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Cassandra Smalley, CFA, CFP®

Tax-smart strategies for women business owners and their families.

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

Serving Clients Nationwide

Tax-smart strategies for women business owners and their families.

11 Certified Advisor Reviews™
Rate this Advisor

Website

Areas of Focus

  • Career
  • Divorce Financial Planning
  • Exit Planning
  • Family and Money
  • Financial Life Planning
  • High Net Worth
  • Inherited Wealth
  • Investing
  • Investment Management
  • LGBTQ Couples
  • Loss of Spouse or Partner
  • Money Psychology
  • Owning a Business
  • Retirement Planning
  • Retiring Early (F.I.R.E)
  • Saving for College
  • Social Security
  • Taxes
  • Women & Wealth

About Me

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 have spent my career helping thousands of families take that leap from career life to living their retirement dream. Working together, you'll get the tools and resources you need to get to that next level. My mission is to elevate women's success too, so at the same time, let's close that gender wealth gap, shall we?!

I have been in the financial services industry for nearly 20 years and after seeing first hand how critical it is for a more inclusive experience when engaging in financial planning conversations, I felt called to publish a book to bring this important message to a wider audience: "The Why of Wealth: Mastering the Steps to a Wealthy Mindset to Live a Joyful Life." You'll find a link to learn more about my book in the 'Highlights' tab below my profile.

Outside of work, I'm the proud mother of two girls and still in the very busy stage of sports mom life (from gymnastics to basketball, swim team, and Girl Scouts) and enjoying every moment. In my downtime, I enjoy visiting the nearby springs to paddleboard, kayak, explore nature, and the getaway is never complete unless there is a tube ride down the river with my family.

Professional Designations

  • CERTIFIED FINANCIAL PLANNER™ Professional
  • Chartered Financial Analyst (CFA)
  • Master of Business Administration (MBA)

Affiliations

  • CFA Institute
  • CFP Board
  • Fee Only Network
  • Financial Planning Association
  • National Association of Personal Financial Advisors
  • XY Planning Network

Primary Location

St. Petersburg, FL 33701

Video

Meeting Options

  • Video Conference
  • Phone
  • Group Classes
  • Online Courses
  • Webinars
Book Intro Call

Compensation Methods

  • Fee Only
  • Flat Fee
  • One-time Financial Plan
  • Percentage of Assets Managed
  • Subscription

What to expect in the first meeting

Click the 'Book Intro Call' button above to schedule a time for us to chat. Our first Introductory meeting should last about 30 minutes and is a chance for us to get to know each other, for you to ask questions, and for us to share how we work with clients to see if there is a mutual fit. If there is a good connection, we’ll meet for a deeper dive Discovery Meeting to discuss the beginning steps of the planning process, onboarding, and most importantly, begin working through some of your highest priorities.

Offers Investment Management

Yes

About our Firm

At Cassandra Smalley Wealth Management we focus on the unique needs of business owners and high-achieving professionals to take the stress out of finances so you can focus on what matters most. We recognize that you deserve more authentic and genuine connections with advice that is aligned with your personal values. We provide true one-on-one support to design your best life.

OUR CORE VALUES

✅ Empower Others: We work with you to take control and feel confident about your future financial success that enables you to do your best work at home, in the office, and in life.

✅ Educate and Grow: We want you to have the knowledge and resources with solutions that not only improve your financial life, but they also make a difference in the legacy you wish to leave behind.

✅ Collaborate Together: We establish partnerships built on honesty, integrity, and transparency with our clients to implement solutions that achieve success.

✅ Lead with Passion and Purpose: We care deeply about the people, missions, and values that are important to you to help you map your journey to an extraordinary life.

HOW WE ARE DIFFERENT:

✨We only take on a limited number of clients. Clients are not just a number. You will always get remarkable service and extremely personalized recommendations for your finances.

✨We are an independent fiduciary. Not just sometimes. All. the. time. This means that we don't get paid by another corporation to encourage you to buy overpriced investment products you don't need or want.

✨We use tax-efficient planning strategies to help you grow, preserve, and enjoy your wealth both in the short-term and the long-term.

✨We are 100% fully digital firm and use world-class technology to provide you with the tools and resources you need to feel confident with your finances as we collaborate together.

HOW CASSANDRA SMALLEY WEALTH MANAGEMENT HELPS BUSINESS OWNERS:

We serve as your dedicated and experienced all-in-one partner that specializes across wealth management, tax planning, multi-generational planning, and risk management.

We serve business owners by giving you back your time to allow you to focus on what is most important – your business and your family.

​As a business owner, you have obligations and assets that need to be managed carefully and strategically to ensure your business wealth can turn into personal wealth and taxes are managed accordingly.

Whether you’re planning on exiting the business soon or are in the wealth-building stage, we help you pursue your financial goals and prepare for the future.

Creating and protecting generational wealth is critical and the result of careful planning and wealth management.

​When it comes to your wealth management and financial planning for business owners, you deserve the best advice and guidance.

​If taking care of your financial future is a priority, let’s see how we can help.

Education

University of North Florida, MBA, Finance | University of Florida, Bachelor of Science, Sport Management

Awards and Honors

  • 2020-2021 Forbes America's Top Women Wealth Advisors
  • 2019-2021 Forbes Best-In-State Wealth Advisors
  • 2017-2020 Forbes Top Next-Gen Wealth Advisors
  • 2017-2020 Working Mother Magazine Top Advisor Moms

Hobbies and Interests

  • Beach
  • Board Games
  • Exercising
  • Family
  • Running
  • Sports
  • Traveling
  • Wine
  • Working Out

SEC Lookup

View Disclosure

Who We Serve

  • Attorneys
  • Baby Boomers
  • Blended Family
  • Business Owners
  • Caregivers
  • Content Creators
  • Corporate Executives
  • Couples
  • Divorce
  • Dual Income Family
  • Educators
  • Entrepreneurs
  • Families
  • Financial Independence Retire Early (FIRE)
  • Gen X
  • Gen Y / Millennials
  • Gen Z
  • Government Employees
  • Individuals
  • Investors
  • LGBTQ
  • LGBTQ Couples
  • Living in Retirement
  • Military
  • Non-Traditional Clients
  • Parents
  • Physicians
  • Remote Workers
  • Single Women
  • Travel Lovers
  • Widow
  • Women in Transition
  • Women Professionals
  • Women’s Finance
  • Young Families

To make Wealthtender free for readers, we earn a nominal monthly fee from financial advisors and firms in exchange for marketing services (including being featured on this profile page), subject to terms of use. This compensation creates a natural conflict of interest when we favor their promotion over others. Wealthtender is not a client of these advisors or firms. Testimonials may not be representative of other clients’ experiences and do not guarantee future performance or success.

Write a Review


By clicking submit, you acknowledge this review is based on your own experience and reflects your genuine opinion. You also agree to our review policy, privacy policy, and terms and conditions, and give this financial advisor permission to publicly display your review on their website.

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: Current Client
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: Current Client
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: Current Client
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: Current Client
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: Current Client
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: Current Client
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: Current Client
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: Current Client
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: Current Client
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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