in, and get the answer in writing.
Paying mail that looks official
Once a new carrier registers, letters and calls about 'required' filings, posters and services tend to follow. Some are real deadlines and many are sales pitches dressed as notices. Check each one on the agency's own website before paying anybody.
Growing on one good month
A strong month tempts owners into a second truck while the first one's figures are still short of a full year. The second truck doubles the fixed costs and adds a driver you have to keep busy. Go back to the conditions you wrote down under Compliance and hiring, and check each one against the books.