Cassandra Smalley, CFA, CFP®
Tax-smart planning for women physicians & practice owners
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Tax-smart planning for women physicians & practice owners
Areas of Focus
- Business Owners
- Business Transitions
- Divorce Financial Planning
- Employee Stock Options
- Equity Compensation Options
- Exit Planning
- Family and Money
- Financial Planning
- High Net Worth
- High Net Worth Retirement Planning
- Inherited Wealth
- Investing
- Investment Management
- Loss of Spouse or Partner
- Retirement Planning
- Social Security Optimization
- Tax-Aware Retirement Income Coordination
- Tax-Efficient Planning
- Tax-Smart Accumulation Planning
- Tax-Smart Distribution Planning
- Taxes
- Travel
- Wealth Management
- Women & Wealth
About Cassandra Smalley, CFA, CFP®
Hi, I'm Cassandra Smalley. I'm a CERTIFIED FINANCIAL PLANNER™ and Chartered Financial Analyst professional. Fewer than 1% of advisors have completed the rigorous coursework, experience, and ethical requirements to earn both designations.I specialize in tax-smart financial planning for women physicians and healthcare practice owners — including family medicine, dermatologists, chiropractors, surgeons, podiatrists, veterinarians, nurse practitioners, DNPs, personal training coaches, and the women who build, run, and eventually sell healthcare businesses. Whether you're managing six-figure student loans in your first years of practice, navigating the financial complexity of owning or buying into a practice, or planning for what comes after a business sale, I bring deep, proactive planning to every stage of your healthcare career.
Women in medicine face financial challenges that general advisors often overlook — pay gaps within physician compensation, career interruptions that compound over time, the unique complexity of practice ownership, and the reality that your most valuable financial years often coincide with your most demanding ones. After nearly 20 years in financial services and seeing firsthand how often women's needs are underserved, I felt called to do something about it — including publishing my book, "The Why of Wealth: Mastering the Steps to a Wealthy Mindset to Live a Joyful Life." You'll find a link to learn more in the Highlights tab below my profile.
Outside of work, I'm the proud mother of two girls and fully immersed in sports mom life — golf, basketball, cheerleading, baton twirling, and Girl Scouts. In my downtime, you'll find me at the nearby springs paddleboarding, kayaking, exploring nature, and no getaway is ever complete without a tube ride down the river with my family.
Professional Designations
- CERTIFIED FINANCIAL PLANNER ®
- Chartered Financial Analyst (CFA)
- Master of Business Administration (MBA)
Affiliations
-
CFA Institute
- CFP Board
- Fee Only Network
- National Association of Personal Financial Advisors
- XY Planning Network
- CFP Board
Primary Location
St. Petersburg, FL 33701
Video
Meeting Options
- Video Conference
- Phone
Compensation Methods
- Fee Only
- Percentage of Assets Managed
What to expect in the first meeting
We work with a limited number of clients, so we use a simple waitlist process to make sure every new client gets the attention they deserve. Click the 'Book Intro Call' button above to fill out a brief questionnaire. This helps us learn a little about you and where you are in your career before we meet. Once complete, we'll invite you to a 30-minute Introductory Meeting during our next onboarding session— a relaxed, no-pressure conversation to get to know each other, answer your questions, and see if there's a mutual fit. If there is and you're ready to move forward, we'll get started on onboarding right away.Offers Investment Management
Yes
About Cassandra Smalley Wealth Management
At Cassandra Smalley Wealth Management, we specialize in the unique financial lives of women physicians and healthcare practice owners — family medicine, dermatologists, chiropractors, surgeons, podiatrists, veterinarians, nurse practitioners, DNPs, personal training coaches, and the women who build, run, and eventually sell healthcare businesses. We take the stress out of your finances so you can focus on what you do best: caring for your patients and building the life you've worked so hard to create.We recognize that women in medicine deserve more than generic financial advice. You deserve a planning partner who understands the intersection of student debt, practice ownership, irregular income, Medicare and billing complexity, employer benefits, and the career transitions that define a life in healthcare — with advice that is aligned with your personal values and your professional reality.
