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Should You Exercise Stock Options During a Pre-IPO Window?
Is exercising stock options right before a company goes public a good idea? Employees with pre-IPO incentive or non-qualified stock options often wonder if they
Selling a Business? Brokers Share Tips on How to Maximize the Sale Price
The sale of a business marks a major life event. It’s emotional, stressful, and exciting all at the same time. And unfortunately, it’s often a
What to do After the Death of a Spouse
Losing a spouse can be an overwhelming and emotional experience. While it’s possible to organize financial documents ahead of time, there’s no way to truly
Financial Planning for a Divorce
There are many financial planning considerations before, during, and after a divorce. A key part of the process from a financial standpoint is dividing the
How to Negotiate Equity in a Private Company or Startup
Working for a startup can pay off big financially, but a lot must go right along the way. If you are considering taking a job
5 Big Changes to Roth Accounts in Secure Act 2.0
The Secure Act 2.0 was signed into law December 29th, 2022, bringing more major changes to tax law. Among the most notable changes include a
Massachusetts ‘Millionaires’ Tax Applies to Sudden Wealth Events
Taxachusetts is back. In November 2022, proponents of the Massachusetts ‘millionaires’ tax won their bid to nearly double the income tax rate on individuals with
Frozen IPO Market Reveals Dangers of Pre-IPO Exercising & Pre-Spending a Windfall
The Instacart IPO is on hold…again. What should employees with stock options do when their employer’s IPO stalls? In truth, best practices around an IPO
The Best Way to Take Required Minimum Distributions (RMDs)
Updated for 2023. Planning can help optimize annual required minimum distributions depending on your goals and cash flow needs. After the passing of Secure Act
What a Down Round Means for Employees with Stock Options
Quite simply, a down round is when a company raises money at a lower valuation per share relative to earlier financing rounds. A simple example:
Returns of Stocks and Bonds Before, During, and After Interest Rate Hikes (Charts)
The Federal Reserve is going to be raising interest rates (via the target Federal Funds rate). This is likely to happen next month. Rising interest
The Stock is Down, But You’re in a Post-IPO Lock-up
More companies entered the public markets in 2021 than any other year on record. From traditional IPOs or SPACs, and even direct listings, it was a banner
What the 4% Rule Gets Wrong About Retirement Income
The 4% rule is one of the most well-known rules of thumb in personal finance. The premise is simple: retirees can withdraw 4% of their
How to Donate Stock to Charity: Donor-Advised Funds
Giving appreciated stocks can be a great way to maximize your gift to charity and your tax benefits. When you donate cash, you’re giving after-tax
Avoid the Double Tax Trap When Making Non-Deductible IRA Contributions
Updated for 2024. Anyone with earned income can make a non-deductible (after tax) contribution to an IRA and benefit from tax-deferred growth. But it may
Explaining the Backdoor Roth and Mega Backdoor Roth IRA
Updated for 2024. Many individuals have heard of the backdoor Roth before, but the mega backdoor Roth is getting a lot of attention recently. Here
Will Tax Hikes Hurt Stocks? Impact of Tax Rates on the S&P 500
Between the Biden tax plans and other bills already before Congress, it’s likely that some level of tax legislation will make its way into law
What Happens to Stock Options in a SPAC Merger?
Although the most common way for a company to go public is through the traditional initial public offering (IPO) process, it’s not the only method.