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Have you ever wondered whether the business structure you chose is actually supporting the brand you’re building?

I know how confusing it can feel — choosing between a Sole Prop, LLC, or S-Corp isn’t just a legal decision, it’s a strategic one… and it shapes your taxes, your protection, and your ability to scale in style.

In this episode of The Systems Boutique Podcast, I sit down with Toki Simmons, a financial expert with 35+ years of experience helping women make confident, data-driven decisions. Together, we break down business structure in a way that finally feels clear and empowering.

We cover:
- Which entity actually protects you
- When an LLC is (and isn’t) the right move
- Why co-mingling funds destroys your protection
- What “reasonable compensation” means for S-Corp owners
- How structure shifts as your revenue grows
- The most common financial mistakes women CEOs make
- How to choose a structure that supports your brand’s long-term vision

If you’re ready for a backend that feels as strong and sophisticated as your brand on the outside, this conversation is your starting point.


Our Guest:
Toki Simmons is a powerhouse Financial Money Manager, business advisor, and the founder of Handle My Books® and the nonprofit Do Money Better®. She is dedicated to transforming the way women manage and grow their business finances to close the gender wealth gap. With over 35 years of experience, Toki simplifies financial complexity and equips women to make confident, data-backed decisions. She has helped hundreds of business owners increase revenue, strengthen profit, and finally pay themselves what they’re worth. Her mission: "Equip and empower for equal representation."


Key Takeaways:
Structure is strategy — not just paperwork.
LLC protection disappears if you mix personal + business funds.
S-Corp status requires payroll and forces you to compensate yourself appropriately.
Your entity should evolve as your revenue, risk, and brand mature.
The right structure saves money, protects assets, and supports scale.

And if you’re ready for hands-on support, come work with me inside The Systems Boutique — where we design operations that scale your business in style.

Your structure shapes your future.
Let’s make sure it’s built beautifully.

📞 Book a Strategy Call: https://thesystemsboutique.com

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• Founder/CEO, The Systems Boutique

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•The Systems Boutique’s Website (for general info and to book a discovery call):The Systems Boutique

• Instagram:@DrRaymonaHLawrence

• Assistant Contact Info: Whitney Hoefer – [email protected] (Please CC on all correspondence)

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