Intelligent
What we do

Most of our executive and other professional clients really had no idea what was in store for them tax-wise, the day they plan to retire from their career… We understand the commitment you’ve made to your profession and career, and the sacrifices you’ve made. We can help you make key decisions in specialized and crucial areas, so that your retirement will be more profitable than you may expect it to be.

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Preparing for retirement

Preparing for retirement has many aspects to consider. Here’s a major one: as your money grows, in most situations, so do your tax-liabilities.

02

Planning

Because of math phenomena like compounding, every day you wait to analyze your planning may cost you more in terms of taxation and fees, and we can help in these areas. Waiting probably is not the best thing to do.

Jay Weinstein,Founder & CEO of Deep Dive Retirement
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We offer

We offer to thoroughly help you understand the hidden financial stresses you’ll face, especially when you retire from your long career and are going to start using the money you’ve built up, saved and invested, to live on. And we can offer viable solutions, that can make a big difference of $100s of thousands or even more, which adhere to the Internal Revenue Code.

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Schedule 15 minute phone

Our offer is based on our strong desire to help you keep more of what you’ve worked hard for your whole life – your money. We welcome you to schedule 15 minute phone chat so we can discuss the most efficient way to proceed.

Leading
Effective Solutions

We work with your company to identify position requirements, implement recruitment programs, and
initiate employee assessments that maximize recruitment efforts

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About Us

Years of experience have prepared us to guide you through life's transitions.

About Us

Years of experience have prepared us to guide you through life's transitions.

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Our Team

Our advisors are ready to evaluate and support all your potential investments.

Our Team

Our advisors are ready to evaluate and support all your potential investments.

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Our Philosophy

Trust. Honesty. Integrity. We believe values matter, and we live by ours every day.

Our Philosophy

Trust. Honesty. Integrity. We believe values matter, and we live by ours every day.

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Schedule a free, no obligation 30 minute Zoom chat.

Let us help you keep more of what you’ve worked hard for – and protect your money. Schedule your 30 minute complementary phone chat so we can discuss the most efficient way to proceed.

Dedicated Team
Our Team

At Our Firm, We Have The Client—And Only The Client—In Mind.

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President and Senior Planner
Jay Winestein
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Director of Client Acquisition
Roman Lejuene
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Events Coordinator
Lisa Lawson
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Office Manager
Trish Gallagher
Testimonials
Customers Experience
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Retired from The Permanente Medical Group

- Leila E, MD
“Jay is a terrific fellow to work with. He's knowledgeable and shares that knowledge in an understandable way. I worked with him as I transitioned from full time work to retiree status.. I was presented with options to maximize my 'retiree' streams of income, but never pressured and we built a great plan for myself and my 2 daughters. I appreciate his guidance and highly recommend him!”
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Virtual Treatment practice, Peter is Jay’s client

- Peter Yellin, CEO - MD (retired)
“Jay's retirement analysis service did a nice job of projecting out what my tax picture would look like, where I was headed was headed with income scenarios, taxes, fees and other expenses. It was an eye opener...there's a lot to it. I have a good chunk in my Profit Sharing and 401ks, and always wondered how that's gonna shake out with the government.”

VA MD, Ohio USA

- Edwin C
“I urge you to heed this message. Jay has helped me develop a tangible and structured plan. And you know I have now and will have increasing amounts of tax advantaged cash that is also very liquid. So when I see an opportunity I’ve got the means to get in, yes at lower levels than before, and stay within my framework Numbers don’t lie! ”

J and JM - North Carolina

- JM
“Jay I love that you listen so well and each time I express a concern you examine it and offer alternatives. That is true customer service, and plain old caring. Yes, let’s meet Tuesday. 6:30 ok??”