Episode 70: Bookkeeping Platform or Bookkeeper? How to Choose (and When to Switch)

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If you’ve ever wondered whether a bookkeeping platform is enough—or if it’s time to hire a bookkeeper for creatives—this week’s episode of Creative Minds, Smart Money is for you.

I’m digging into the real-world trade-offs between platform bookkeeping (think Bench, Collective, Pilot, Xendoo, inDinero, Paro, KPMG Spark) and working with a dedicated bookkeeper who knows your business inside and out. You’ll walk away with a simple decision rubric you can reuse every 6–12 months, plus guardrails to protect data ownership so bookkeeping migration never turns into a mess.

Why this conversation matters

So many creatives get stuck in one of two places:

1. They choose a platform too fast and end up with tidy reports that don’t answer real decisions, or
2. They stick with a platform too long and try to force “books done” to do the job of strategy.

This episode helps you match the level of support to the real job your numbers need to do—record or decide—so your bookkeeping actually moves the business forward.

Look, I’ve been on both sides of this. When I was running my handmade clothing store and my sticker and pin shop, I thought if my books were “done,” that was enough. Spoiler: it wasn’t. I had no idea if my pricing was covering my costs or which products were actually profitable. That’s the difference between having your books categorized and having numbers that help you make decisions.

What you’ll learn in this episode

• Platform bookkeeping vs. a dedicated bookkeeper—what you’re actually buying (beyond “my books are done”)
• How your business model changes the answer—Stripe, Square, ThriveCart, sales tax, payroll all matter
• Data ownership + portability—keeping your QuickBooks or Xero clean, accessible, and exportable so you’re never stuck
• The red flags it’s time to switch—multiple revenue streams, contractor complexity, custom reporting needs
• The questions to ask before you sign—scope, SLAs, reporting, migration and export terms
• A decision rubric you can reuse—choose your best fit today and revisit as things grow

A quick preview

I share:

• The exact checklist I use with clients to decide between a bookkeeping platform vs bookkeeper
• What to watch for in your contracts around data ownership and exports (this is non-negotiable, trust me)
• Why continuity—one point of contact—can save you time and mistakes as your offer suite grows
• When to keep it lean with a platform and when to upgrade for context and speed

Is this episode for you?

You’ll especially benefit if…

• You’re launching new offers or a membership and payouts/refunds are getting messy
• You’re juggling contractors or payroll and need clearer, faster answers
• You’re asking “Can I afford this?” more than once a month
• You’ve outgrown a basic P&L and need offer-level reporting

Basically, if you’ve ever stared at your profit and loss and thought, “Cool numbers… but what do I do with this?”—yeah, this episode is for you.

Next steps

Listen & subscribe:

• Apple Podcasts
• Spotify
• Episode Page

Want help mapping this to your business? If you’re ready to choose with confidence—or you sense you’ve outgrown your current setup—book a discovery call and I’ll walk you through this rubric with your actual numbers and business model.

P.S. Got a question you want me to cover on the show? Drop it here and I’ll add it to the list.

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