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Timothy LeGendre CPATimothy LeGendre CPA LLC

56 answers, written by me

Frequently asked questions.

The questions I hear most, about taxes, bookkeeping, pricing, and what it's like to work with my practice.

Start here

The ones everyone asks first.

Should I elect S-Corp status for my business?

S-Corp election can save you significant money on self-employment taxes once your net income exceeds roughly $40,000 annually. However, it comes with additional requirements like running payroll for yourself and filing a separate corporate return. I evaluate each client's situation individually to determine if the tax savings outweigh the added compliance costs.

How much does a CPA cost?

It depends on your business. Your revenue, transaction volume, how many entities you have, and what you need done. I scope every engagement to the business it serves. Book a discovery call and I'll walk you through what it would look like.

How do I switch from my current CPA?

Switching is straightforward. I request a copy of your prior year returns and any relevant workpapers from your current CPA (with your authorization). There is no need to notify them in advance. I handle the transition seamlessly. Most clients are fully transitioned within one to two weeks with zero disruption to their business.

When are quarterly estimated taxes due?

Quarterly estimated tax payments are due April 15, June 15, September 15, and January 15 of the following year. If a due date falls on a weekend or holiday, the payment is due the next business day. Missing a deadline can result in underpayment penalties, so I recommend setting calendar reminders well in advance.

Browse all 56 questions below, or search for what you need.

Tax

18 questions

The questions I hear most during tax season, deadlines, deductions, and what actually saves you money.

Bookkeeping

11 questions

How bookkeeping should work, and why shoeboxes in April cost more than monthly books.

Business

6 questions

LLC vs S-Corp, what you can deduct, and the operational questions founders ask me over coffee.

Pricing

6 questions

Every engagement is scoped for the business it serves. Here's how that works.

Want a real number for your business?

A few questions, then pick a time.

Book a Discovery Call

Getting Started

4 questions

What the first 30 days look like when you hire me, and what you'll need to bring.

Ready to get started?

I'll walk you through exactly what I need.

Book a Discovery Call

About Timothy

11 questions

The small-shop questions, who I am, how I operate, and why I'll always pick up the phone.

Didn't find it?

Ask me anything I read every note.

Send me your question and I'll get back to you, usually same day.

