How to Choose the Right Business Structure: LLC, S-Corp, C-Corp, or Sole Proprietorship?
A clear, simple guide for new small business owners
Starting a business comes with excitement, ideas, and plans — but one of the most important decisions you’ll make early on is choosing the right business structure. The structure you choose affects your taxes, personal liability, how you pay yourself, and even how easily you can grow. At Connell Tax & Advisory, we help new entrepreneurs choose the structure that protects them, maximizes tax benefits, and aligns with their long-term goals. This guide breaks down the major business structures in plain language so you can feel confident moving forward.
1. Sole Proprietorship
Best for: Simple one-person businesses, side hustles, early-stage testing
A sole proprietorship is the simplest form of business — and the most common for new entrepreneurs.
Pros:
Easiest and cheapest to start
Very little paperwork
You report everything on your personal tax return
Great for testing a business idea before formalizing it
Cons:
No liability protection — your personal assets are at risk
Harder to separate business and personal finances
No real tax planning flexibility
Insight:
If you’re making more than a few thousand dollars or working with customers regularly, it’s usually time to upgrade to an LLC for protection.
2. Limited Liability Company (LLC)
Best for: Small to midsize businesses, service businesses, real estate investors, contractors
An LLC is the most popular structure for small businesses — and for good reason.
Pros:
Liability protection (your personal assets are shielded)
Flexible tax treatment
Minimal ongoing paperwork
Can have one or multiple owners
Professional and credible for customers
Cons:
You still pay self-employment taxes unless you elect S-Corp status
Rules vary slightly by state
Not ideal for businesses seeking outside investors
Tax Flexibility
An LLC can choose how it wants to be taxed:
As a sole proprietor (default for single-member)
As a partnership (default for multi-member)
As an S-Corporation (tax election)
As a C-Corporation
This flexibility makes LLCs extremely powerful for tax planning.
Insight:
For most early-stage service businesses or consultants, LLC + S-Corp election is often the sweet spot (depending on your income level).
3. S-Corporation (S-Corp)
Best for: Active businesses earning ~$60k+ in profit; service businesses; contractors; freelancers with steady income
An S-Corp is not a type of business entity — it’s a tax election available to LLCs and corporations.
It allows you to split your income between:
Reasonable salary (subject to payroll taxes)
Distributions (not subject to payroll taxes)
This split can significantly reduce your overall tax burden.
Pros:
Reduced self-employment taxes
Owners can take tax-advantaged distributions
Good for growing service businesses
Still provides liability protection (through an LLC or corporation structure)
Cons:
You must run payroll
More IRS scrutiny around “reasonable compensation”
Additional filings and bookkeeping
Insight:
If your business earns enough to pay yourself a reasonable salary and still produce extra profit, an S-Corp can save thousands annually.
4. C-Corporation (C-Corp)
Best for: High-growth companies, startups seeking investors, companies planning to reinvest profits
A C-Corp is a more complex structure designed for scalability and investment.
Pros:
Unlimited owners
Attractive to investors and venture capital
Lower flat federal corporate tax rate
Can retain earnings in the company for growth
Cons:
Double taxation (the corporation pays taxes, then shareholders pay taxes on dividends)
More regulatory requirements
Higher accounting cost
When a C-Corp makes sense:
You plan to raise money
You want to offer stock to employees
You plan to reinvest profits rather than distribute them
Insight:
Most small local service businesses do not need a C-Corp — an LLC or S-Corp is usually the better fit. But for scalable ventures, this is often the right choice.
Key Questions to Ask Before Choosing
Before selecting a structure, consider these important questions:
✅ Do you want liability protection? If yes, eliminate sole proprietorship immediately - LLCs could be the best option.
✅ How much profit do you expect in year one? Higher profits often favor an S-Corp for tax benefits.
✅ Do you plan to add partners? LLCs and corporations handle multi-owner structures best.
✅ Do you need outside investors? Investors almost always prefer C-Corps.
✅ How important is tax flexibility? LLCs offer the broadest range of options.
Our Recommendation Framework
Here’s a simple way Connell Tax & Advisory typically guides new entrepreneurs:
💼 Side hustle or early testing
→ Start as a sole prop, move to LLC when income stabilizes.
🧰 Local service business (contractor, consultant, handyman, designer, etc.)
→ LLC with option to elect S-Corp when profits rise.
🏢 Growing small business with steady profit
→ LLC taxed as S-Corp for maximum tax efficiency.
🚀 Scalable or investor-focused startup
→ C-Corp from day one.
This framework ensures entrepreneurs choose the structure that fits both their current needs and future ambitions.
