Evan Eastman

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.

Carter Hansen is a Vice President and Financial Consultant at Fidelity Investments, a position he has held since 2019. He has been with Fidelity Investments since 2010, progressing through various roles including Financial Consultant, Investment Consultant, Investment Solutions Representative, Premium Relationship Associate, and Financial Representative. Prior to joining Fidelity, he worked as a Financial Services Representative at Wells Fargo Investments from 2008 to 2009 and at Etrade Securities from 2006 to 2008. Throughout his career, Carter has focused on assisting clients in creating financial plans based on their individual needs and goals, utilizing solid financial practices and resources. He emphasizes open and honest communication and aims to build trust with clients at every step. His experience spans financial consulting, investment advising, and relationship management within the financial services industry.

Dino Jambresic is a Planning Consultant at Fidelity Investments, where he guides clients through their financial planning needs. He collaborates closely with clients to develop plans tailored to their goals, time horizons, and investment requirements. Dino emphasizes building strong client relationships through close collaboration. He has been with Fidelity Investments since 2010, holding various roles including Relationship Manager, Financial Representative, Retirements Specialist, Investment Solutions Representative, and Premium Relationship Associate. This progression reflects his extensive experience within the firm and expertise in financial planning. Outside of his professional work, Dino enjoys cooking and baking, exploring food, attending social events with friends, watching movies, spending time with pets, and playing soccer.

Nick Redhead is a Financial Consultant who focuses on helping clients simplify their financial lives by developing strategies to accumulate, preserve, and transfer wealth. He works closely with clients to understand their needs and build financial confidence through personalized guidance and ongoing partnership. Nick has experience as a Financial Representative at Charles Schwab from 2022 to 2023 and served as a Financial Consultant partner at Equitable Advisors from 2019 to 2021. Outside of his professional work, Nick has personal interests in fitness, food, football, golf, and movies.