Starting a business can feel exciting, overwhelming, and wildly confusing all at the same time. Whether we’re growing flowers, quilting, selling handmade goods, offering a service, or finally turning a passion into something more official, there are so many moving pieces that it can be hard to know where to begin.
In Episode 116 of The Flower Files, Liza sits down with Shannon Everhart, an enrolled agent, small business tax professional, and fractional CFO, to talk through the foundational financial pieces every new business owner should understand. From choosing a business name to keeping receipts, separating business and personal finances, understanding LLCs and S corps, and charging what we’re worth, this episode is packed with practical advice for anyone building a business from the ground up.
Meet Shannon Everhart
Shannon Everhart began her career in the financial industry working with profit-sharing plans, retirement plans, 401(k) plans, tax returns, and participant reporting. After moving to Maryland, she joined her husband’s HVAC business and handled the back-office side of the company, including payroll, taxes, bookkeeping, and administrative operations.
That experience eventually led her to launch her own tax and bookkeeping business, now branded as The Tax Chick. Today, Shannon works with small business owners on taxes, bookkeeping, payroll, planning, and fractional CFO services.
What makes Shannon’s approach so valuable is that she has been on both sides of the table. She is not just reading business theory from a book. She has lived the realities of payroll stress, cash flow concerns, business transitions, and late-night problem solving. That kind of experience matters when we’re trying to understand the numbers behind our business.
Why Small Business Owners Need Financial Guidance
Many of us start a business because we love the thing we do. We love flowers, plants, design, farming, teaching, creating, or serving our community. Very few of us start a business because we are excited about QuickBooks, tax codes, or financial reports.
That is why having someone who can explain the numbers in normal language is so important.
A good tax professional or fractional CFO can help us understand not just what is happening in the business, but why it is happening. When we understand the why, we can make better decisions about pricing, expenses, marketing, payroll, growth, and profitability.
As Shannon explains in this episode, the numbers do not lie. If money is coming in but nothing is left at the end, we have to look deeper. Are we charging enough? Are expenses too high? Are we taking on too much work for too little profit? Are we working harder instead of smarter?
Those are the kinds of questions every small business owner needs to ask.
Start With the Right Business Name
One of the first steps in starting a business is choosing a name. It sounds simple, but a business name carries a lot of weight.
A strong business name should be memorable, clear, easy to say, and easy to spell. It should also be checked carefully before we get too attached to it.
Before settling on a name, Shannon recommends checking:
- Whether the name is already being used
- Whether the domain is available
- Whether the acronym creates anything awkward
- Whether people naturally reverse or mishear the name
- Whether the name will still make sense if the business grows or moves
Liza shares that with Wildly Native, people sometimes flipped the name around, calling it “Natively Wild.” Because of that, grabbing related domains became an important step in protecting the brand.
Even if we are not ready to build a website right away, buying the domain early can save a lot of money and frustration later. Once a domain is taken, we may be forced to choose another name or pay much more to get it back.
When Do You Have to Report Business Income?
One of the biggest questions new business owners ask is: when do we have to become official?
Shannon’s answer is simple: when we make money, we are supposed to report it.
Even if we are just selling a few bouquets, quilts, crafts, or services, income should be reported. There is not a magical threshold where income suddenly “counts.” If we make a dollar, it is income.
For someone just starting out, that may mean operating as a sole proprietor and reporting business income and expenses on a Schedule C with a personal tax return. As the business grows, it may make sense to consider forming an LLC or electing S corporation tax treatment, but those decisions depend on the business, risk, income, goals, and tax situation.
Sole Proprietor, LLC, and S Corp: What’s the Difference?
This episode breaks down one of the most confusing topics for new business owners: the difference between being a sole proprietor, an LLC, and an S corp.
A sole proprietor is often the simplest starting point. We earn income, track expenses, and report the profit or loss on our personal tax return. A sole proprietor can have employees, but the owner is not treated as an employee of the business.
An LLC, or limited liability company, is generally about liability protection. It helps create separation between the business and the owner personally. However, that protection only works if we keep the business truly separate from our personal finances.
