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Your talent can be your side hustle

Dave Ramsey

Dear Dave,

I’m currently in Baby Step 2 of your plan, and I’ve been intense about paying off debt. I make about $80,000 a year in sales and recently received a windfall of $4,400. I have an idea to use the money to open a trailer rental business as a side hustle to pay off debt faster. Do you think this is a good idea, or should I use all the money to help pay off debt?

— Mike

Dear Mike,

I like that you’re trying to find a way to pay off your debt even faster. But no, I wouldn’t use the windfall to open a trailer rental business.

I want you to get rid of your debt as fast as possible. But the problem with throwing all that money at two or three trailers is that you might not rent them one single time. That’s a very real possibility.

You’ve got to consider all the downsides and all the possible negative scenarios. If there are more negatives than there are positives, your idea’s probably not going to work.

Now, I don’t mind the idea of you taking a small part of the $4,400 to get something going on the side. I’d rather see you take $400 to $500 of the money and put it into something where you’re pretty sure you’re going to get $500 to $1,000 back within the first month or so.

In that kind of situation, even if the idea doesn’t work out, you’ve only burnt a little bit of the money. You’d still have around $4,000 left to help pay off debt.

But here’s something else I want you to think about: it sounds like you’re making a pretty good living as a salesman.

If I were in your shoes, I’d find a part-time job selling a quality product I was excited about and believed in, something that does not compete with what I’m selling at my day job. I mean, selling is selling.

If you could get with a company that would let you sell on nights or weekends, you could probably make a nice chunk of cash. That’s a lot better plan than setting a couple of trailers in your yard and hoping someone rents them.

Good luck, Mike!

— Dave

Dave Ramsey is a nine-time national bestselling author, personal finance expert and host of The Ramsey Show. He has appeared on Good Morning America, CBS This Morning, Today, Fox News, CNN, Fox Business and many more. Since 1992, Dave has helped people take control of their money, build wealth and enhance their lives. He also serves as CEO for Ramsey Solutions

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Published May 02, 2026 at 7:19 am (Updated May 02, 2026 at 7:19 am)

Your talent can be your side hustle

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