Tim

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Frequently asked questions

When are quarterly estimated taxes due?
Quarterly estimated tax payments are due April 15, June 15, September 15, and January 15 of the following year. If a due date falls on a weekend or holiday, the payment is due the next business day. Missing a deadline can result in underpayment penalties, so I recommend setting calendar reminders well in advance.
Should I elect S-Corp status for my business?
S-Corp election can save you significant money on self-employment taxes once your net income exceeds roughly $40,000 annually. However, it comes with additional requirements like running payroll for yourself and filing a separate corporate return. I evaluate each client's situation individually to determine if the tax savings outweigh the added compliance costs.
What's the standard deduction?
For the 2025 tax year (the return you file in 2026), the standard deduction is $15,750 for single filers, $31,500 for married filing jointly, and $23,625 for head of household under the One Big Beautiful Bill Act. It is adjusted for inflation every year, so check IRS Publication 501 for your filing year. If your itemized deductions (mortgage interest, state taxes, charitable contributions) exceed the standard deduction, itemizing may save you more.
How do I deduct my home office?
You can use either the simplified method ($5 per square foot, up to 300 sq ft for a $1,500 max deduction) or the regular method, which calculates the actual percentage of home expenses used for business. The space must be used regularly and exclusively for business. I typically recommend the simplified method for most clients unless your home office is large or your housing costs are high.
I'm paying too much in taxes and I don't even know why. Can you really reduce that?
If you're overpaying, it usually means poor structure, missed strategy, or both. I specialize in identifying where taxes are being paid unnecessarily and restructuring the setup, legally, to reduce exposure going forward.
Is tax planning something you do year-round, or only when it's time to file?
Real tax planning happens before December, not in April. I watch client numbers as the year develops, reviewing projections, adjusting estimated payments, evaluating major purchases, and implementing year-end strategies like retirement contributions and equipment depreciation while the moves still count. By the time we file, the work to minimize your bill is already done.
Can you show me how to legally pay less in taxes?
That's a core part of what I do. I look at your entity structure, income allocation, timing of expenses, retirement contributions, and depreciation strategies. Every business has legal ways to reduce its tax burden. Most owners just don't know what they are until a CPA shows them.
When should I start thinking about my taxes?
Ideally, before the year ends. The best moves to lower your taxes (like purchasing equipment or funding retirement accounts) must happen before December 31st.
What is the difference between a CPA and a regular tax preparer?
A CPA (Certified Public Accountant) is a state-licensed professional held to the highest ethical and educational standards. Unlike non-certified preparers, I can represent you before the IRS and offer deep strategic advice, not just data entry.
My last CPA just "filed the return." I need someone who actually understands business.
That is exactly the difference here. I do not operate as a form-filler. My background includes real business operations, real estate, lending, and valuation. I understand how your decisions today affect your position six months or three years from now.
Can you help me decide whether a business or property is actually worth buying?
Yes. I analyze value, risk, cash flow, hidden liabilities, and long-term viability. I do not rely on "potential" or hype. I rely on numbers and reality.
My business isn't profitable on paper, but I feel like I'm working nonstop. What gives?
This is usually a structure or margin problem. More work does not equal more profit. I will identify where the money is being lost, whether it's overhead, pricing, inefficiency, or tax drag.
What documents do I need to bring for our first meeting?
For our initial consultation, having your previous year's tax return and a current P&L (Profit and Loss) statement is very helpful.
I don't just want "tax prep." I want someone in my corner long-term.
Then you're looking for a strategic relationship, not a once-a-year service. That is exactly how I operate. My role is to help you make better financial decisions over time, not just meet a deadline.
What does tax advisory include?
Tax advisory is the planning side of tax work, entity structure, how you pay yourself, retirement contributions, the timing of equipment purchases and income, and the write-offs your situation actually supports. Tax preparation files the year that already happened; advisory shapes the year that has not. The strategies that apply depend on your numbers, which is exactly what a discovery call sorts out.
What kinds of tax strategies do you actually use?
The ones the tax code provides and your numbers support: S-Corp compensation structure, retirement plan stacking, hiring family members correctly, accountable plan reimbursements, vehicle and equipment timing, the home office done right, and more. Every strategy I recommend is grounded in the statute and documented properly, no gray-area schemes. Which ones fit your business is the first thing I look at.
When should a business owner start tax planning?
Before year-end. Most of the moves that actually lower a tax bill close on December 31, not in April. And the more your profit grows, the more each planning decision is worth. If you are past roughly six figures of net income and no one has walked you through your options, you are almost certainly leaving money on the table.
How do I stop getting surprise tax bills?
Surprise bills come from finding out what you owe after the year is over. The fix is knowing the number while you can still do something about it: books that stay current, a running profit picture, estimated payments that adjust as the year moves, and planning conversations before December instead of a scramble in March. That is the core of the tax advisory work I do.