An S corp is not exactly a type of business we form at the state level. Instead, it is a tax election with the IRS. A business, such as an LLC, may elect to be taxed as an S corporation. This can create tax planning opportunities, but it also adds complexity, including payroll, separate tax returns, bookkeeping requirements, and stricter separation of funds.
The key takeaway is that there is not one perfect structure for every business. We need to look at our income, liability, expenses, goals, family situation, and long-term plans with a qualified tax professional.
Keep Business and Personal Finances Separate
One of the biggest mistakes Shannon sees is commingling funds.
Commingling means mixing personal and business money. For example, paying business expenses from a personal account or using the business account for personal purchases.
This can create serious problems, especially for an LLC. If we form an LLC for liability protection but do not keep finances separate, we may weaken that protection.
A better system is to:
- Open a separate business bank account
- Pay business expenses from the business account
- Deposit business income into the business account
- Pay yourself through an owner’s draw or proper payroll structure
- Keep clean records
This separation helps with taxes, bookkeeping, legal protection, and decision-making.
Keep Receipts for Everything
If there is one message Shannon repeats loud and clear, it is this: keep your receipts.
A bank statement or credit card statement may show that we paid a company, but it may not prove exactly what we bought. Shannon shares an audit example where a business owner could show payments to a cell phone company, but because he did not have the detailed bills, the expenses were thrown out.
Digital receipts are fine, but we have to save them. We should not assume a company will keep records forever. Phone bills, bank statements, invoices, receipts, and supporting documents should be downloaded and backed up.
A good habit is to take a photo of receipts, save PDFs, upload records to cloud storage, and keep backups on an external drive or in another secure location.
Charge What You’re Worth
Another major mistake new business owners make is undercharging.
This is especially common when we are working with friends, family, neighbors, or early customers. We want to be generous. We want to be helpful. We want people to say yes. But if we do not charge enough, we may not cover our overhead, time, education, tools, materials, software, insurance, taxes, and experience.
Shannon reminds us that there is value in what we know.
Whether we are preparing tax returns, growing flowers, designing weddings, teaching workshops, or creating custom products, our pricing needs to reflect the full cost of doing business.
There is a difference between selling something and making a profit. As Shannon jokes through the “bigger watermelon truck” example, if we buy watermelons for five dollars and sell them for five dollars, getting a bigger truck does not solve the problem. We are still not making money.
More volume is not always the answer. Better pricing, smarter systems, clear boundaries, and stronger planning often matter more.
Work Smarter, Not Harder
Liza shares an example from Wildly Native where the team completed six weddings in one weekend. On paper, it looked like more work should equal more money. But when they looked at the bottom line, the profit was not meaningfully different from doing fewer weddings.
That kind of realization is exactly why reviewing the numbers matters.
Sometimes more work creates more expenses, more stress, more payroll, more exhaustion, and very little additional profit. A fractional CFO or financially minded advisor can help us look at capacity, pricing, staffing, and profitability so we can make better choices.
As business owners, we have to ask:
Are we building a business that supports our life, or are we just creating a stressful job for ourselves?
Plan for the Business You Actually Want
Another important topic in this episode is long-term planning.
Do we want to sell the business someday? Do we want it to run without us? Do we want to retire from it? Do we want it to support our family, employees, or community long term?
If we are the entire business, it may be hard to sell. If everything depends on us, we may not have flexibility or freedom. That does not mean every business has to become huge, but it does mean we need to be honest about our goals.
The earlier we understand the numbers, systems, and structure, the easier it becomes to build a business that matches the life we want.
Final Takeaways for New Business Owners
Starting a small business can feel messy, but we do not have to figure it all out alone. The biggest lessons from this episode are simple and powerful:
Choose a strong business name. Check the domain. Report income. Keep receipts. Separate business and personal funds. Ask questions. Find professionals you trust. Charge what you are worth. Understand your numbers. And above all, build a business that supports your life instead of consuming it.
When we understand the financial foundation of our business, we can make decisions with more confidence, less stress, and a clearer path forward.