Final Thoughts
Choosing the right business structure doesn’t just affect taxes — it influences your protection, credibility, and long-term financial success. The good news? You don’t have to figure it out alone.
At Connell Tax & Advisory, we help entrepreneurs and small business owners select the structure that protects their personal assets, minimizes taxes, and sets a stable foundation for long-term growth.
Whether you’re launching your first business or transitioning an existing one, we’re here to guide you with clarity and confidence.
10 Overlooked Tax Deductions Most Individuals Miss Every Year
Most people file their taxes thinking they covered everything… only to discover they left money on the table. The U.S. tax code is full of deductions and credits designed to reduce your tax bill — but many of the most valuable ones are also the easiest to miss. At Connell Tax & Advisory, we help families and individuals take advantage of every tax-saving opportunity.
Below are 10 commonly overlooked deductions and credits that could meaningfully lower your tax burden this year.
1. State Sales Tax Deduction (Even If You Don’t Itemize Often)
Most people assume they can only deduct state income taxes — but you can choose to deduct state sales tax instead.
This is valuable if:
You live in a state with high sales tax and low income tax
You made large purchases (car, RV, appliances, furniture)
You had major renovation or construction expenses
Even if you didn’t track receipts, the IRS provides a sales tax calculator you can use.
2. Medical Miles Driven to Appointments
You can deduct miles driven for medical appointments, prescriptions, therapy visits, and certain health-related errands.
For 2025, the IRS medical mileage rate is eligible as long as:
The mileage is documented
The medical expenses exceed 7.5% of your AGI when itemizing
People often forget this — but it adds up quickly.
3. Student Loan Interest Paid by Someone Else
If someone makes student loan payments on your behalf, the IRS generally treats it as though you received the money first, then paid the loan — meaning you may be able to take the deduction. This applies even if the payer isn’t a dependent.
4. Educator Expenses for Teachers
Teachers, instructors, classroom aides, and principals may deduct:
Classroom supplies
Books
Software
Professional development
Classroom materials purchased out-of-pocket
This deduction increases periodically and is available even if you do not itemize.
5. Job Search and Career Development Costs (Often Missed)
While not all job-search costs are deductible, certain professional-development and education expenses related to your current career may still qualify, including:
Industry certifications
Continuing education
Certain licensing fees
Professional dues
If the expense maintains or improves your skills, it may be deductible or qualify for a credit.
6. Home Office Deduction — Even for Partial Use
If you are self-employed, gig-working, or freelancing, you may qualify for a home office deduction — even if:
Your workspace is small
It's a sectioned-off corner of a room
You only use part of a room exclusively
You can choose the simplified method or calculate actual expenses.
7. Charitable Contributions You Didn’t Realize Were Charitable
Most people think of cash donations, but you can also deduct:
Clothing and household goods donated to nonprofits
Mileage driven for volunteer work
Out-of-pocket expenses for volunteering
Supplies purchased for charitable events
Donations of appreciated stock (a powerful tax-saving move)
Just remember: donations must go to a qualified charity.
8. State Tax Refunds (If You Itemized Previous Year)
Many individuals forget that state refunds may be taxable — but also forget they may be negative income (a deduction) in certain situations.
A proper review helps prevent surprises.
9. Energy Efficiency Home Credits
If you improved your home this year, you may qualify for a credit for:
Insulation
New windows or doors
Heat pumps
Water heaters
Solar and renewable energy systems
These credits can be generous and are often missed because people assume they need extensive documentation (which is not always the case).
10. Health Insurance Premiums for Self-Employed Individuals
If you’re self-employed and pay for your own health insurance, you may be able to deduct:
Health premiums
Dental premiums
Vision premiums
Long-term care insurance (up to limits)
This deduction reduces AGI, which can increase eligibility for other credits.
The Bottom Line: Small Deductions Add Up to Real Savings
Most individuals overlook at least one of these opportunities each year — especially if they file quickly, rely solely on software, or don’t review their full financial picture.
At Connell Tax & Advisory, we help families and professionals uncover every deduction, every credit, and every tax-saving option available to them. The result? Less stress, more clarity, and a tax bill that reflects the small advantages that add up in a big way.
If you’d like a personalized deduction review, we’re here to help.
Smart Year-End Tax Strategies for Individuals: Maximize Your Savings Before December 31st
As the year winds down, most people turn their attention to holidays, travel, and family. But there’s one more item worth checking off your list before December 31st — a year-end tax review. With a few intentional moves, you can still meaningfully reduce your tax bill, set yourself up for a stronger financial year ahead, and avoid surprises come April.
At Connell Tax & Advisory, we help individuals and families make confident, proactive decisions before the year closes. Below are the most impactful, easy-to-understand year-end strategies that can help you keep more of your hard-earned money.
