Thomas Alford

Hi, I'm Chris - Founder and Financial Planner at Southshore Financial Planning. I enjoy partnering with individuals and families to guide them to and through retirement so they can live life to the fullest. This is accomplished by first taking a deep dive into where clients are now financially and where they want to be. Then ideas are weaved together in the areas of cash flow, investments, taxes, insurance, debt and estate planning into one financial roadmap. Professionally, I am a CFP® Practitioner and have two finance-related degrees from the University of North Florida. My entire 19 year career has been dedicated to serving individuals and families in the financial services industry. Before founding Southshore Financial Planning, I spent 11 years at one of the largest financial institutions in the country where I was directly responsible for a $700 million client practice. On a personal note, my wife Heather and I are parents to three wonderful boys. In our free time we enjoy spending time with family, traveling, fishing, and watching the Tampa Bay Lightning.

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.

Hello, I'm Amy, the founder of AFT Planning. While AFT Planning was officially established in 2023, I've been working in the financial advice industry since 2012, honing my skills at a Broker-Dealer/Corporate IRA. Although I'm based in Florida, I enjoy working remotely and assisting clients from all over the US. My ultimate goal is to encourage people to rethink what a fulfilling life can look like outside of the traditional 9-5 until 65 paradigm. I do this by helping clients organize their current financial situation, develop adaptable life plans, and achieve financial independence by identifying ways to create sustainable and flexible income streams. Outside of work, I like niche museums,failing upwards at new hobbies, and I'm decidedly a cat person.

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.