Tax strategy for business owners
Cassie Kirwan is an IRS tax professional with an MBA. She prepares every return with a strategy lens and builds year-round tax plans for business owners and the self-employed, so there are fewer surprises and smarter decisions.
Hindsight vs. foresight
Drag the divider across the same twelve months. On the left, a year you only see in the rear-view mirror. On the right, a WhipSmart CEO™ year, with every milestone set before it arrives.
Hindsight A filing-only year
Foresight A WhipSmart CEO™ year
Services
Start with a clean, accurate return or go all in on a year-round strategy. Either way, you work directly with Cassie, and every return is prepared with an eye on what comes next.
12-month engagement
A high-touch, year-round strategy relationship for business owners and self-employed professionals who want to stop reacting at tax time and start leading their finances with intention.
Individuals + business
Accurate, compliant returns prepared with a strategy lens: individual returns, Schedule C and single-member LLC returns, federal and state filing, and a year-end review before anything is filed.
Targeted sessions
Focused planning conversations before decisions are made: estimated tax guidance, a review of how income and deductions are structured, and scenario planning for life and business changes.
Excel tool
A downloadable Excel dashboard to track income, expenses and mileage, with totals that calculate themselves. No apps. No subscriptions.
The signature program
A 12-month strategic engagement for business owners and self-employed professionals who are done finding out what they owe after it’s too late to change it.
Twelve months of planning, guidance and execution support, not one meeting in April.
Income and projected obligations reviewed every quarter, so estimated payments stop being guesses.
How your business is structured and how you pay yourself, revisited as you grow.
Planning milestones, estimated tax timing, strategy checkpoints and recommended actions, on your calendar.
When a decision comes up mid-year, you ask before you act, not after.
Tax preparation is a separate service and can be added so your filings line up with the plan.
How it works
A free 15-minute Zoom discovery call to understand your income, your business and what is keeping you up at tax time.
Cassie reviews your information and identifies opportunities based on your situation: clarity, planning and intention, not guesswork.
Returns are prepared accurately and compliantly, and planning moves get put on the calendar so they actually happen.
Check-ins and guidance as your income, business or life changes, so next year starts ahead instead of behind.
Fast once you’re ready: after all your documents are in, Cassie aims to complete your filing within 24–48 hours.
Second Look
“We had a CPA who said our ridiculously high tax bill was our fault. I reached out and found Cassie — and she found the error.”
Book the 15-minute discovery call and mention last year’s return. Don’t send anything ahead: after booking you receive a personalized checklist, and Cassie will tell you plainly whether a deeper review makes sense.
A bill that felt wrong is worth a fresh set of eyes, especially if your income or business changed.
Notice and transcript review is one of the things Cassie helps with through planning engagements.
Prior-year catch-up and non-filer situations are a starting point, not a judgment.
In clients’ words
She was able to really dig into my information and books to maximize our deductions. She saved us $8,000 in our tax returns this year. I cannot recommend her enough for families with multiple W-2s and business owners.
We had a CPA who said our ridiculously high tax bill was our fault. I reached out and found Cassie — and she found the error. She saved us $4,000. Reach out to Cassie. She is fantastic and I am so glad we found her.
Quoted as published on kirwanfinancial.com. Individual results depend on each client’s situation.
Meet Cassie
Cassie Kirwan is the founder and tax strategist behind Kirwan Financial Services, an IRS tax professional with an MBA and a background in analytical, process-driven work.
She built the firm after seeing how many people only think about taxes once a year, plugging in numbers and hoping for the best. Her approach is the opposite: clarity, planning and intention. You work with her directly, from the first call to the final filing.
Read Cassie’s full storyThe details are handled with care and precision, so filing feels organized and manageable, not overwhelming.
Every return is prepared with a forward-looking mindset, so you can think beyond the current year.
An IRS tax professional with an MBA, bringing accuracy and integrity to every client relationship.
You work directly with Cassie. A relationship-driven practice, not a one-size-fits-all service.
Tax-ready resources
Tools and plain-language guides from Kirwan Financial, plus the official IRS and Florida links in the footer.
Tool WhipSmart Tax Dashboard An Excel dashboard for income, expenses and mileage, with totals that calculate themselves. No apps. No subscriptions. See Tax-Ready Tools Guide Proactive Tax Planning What a targeted planning session covers, who it’s for, and how it differs from filing season help. Read the planning page Program WhipSmart CEO™ overview The full 12-month engagement: quarterly reviews, implementation schedule and FAQs. Read the program page Checklist Tax Preparation & Compliance What’s included in individual and business returns, plus the documents to start gathering. See tax services FAQ
Question not here? Ask Cassie on a 15-minute discovery call or by email.
Book a discovery call hello@kirwanfinancial.comTax preparation is focused on accurately filing your return for a completed tax year. Proactive tax planning focuses on evaluating upcoming income, changes and decisions so you can plan ahead, before decisions are made rather than reacting at filing time.
Yes. WhipSmart CEO Tax Strategy is a 12-month strategic engagement with consistent planning, guidance and execution support throughout the year, including a customized implementation schedule of planning milestones, estimated tax timing, strategy checkpoints and recommended actions.
Tax preparation and tax strategy are offered as separate services. Tax preparation can be added so your filings align with your overall plan.
Proactive Tax Planning offers targeted planning sessions as needed. WhipSmart CEO provides a structured, annual strategy with ongoing guidance, accountability and implementation support.
Yes. Cassie works with freelancers, independent contractors and small business owners to prepare accurate and compliant returns based on business income and expenses, including Schedule C and single-member LLC returns.
Once all your documents are in, the aim is to complete your filing within 24–48 hours.
Income documents such as W-2s and 1099s, plus documents for deductions or credits you may qualify for (education expenses, charitable contributions, business expenses and so on). You receive a personalized document checklist after booking.
IRS notice support and representation are not included with standard tax preparation. They are available through proactive tax planning or ongoing strategy engagements.
Yes. Kirwan Financial Services is based in St. Augustine, Florida and serves clients virtually throughout Florida and beyond. The discovery call happens over Zoom.
Final call
Book a free 15-minute discovery call over Zoom. Pick a time that suits you and talk with Cassie directly. Prefer to write? Email works too.
