Introducing Tailwind CPA

When I founded Deep Dive Financial in 2014, my goal was to create a virtual firm that allowed me to serve clients while living in the Florida Keys—where I could also dive as much as I wanted. I chose the name "Deep Dive Financial" to reflect both my passion for diving and my commitment to providing in-depth, personalized services. For eight years, I focused on tax preparation, bookkeeping, and, of course, plenty of diving.

During this time, I pursued a master's degree in tax and began working on more complex tax matters. Our firm has grown alongside our clients’ needs. Donette Conrad joined in 2016 and Karyna Hawthorne joined in 2024. As our clientele expanded, so did the complexity of the services we provide. Today, many of you require advanced strategies that encompass not just tax planning but also estate planning, insurance evaluations, and retirement planning.

As our services have evolved, so has our vision for the future. We are no longer just providing tax compliance—we are partners in helping you plan for the future and achieve your financial goals. With this broader scope in mind, we are excited to announce our rebrand to Tailwind. Tax planning, compliance and accounting services that we are currently providing under Deep Dive Financial will be provided under Tailwind CPA. You will see our logo and branding change, but it is still Diana, Donette and Karyna providing the same services as we have in the past.

The name Tailwind reflects our mission: just as a tailwind propels an aircraft forward, we aim to accelerate your progress toward achieving your financial objectives. It’s about moving forward, faster, with a clear sense of direction.

We are grateful for your continued trust and partnership, and we are excited about the opportunities and expanded services this evolution will bring. Stay tuned for more updates!.