Bookkeeping Platform or Bookkeeper? How to Choose (and When to Switch)

Creative Minds, Smart Money: Finance & Business Tips for Creatives

Everyone online makes bookkeeping platforms sound like a magic fix: low cost, hands-off, done-for-you. But here’s the truth—I see creatives pick a platform too fast (or switch too late) and end up with messy categorization, limited data ownership, and zero strategic insight. In this episode of Creative Minds, Smart Money, I break down how to choose between a bookkeeping platform vs. a bookkeeper, when to switch, and how to keep your bookkeeping data portable no matter what you pick.

I walk through the real trade-offs between popular platform bookkeeping options—Bench, Collective, Pilot, Xendoo, inDinero, Paro, KPMG Spark—and hiring a dedicated bookkeeper for creatives who knows your business inside and out. You’ll leave with a simple decision rubric to evaluate scope, continuity, and bookkeeping migration concerns, so your numbers actually help you make decisions.

In this episode, I cover:

• Platform bookkeeping vs. dedicated bookkeeper—what you’re truly buying (beyond “my books are done”)

• How your business model (offers, payment processors like Stripe/Square/ThriveCart, sales tax, payroll) changes the answer

• Data ownership & portability: set up your stack so you’re never stuck if you switch (think QuickBooks or Xero access, exports, reporting)

• Continuity & context: why a single point of contact can prevent rework and errors as you grow

• Red flags it’s time to switch: multiple revenue streams, contractors, inventory, or new growth plans

• Questions to ask before choosing (scope, SLAs, cleanup policies, reporting, migration/export options)

• A quick decision rubric to pick your best-fit today—and revisit in 6–12 months

If you’ve wondered whether a platform or a person is the smarter move for your stage, this episode gives you a clear, no-BS way to decide—without pressure, panic, or FOMO.

🎧 Hit play now and find your best-fit bookkeeping support—so your numbers actually help you run the business.

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