How often should I reconcile my books?
Monthly reconciliation is the gold standard. It ensures your records match your bank and credit card statements, catches errors or fraudulent charges early, and keeps your financials accurate for decision-making. Waiting until year-end to reconcile often means scrambling to fix months of discrepancies under time pressure.
What's the difference between cash and accrual accounting?
Cash basis records income when you receive payment and expenses when you pay them. Accrual basis records income when earned and expenses when incurred, regardless of when money changes hands. Most small businesses start with cash basis for simplicity, but businesses with inventory or over $30 million in gross receipts are generally required to use accrual.
Do I need a separate business bank account?
Yes. A separate business bank account is essential. It simplifies bookkeeping, provides a clear audit trail, and protects your personal liability shield if you operate as an LLC or corporation. Mixing personal and business funds (commingling) can lead to the IRS or a court "piercing the corporate veil," leaving your personal assets exposed.
How long should I keep my financial records and receipts?
The IRS generally recommends keeping tax records for at least three years from the filing date. However, I advise keeping records for seven years to cover situations like unreported income or fraud claims. Digital copies (scans or photos) are acceptable, just make sure they are legible and organized by year and category.
My books are a mess. Can you actually fix them or are you just going to judge them?
Yes, I fix them. I've seen everything: missing transactions, mixed personal and business expenses, incorrectly filed returns, messy QuickBooks files, and years of disorganization. This is not theory for me. I isolate the problems, rebuild clean records, and get you back to a stable, usable financial foundation.
I don't understand my own financial statements. Should that be a red flag?
Yes. If you don't understand your numbers, you don't control your business. I break them down until you fully understand what they're telling you. A business owner who can't read their statements is making blind decisions.
Can you take over my bookkeeping, or do I still have to do all that?
Both options exist. I can fully manage your bookkeeping on a monthly basis, clean up and reconcile past records, review what you've done yourself, or help you set up a system you can maintain with confidence. Most clients prefer full management so they can focus on running their business.
I don't want to waste time on complicated software. Are you going to force me into something?
No. The tool must match the user. Complicated systems are worthless if they don't get used correctly. I focus on what actually works long-term.
Can you help me find where I'm wasting money every month?
Yes. Most businesses leak money in small, consistent ways, duplicate subscriptions, miscategorized expenses, overpaying for services, or missing early payment discounts. During the first month of bookkeeping, I typically find at least a few areas where spending can be tightened without affecting operations.
What if I've been doing things "wrong" for years? Am I in trouble?
In most cases, it's fixable. The IRS has a three-year statute of limitations for standard returns and six years for significant underreporting. If there are errors, I can file amended returns and get things corrected. The real risk isn't what you did wrong in the past. It's continuing to avoid dealing with it.
Do I have to sign a long-term contract?
No. My bookkeeping services are month-to-month. You can cancel at any time with 30 days' notice.
LLC vs S-Corp: which is better for my business?
An LLC is a legal entity type that provides liability protection and flexibility. An S-Corp is a tax election that can be applied to an LLC. Many business owners form an LLC and then elect S-Corp status once their income justifies the self-employment tax savings. The right choice depends on your income level, growth plans, and willingness to handle payroll compliance.
How much should I pay myself as an S-Corp owner?
The IRS requires S-Corp owners who perform services to pay themselves a "reasonable salary" before taking distributions. Reasonable means comparable to what you would pay someone else to do the same work. Setting your salary too low risks IRS scrutiny and reclassification of distributions as wages with back taxes and penalties.
What business expenses can I write off?
Common deductible business expenses include office supplies, software subscriptions, professional services, advertising, vehicle use (mileage or actual expenses), travel, meals (50% deductible when business-related), insurance premiums, and home office costs. The key test is that the expense must be ordinary and necessary for your business. I help clients identify deductions they often overlook.
I just started a business. What do I need to set up financially?
At a minimum, you need a separate business bank account, an EIN (Employer Identification Number) from the IRS, a bookkeeping system to track income and expenses, and a plan for quarterly estimated tax payments. Depending on your entity type, you may also need to register with your state and set up payroll. I walk new business owners through the entire setup process.
I'm a barber / landscaper / beekeeper / tradesman / niche operator. Do you really understand my type of business?
Yes, because I understand systems, not just industries. Every business runs on the same fundamentals: income, expense, margin, labor, timing, and cash flow. The specifics change. The structure doesn't.
My business isn't "formal." Cash, Venmo, side jobs, etc. Is that a problem?
It's more common than you'd think, and it's not a deal-breaker. But income from cash, Venmo, Zelle, and side work is still taxable. I help you organize what exists, set up a simple tracking system going forward, and make sure you're reporting accurately so there are no surprises from the IRS.
How much does a CPA cost?
It depends on your business. Your revenue, transaction volume, how many entities you have, and what you need done. I scope every engagement to the business it serves. Book a discovery call and I'll walk you through what it would look like.
