You know how it goes. Everyone says, “Keep your books in order,” but only a few will tell you how tough that actually is.

Between running your business, managing customers, and trying to find five minutes to breathe, bookkeeping often takes a backseat — until something gets missed, and suddenly you’re scrambling to catch up.

But here’s the good news: staying on top of your books doesn’t have to be a grind. There are a few lesser-known tactics that make it a lot easier. Not the usual advice you hear, but the kind that actually helps when you’ve got a million other things going on.

Let’s dive in. Here are some practical bookkeeping tips for startups and entrepreneurs to help you stay financially healthy.

And if you’re ready to jump straight into a solution that can take all your bookkeeping worries off your plate, feel free to book a consultation with our experts.

1. Separate Personal and Business Finances

One of the most common mistakes entrepreneurs make, especially in the early days, is mixing personal and business finances. It might seem harmless at first — using your personal credit card for a business purchase or transferring funds back and forth — but this tiny mistake can turn into a nightmare come tax time or when you’re trying to gauge the actual health of your business.

Separating your personal and business finances ensures clarity in your books and saves you time during tax season. It’s also a great way to shield yourself from liability. If your business runs into legal or financial trouble, you don’t want your personal assets entangled.

What to do:

➡️ Set up a business account and credit card as soon as you get that startup rolling. Mercury and Brex are great options if you want something designed for startups.

➡️ Keep everything business-related on those accounts — no excuses. Every penny should run through them, from income to expenses.

➡️ And please, please don’t mix personal stuff with your business account. It’ll save you time and lawyer fees if things go south.

2. Track Every. Single. Expense.

Okay, this one sounds tedious, but stay with us. Every little expense — whether it’s that subscription to Canva or the ten-dollar cab ride to meet a client — needs to be logged. 

Why? Because all those small purchases pile up and can either help you out when it’s time to file taxes or sneak up on you like a bad surprise.

Plus, if you’re not tracking everything, you’re throwing away potential tax deductions. Plus, you want to have a crystal-clear view of where your cash is going, so you can actually keep more of it.

Here’s what you can do:

➡️ Use an expense-tracking tool like QuickBooks. These tools can sync with your business accounts and do the heavy lifting for you.

➡️ Take pictures of receipts on the go and store it in digital format. There’s no need to drown in paper.

Pro tip: Make a habit of tracking your expenses at the end of the day. Not only will this give you peace of mind, but you’ll also thank yourself later when tax deductions start rolling in.

3. Don’t Be Afraid of Accounting Software

Look, if you’re still using spreadsheets, we’re here to tell you that here’s a better way. Accounting software might sound intimidating, but it’s a game-changer for startup bookkeeping. 

Not only does it help you manage everything from payroll to taxes, but it also lets you see exactly how your business is performing without having to become a full-blown accountant.

Why it matters:

Mistakes in bookkeeping are no joke, and even a small misstep can cost you big. Accounting software makes sure everything is accurate, automates the mundane stuff, and gives you a clear picture of your financial health.

What to do:

➤ Pick software that works for your startup size. Xero and Wave are good options for beginners, but QuickBooks is the go-to for a lot of small businesses.

➤ Don’t just set it up and forget it. Take time to explore its features carefully.

4. Keep an Eye on Cash Flow (It’s your business’s heartbeat)

Your business can be profitable, but if you run out of cash, it’s game over. Many businesses fail because they don’t have enough money in the bank to cover expenses, even if they’re technically making a profit. To avoid this, you need to know exactly how much cash is flowing in and out of your business at all times.

Here’s the reality: You might have customers who take their time paying, but your bills and employees can’t wait. That’s why steady cash flow is critical—it keeps your business running smoothly without unexpected financial hiccups.

How to manage it:

➜ Track your cash flow regularly. Make it a habit to review it at least monthly, or even weekly if your funds are tight. Spot trends — are there certain times when you’re low on cash? Plan ahead for those dips.

➜ Create cash flow projections. It’s simpler than it sounds. Just look at your past numbers and predict when cash might get tight so you can prepare.

