Wealth Management Insights

Kristin McKenna, CFP® covers a range of financial planning and investing topics with an emphasis on stock options and sudden wealth events.

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ISOs and the AMT
ISOs

Incentive Stock Options: Navigating AMT and AMT Credits

Updated for 2025 and 2026. If you have incentive stock options, you’ve probably heard of the alternative minimum tax (AMT). Essentially, the alternative minimum tax is a prepayment of taxes. In years when not subject to the AMT, you can receive an AMT credit. The credit reduces your tax liability

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10b5-1 Trading Plans for public company insiders
Stock options

10b5-1 Trading Plans: Sales Strategies for Insiders

Rule 10b5-1 allows insiders to create pre-arranged trading plans as a way to remain compliant when managing their stock compensation. When structured properly, a 10b5-1 trading plan can provide corporate insiders an affirmative defense against insider trading allegations. This serves to balance the executives’ need to diversify with adequate measures

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Managing and investing wealth inherited from parent
Inheritance

Options and Rules When Inheriting an IRA From a Parent

What to do after inheriting an IRA from a parent If you’ve inherited an IRA from a parent, you may be wondering what your options are. Though there are some exceptions, most adult children inheriting an IRA or 401(k) from a parent will need to take the money in 10

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pension or lump sum
Employee benefits

Should You Take a Pension or a Lump Sum?

Should You Take a Pension or a Lump Sum? Deciding between a lump sum or receiving pension benefits monthly requires careful planning and consideration. Though your personal situation and circumstance will always be the most important factor in any major financial decision, there are several key considerations to keep in

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Managing concentrated stock positions
Diversification

7 Ways to Manage Concentrated Stock Positions

What is a concentrated stock position? If one stock makes up more than 10% of your overall asset allocation, it’s probably too much. A diversified portfolio is the cornerstone of a risk-adjusted investment strategy. Since single stocks don’t move like the broader market, you’re exposed to much greater risk. Whether

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Tax law changes - 2025 OBBB
Tax planning

Major Tax Changes: The 2025 One Big Beautiful Bill (OBBB)

The “One Big Beautiful Bill Act” (OBBB Act), signed into law by President Trump on July 4, 2025, represents a massive overhaul of federal tax policy. The expanse and complexity of the new tax bill cannot be understated. Given the breadth and recency of the bill, tax, financial, and legal

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Should I Accept a Tender Offer for Company Stock
Diversification

Should I Accept a Tender Offer For My Stock Options?

As a startup or private company employee, you may have the option to participate in a tender offer from your employer. Accepting a tender offer means the company buys back some of your stock or options. While it won’t always make sense to participate, any opportunity for liquidity as a

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Restricted Stock Awards RSAs
Restricted Stock Equity Awards

Restricted Stock Awards: Guide to Your Grant

A restricted stock award (RSA) is a form of equity compensation. RSA grants are commonly issued by private companies, particularly early-stage startups, and may be referred to as founder’s stock or simply restricted stock grants awarded to employees. When restricted stock is granted, shares of company stock are held in

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Inheriting IRA from Spouse
Inheritance

Inheriting an IRA from Your Spouse

Losing a spouse is a difficult time, and navigating the complexities of inherited assets can feel overwhelming. If your spouse named you as the sole beneficiary of their traditional IRA, understanding your options is a crucial first step. The most common options after inheriting an IRA from your spouse are

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Putting home in trust
Estate Planning

Should I Put My House in a Trust?

Why own a home in a revocable trust? There is one main reason to consider putting a house in trust: to avoid probate court. Although a living trust can be an effective estate planning technique, it is important to understand the benefits it can and cannot provide. A living trust

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83b election stock options restricted stock
ISOs

83(b) Election for Stock Options and Restricted Stock

For individuals with stock-based compensation, an 83(b) election has the potential to greatly reduce taxes on stock options or restricted stock. When you purchase unvested stock compensation and make the election, you recognize the taxable gain now (if any), instead of when the shares vest. What is an 83(b) election?

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Best time for Roth conversions
401(k) Plans

When is the Best Time for a Roth Conversion?

Is there an optimal time to convert a traditional IRA or old 401(k) to a Roth IRA? While a Roth conversion may never make sense for some individuals, for others, early retirement years may be the best time to convert pre-tax accounts to tax-free Roth. Your current and projected future

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What happens to stock options if I quit
ISOs

What Happens to Your Stock Options When You Quit or Leave the Company?

What happens to employee stock options or equity compensation if you leave the company? Before giving notice, understand how vested and unvested stock options and restricted stock units are treated if you quit, retire, or leave the company for other reasons. In brief, here’s what usually happens to stock options

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Is it worth it to work with a financial advisor?
Cash Management

Are You Holding Too Much Cash?

You may want to think twice before taking the old saying cash is king too literally. Even though interest rates have risen in the last few years, over time, holding cash will yield a real negative return after inflation and taxes. Keeping cash is important, the key is finding the right

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Stocks vs bonds historical returns by calendar year
Bonds

Stocks vs. Bonds: Historical Returns, Risk, and the Case for Both

Stocks and bonds differ in many aspects, including the risk and return investors can expect. Because of these differences, stocks and bonds accomplish different things in an asset allocation. When you own a stock, you’re buying a piece of equity ownership in the company. With bonds, you’re buying the issuer’s

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what happened to the bond market in 2008
Bonds

Are Bonds Safe During a Recession or Market Crash?

Although past performance is not indicative of future results, history can be a helpful lens to view bond performance during past recessions and bouts of volatility. Swings in the financial markets also highlight the benefits—and limitations—of diversification. During times of economic, financial, and political uncertainty, investors often wonder where to

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Early exercise stock options
ISOs

What Is An Early Exercise of Stock Options?

If you work for a private startup, you may be able to exercise your stock options early. Early exercisable stock options means you can exercise your option to buy the stock before the vesting date. When should you exercise an option early? In the right situations, early exercising stock options

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