Gary Wintermeier Sr.

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.