One Owner, One Truck, and Seven Questions Before the Money

I tell people who are afraid to start a business the same thing every time. Start and fail. Once the fear of failure is gone, you already have your no, and you can stop carrying it around. So what if it does work out?

Borrowing is different. When you borrow, the fear is the useful part. So let me walk through one decision the way I would want an owner to walk through it, with me asking the questions across the table. The owner is made up. The questions are the ones I ask.

The truck

Say you run a plumbing company with two trucks and three plumbers. One plumber rides along because there is no third truck. You are turning away two or three jobs a week. You want $40,000 for a used truck, fitted out, and you want it this month.

Good. That is already better than most applications, because you can name the thing. "I need capital" tells me nothing. A truck tells me what the money does on day one. It also tells me the amount. Owners who cannot name the thing ask for too much or too little, and both cost them. Our own application asks what the funding is for, and this is why.

Now the second question. What does the truck bring in? Not "more business". A number. Two jobs a week the third plumber can now do alone, at whatever an average job pays you. Multiply it out for a month. Write it down. If you cannot, you do not know yet whether the truck pays for itself, and neither do I.

Third. Which dollars make the payments? The new jobs, or the money the two trucks already bring in? Either is fine. But be honest about the order things happen in. The payments start the week the money lands. The new jobs start when the truck is on the road, the plumber is set up on it, and the calendar fills. That can take a month. So for that month, the old trucks carry the new payment. Can they?

The bad month

Here is where I turn my own advice around. Before you sign, I want you to think about what happens if it does not work out.

The truck needs a transmission in week three. Your best plumber leaves. It rains for two weeks and the jobs you were turning away stop coming in. The payment still comes out on schedule. Nothing about the payment knows you had a bad month.

So tell me now, while nothing has gone wrong, how you would cover it. Maybe the two old trucks cover it with room to spare. Maybe you have savings you would rather not touch but could. Maybe the answer is a cheaper truck and a smaller payment. Any of those is a plan. "It will work out" is not a plan. It is a hope, and I do not like to fund hope.

If you cannot answer this one, you are not ready to sign. That is not a judgment on you or on the business. It is one more piece of homework, and it is the piece most owners skip.

The paperwork

Now the part people rush. Put the payment schedule next to the days your customers actually pay you. A plumber who collects at the door can handle a daily or weekly payment. A contractor who waits for a progress check at the end of each phase cannot, and a daily payment will drain the account between checks. Same money, different fit. Working capital from us comes with a fixed daily or weekly payment, and you choose which, so this is a real choice and you should make it on purpose.

Then ask two questions out loud, and get the answers in writing. What happens if I pay this off early? What happens if I miss a payment? Both of those will matter to you one day. Better to know the answers on a good day.

Ask what the whole thing costs, in dollars, start to finish. I will not repeat the math here, because how business funding costs work, our guide to it, does that properly, and you should read it before you compare two offers.

And one last one. If a slow month comes, does the payment change with it, or stay the same? For some businesses a fixed payment is the right shape, because it is predictable. For a business whose sales swing from day to day, there is revenue-based financing, where the payment is a small percentage of each day's sales, so a slow day means a smaller payment. Neither one is better. One of them fits you. Knowing which is the seventh question.

Count what you would have at the end of that conversation. What the money buys. What it brings in. Which dollars pay it back. How you cover a bad month. Whether the payments fit how you get paid. What early payoff and a missed payment cost. What a slow month does to the payment. Seven answers, and none of them needed an accountant.

Our guide to getting funded in 2026 picks up from here, with four questions for choosing where to apply. That is the next conversation. And if you are not sure your low account is a timing problem at all, my essay on cash flow problems and business problems comes first.

Write the seven answers down before you apply, and bring them with you. Applying begins with a soft credit pull, which does not affect your score, so there is no cost to starting. If one of the seven is blank, work on that one first. The application will still be there when you have the answer.