If you’re trying to decide between doing your own books or hiring help, you’re not alone. It’s one of the first major decisions most founders face after making a little money.
This guide will help you figure out which route makes the most sense—based on your business, not just your budget.
DIY Bookkeeping: The Pros & Cons
“If you’re organized and consistent, DIY can work in the early days. But most people aren’t.”
— Kimi, Co-founder ofSam’s List
Pros:
Save money upfront
Learn your numbers and systems
No need to manage anyone else
Cons:
Easy to fall behind
High risk of categorization mistakes
You’re using founder time on non-revenue tasks
Stressful during tax season
Outsourced Bookkeeping: The Pros & Cons
Pros:
Experts handle categorization, reconciliation, reports
Saves 10–15+ hours/month
Clean books = better tax prep and faster decisions
Monthly reporting and check-ins
Cons:
Monthly cost (usually $300–$1,500)
Some firms may not be responsive or specialized
“You get what you pay for. Cheap AI bookkeeping can work for simple businesses—but breaks down fast when complexity kicks in.”
When It’s Time to Outsource
Here are the clearest signals that you need to hand off your books:
You’re making $250K+ in revenue
You haven’t reconciled in 2+ months
You’re behind on 1099s or tax prep
You’ve got contractors, inventory, or multiple bank accounts
You’re making decisions without financial reports
A Simple Framework
If You're... | Go With... |
Making under $100K/year | DIY or simple software |
Between $100K-$250K | Software + monthly check-ins |
Earning $250K+ or time-strapped | Outsourced bookkeeper |
👉Find a bookkeeper who matches your industry + income level
FAQ
Is it worth outsourcing bookkeeping?
Yes—especially if you're earning $250K+ or spending more than 5–10 hours a month trying to stay organized.
What are the risks of DIY bookkeeping?
Missing deductions, inaccurate books, and spending founder time on low-leverage tasks.
Can I switch from DIY to outsourced bookkeeping mid-year?
Absolutely. Most bookkeepers can clean up past months and take over moving forward.
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Author: Kimi, Co-founder of Sam's List
Kimi writes about what she's learning while building Sam's List and shares honest takeaways from her conversations with accountants and financial advisors across the country. None of this is financial advice—just the stuff most people wish someone told them sooner.