Tampa bay Advisory
Crafting your
retirement strategies
with confidence
Consulting
Michael Watkins
As the Founder of Tampa Bay Advisory, Michael has strong ties to the Tampa Bay community and specializes in helping business owners, families, and individuals develop comprehensive financial strategies tailored to their unique needs and goals.
Michael Watkins’ journey to financial advisory reflects a career built on real-world experience, trust, and a genuine commitment to helping others achieve financial success.
Since making Pinellas County his home in 1980, Michael has developed a deep understanding of business, relationships, and financial planning, which has shaped his approach as a Fiduciary Advisor.
Join our watch party waitlist!
A Foundation Built on Real-World Business Experience
Michael Watkins brings a rare depth of perspective to financial advising, shaped by decades of hands-on business leadership before ever entering the financial services industry.
He began his professional career in commercial construction, advancing into project management roles where he worked closely with business owners throughout the Tampa Bay area.
Those early years honed his ability to manage complexity, lead teams, and understand the financial pressures faced by owners responsible for payroll, growth, and long-term sustainability.
More importantly, they instilled a lifelong respect for disciplined planning, accountability, and trust.
Entrepreneur, Employer, and Business Owner
Driven by an entrepreneurial mindset, Michael went on to found and scale a building maintenance company that grew into a multi-division operation employing more than fifty people during the 1980s and 1990s.
As a business owner and employer, he was responsible not only for profitability, but for the livelihoods of dozens of families — an experience that profoundly shaped his approach to risk, cash flow, and long-term planning.
He later expanded into manufacturing, where he successfully secured both a U.S. Trademark and Patent, further deepening his understanding of operational efficiency, intellectual property, and strategic growth.
These years provided Michael with firsthand insight into the real challenges business owners face — insights he now brings to every client relationship.
A Purposeful Transition into Financial Services
In 2010, Michael transitioned into the financial services industry, founding Tampa Bay Advisory to combine his extensive business experience with his passion for helping individuals and families make confident financial decisions.
Today, Michael serves as an Investment Advisor Representative with TruVestments Capital Management in the Tampa Bay area. He holds a Series 65 Registration and Florida Life, Health, and Annuities license, along with several advanced professional designations:
- Registered Financial Consultant (RFC)
- Certified Dementia Practitioner (CDP)
- Certified IRMAA Planner
These credentials reflect his commitment to fiduciary responsibility, ethical guidance, and ongoing professional education.
A Fiduciary Perspective Clients Can Trust
With more than four decades of practical business experience, Michael offers clients something increasingly rare: advice grounded not just in theory, but in lived experience.
As a Fiduciary Advisor, he is committed to transparency, clarity, and education — empowering clients to understand their options, reduce uncertainty, and make informed decisions aligned with their long-term goals.
Deep Roots in the Tampa Bay Community
Michael and his wife, Annie, reside in Dunedin, Florida, where they enjoy life with their three daughters and seven grandchildren.
His long-standing ties to the Tampa Bay community reinforce his dedication to helping local families, retirees, and business owners build secure financial futures with confidence and purpose.
Rebecca Keller
Client Services
Rebecca Keller is an experienced Administrative and Business Operations Specialist with a strong background supporting professionals in the financial and insurance industries.
She works directly with Michael and his team to ensure day-to-day operations run smoothly, client interactions are handled with care and consistency, and behind-the-scenes details are managed efficiently so clients receive a seamless, high-quality experience. Rebecca’s proactive approach and attention to detail bring clarity and consistency.
Her career began in hands-on service roles and evolved into executive-level administrative support. Rebecca offers a grounded, real-world perspective on business operations. She takes pride in being a reliable extension of Michael’s team.
Outside of work, she enjoys spending time with her family, daughters, and rescue dogs. She loves being active outdoors and continuing to learn and grow both personally and professionally.
Lindsey Kirk
Operations Specialist
In her 20+ years in the insurance and financial services industry, Lindsey has founded and lead several businesses including the one that brings her to us: LevelUp Administrative Services.
Lindsey has worked for and even started a handful of insurance companies, so she knows how they work internally and uses this experience to our advantage!
She specializes in annuity and life insurance and knows how to coordinate best with carriers. She enjoys helping people navigate the daunting task of dealing with financial institutions efficiently and quickly.
At home, Lindsey recently moved with her family and 3 cats from her home of Atlanta, GA to Monterey, CA for the ocean life! She just celebrated her 20th wedding anniversary last fall to her husband, Stuart – and they have 2 daughters together: Audrey (16) & Reese (13)
Retirement Planning
- Lifetime Income Strategies
- Inflation and Tax Planning Approaches
- Preparing for Health Care Costs in Retirement
- Clear, Written Plans and Directives
- Identifying and Addressing Income Gaps
- Strategies to Optimize Social Security Benefits
- Managing Market Volatility and Risk
- Tax-Efficient Retirement Planning