Diane Kennedy, CPA

Strategic Tax Consultant, Bestselling Author, Founder of USTaxAid & KennedyTax.Tax
Diane Kennedy, CPA, is a leading expert in tax strategy for entrepreneurs and real-estate investors. She is the founder of USTaxAid and KennedyTax.Tax, where she helps business owners reduce taxes, strengthen structure, and turn complex tax rules into clear, actionable steps.

A bestselling author, Diane wrote Loopholes of the Rich and more than a dozen additional books on business and real-estate tax planning. She has been featured on CNN, Bloomberg TV, and in Forbes, The Wall Street Journal, and CNBC. She also received the State of Nevada Small Business Owner of the Year award and previously co-hosted Wealth Talk Radio, bringing practical financial education to a national audience.

Diane teaches weekly Tax Strategy Labs, where she answers live questions and works through real-world tax scenarios, and she advises private clients through a strategy-driven, implementation-focused consulting practice. She holds a BS in Accounting from the University of Nevada, Reno, where she has also taught.

She was invited to the White House for a roundtable on how small businesses and local charities can partner to support entrepreneurial community initiatives.

  • There are no suggestions because the search field is empty.

4 min read

How Are Real Estate Team Leaders Taxed? Commission Splits, Overrides & Payroll Rules Explained

Team leaders can receive income through personal commissions, team splits, and overrides. The way funds flow determines what you must report and whether...

women at home office

5 min read

How Real Estate Agents with Brokerage Offices Can Still Deduct a Home Office—and when the Augusta Rule Applies

Agents can have both a brokerage desk and a deductible home office if the home office is your principal place of business for admin work. That...

man and woman shaking hands in front of a sold home

4 min read

What Can Real Estate Agents Actually Deduct?

Generic tax checklists often miss these real estate-specific deductions, like commission splits, high-mileage fieldwork, and listing prep costs. Learn...

man looking stressed about taxes

3 min read

What to Do If You Can’t Pay Your Tax Bill

Owing more in taxes than you can pay is stressful, but it’s usually manageable. Acting early, filing on time, and communicating with the IRS can preserve...

man outside sitting at a laptop

3 min read

What to Do If Your Books Are a Mess and Taxes Are Due

If your bookkeeping is behind and a tax deadline is looming, accuracy matters more than speed. This guide explains what not to do, what to prioritize...

A woman talking to a client using a tablet

2 min read

Your Tax Return Is Only as Good as Your Bookkeeping

Clean bookkeeping isn’t about perfection; it’s about accuracy and consistency. Incomplete or outdated books directly affect your tax return, limiting...

Podcaster recoding in their studio

4 min read

Are You Missing These Creator-Specific Deductions?

Many creators miss valuable tax deductions because traditional small-business advice doesn’t reflect how content businesses actually operate. From...

video blogger setting up on the couch

3 min read

When Does a Creator Outgrow DIY Taxes?

As creator income grows, tax complexity often increases faster than expected. Multiple revenue streams, state obligations, and entity decisions can...

video blogge at home setting up the camera

3 min read

Does Your Accountant Understand Affiliate, Sponsorship, And Platform Income?

Creators earn from multiple streams including platform ads, affiliate commissions, sponsorships, and digital products. Each revenue type has unique tax...

A man working in a brightly lit office

2 min read

Can I Do My Own Bookkeeping? Here’s the Real Answer

You can do your own bookkeeping, but accuracy, consistency, and tax readiness matter more than control. Learn when DIY works, when it breaks down, and how...

woman small business owner sits at desk with laptop

3 min read

How the Augusta Rule Works for Small Business Owners

The Augusta Rule lets small business owners rent their home to their business for up to 14 days a year, creating a business deduction without taxable...

solopreneur speaking

3 min read

Tax Breaks Solopreneurs Get That Big Businesses Don’t

Did you know that solopreneurs can access more flexible tax breaks than larger businesses? This is thanks to simpler ownership and fewer nondiscrimination...

solopreneur talking on the phone

4 min read

Solopreneur Action Plan: Simple Tax Moves That Save You Money

A solid solopreneur action plan starts with structure, not just income. Many solopreneurs watch their tax bills climb as they grow, not because they're...

solopreneur siting at a desk looking at financials

4 min read

What Solopreneurs Need to Know About the OBBB

Headlines around the OBBB can be misleading for solopreneurs, so the real focus should be on how IRS guidance and income definitions like AGI and MAGI...

3 min read

Solopreneurs Should Do These 5 Things Before December 31st

This article was originally published in Accounting Today and written by Ran Harpaz, CEO of Lettuce, and Diane Kennedy, Head of Tax Education at Lettuce.

Got a tax question?

Got a tax question? 

Group 1000002431-2