Robert Anderson

At Cassandra Smalley Wealth Management we work with women business owners and high-achieving professionals to take the stress out of finances so that you can focus on your zone of genius and what matters most to you. We focus on the unique needs of women building wealth with the mission to help close the gender wealth gap and empower you to design your best life. Cassandra has helped thousands confidently take the leap from career life to retirement dream. Finances are deeply personal, but your goals are uniquely yours and do not need to fit into the traditional retirement ideals sold by the financial advice industry. Recognizing that women deserve more authentic connections with advice that is better aligned with their personal values, Cassandra’s practice gives you true one-on-one support to help you achieve success. Her areas of expertise include retirement planning, small business retirement plans, college planning, investing, tax planning, insurance needs, Social Security optimization, inherited wealth and life transitions, estate planning, employee benefits optimization, and strategies for business owners. With 20 years in financial services and seeing first-hand how critical it is for women to be engaged in financial planning conversations, Cassandra felt called to publish a book based on her experiences. Through stories in "The Why of Wealth: Mastering the Steps to a Wealthy Mindset to Live a Joyful Life," finances become more approachable, relatable, and applicable to the unique challenges women face. Topics range from career, motherhood, relationships, elder care, gender wealth gaps, life transitions, retirement needs, setting our kids up for success, creating a lasting legacy, and most importantly, building the joyful life you deserve. Cassandra is the proud mother of two daughters and is still in the very busy stage of sports mom life (from gymnastics to basketball, swim team, and Girl Scouts) and enjoying every moment. In her downtime, she enjoys visiting the nearby springs to paddleboard, kayak, explore nature, and tube down the river with her family. Accolades and recognition: Forbes and SHOOK Research as America’s Top Women Wealth Advisors 2020-2021, Top Next-Gen Wealth Advisor 2017-2020, Working Mother Magazine and Top Wealth Advisor Moms 2017-2020. Located in St. Petersburg/Clearwater/Tampa Bay area, Cassandra serves clients virtually across the US.

You’re making good money. So why does it still feel like you’re always behind? You’re the one everyone depends on. You manage the bills, the schedules, the big decisions and somehow still lie awake wondering if you’re missing something. On the outside, it looks like you’ve got it together. But inside? Money still feels stressful. Disorganized. Like one more thing you should’ve figured out by now. You don’t just want things “under control.” You want space to enjoy your life. To book the trip. To say yes without guilt. To feel steady and secure and have fun along the way. That’s where I come in. I work with women who manage the money in their households, including many in the LGBTQIA+ community, and create a safe, judgment-free space for honest conversations about what’s really going on with your finances. Through my Financial Happiness Method, I help you sort through the chaos, clear the mental clutter, and build a rhythm that actually supports your life not someone else’s idea of what it should look like. Together, we: ✅ Get things organized so it finally feels manageable ✅ Build systems that support your values and your version of joy ✅ Make room for things that light you up not just what’s “responsible” ✅ Quiet the noise so you can focus on what matters most This isn’t about being perfect with money. It’s about feeling free, clear, and confident. It’s about dinners with people you love. Quiet weekends. Big dreams. Soft mornings. A little breathing room. A life that actually feels like yours. If you’re tired of carrying the weight of it all alone, I’ve got you.

Tom LeClaire is the Principal and a Senior Wealth Manager at Caliber Wealth Advisory based in Tampa, FL. Tom holds the CERTIFIED FINANCIAL PLANNER™ designation and graduated from Stetson University with a Master of Business Administration and a Bachelor’s degree in Political Science. Prior to starting Caliber Wealth Advisory, Tom worked for Charles Schwab & Company for ten years, primarily as a Financial Consultant, where he developed and maintained client relationships focusing on financial planning, investment analysis, and portfolio management. In addition to leading a team of qualified professionals, his core responsibilities at Caliber Wealth Advisory include wealth management covering financial planning, strategic investment management, and client education. Since 1994, Tom has served in the Army Guard, deployed overseas three times, and currently works with the 50th Regional Support Group in Homestead, FL. Tom was born and raised in Central Florida and resides in Tampa. He is the proud husband of his wife, Michelle, and he spends his free time with her, raising their newborn daughter.

