Small Business money tools to ease your midnight worry

5 min read · 6 years ago


It is one of the persistent paradoxes of running a small business. You do it – to some extent – for the money. But you can’t stop for long to count your pennies if you hope to keep making it. So you fly by the seat of your pants when it comes to money management. Luckily getting a miser’s grip on your finances no longer requires specialized knowledge. All you need is
the right tool. There are geeky accountant types out there who live and breathe fiscal accountability and they built awesome tools just for you. We rounded up some those modern tools that help you watch the cash box. Whether your business is lurking coiled in your parents’ basement, rattling around in the front seat of a pickup truck, or you are memsahib to a horde
of hirsute hipsters, your money is the beating heart of your business. One of these tools – or perhaps a handful of them – will help you count it, collect it, and – when the time comes – slice off a pound of flesh for the usurious tax man.

PayPal Invoicing

Stop sending invoices you created in Word or a spreadsheet. You may not realize it but that is making work for you – and your customers. Paypal has a nice email invoicing function that requires no monthly membership fee. (There is a transaction fee that takes a percent of your invoice.) But it also lets your customers click a button right in the invoice to pay you. And that will help you get paid. Also? If you sell goods and use Paypal to create the invoices, PayPal will offer your customers free return shipping. That will help you compete with bigger outfits who all offer free return shipping. You can keep track of who paid you online, trick out your invoices so they look like your brand, and attach all related documents to your invoices online.


Accounting does not have to be hell. Or at least that what’s the folks at Xero are suggesting. This program will reign in the chaos without assuming you know what you are doing. It is more than an invoicing program. (Though it does do invoicing.) It is more than an expense categorization program. It is, in its own gentle way, a complete accounting program. It will even do payroll. It will ask you to reconcile your expenses and income. But it will not insist you pull your hair out in the process. In fact, it might calm you down. It lives online, has apps for your phone or tablet, is thoroughly modern, and is easy on the eyes. If you log on for just a few minutes every day, reconcile a few transactions, send some invoices, or do whatever it is the program prompts you to do, you will develop a clear picture of where your money comes from and where it goes. And that is the secret to making business decisions that lead to profit.

Xero plays nicely with some of the other tools in this story – as well as a host of add-on products. So it can scale up as you need. For example, you can connect it to Freshbooks (below) if you like the way that program handles time tracking and invoicing. And it will keep track of those invoices, along with your money, for you. And it has a marketplace of third-party apps that add other features.


If you are a freelancer or consultant, this is the way to go. You can create estimates for clients that convert neatly to invoices. Your clients can log on and comment on those estimates and you can make adjustments right from there. Use Freshbooks to track your time and it will create an invoice from your logged hours. Connect a bank account or credit card to Freshbooks and
pull your transaction in so you can charge expenses back to your clients. And then send the entire, accurate thanks to technology, invoice to your client via
email. You can see when they have viewed it. They can pay you online. When they do pay, that’s easy to record, too – and to thank your clients. You can even let clients give you feedback right from the invoice. And you can log on from anywhere – the apps, a Web site – to do any of this.

QuickBooks Self Employed

When you wear all the hats in the business, you need hats you can put on and take off easily. This version of Quickbooks is down and dirty – and super easy.  Connect it to the bank account or credit card you use for work deposits and expenses. Then spend a few minutes every week answering questions that fly across the screen. Is this charge personal or business? Do you have a home office? It will keep a running tally of how much you should pay in estimated taxes, how much money you are earning, and how much of that is profit. It won’t ask you to reconcile anything. It won’t demand you categorize every penny. But it will keep you up to date on quarterly taxes and save you from that awful moment at the end of the year when you owe more taxes than you have money to pay. At tax time, just pull all this data directly into TurboTax (below) and it will fill out your Schedule C.


Freelancer and small business taxes are complicated. Too unique and time consuming for your accountant to pay the kind of attention to you would. This program is like an accountant in a box. It asks the questions, you find the answers. Often those answers are easy: Just type in a few numbers from your 1099s and it auto-fills, for example. Or the question might seem arcane. But it turns out – when you answer it – the answer is a tax deduction that saves you money. Some of the questions require you to dig through receipts and credit card transactions to come up with totals. But the software is in no hurry. And it isn’t charging by the hour. Feel free to dig around in your receipts, bank accounts, and records to make sure you capture every possible deductible expense. Log on, answer a few questions, and get back to work.  Do a little every day. Taxes are no fun. But if you are getting paid in tax savings instead of paying someone so you can outsource the dread, you might find the pain is mitigated by an awesome payday. And it gets easier every year because it remembers relevant answers from last year.


Your business may be large enough to have a few employees but that doesn’t mean you are rich enough to pay someone to handle the business of employing people: Payroll, benefits, worker’s compensation compliance. So you probably spend nights and weekends dealing with it – or fretting over it. Gusto steps in and acts like the machine version of that person you wish you could
hire. It handles running your payroll. But, since you have already entered employee data to make that happen, it also manages benefits and worker’s compensation compliance from the same place. You choose the benefits you want to offer. And your employees can do their own onboarding. You just keep working.