I used to send invoices as PDF attachments from Gmail. Then I'd forget who paid and who didn't. Then I'd feel weird following up. Then I'd realize someone owed me $1,200 from two months ago.
Invoicing software fixes all of this. It sends the invoice, reminds the client automatically, lets them pay online, and tracks everything so you're not scrambling at tax time. The right tool pays for itself the first time it chases a late payment you forgot about.
The short answer
Wave is the best free option. Unlimited invoices, online payments, and basic accounting. Costs nothing. FreshBooks is the best paid option. Worth the $17/month if you have more than 5 clients or need time tracking and expense management.
Quick comparison
| Tool | Price | Free invoices | Best for |
|---|---|---|---|
| Wave Best free | Free | Unlimited | Side hustles on a budget |
| FreshBooks Best paid | $17/mo | 5 on Lite | Growing freelance businesses |
| Zoho Invoice | Free up to 5 clients | Yes | Zoho ecosystem users |
| QuickBooks Self-Employed | $15/mo | No free tier | Tax prep + invoicing combo |
| HoneyBook | $19/mo | No free tier | Service businesses (photography, design) |
Dad Math: How We Ranked These
Every ranking on Dadzilluh uses a simple scoring system. No black boxes. Here's what we weighed:
Wave
Best for: Any dad with a side hustle who doesn't want to pay for invoicing.
✓ Completely free invoicing, unlimited clients
✓ Online payment built in (clients pay by card)
✓ Automatic payment reminders
✓ Basic accounting and expense tracking included
— Payment processing fees come out of what you collect
— Interface feels dated compared to FreshBooks
— No time tracking
— Customer support is limited on free plan
FreshBooks
Best for: Dads whose side hustle has grown past 'just a few gigs.'
✓ Beautiful, professional invoice templates
✓ Time tracking built in
✓ Expense tracking with receipt scanning
✓ Late payment reminders are aggressive (in a good way)
✓ Excellent mobile app
— Lite plan caps at 5 clients
— $17/month is steep if you only invoice 2-3 times a month
— Some features locked behind higher tiers
Best for: Dads who want invoicing and tax prep in one place.
✓ Automatic tax categorization of expenses
✓ Quarterly tax estimate calculator
✓ Direct integration with TurboTax
✓ Mileage tracking
— No free tier
— Interface can feel bloated for simple invoicing
— More accounting tool than invoicing tool
— Pricing has crept up over the years
The real cost of not invoicing properly
Here's what I learned the hard way: the money you lose isn't from bad pricing. It's from invoices you forget to send, payments you forget to follow up on, and expenses you forget to track.
In my first year of side work, I found $2,400 in invoices I'd sent but never followed up on. Two clients had simply forgotten. One was waiting for a "final version" I'd already sent. All three paid within a week once I followed up. An invoicing tool with auto-reminders would have caught all of that without me lifting a finger.
And at tax time, I spent an entire weekend sorting through bank statements trying to find deductible expenses. Now FreshBooks does that automatically. The $17/month saves me a weekend every April. That's Dad Math.
About these links: Dadzilluh may earn a commission when you sign up through links on this page. It costs you nothing extra. Rankings use Dad Math. Prices accurate as of March 2026.