Michael Noce, ChFC®, is an Investment Adviser Representative with Olsen Family Financial, LLC. Mr. Noce graduated Magna Cum Laude from Tulane University in 2009 with a Bachelor of Science in Management, Majoring in Finance. He was commissioned through the Navy ROTC program at Tulane and was named the Chief of Naval Operations 2009 Distinguished Graduate. Mr. Noce was also a member of the Sigma Phi Epsilon Fraternity and the Beta Gamma Sigma Business Honor Society. He graduated with a Master of Liberal Arts, Finance degree from the Harvard Extension School in 2020 with the Dean’s List Academic Achievement Award and Graduate certificates in Real Estate Investing and Corporate Finance. In 2023, he completed the Chartered Financial Consultant program from The American College of Financial Services. In his military career, Mr. Noce served as a Surface Warfare Officer in the United States Navy, deploying on numerous ships throughout the Middle East and Pacific theaters. He held various leadership roles in Engineering, Combat Systems, and Operations departments, and was recognized by Accenture as part of their “Top 40 Under 40 Military” for 2012. He transitioned to the Navy Reserves in 2015 and became the Senior Manager for US Factory Service at Whirlpool Corporation. Mr. Noce returned to active duty in 2018, supporting cultural initiatives for the Secretary of the Navy and the Chief of Naval Operations. During this time in Washington DC, he was selected as a White House Social Aide, serving for both the Trump and Biden administrations. He recently completed two-year Mobilization orders working as a Strategic Operations Planner for US Central Command in Tampa, Florida and Saudi Arabia. He continues to serve as a Commander (Select) in the Navy Reserve. After 15 years in the military, the concept of Service has been a guiding principle in my life. Now as a fiduciary advisor, I am committed to serving others by helping them build a richer and more fulfilling life.

Jonathan Bik is a Wealth Management Advisor with Merrill Lynch Wealth Management. In his role, he focuses on delivering a comprehensive wealth management approach that begins with understanding clients and their families, financial situations, and priorities. He works to create customized strategies that adapt to clients’ evolving needs and market conditions, leveraging Merrill’s investment insights and the banking services of Bank of America. Jonathan specializes in managing new wealth, personal retirement planning, tax minimization, and retirement income strategies. He collaborates closely with clients to align wealth management plans with their values and goals. His expertise includes retirement planning, 401(k) analysis, portfolio strategies, education planning, cash flow modeling, estate planning services, and tax minimization. He also facilitates access to banking support for large purchase financing as part of addressing clients’ broader financial needs. He holds a Bachelor’s Degree from the University of Kentucky and an MBA from Saint Leo College. Jonathan has earned several professional designations, including Chartered Financial Consultant (ChFC), Certified Plan Fiduciary Advisor (CPFA), Personal Investment Advisor (PIA), and Retirement Accredited Financial Advisor (RAFA). Outside of his professional work, he volunteers with the Florida Holocaust Museum and enjoys boating, football, golfing, ice hockey, music, reading, running, spending time with his family, and watching movies.

Andrew DiFiore is a Financial Consultant at Fidelity Investments, a role he has held since 2025. Prior to this, he served in several positions within Fidelity, including Planning Consultant, Relationship Manager, and Central Relationship Manager between 2023 and 2025. His career in financial services began with Charles Schwab as a Financial Services Representative in 2022, following an internship at Virtus Financial Partners in 2021. Andrew and his team focus on creating an environment of trust to help clients and their families feel confident in their financial plans, enabling them to concentrate on their personal passions. He aims to be the primary resource for clients when life events impact their finances. Outside of his professional work, Andrew enjoys spending time at the beach, engaging in fitness activities, playing football and golf, traveling, and caring for pets.