Pro tip: Set up a business line of credit. This gives you quick access to cash if things get tight, so you’re not scrambling to cover expenses when clients are slow to pay.

5. Get Ready for Tax Season Before It Sneaks Up on You

Tax season can feel like a looming deadline, but it doesn’t have to be the stressful, anxiety-filled rush we all dread. The key is preparation — treat it like a marathon, not a sprint. You don’t want to end up rushing at the last minute, missing out on potential deductions, or worse, facing penalties. With a few simple steps, you can make tax season way more manageable.

How to get ready for the tax season?

➜ Start a tax savings habit. Every month, set aside a portion of your income specifically for taxes. Don’t wait until the end of the year to scrape funds together. 

By building a habit of regularly saving for taxes, you’ll avoid the shock of a large bill come tax time. It’s a simple way to protect your cash flow and reduce stress when filing season hits.

➜ Know your deadlines and requirements. Depending on how your business is structured (whether it’s an LLC, S Corp, or sole proprietorship), your tax obligations and deadlines will differ. Make sure you know exactly what forms to file and when. 

Keep a calendar or reminder system in place for key dates. Missing these deadlines can lead to unnecessary penalties, and the IRS isn’t exactly forgiving when it comes to late filings.

➜ Organize your records. Throughout the year, track all business expenses, income, and receipts. This way, you’ll be able to easily identify what’s deductible when tax time comes. 

Categories like office supplies, marketing costs, and even home office deductions can add up to significant savings. It’s crucial to stay on top of this paperwork so that come tax time, you’re not scrambling to find receipts or reconstructing your finances from memory.

➜ Hire help if needed. If managing your own taxes seems overwhelming, don’t hesitate to hire a professional or use tax software specifically designed for small businesses. 

doola can help take the confusion and complications out of tax preparation, especially for startups, by filing your taxes on time and making sure you’re compliant with the latest regulations. Plus, having a tax pro in your corner ensures you’re maximizing deductions and not making costly mistakes.

Pro tip: If your business is doing well, consider paying quarterly taxes. Instead of one big tax bill at the end of the year, break it into smaller, more manageable payments throughout the year. 

This not only reduces the financial hit but also prevents potential underpayment penalties from the IRS. Plus, it makes cash flow planning easier, and by the time the year wraps up, you’ll have far less to worry about.

6. Don’t Skimp on Payroll (And yes, pay yourself too)

Payroll might not be the most exciting task on your list, but it’s one of the tasks you absolutely need to get it right. Plus, if employees aren’t paid on time, it leaves a bad taste, and honestly, that’s the last thing you want when you’re trying to build a solid team. 

Here’s how to keep the payroll process simple:

➜ Use Gusto to handle payroll for you. It’s a game changer, especially for startups. Gusto takes care of payroll, tax filings, benefits, and even direct deposits so you don’t have to stress over the details. Plus, it makes sure you’re staying compliant with tax laws, which is huge if you want to avoid fines.

Whether you’ve got a few employees or a growing team, Gusto scales up with you and integrates with your accounting software, so when tax season rolls around, you’re already ahead.

➜ Don’t forget to pay yourself. It’s easy to get so focused on paying everyone else that you skip your own paycheck. Set up a regular payment schedule for yourself, just like any other employee. 

➜ Keep personal and business funds separate. We already talked about this, but it’s worth repeating because mixing up personal and business finances is a recipe for chaos. A smart way to keep things separate is by opening a business account with Mercury.

It’s a modern banking platform built for startups, and it integrates seamlessly with tools like Gusto, making it easier to manage payroll and finances. 

With a Mercury account, you’ll have a clear separation between personal and business expenses, which will make tracking your business’s financial health much simpler. Plus, their digital-first platform is perfect for entrepreneurs who want an efficient way to manage everything online, from banking to payments.

7. Get Organized (Because chaos will catch up to you)

No one loves sorting through receipts or chasing down invoices. But staying organized isn’t just about being neat — it’s about avoiding those “oh no” moments when you realize you’ve missed something important, like a big payment.

That can snowball into cash flow problems faster than you think. 

