The Massimo-Anastasian Team

Serving the greater Deer Park, NY, area.

A team behind every plan

At the Massimo‑Anastasian Team, we help clients keep more of what they’ve built by focusing on outcomes—not just investments. Led by Charles Massimo and Peter Anastasian, our team brings more than 60 years of combined experience and delivers the resources of a national firm with the personalized attention of a boutique practice.

Most advisors concentrate on market performance. We concentrate on what you actually keep after taxes and planning decisions are made. In our experience, the greatest threat to long‑term wealth isn’t short‑term market volatility, but unnecessary tax drag, poor coordination between advisors, and missed planning opportunities around major financial events.

Our clients typically come to us at pivotal moments—selling a business or real estate, transitioning into retirement, or managing large taxable portfolios or concentrated positions. These are decisions where timing and structure matter, and where the opportunity to improve outcomes can be limited once a decision is made.

We serve as your Personal CFO, coordinating investment strategy, tax planning in collaboration with your CPA, estate and legacy considerations, and income and distribution planning. Our goal is to ensure every decision works together—so nothing falls through the cracks.
Rather than trying to beat the market, we focus on disciplined, tax‑aware planning built for real life. Saving on taxes, aligning advisors, and getting the structure right often has a greater impact than chasing returns.

We also provide specialized guidance for women navigating major life transitions such as divorce, widowhood, or stepping into greater financial leadership. Through our Life by Design program, we offer education, clarity, and deeply personalized planning designed to create confidence and control.

If you’re approaching—or have recently experienced—a major financial event, this may be one of the most important planning windows you’ll have. We start with a conversation focused on where you are today and how to position your wealth for efficiency, flexibility, and long‑term clarity.

Meet Our Team

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Advisory Team
Client Service Team
Comprehensive Wealth Management

Every detail of your big picture

Beyond the six core areas of wealth management, we also offer specialized solutions including employee retirement account management, trust services, tax preparation, and business owner consulting. For businesses, we provide guidance for plan sponsors, plan participant education, and employee benefits programs.

Planning for retirement

Financial freedom in retirement is about creating a strategic plan for a viable, predictable, tax-efficient stream of income. 

Explore Retirement Planning

Investing with a plan-first mindset

We offer investment guidance designed to strike a balance between risk/return and align with your financial goals.

Explore Our Investment Approach

Preparing for the unexpected

Risk management is about being prepared. We can help verify that your current insurance policies fit your unique needs.

Review My Coverage

Managing my tax strategy

Every effective plan starts with an integrated tax strategy. Our team can help you manage your tax liabilities. 

Explore Tax Strategy

Building my legacy

Our team can build a plan that reflects your passions and provides for your loved ones, now and in the future. 

Explore Legacy Planning

Creating a financial plan

We will help you assess your situation, recognize and pursue opportunities, and craft a detailed financial plan.

Start My Financial Plan

Where we are

Our offices, one team

The primary office is listed first, followed by the remaining offices alphabetically. The team serves clients from every office and meets virtually across the region.

Our Approach

What working together looks like

01

Discover

A no-cost conversation about where you are, what you own, and what you want money to do for the people you love.

02

Plan

A written plan covering income, tax, estate, and insurance — reviewed by a planner, a tax professional, and a strategist before you see it.

03

Implement

We put the plan to work: portfolios built to your risk tolerance, accounts consolidated, beneficiaries and documents aligned.

04

Review

Scheduled reviews each year — and a team that picks up the phone when life changes between them.

Insights from Massimo-Anastasian Team

What we’re thinking about

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Your Pathways To Wealth Podcast

Wellness & Wealth for Women: Why Confidence Begins with Caring for Yourself

Wellness & Wealth for Women: Why Confidence Begins with Caring for Yourself

Jan 22, 2026

Why Confidence Doesn’t Come From Beating the Market

Why Confidence Doesn’t Come From Beating the Market

Jan 22, 2026

Designing a life with intention: building wealth, wellness, and community

Designing a life with intention; building wealth, wellness, and community

Sep 2, 2025

Mastering Mindset

Mastering Mindset

Aug 19, 2025

Think Like a CEO - Treating Your Investments as a Family Business

Think Like a CEO - Treating Your Investments as a Family Business

Jul 15, 2025

Special Needs Planning: Building a Future with Intention

Special Needs Planning: Building a Future with Intention

Jul 15, 2025

Fixed Income, Market Efficiency, and How to Think About Bonds

Fixed Income, Market Efficiency, and How to Think About Bonds

Nov 18, 2025

When Markets Go Down – How to Stay Invested Without Fear

When Markets Go Down – How to Stay Invested Without Fear

Jul 15, 2025

Understanding Medicare in 2025

Understanding Medicare in 2025

Dec 26, 2025

Understanding Bonds: Simplifying One of the Most Misunderstood Investments

Understanding Bonds: Simplifying One of the Most Misunderstood Investments

Jul 15, 2025

Preparing for the 2030 Economic Depression

Preparing for the 2030 Economic Depression

Jul 15, 2025

Debunking Five Common Medicare Myths with Kevin Lawrence

Debunking Five Common Medicare Myths with Kevin Lawrence Episode 19

Jul 15, 2025

The Current State of Medicine with Dr. Dicapua

The Current State of Medicine with Dr. DiCapua

Jul 15, 2025

The Value-Driven Path to Wealth with Elena Beckius

The Value-Driven Path to Wealth with Elena Beckius

Jul 23, 2025

Women Who Inspire Us - Allison Kleinman and Alex LoPinto Future Centered Care

Women Who Inspire Us - Allison Kleinman and Alex LoPinto Future Centered Care

Aug 1, 2025

Women Who Inspire Us - Becky Fawcett (Help Us Adopt)

Women Who Inspire Us - Becky Fawcett (Help Us Adopt)

Jul 15, 2025

Women Who Inspire Us - Laurie Spampinato

Women Who Inspire Us - Laurie Spampinato

Jul 31, 2025

How to Navigate Upcoming Tax Law Changes with Kate Maier

How to Navigate Upcoming Tax Law Changes with Kate Maier

Jul 15, 2025

Living a Vibrant Social Life After Retirement

Living a Vibrant Social Life After Retirement

Aug 1, 2025

Solving the Social Security Puzzle with David Freitag

Solving the Social Security Puzzle with David Freitag Episode 17

Aug 11, 2025

Couple Walking in Vineyard with dog
Why Wealth Enhancement

One coordinated team, built around your plan

Our advisory teams work best with households that have $500,000 or more in investable assets.

Ready to talk now? Call 763-401-5685.

(Weekdays 8am–6pm Central)

Get your second opinion

Meet with us and get your complimentary, hand-crafted Wealth Blueprint to serve your financial goals.

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