OUR CORE VALUES
✅ Empower Others: We work with you to take control and feel confident about your financial future — so you can do your best work in the exam room, the operating suite, the boardroom, and at home.
✅ Educate and Grow: We want you to understand every strategy we implement, because an informed client makes better decisions. We bring the planning; you bring the expertise — and together we build something that lasts.
✅ Collaborate Together: We establish partnerships built on honesty, integrity, and transparency. Your goals drive every recommendation we make.
✅ Lead with Passion and Purpose: We care deeply about the people, missions, and values that matter to you — including the legacy you build for your patients, your family, and your community.
HOW WE ARE DIFFERENT
✨ We specialize in healthcare. Most financial advisors treat physicians like any other high-income professional. We don't. We understand the financial realities of medical education debt, practice ownership, navigating insurance billing, negotiating contracts and benefits, buy-ins and buyouts, cash balance plans, and the eventual business exit — because we've navigated every stage alongside our clients.
✨ We only take on a limited number of clients. You are not a number. You will always receive remarkably personalized service and recommendations built specifically around your financial life — not a template.
✨ We are an independent fiduciary. Always. We are never paid by a corporation to sell you overpriced products you don't need. Our only job is to act in your best interest, every single time.
✨ We use tax-smart planning strategies. Physician-level income creates tax complexity — the backdoor Roth, estimated quarterly taxes, practice retirement plan design, and capital gains management when you sell your business. We use dedicated tax planning software to analyze your return and build forward-looking strategies every year.
✨ We are a 100% fully digital firm. We use world-class technology to give you real-time visibility into your financial plan — from anywhere, on your schedule, because we know your calendar doesn't leave much room.
HOW CASSANDRA SMALLEY WEALTH MANAGEMENT HELPS WOMEN IN HEALTHCARE
Your financial life is unlike anyone else's. You spent years — and often hundreds of thousands of dollars — building the expertise to practice medicine. Now you deserve a financial plan that reflects that investment and the unique path ahead.
We help you at every stage of your healthcare career:
Early career: Managing student loan repayment strategy, maximizing employer benefits, building wealth from the ground up, and protecting your most valuable asset — your ability to work.
Practice ownership: Designing tax-efficient retirement plans, managing business and personal cash flow, navigating buy-ins and partnership agreements, and planning for growth.
Business transition and exit: Planning for the sale of your practice, managing the tax impact of proceeds, building a retirement income strategy, and coordinating your estate.
Retirement: Social Security timing, RMD planning, pension benefits, and making sure the wealth you built in medicine supports the life you want next.
Whether you are in your first year of practice or preparing to hand over your keys for the last time, we are your dedicated, experienced partner — bringing proactive strategies to every conversation so you never have to wonder if you're on the right track.
If taking care of your financial future is a priority, let's talk.
Education
University of North Florida, MBA, Finance | University of Florida, Bachelor of Science, Sport Management
Hobbies and Interests
- Beach
- Board Games
- Exercising
- Family
- Running
- Sports
- Traveling
- Working Out
SEC Lookup
View DisclosureWho We Serve
- Attorneys
- Blended Family
- Business Owners
- Caregivers
- Content Creators
- Couples
- Dentists
- Divorce
- Dual Income Family
- Entrepreneurs
- Families
- Gen X
- Gen Y / Millennials
- Gen Z
- Government Employees
- Healthcare Professionals
- High Net Worth
- Individuals
- Investors
- Living in Retirement
- Mid-Career Professionals
- Military
- Nurses
- Parents
- Pharmacists
- Physician Assistants
- Physicians
- Pre-Retirees
- Remote Workers
- Single Women
- Technology Professionals
- Therapists
- Travel Lovers
- Veterans
- Widow
- Women in Transition
- Women Professionals
- Women’s Finance
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5 Stars
5 Stars
PEACE OF MIND
5 Stars
5 Stars
If you're looking for the best.... here she is
5 Stars
Wonderful to work with
Incredibly intelligent, knowledgeable, and thoughtful with her guidance.
Cassandra is amazing!
Won me over
5 Stars
Extremely thorough, a great planner, and an effective teacher
Ms. Smalley is the calm in the face of financial storm
Highly Skilled Dedicated Financial Advisor
5 Stars
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FAQs
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