Tampa Bay Registered Investment Advisor for over 30 years
H O W L A N D
30+ YEARS OF PROVEN RESULTS
CFA® and CFP® leadership
Testimonials
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(727) 491-7777 | (813) 333-2900
Our Team

Dee S. Howland
President
As a Chartered Financial Analyst with over 30 years of market experience, Dee Howland makes certain every investment decision is rooted in valuation principles and disciplined research.

Robert C. Howland
Vice President
Rob Howland serves as VP and Portfolio Strategist at Howland and Associates, where he oversees portfolio construction, risk management, and day-to-day trading operations.

Ross Thomas
Senior Equity Analyst
Ross Thomas focuses on market analytics, data modeling, and company-specific research that inform and contribute to maintaining Howland’s disciplined, evidence-based portfolio process.

Alex Tavares
Director of Communications Investment Advisor
Alex Tavares oversees client relationships and strategic development at Howland, translating complex financial strategies into clear, actionable guidance.
Guidance When Life Changes Overnight
Some of the most important financial decisions happen during unexpected life events. Whether you’ve recently inherited assets, sold a business, received a trust distribution, gone through a divorce, lost a spouse, or experienced another major life transition, the choices you make today can have a lasting impact on your financial future.
At Howland and Associates, we help individuals and families navigate these pivotal moments with clarity and confidence. We take the time to understand your unique situation, evaluate your options, and develop a thoughtful strategy designed to protect and grow your wealth while aligning with your long-term goals.
We Commonly Help Clients Navigate
Inheritances and estate distributions
Trust beneficiary planning
Business sales and liquidity events
Divorce and asset division
Retirement transitions
Sudden wealth situations
Loss of a spouse or loved one
Major career changes and executive compensation
When life changes, your investment strategy should adapt with it.
We’re here to help you make informed decisions every step of the way.
We create customized investment portfolios
Founded in 1992 by Dee S. Howland, CFA®, our family-owned firm combines deep fundamental research with personalized investment planning to help clients achieve growth without unnecessary risk. As an independent Registered Investment Advisor (RIA), we act solely in your best interest — offering transparency, fee clarity, and direct access to decision-makers.
Our approach emphasizes long-term wealth preservation and hands-on guidance through every market cycle. Whether you’re preparing for retirement, managing a family trust, or seeking a more customized investment strategy, Howland and Associates provides concierge-level service backed by over 30 years of proven performance.
Our clients don’t wait days for a call back or get routed through layers of staff. They have direct access to their advisor—by phone, text, or in person—whenever they need perspective or guidance. Every conversation is personal, timely, and handled by the people who actually manage their portfolios. Schedule a portfolio review or explore our latest insights to see why so many families have trusted Howland since 1992.
Built to your needs, goals, risk tolerance, and time horizon.
Guiding Widows Through Inheritance with Clarity and Care
Whether you’re navigating an inheritance, managing accounts that were always in your spouse’s name, or simply trying to understand what comes next, we’ve guided families through these transitions for over 30 years. We’ll help you make sense of what you have, protect what matters, and build a plan for the life ahead of you.

Wealth Concierge
Tailored Investment Strategies
Rooted In Your Life
and neither should their portfolios.
Unlike big corporate firms, we track and consider taxes in every transaction.
In the end, our clients often make more money and save more on taxes.
This allows us to not only build resilient portfolios, but also to integrate investment decisions seamlessly into your broader financial plan.