1. Max Out Tax-Advantaged Retirement Contributions
Contributing to retirement accounts is one of the most effective ways to reduce taxable income.
401(k), 403(b), and Employer Plans
2025 employee contribution limit: $23,500
Age 50+ catch-up: additional $7,500
Every dollar you contribute lowers your taxable income today and grows tax-deferred for the future.
Traditional IRA
Contribution limit: $7,000
Age 50+ catch-up: additional $1,000
Depending on your income and employer plan coverage, IRA contributions may be deductible.
If you received a year-end bonus, consider directing part of it toward your retirement plan to reduce your tax burden.
2. Use the “Backdoor Roth” if You’re a High Earner
If your income is above IRS limits for direct Roth IRA contributions, a backdoor Roth IRA can still allow you to build tax-free retirement income.
This involves:
Contributing to a non-deductible IRA
Converting it to a Roth IRA
This strategy can be powerful, but it must be done properly to avoid unexpected tax implications.
3. Harvest Investment Losses to Offset Gains
If you sold investments this year for a profit, you may face capital gains taxes. But you can reduce or eliminate those taxes using tax-loss harvesting:
Sell investments that have dropped in value
Use the loss to offset gains
Offset up to $3,000 of ordinary income if losses exceed gains
Carry forward unused losses indefinitely
This strategy should be approached thoughtfully to avoid the “wash sale rule,” which disallows the loss if you repurchase a substantially identical investment within 30 days. Even passive investors can benefit from harvesting losses periodically — especially in volatile markets.
4. Boost Your HSA or FSA Before It's Too Late
Health Savings Account (HSA)
HSAs offer triple tax benefits:
Deductible contributions
Tax-free growth
Tax-free withdrawals for medical expenses
2025 Contribution limits:
$4,300 for individuals
$8,550 for families
$1,000 catch-up for age 55+
If you’re enrolled in a high-deductible health plan, maxing your HSA is one of the smartest financial decisions you can make.
Flexible Spending Accounts (FSA)
Most FSAs are “use it or lose it.” Check your balance now — glasses, prescriptions, dental work, and other health expenses often qualify.
5. Make Strategic Charitable Donations
If you itemize deductions, year-end giving can significantly reduce your taxable income.
Ways to donate:
Cash donations to qualified charities
Donor-Advised Funds (DAFs) — contribute now, distribute later
Non-cash items such as clothing or household goods
Appreciated stock — avoid capital gains and receive a full-value deduction
Even if you take the standard deduction, there may still be opportunities depending on future tax law changes or bunching strategies.
6. Prepay Certain Expenses to Unlock Deductions Early
For individuals who itemize deductions, prepaying certain expenses before year-end can increase deductions in the current tax year.
Common examples:
State estimated tax payments
Property taxes
Mortgage interest (depending on your lender)
Medical expenses if you’re close to exceeding 7.5% AGI threshold
This strategy is especially helpful if you’re planning a large medical procedure or home tax payment in January — shifting it to December may increase your totals.
7. Review Withholdings and Avoid a Surprise Tax Bill
If you switched jobs, earned bonuses, or had unexpected income, your withholdings may not reflect your total tax liability.
A quick year-end check can:
Prevent underpayment penalties
Help you adjust last paycheck withholdings
Ensure you start the next year on the right foot
Most people wait until filing time — but by then it’s too late to correct a shortfall.
8. Take Advantage of Education Tax Credits
If you or your dependents paid for education this year, explore:
American Opportunity Tax Credit (AOTC): Up to $2,500 per student
Lifetime Learning Credit (LLC): Up to $2,000 per return
Keep receipts for books, tuition, and required materials.
9. Use Your Annual Gift Tax Exclusion
If you’re planning family gifts or supporting younger generations:
You can give up to $19,000 per recipient in 2025
Married couples can gift $38,000 per person
These gifts reduce your taxable estate and help family members without generating any tax burden for either side.
10. Look Ahead: Create a Simple Tax Plan for Next Year
Year-end planning isn’t just about minimizing this year’s taxes — it’s also about starting the next year with clarity. Consider:
How your income will change
Expected bonuses, investments, or life events
Whether to adjust withholdings or estimated payments
Whether you’ll itemize or take the standard deduction
Opportunities to structure income or deductions strategically
Final Thoughts
The best opportunities to lower your tax bill don’t happen in April — they happen right now, before December 31st.
Whether you’re navigating investments, charitable giving, healthcare accounts, or simply want to avoid surprises at tax time, year-end planning gives you control and confidence.
If you’d like personalized recommendations tailored to your income, goals, and tax situation, Connell Tax & Advisory is here to help you start the new year on solid financial ground.