Cassandra Smalley, CFA, CFP®

Tax-smart planning for women physicians & practice owners

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Cassandra Smalley Wealth Management Cassandra Smalley, CFA, CFP®
St. Petersburg, FL

Serving Clients Nationwide

Tax-smart planning for women physicians & practice owners

16 Certified Advisor Reviews™
5 out of 5 Stars
Jump to Reviews

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

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

Who 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

Wealthtender® is a trusted, independent financial directory and educational resource governed by our strict Editorial Policy, Integrity Standards, and Terms of Use. While we receive compensation from featured professionals (a natural conflict of interest), we always operate with integrity and transparency to earn your trust. Wealthtender is not a client of these providers. Testimonials may not be representative of other clients’ experiences and do not guarantee future performance or success.

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5 Stars

✅ Wealthtender Certified Advisor Review™
Nov 2, 2026
We are extremely happy with Cassandra Smalley Wealth Management. Having worked with Cassandra for over 10 years, Not only does she have a wealth of knowledge, she knows how to implement that knowledge in ways that have met our needs over and over. On top of this, she is also a fee-only fiduciary which is the only kind of financial advisor I will work with. I trust her. I am not a "numbers guy" and I rely on her to explain things to me and to talk me back from the edge when I get needlessly anxious over financial news. Our investments have done very well.
Relationship to Financial Advisor: Client as of Nov 2, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
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Mr Boberg

5 Stars

✅ Wealthtender Certified Advisor Review™
Oct 17, 2026
I trust Cassandra to give me sound financial advice and direction. She has empowered me to take control of my money so I feel excited about the future. I recommend you contact Cassandra about your financial plans.
Relationship to Financial Advisor: This reviewer has never been a client.
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Jackie Sager
Jackie Sager

PEACE OF MIND

✅ Wealthtender Certified Advisor Review™
May 19, 2025
Cassandra is extremely knowledgeable and is an ultimate professional. We have worked with her for several years, both before and after retirement. She is a great communicator who specializes in tax implications for our finances. Cassandra always follows up immediately and in writing and is easily available if you have questions. We have total peace of mind that we are in good hands.
Relationship to Financial Advisor: Client as of May 19, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Sherry M.
Sherry M.

5 Stars

✅ Wealthtender Certified Advisor Review™
Apr 6, 2025
My husband and I had had meetings with quite a few financial advisors in the past, but we never found any that were a good fit. We always felt like we were being sold to. I had a couple of meetings with Cassandra on my own and had already felt confident in her knowledge and advice (she had already started helping me even though I wasn't even a client yet!) Then my husband and I had a chance to have a meeting with Cassandra together, and we both agreed that we had found someone that actually had our family's best interests in mind. During our meeting, we felt confident in her ability to tailor her guidance to our specific financial situation and even walked away with some action steps we could implement right away even though we had not committed to working with her yet. Needless to say, we just signed up with her and look forward to having an honest, caring, and knowledgeable guide on our journey to financial freedom! I highly recommend everyone meet with her!!
Relationship to Financial Advisor: Client as of Apr 6, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Patricia D.
Patricia D.

5 Stars

✅ Wealthtender Certified Advisor Review™
Apr 2, 2025
Cassandra is an absolute wealth of knowledge! Her expertise, insightful advice, and thoughtful guidance are truly appreciated. She takes the time to thoroughly explain complex concepts in a way that’s easy to understand leaving you feeling completely at ease with your future investments. I highly recommend her to anyone seeking expert financial planning!
Relationship to Financial Advisor: This reviewer has never been a client.
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Stephanie K.
Stephanie K.

If you're looking for the best.... here she is

✅ Wealthtender Certified Advisor Review™
Jul 8, 2024
We've been lucky enough to work with Cassandra for several years. She's just so full of knowledge. She is there to address our concerns, answer questions as well as reassuring us that we're on track for success! I especially like the tools she uses so that at a glance we can keep up with our growth. We really do feel lucky to have her managing our retirement and investments.
Relationship to Financial Advisor: Client as of Jul 8, 2024
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Mike Cindy
Mike Cindy

5 Stars

✅ Wealthtender Certified Advisor Review™
Jun 23, 2024
Well, I cannot express how thankful I am to have such an experienced financial expert looking after our retirement. Cassandra is so tuned into her clients current and FUTURE needs. I will pass her name around to family and friends. The personalized attention we are getting from you is so welcoming... Thanks for being you Cassandra!
Relationship to Financial Advisor: Client as of Jun 23, 2024
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Mike Ferguson
Mike Ferguson

Wonderful to work with

✅ Wealthtender Certified Advisor Review™
Jun 19, 2024
Newly working with her to navigate multiple big life and career changes. Cassandra was extremely helpful in helping me navagate purchasing a new car while separating finances from my ex husband. She was also very reassuring to me in areas where I thought I was struggling. She can give advice and help lead while simultaneously reinforcing the good things that I was already doing. Also she's just pleasant and wonderful to work with.
Relationship to Financial Advisor: Client as of Jun 19, 2024
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Sarah B
Sarah B

Incredibly intelligent, knowledgeable, and thoughtful with her guidance.