What's included in monthly bookkeeping?
Monthly bookkeeping includes categorizing all transactions, reconciling bank and credit card accounts, generating financial statements (Profit & Loss, Balance Sheet), and ongoing communication about your financial position. Depending on the engagement, sales tax filings and coordination with your payroll provider are part of the work too.
Do you offer free consultations?
Yes, I offer a 30-minute discovery call to learn about your business, understand your needs, and explain how I can help. This is a no-pressure conversation. I want to make sure we are a good fit for each other before you commit to anything. You can book a time directly on my website.
How quickly will my tax return be completed?
For clients who provide all documents promptly, I typically complete individual returns within 1–2 weeks and business returns within 2–3 weeks. During peak season (March–April), timelines may extend slightly. Year-round bookkeeping clients get priority scheduling since their financials are already up to date.
Can I actually afford you, or is this going to be out of my league?
Most people think in terms of "cost." I work in terms of "net result." If I'm not helping you save more, run cleaner, or earn more than I cost, then it doesn't make sense for either of us.
Do you charge by the hour or by the project?
It depends on the type of work. Every engagement is scoped for the business it serves. I am clear upfront. No surprises. No ambiguity.
What do I need to get started?
To get started, I need your prior year tax return (if available), government-issued ID, bank and credit card statements for the current year, and any relevant tax documents (W-2s, 1099s, etc.). For business clients, I also need access to your accounting software or a summary of income and expenses. I provide a detailed checklist once we begin.
How does onboarding work?
After your discovery call, I send a proposal outlining exactly what I will handle. Once accepted, you get access to a secure client portal where you can upload documents, send messages, and track progress. I review your prior returns, set up your books, and schedule a kickoff call to align on goals and timelines. The entire process typically takes less than a week.
Can you help with catch-up bookkeeping?
Absolutely. Many new clients come to me with months or even years of unorganized records. I clean up and reconcile your books from wherever they left off, categorize transactions, and bring everything current. I scope the work and quote it up front after a look at your accounts, so you know where you stand before anything starts.
How do I switch from my current CPA?
Switching is straightforward. I request a copy of your prior year returns and any relevant workpapers from your current CPA (with your authorization). There is no need to notify them in advance. I handle the transition seamlessly. Most clients are fully transitioned within one to two weeks with zero disruption to their business.
How do I know you actually understand people like me?
Because I've lived in the same world as the people I serve. I've worked for business owners, alongside business owners, and I am one myself. I understand the pressure, the uncertainty, and the responsibility you carry every day. You won't have to translate your life into accounting language for me.
Will I actually be able to communicate with you?
Yes. No ticket systems, no runaround. You get a direct line and a real answer. I'm known for being responsive, direct, and honest, even when the answer isn't what you want to hear.
I left my last CPA because I never knew what was going on. How transparent are you?
Completely. I explain what I'm doing, why I'm doing it, and what it means for you. If you don't understand something, that's a failure on my end, not yours.
Who is not a good fit for you?
If you want a 'yes-man', bargain pricing, or minimal involvement in your own finances, I'm not the right fit. If you want clarity, order, truth, and accountability, then we'll work very well together.
I've felt judged or talked down to by CPAs before. Are you like that?
No. My job is not to judge. My job is to help you see clearly and then move forward intelligently. Shame and confusion keep people stuck. Clarity and direction change everything. That's where I operate.
I've been ignored by accountants in the past once they had my money. Will that happen with you?
No. I don't take on more clients than my practice can serve well. That is why I turn people away. My reputation matters more than volume.
Do you actually care about my situation or am I just another account?
I work with a limited number of clients by design. I know their businesses, their patterns, and their pressure points. You are not a number in a system. You're a person whose financial decisions affect your entire life.
Are you more 'corporate' or more grounded?
Grounded. I'm professional, but I'm still a human being. I speak plainly. I don't use jargon to hide behind intelligence. I value truth, discipline, responsibility, and stewardship over appearances.
What type of clients do you work best with?
I do my best work with trade businesses, plumbers, HVAC, electrical, outdoor services, and established small businesses in the $750K–$5M revenue range that are ready for better systems, clean books and records, and tax done the right way. I also work with S-Corp owners and real estate investors. I intentionally do not work with organizations over $25M in revenue or businesses managing more than 15 bank/credit accounts. I keep my client base focused so every client gets real attention, not outsourced attention.
I've had bad experiences with CPAs in the past. Why would this be different?
Most CPAs have only lived inside an office. I've lived in multiple industries, multiple roles, and multiple income structures. I understand real-world problems because I've actually dealt with them myself.
Do you work better with individuals or business owners?
I work best with business owners and serious individuals who want to understand and improve their financial position. If you're willing to face reality, I can help you change it.

Timothy LeGendre CPA LLC | Florida CPA License #AC62625 (firm #AD72267) | Mount Dora, FL | (407) 417-1064 | Contact