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Blog

Matthew Cuplin | Oct 7, 2026

Six Estate Planning Assumptions Worth a Second Look

Estate Planning
Family
Insurance
Retirement
Tax Planning

It's easy to set estate planning aside once you've done a version of it. You sign the paperwork. You name a beneficiary. You mentally close the file.

The only

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Matthew Cuplin | Sep 21, 2026

More Than a Number: The Four Risks That Shape Your Retirement

Retirement
Risk Management
Health
Investments
Finance

Many people can tell you their portfolio balance. Far fewer can tell you what else determines whether their retirement actually works.

That's understandable. The

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Matthew Cuplin | Sep 8, 2026

Retirement Isn't Just About How Much You Save. It's About When.

Retirement
Risk Management
Investments
Finance
Savings

You can do everything right on paper — save diligently, spend reasonably, stay invested for the long haul — and still land in a very different retirement than

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Matthew Cuplin | Aug 27, 2026

Permission to Spend in Retirement: A Skill Rarely Taught

Retirement
Lifestyle
Finance
Savings
Family

For decades, you trained one financial muscle: save, invest, don't touch it. Then retirement arrives and asks you to do the opposite.

Nobody teaches that part

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Matthew Cuplin | Aug 5, 2026

What to Do With Your Next Dollar: A Financial Order of Operations

Finance
Savings
Investments
Retirement
Risk Management

What do you do when you earn well and have generally dialed in the fundamentals: save, invest, reduce debt, stay protected? The challenge was never knowing what

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Matthew Cuplin | Jul 17, 2026

Trump Accounts: What Parents and Grandparents Should Know

Education
Savings
Family
Tax Planning
Finance
Investments

Trump Accounts have been in headlines for months. Few of those headlines explain them the same way.

Depending on the article, they sound like a college fund, a

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Matthew Cuplin | Jul 2, 2026

How Retirement Has Changed Over the Last 75 Years (And What It Means for Your Plan)

Retirement
Lifestyle
Finance

Retirement used to mean a short, quiet final chapter. For many people today, it's something else entirely.

For much of the last century, retirement followed a

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Matthew Cuplin | Jun 4, 2026

Business Succession Planning: Built to Last vs. Built to Transfer

Finance
Retirement
Estate Planning
Family
Investments

Many business owners spend decades building something that works. The team. The reputation. The customers who keep coming back.

Then comes a quieter assumption

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Matthew Cuplin | May 30, 2026

Checking Your Portfolio Isn't the Same as Reviewing It

Investments
Retirement
Tax Planning
Risk Management
Estate Planning

Nearly half of investors check their portfolio at least once a day.1

Many of them aren't reviewing anything.

They're refreshing a number. Watching it move

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Matthew Cuplin | May 6, 2026

The Estate Plan That Looks Complete on Paper

Estate Planning
Tax Planning
Real Estate
Property
Family
Retirement
Risk Management
Finance
Investments

Many estate planning failures aren't dramatic. There's no missing will, no family feud, no document anyone forgot to sign.

The plan is right there in the drawer

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Matthew Cuplin | Apr 10, 2026

When Your Company Gets Acquired: What Your RSUs and Vested Shares Really Mean for Your Financial Future

Investments
Finance
Risk Management

When Your Company Gets Acquired: What Your RSUs and Vested Shares Really Mean for Your Financial Future

If your company has recently announced an acquisition

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Matthew Cuplin | Apr 9, 2026

What $100 Invested in 1928 Would Be Worth Today

Investments
Finance
Savings
Retirement
Risk Management

Many people think the biggest risk with money is losing it. A bad investment. A market crash. A bet that doesn't pay off.

But what if the most expensive

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