Small Business Tax Savings Podcast
Jul 22, 2026 · 34 min · 10 segments
👉 Ready to simplify your recordkeeping? Check out Shoeboxed to organize receipts, track mileage, and keep your business expenses audit-ready. Visit…
Doug BreakerGuestI wanna hear from kinda your sp- perspective when you're talking to business owners.
What are they getting wrong? Why do business owners underestimate this idea of documenting? Because, you know, we see it on our end.
And so are you seeing the same thing? What are you kinda seeing when you're talking to business owners when it comes to this idea of having accurate tracking of whether it's receipts, mileage, whatever it might be?

Yeah, and I have to admit, I listened to every one of your podcasts as I was preparing to, to buy Shoeboxed, just because going from a W2 a business owner, I wanted to make sure I, I had all of the strategies in place and everything else.

And even with that, like, I, I still fall down here and there on tracking myself.

But the key thing that I see for myself, and then for our clients and customers too, is just setting up the systems and making it easy to track.

So there's so much money to be saved if you work from a home office, or if you can do the Augusta rule, or if you drive for business.

That's, that's a lot of money if you're doing, you know, a fair amount of mileage.

But you know, like anything in life, if you don't have a system to track it, and if you don't make it a priority to track it, you don't.

And then come tax time, you're kicking yourself 'cause you think, "Oh, man, all those business trips I didn't track, all that mileage I didn't track," or, "The home office, I screwed it up and I can't get this $8,000 deduction." That's what we see.

It's just setting up the systems correctly and making it easy for themselves to, to track all the receipts and the donations and the mileage.
I think it's so important, that concept of making it easy to implement and easy to do because, you know, when you're talking about a receipt, let's say it's you go out to the lunch, talk, have a business meeting.
You know, the concept of just taking a picture of that receipt, that doesn't provide you any value.
I wanna hear from kinda your sp- perspective when you're talking to business owners.
What are they getting wrong? Why do business owners underestimate this idea of documenting? Because, you know, we see it on our end.
And so are you seeing the same thing? What are you kinda seeing when you're talking to business owners when it comes to this idea of having accurate tracking of whether it's receipts, mileage, whatever it might be?

Yeah, and I have to admit, I listened to every one of your podcasts as I was preparing to, to buy Shoeboxed, just because going from a W2 a business owner, I wanted to make sure I, I had all of the strategies in place and everything else.

And even with that, like, I, I still fall down here and there on tracking myself.

But the key thing that I see for myself, and then for our clients and customers too, is just setting up the systems and making it easy to track.

So there's so much money to be saved if you work from a home office, or if you can do the Augusta rule, or if you drive for business.

That's, that's a lot of money if you're doing, you know, a fair amount of mileage.

But you know, like anything in life, if you don't have a system to track it, and if you don't make it a priority to track it, you don't.

And then come tax time, you're kicking yourself 'cause you think, "Oh, man, all those business trips I didn't track, all that mileage I didn't track," or, "The home office, I screwed it up and I can't get this $8,000 deduction." That's what we see.

It's just setting up the systems correctly and making it easy for themselves to, to track all the receipts and the donations and the mileage.
I think it's so important, that concept of making it easy to implement and easy to do because, you know, when you're talking about a receipt, let's say it's you go out to the lunch, talk, have a business meeting.
You know, the concept of just taking a picture of that receipt, that doesn't provide you any value.
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