The Successful Bookkeeper · 500+ Episodes + 100+ Articles

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Ten years of conversations with the bookkeepers who built real businesses, plus every Successful Bookkeeper article — searchable, askable, actionable. One question, answers from the entire TSB archive.

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500+ episodes 100+ articles 43,000+ bookkeepers listening
Ask TSB · Answered from 3 episodes
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How do I raise my prices without losing clients?
Answer

Across the episodes, the bookkeepers who raised prices successfully did three things in common — and the order matters.

1. They got crystal clear on the value before the conversation. Every pricing shift in the library happens at a catalyst moment, not from learning a methodology. For Kimme Lafayette it was COVID hitting her cash flow. For Dan Baker it was a client doing $600K in revenue with a $19K T4 — the number was undeniable.

2. They structured the conversation as an invitation, not an announcement. Brad Wolford's "reverse opt-out" letter is the cleanest template: clients had to opt out of the new pricing, not in. Almost nobody opted out.

3. They accepted that some clients would leave — and that's the point. The clients who don't pay more are usually the clients draining your evenings and weekends. Letting them walk is what unlocks the capacity for the next tier.

2 of 3 free questions used today Members ask unlimited questions — plus download Brad's actual letter as an Action Pack.
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Browse the archive.

Showing 522–516 · 527 total
EP528
EP528 · Apr 21, 2026

Teresa Slack - From $18/Hour To Million-Dollar Firm:The Pricing Shift

30-sec brief
Teresa Slack shares how pricing mistakes nearly broke her business—and how she fixed them to build a million-dollar firm.
EP527
EP527 · Apr 14, 2026

Justin Atherton - The Clarity Advantage Most Bookkeepers Ignore

30-sec brief
Justin Atherton shares how your words impact trust, deadlines, and results—and how to fix it fast.
EP526
EP526 · Apr 7, 2026

David Homan - Why Networking Feels Broken & What Actually Works - Part 2

30-sec brief
David Homan shares how to build real relationships, overcome hesitation, and turn everyday connections into lasting business growth.
EP525
EP525 · Mar 31, 2026

David Homan - Why Networking Feels Broken & What Actually Works - Part 1

30-sec brief
David Homan shares a practical approach to building trust, creating real connections, and turning your network into meaningful opportunities.
EP524
EP524 · Mar 24, 2026

Gina Cotner – The Simple Accountability System That Gets Work Done

30-sec brief
Gina Cotner shares a practical framework for holding your team accountable, improving delegation, setting clear deadlines, and building high-performing leaders inside your bookkeeping firm.
EP523
EP523 · Mar 19, 2026

Spotlight - Joe Woodard - How To Stay Relevant In The AI Era

30-sec brief
Discover how AI is reshaping bookkeeping with insights from Joe Woodard. Learn how to evolve your services, pricing, and role to stay relevant.
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Michael is the co-founder of The Successful Bookkeeper Global and has spent the last decade talking with the bookkeepers quietly building extraordinary firms. What started as a handful of conversations is now 500+ episodes — and one of the largest bookkeeping communities in the world.

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From $50/Hour to Value Pricing — How Rebecca Tran Rebuilt Her Firm
EP 528 · Rebecca Tran
17:42
54:08