How to stay organized (and sane)?

➜ Go digital, for real. Instead of storing receipts in your study table drawer or having random PDFs floating in your inbox, set up a digital filing system.

Consider Google Drive, Dropbox, or your accounting software — whatever works for you. Label everything clearly by month and category, so when tax time comes, you’re not stuck digging through a mess. 

➜ Monthly check-ins. Set a reminder on your calendar to go through your receipts, invoices, and bank statements once a month.

Do it regularly, and you avoid major problems down the road. Plus, it’s way easier to handle smaller tasks regularly than to deal with a big chaos at the end of the year.

➜ Hire a bookkeeper if you can. Now,  if you’re spending hours trying to sort out your finances and feeling like you’re barely keeping up, you could use some help.

A bookkeeper can handle all the day-to-day tracking of expenses, reconciling accounts, and even preparing reports. This frees you up to focus on your business. 

And don’t worry, doola is right here for you. We offer bookkeeping services that are designed specifically for startups and small businesses. Our bookkeeping experts can handle income and expense tracking, reconcile accounts, and prepare detailed financial reports — so you don’t have to spend hours hunched over spreadsheets. 

➜ Back everything up. Think about how many times you’ve accidentally deleted an important file or lost something to a computer crash. Now imagine that happening with your financial records.

Backup your files — either through cloud storage or an external drive—so you’re covered if things go sideways.

Best Bookkeeping Practices for Entrepreneurs

Here are some best bookkeeping practices you might not hear about as often but are game-changers for entrepreneurs:

Use a bookkeeping calendar

A calendar dedicated just to bookkeeping might sound old-school, but it’s actually a game-changer. Set specific dates for reviewing your finances, sending invoices, paying bills, and reconciling accounts.

It’s like setting up non-negotiable “money meetings” with yourself, so things never pile up.

Keep an eye on client payment habits

You may not think about it often, but late payments from clients can mess with your cash flow. Keep track of which clients pay on time and which ones are consistently late. Consider implementing late fees or setting up automated reminders to ensure timely payments.

This way, you can better predict when the money will actually hit your account.

Record future expenses as soon as you know about them

If you know an annual subscription or big bill is coming up, record it ahead of time. Even if the payment isn’t due for months, adding it to your bookkeeping software helps you see a more accurate picture of what’s going to come out of your account.

It’s a proactive approach that helps with planning and avoids surprises.

Embrace financial forecasting

Financial forecasting is like peeking into the future of your business. It helps you predict your revenue, expenses, and cash flow based on past trends. You don’t need to be a finance guru — use simple tools or templates to estimate what the next quarter or year might look like financially.

This gives you insight into potential issues before they become real problems.

Regularly audit your subscriptions and recurring expenses

Subscriptions pile up quickly — software, services, tools, and platforms you may not even use anymore. Do a regular audit of all recurring expenses and cancel anything that’s no longer serving you.

It’s an easy way to cut costs and avoid unnecessary drain on your cash flow.

Understand your break-even point

A lot of entrepreneurs overlook this one. Your break-even point is the moment where your business revenue covers all your expenses. Knowing this figure is crucial — it tells you how much you need to make each month just to keep your business afloat.

Once you have that number, you can make smarter pricing and budgeting decisions.

Set aside time for financial learning

Entrepreneurs often avoid the financial side of things because it feels complicated. But setting aside time each month to learn something new about bookkeeping or finances (even 30 minutes) can help you get a better handle on your business.

Whether it’s understanding tax deductions or learning how to read financial statements, the more you know, the more empowered you’ll feel in managing your money.

For Everything Else, You’ve Got doola

Okay, that’s a wrap. But, if you’re still curious about how other entrepreneurs around the world have tackled their own bookkeeping struggles, tune into our podcast: 15 Minute Founder. You’ll hear real stories about the ups, downs, and everything in between — and maybe pick up a few bookkeeping tips along the way.

And, if you’re more of a “let’s get straight to the point” kind of person, book a free consultation with our bookkeeping experts. Bring all your questions, no matter how big or small, and we’ll be happy to guide you through it.