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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 (question 1) won their bid to nearly double the income tax rate on
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’s The Best Thing To Do With Inherited Money?
Updated for 2024. There are lots of ways to spend an inheritance. But just because you have options, doesn’t mean they’re all good options. After
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:
3 Biggest Mistakes Investors Make in Volatile Markets
Investing through market volatility can be challenging. Should you go to cash? What investments perform the best during a market selloff? Is it a good
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
Is 10 Million Enough to Retire?
Can you retire on 10 million dollars? For many Americans, this hefty sum would far exceed retirement needs and may even lead to generational wealth.
Qualified Small Business Stock Gain Exclusion (Section 1202)
If you invested in a startup or small business (founders, employee exercise of stock options, business owner), you need to know about qualified small business
When to Exercise Stock Options
When should you exercise stock options? With stock options, employees have the right (not obligation) to buy the shares (called exercising). Vesting is often the
Here’s Why it Might be a Good Time to Rebalance Your Portfolio
Rebalancing your portfolio is an important part of managing your money. Rebalancing means buying and selling positions in your portfolio to get back to your
Expecting a Windfall from Stock Options or Selling a Business? New Tax Proposals May Cost You.
Tax planning for a sudden liquidity event just got more complicated. If you’re expecting a big windfall from selling a business or employee stock options
Worried About Taxes Going Up? 9 Ways To Reduce Tax
While there likely isn’t a magic bullet to wipe out your tax bill, there are ways to layer tax-efficiency into your plan. If you’re concerned
2022 IRS Contribution Limits
The IRS has released the 2022 contribution limits for retirement plans and other cost-of-living adjustments.
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