Mini Case Study: Using RSUs for Charitable Giving
Instead of donating to charity by writing checks from your brokerage account, you can donate your RSUs into a donor-advised fund. This gives you a double tax benefit.
Employee Stock Purchase Plans: The Low-Hanging Fruit Too Many Employees Ignore
When you buy stock in a traditional brokerage account, you pay the current market price. An Employee Stock Purchase Plan (ESPP) is attractive because it allows you to buy your company’s stock for less than its current market value.
How To Catch Up on Retirement Savings if You’re Between 55 and 65 and Feel Behind
Surveys consistently show that most people between 55-65 believe they haven't saved enough for retirement. The good news is that this decade is one of the best times to close the gap.
If It Were Easy, Everyone Would Do It: Creating and Sticking to a Financial Plan as a Sales Professional
The hardest part about achieving a $1M portfolio is the discipline required. And it’s more complicated when you work in a sales role and have lumpy pay.
Selling Company Stock? Make Sure Your 1099-B Does Not Cause You to Pay Tax Twice
If you earn equity compensation, there is an easy mistake you could make that causes you to pay taxes twice on the same income. Read to learn why this happens and how you can avoid it.
What is The Three-Bucket Retirement Withdrawal Strategy?
In retirement, how you withdraw money matters as much as how much you've saved. The lack of a plan can cost hundreds of thousands in taxes and missed growth. The three-bucket strategy is a framework that helps avoid that.
Five Trust Mistakes That Can Cost Your Family Time, Money, and Peace of Mind
A trust is a powerful estate planning tool, if it’s set up correctly. Whether you're considering creating a trust or already have one in place, here are five of the most common trust mistakes.
Choosing Your Pension: One of the Most Important Retirement Decisions You'll Make
Many retirees, especially those who spent careers with public agencies, have a defined benefit pension coming to them. The decision on how to take that income can shape your retirement.
Advanced Roth Conversion Strategies – For Taxpayers with IRAs worth $3M or more
A friend recently told me he had $5M in his IRA and was contemplating converting the entire thing to a Roth. He asked me for my opinion, but there is no “one size fits all” answer.
Mini Case Study: 351 Exchange (Intel)
One of our clients received stock options from his company that was later acquired by Intel, so his shares converted to Intel stock. Now that Intel is up more than 4x over the past year, selling would have triggered a substantial capital gain. Enter the 351 exchange.
Mini Case Study: Saving Over $370K Per Year for Retirement
I helped one of my business owner clients set up a plan to save almost $400k per year for retirement, thanks to a combination between his 401(k) + Safe Harbor contribution + Cash Balance Pension Plan.
What Happens After Death? Understanding the Role of an Administrative Trust
A revocable living trust doesn't end at death, it enters a new phase known as an administrative trust. During this time, the trustee has to gather and value assets, get a new EIN, pay off debts, file final tax returns, and only then distribute what's left.
Mini Case Study: Selling Rental Properties
Owning rental property can be a great source of income, but it can also come with headaches. If you’re tired of running a property and looking to sell, remember that the timing of a real estate sale can be just as important as the sale itself, from a tax perspective.
Treasury Bills vs. High Yield Savings Accounts: The Tax Angle Most People Miss
High Yield Savings Accounts are a popular option for investors who want to save some cash and still earn a return on it. Treasury Bills are a lesser-known alternative and unlike HYSAs, all interest income earned is exempt from all state and local income taxes.
What Leverage Actually Means When It Comes to Stock Options
Most people understand the basics of their stock options. They know the strike price is what they can buy company stock for, and they know the fair market value is what the stock is currently worth. Leverage is where some get confused.
Why We Passed on Private Credit & Private Equity
Last year, we decided against adding any private credit or private equity into our clients’ portfolios. Last month, the largest private credit interval fund redeemed less than 1/3 of their withdrawal requests. The private space looks to be a place where permanent, irreplaceable capital should not be allocated.
Mini Case Study: Wealth Transfer Tax Planning
When your portfolio has a large amount of concentrated stock, selling either means a large tax bill or an opportunity for strategic planning.
How the One Big Beautiful Bill Will Reshape Retirement
The One Big Beautiful Bill Act (OBBB) is a significant overhaul of the U.S. tax code. For families with significant assets and income, it creates planning opportunities and risks for retirement.
SpaceX vs. AOL: We've Seen This Movie Before, and We Know How It Ends
In 2000, AOL announced it would acquire Time Warner in an all-stock deal, using its extraordinary stock price to acquire assets it could never justify purchasing with real money. SpaceX replicated this when it absorbed xAI in 2026.
Mistakes to Avoid with Your Equity Compensation
Equity compensation is becoming increasingly common as a key piece of many people’s salaries, and many employees have been in favorable positions to "cash in" on it. As with anything, more digits after a dollar sign equate to the possibility of bigger mistakes.