✅ Wealthtender Certified Advisor Review™
Jun 6, 2024
I have worked with Cassandra for about 10 years now and she is fantastic. I started with low expectations for the future, but Cassandra has been wonderfully successful helping me build wealth and a solid financial future. I highly recommend working with Cassandra.
Relationship to Financial Advisor: Client as of Jun 6, 2024
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Douglas B.
Douglas B.

Cassandra is amazing!

✅ Wealthtender Certified Advisor Review™
May 22, 2024
Cassandra has always been extremely helpful with explaining things, as well as handling things we may not be able to do. She also cares about what we are doing and how we are doing in life. We would not be where we are with out her!
Relationship to Financial Advisor: Client as of May 22, 2024
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Kristin and Ronnie
Kristin and Ronnie

Won me over

✅ Wealthtender Certified Advisor Review™
May 22, 2024
I had a generally negative opinion of people in wealth management because of watching my parents go through a terrible past experience with different firm in another state. I was upfront with Cassandra about my skepticism, and she explained to me how she is different from some financial advisors. (She is a highly qualified independent fiduciary -look that up) I gave her a chance, and now I feel at ease and confident working with her. Her professionalism, attention to detail, follow-through, knowledge and ethics are remarkable. I really have nothing critical to say. I'm highly impressed.
Relationship to Financial Advisor: Client as of May 22, 2024
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for G.L.B.
G.L.B.

5 Stars

✅ Wealthtender Certified Advisor Review™
Mar 21, 2024
Cassandra is a wealth of knowledge. Her expertise has been so valuable for my clients. I really trust her ability to help them in all facets of their life. Whether they are in the middle of growing their business, looking to sell their business, or looking to retire, I trust Cassandra with giving them the advice they need for their financial future.
Relationship to Financial Advisor: This reviewer has never been a client.
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Christina Dickson
Christina Dickson

Extremely thorough, a great planner, and an effective teacher

✅ Wealthtender Certified Advisor Review™
Nov 10, 2023
I started with Cassandra early in 2023 as I was looking towards retiring by the end of the year. I knew almost nothing about finances, taxes, and investments. Cassandra was very patient in explaining the whys and how-tos. She looks at more than finances, she helps develop workable plans in order to create a lifestyle. I am very happy with her services and highly recommend her!
Relationship to Financial Advisor: Client as of Nov 10, 2023
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Felicia
Felicia

Ms. Smalley is the calm in the face of financial storm

✅ Wealthtender Certified Advisor Review™
Oct 30, 2023
I equate Ms. Smalley to my Coast Guard career. After retiring from a total of 42 years Coast Guard and Federal Service, I sought out Ms. Smalley to manage my investments. Much like the CG, she navigates our current financial storm with sound judgement, a steady course and a firm hand on the helm to keep us upright and on a safe course. I trust her implicitly to help us weather these tumultuous times. I would highly recommend her to anyone seeking financial advice in these troubling times.
Relationship to Financial Advisor: Client as of Oct 30, 2023
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Disclosure: This reviewer is related to the advisor.
Avatar for Frank
Frank

Highly Skilled Dedicated Financial Advisor

✅ Wealthtender Certified Advisor Review™
Oct 27, 2023
Cassandra has been our financial advisor for many years and it was a no-brainer that we would follow her when she started her own wealth management firm. She is dedicated to her clients and their financial success. Without Cassandra's support, coaching, and sometimes tough conversations, our family would not have been as financially successful.
Relationship to Financial Advisor: Client as of Oct 27, 2023
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Melissa
Melissa

5 Stars

✅ Wealthtender Certified Advisor Review™
Oct 26, 2023
Great financial advisor! Many of our clients have used Cassandra's services and only have wonderful things to say about her. She is skilled, compassionate, and dedicated to her clients' success.
Relationship to Financial Advisor: This reviewer has never been a client.
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
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Finley Williams Law Firm
Get answers to frequently asked questions regarding the services offered by Cassandra Smalley, CFA, CFP® View Disclosures

