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We love good branding. We love visibility. We love looking successful.
But in this episode, I’m challenging you to ask a deeper question: Is your business actually profitable?

I’m joined by financial powerhouse Toki Simmons, and together we break down what it really takes to make—and keep—money as a business owner. We talk about the difference between revenue, profit, and cash flow, why high income doesn’t always equal success, and how paying yourself starts with mindset, habits, and systems—not just more sales.

We dig into pricing for profit (not popularity), how emotional pricing hurts your bottom line, when to hire support without breaking your business, and why structure doesn’t limit creativity—it creates freedom. Toki also shares how to forecast realistically, plan for seasonal cash flow, and make confident financial decisions heading into the next year.

If you’re tired of building a “pretty” business that doesn’t actually pay you, this conversation will help you shift from fear and avoidance to clarity, confidence, and control over your money.

This episode is about listening to the story your numbers are telling—and finally letting your business work for you.

Our Guest;
Toki Simmons is a Financial Money Manager, business advisor, and the founder of Handle My Books® and the 501(c)(3) nonprofit Do Money Better®—two platforms dedicated to transforming how women manage, grow, and lead with money to help close the gender wealth gap.

With over 35 years of experience, Toki is known for simplifying complex financial concepts and equipping women with the tools to make confident, data-driven decisions. She has helped hundreds of business owners increase revenue, improve profitability, and pay themselves what they’re truly worth.

From boardrooms to television segments, Toki delivers practical truth that shifts how women think about money, leadership, and sustainability. Her mission is clear: Equip and Empower for Equal Representation.

Connect with Toki Simmons
LinkedIn: Toki Simmons
Facebook: Toki Simmons
Website: TokiSimmons.com
Email: CFO@handlemybooks.net

Stay Connected with Dr. Raymona

• Founder/CEO, The Systems Boutique

Want Personalized Help?
Book a Systems Style Strategy Call to get a customized plan for your business: Book Here

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

• Instagram:@DrRaymonaHLawrence

• Assistant Contact Info: Whitney Hoefer – hello@whitneyhoefer.com (Please CC on all correspondence)

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Subscribe to The Systems Boutique Podcast and leave a review if you found this helpful!

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If numbers, spreadsheets, or P&Ls make you want to shut down, this episode is your reset.

In Episode 2 of our Financial Series, I sit down with Toki Simmons — Financial Money Manager, business advisor, and founder of Handle My Books® and Do Money Better®. Together, we break bookkeeping and accounting down into clarity, confidence, and CEO-level strategy.

Whether you’re still tracking expenses in your Notes app or deciding if it’s time to hire support, this conversation simplifies the real financial foundations boutique brands need to scale with intention.

We dive into the essential systems for tracking income and expenses, the moment when pen-and-paper or spreadsheets no longer support growth, and the difference between a bookkeeper and an accountant — including who you actually need. We talk about why CEOs should stop DIY’ing their finances, the “monthly money date” every business owner should have, and what it really means to reconcile your books. She also explains how to spot financial leaks draining your profit, what your P&L truly reveals about your business, how to make smarter decisions using your financial data, and why negative numbers aren’t failure but guidance.

Toki brings honesty, clarity, and a no-jargon approach that makes finance feel empowering instead of overwhelming.

👑 About Our Guest: Toki Simmons

With 35+ years of financial management experience, Toki Simmons has helped hundreds of women strengthen profit, streamline their financial operations, and finally pay themselves what they’re worth. Through Handle My Books® and Do Money Better®, she equips women to make confident, data-backed decisions and close the gender wealth gap.

✨ Key Takeaways

Your numbers are information — not judgment. Bookkeepers handle the details, while accountants provide strategic guidance. Growing businesses shouldn’t be managing their own books. Your P&L tells the true story of your business health. Strategic shifts in pricing and spending can dramatically impact your margins. Most importantly, you deserve to feel powerful and informed when looking at your finances.

If you’re ready to build systems that support your revenue goals and elevate your operations, come work with us at The Systems Boutique.

Your numbers are speaking — this episode helps you finally understand the story.

📞 Book a Strategy Call

https://thesystemsboutique.com

🎧 Listen & Subscribe

YouTube | Apple Podcasts | Spotify | Google Podcasts

Stay Connected with Dr. Raymona

• Founder/CEO, The Systems Boutique

Want Personalized Help?
Book a Systems Style Strategy Call to get a customized plan for your business: Book Here

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

• Instagram:@DrRaymonaHLawrence

• Assistant Contact Info: Whitney Hoefer – hello@whitneyhoefer.com (Please CC on all correspondence)

Never Miss an Episode!

Subscribe to The Systems Boutique Podcast and leave a review if you found this helpful!

Send us a text

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

🎧 Listen & Subscribe
YouTube | Apple Podcasts | Spotify | Google Podcasts

Stay Connected with Dr. Raymona

• Founder/CEO, The Systems Boutique

Want Personalized Help?
Book a Systems Style Strategy Call to get a customized plan for your business: Book Here

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

• Instagram:@DrRaymonaHLawrence

• Assistant Contact Info: Whitney Hoefer – hello@whitneyhoefer.com (Please CC on all correspondence)

Never Miss an Episode!

Subscribe to The Systems Boutique Podcast and leave a review if you found this helpful!