FAQs

Who is Cassandra Smalley and what does she do?
Cassandra Smalley is a CERTIFIED FINANCIAL PLANNER™ professional, Chartered Financial Analyst, MBA, author, and Founder of Cassandra Smalley Wealth Management in St. Petersburg, Florida. With more than 20 years in financial services — including a role as Director of Financial Planning overseeing a team of CFPs and CPAs — Cassandra has dedicated her career to one mission: closing the gender wealth gap and giving women a powerful voice at the financial table. She specializes in tax-smart financial planning for women physicians and healthcare practice owners. From the first years of practice to navigating a practice sale after decades of building something meaningful, Cassandra is by your side.
Why does Cassandra Smalley specialize in women physicians and healthcare practice owners?
Because women in medicine face financial challenges that most advisors are simply not equipped to handle and Cassandra decided to change that. She has spent more than 20 years watching what happens when high-achieving women receive generic financial advice that ignores their reality: pay gaps that persist even at the physician level, the complexity of owning or buying into a practice, and the fact that your most financially critical years often coincide with your most demanding ones personally and professionally. They don't get a one-size-fits-all plan. They get a partner who truly understands their profession, their pressures, and their potential.
Where is Cassandra Smalley Wealth Management located, and who do they serve?
Cassandra Smalley Wealth Management is based in St. Petersburg, Florida, and proudly serves clients nationwide. As a 100% fully digital, virtual firm, Cassandra uses world-class technology to collaborate with clients wherever they are, from Florida to Alaska and abroad. Her clients include women physicians, podiatrists, chiropractors, dermatologists, veterinarians, nurse practitioners, DNPs, health coaches, and healthcare practice owners at every career stage — whether they are early in their career, growing a business, or planning an exit. Geography is never a barrier. Cassandra's clients get the same dedicated, white-glove experience whether they are down the street or across the country.
What makes Cassandra Smalley's credentials stand out?
Fewer than 1% of financial advisors in the country hold both the CFP® and CFA designations — and Cassandra is one of them. The CERTIFIED FINANCIAL PLANNER™ certification requires rigorous coursework in financial planning, taxes, retirement, and estate planning. The Chartered Financial Analyst designation demands three years of post-graduate study in investment analysis and portfolio management and has a historically low pass rate. Add an MBA with a finance concentration, 20+ years of direct client experience, and recognition by Forbes as one of America's Top Women Wealth Advisors — and you have an advisor whose depth of expertise is exceptionally rare.
Is Cassandra Smalley a fiduciary? How does she charge for her services?
Yes — Cassandra is a fee-only fiduciary, which means she is legally obligated to act in your best interest at all times. She never receives commissions, never sells insurance or annuities, and has no financial incentive to recommend any product. You pay for advice and investment management, period. Cassandra charges an annual advisory fee of 0.50%–1%, with a $1,000,000 asset minimum; annual fees start at $9,000. Transparency in finances is the only way Cassandra operates. When you work with her, you can trust that every recommendation is made for you, not for a commission check.
Can Cassandra Smalley help ensure my spouse will be financially taken care of?
Yes — and it is one of the most meaningful conversations Cassandra has. A spouse often reaches out with a quiet, loving concern: if something happens to me, I need to know they will be okay. Cassandra brings both partners into the process so each feels confident managing finances independently. She also ensures the next generation knows who to call and how to navigate the family's financial life if an elder parent is no longer able to. True financial security means the people you love most never face the future alone.
How does Cassandra Smalley help with tax-smart financial strategies?
Taxes touch every aspect of your financial life — your practice income, your investments, your retirement accounts, your estate — and Cassandra approaches all of it proactively. With experience working alongside CPA teams as Director of Financial Planning, she brings a level of tax fluency that most advisors simply do not have. For women in healthcare, this means strategies tailored to your profession: maximizing practice retirement plans like cash balance plans, solo 401(k)s, and SEP IRAs; managing taxes on self-employment income; and planning for the capital gains impact when you sell your practice. Cassandra uses dedicated tax planning software to help you keep more of what you earn.
Can Cassandra Smalley help me navigate a major life transition?
Yes — and this is where Cassandra's work often matters most. Life does not always go according to plan, and for women in healthcare, major transitions take many forms: leaving a hospital system to start your own practice, buying into or out of a partnership, stepping into retirement. Personal transitions matter just as much — divorce, the loss of a spouse, an inheritance, or a career change can be financially overwhelming without the right guidance. Cassandra has helped clients through each of these moments. She does not just manage the numbers; she helps you organize your financial life, understand your options, and move forward with confidence into whatever chapter comes next.
What do clients say about working with Cassandra Smalley?
Cassandra has earned glowing Certified Advisor Reviews™ on Wealthtender — all 5 stars — from clients who describe her as extraordinary in her knowledge, attentiveness, and ability to make complex financial topics feel approachable. Clients say she brings "total peace of mind," that she is "the calm in the face of a financial storm," and that she is "incredibly intelligent, knowledgeable, and thoughtful." She has been recognized by Forbes as one of America's Top Women Wealth Advisors. Many of her clients have followed her for years and through major life changes — a testament to the trust she builds and the results she delivers. Read their stories on her Wealthtender profile.
How do I get started working with Cassandra Smalley?
It begins with a complimentary introductory meeting — no pressure, no sales pitch. Just a genuine conversation about where you are, where you want to go, and whether Cassandra Smalley Wealth Management is the right fit for you. Cassandra believes the best planning relationships start with trust, and she takes the time to understand your goals, your values, and what a joyful, well-designed life looks like for you. Schedule your complimentary meeting today and take the first step toward aligning your wealth with the life you are meant to live.

FAQ Disclosures

Still have questions? Please reach out directly and I’ll be happy to assist.