Ask Tim: The True Cost of Being a Las Vegas Raiders Fan
Summer has arrived, which means the calendar is full of camp gear, baseball scores, sunscreen arguments, and at least three family chats with way too many exclamation marks. Somewhere between booking flights and chasing a wiffle ball into the hydrangeas, Washington decided families needed fresh financial puzzles. Some involve babies. Some involve trusts. All involve […]
Market Flash: Warsh Grabs the Wheel, AI Hits a Pothole, and Shinnecock Gets Loud
U.S. equities lost altitude Tuesday as selling centered on semiconductors, AI infrastructure names, and other growth stocks that had been carrying the market. The Nasdaq and S&P 500 fell to one-week lows as investors questioned whether debt-heavy AI spending can keep clearing a higher-rate hurdle.
Ask Tim: Can I Sell My Rental, Use a DST, and Retire From Being a Landlord?
It’s peak “I am tired of dealing with this property” season. A rental that felt clever at 52 can feel like a second job at 67. Add tax bills, tenant calls, insurance hikes, and a roof that keeps making eye contact with your savings account, and suddenly passive income feels pretty chatty. This week, we […]
Market Flash: Inflation Gets Loud and New York Finally Gets Its Parade
The inflation story got harder to ignore this week. The May CPI report showed headline inflation rising 4.2% year over year, up from 3.8% in April, while core CPI rose 2.9%. Energy did most of the headline damage, but the broader message was simple: the glide path back toward 2% has picked up some turbulence.
Quick Answers: 3 Smart Ways to Reduce Taxes After a Business Sale
A business sale can trigger several layers of taxation: capital gains, depreciation recapture, and potentially ordinary income depending on how the deal is structured. Without planning, a large portion of the proceeds can end up with the IRS rather than your family, your next venture, or your charitable goals.
Beyond the Gala Table: Charitable Giving Strategies for High-Net-Worth Families
The inflation story got harder to ignore this week. The May CPI report showed headline inflation rising 4.2% year over year, up from 3.8% in April, while core CPI rose 2.9%. Energy did most of the headline damage, but the broader message was simple: the glide path back toward 2% has picked up some turbulence.
Ask Tim: I Want to Kill the Mortgage but My Spouse Wants to Keep the Cash
Summer has a funny way of turning small bills into big debates. The grill needs propane, the air conditioner sounds tired, and the house seems to ask for cash every time you walk by it. That is why mortgage talk heats up before retirement. A house payment can feel like a rock in your shoe. […]
How DSTs Help Real Estate Owners Step Away — Without Generating a Massive Tax Bill
A DST can give certain real estate owners a way to move from direct property ownership into a more passive real estate structure while preserving the possibility of 1031 tax deferral. It can help solve a real problem: how to stop being a landlord while avoiding an immediate full tax hit from the sale.
Market Flash: Jobs Won’t Blink, Chips Catch a Cold, and Finals Get Interesting
U.S. stocks opened June with the same message they have been sending for much of the spring: investors still have appetite for the AI trade. The Dow and S&P 500 reached new record highs on June 2, helped by strength in AI-linked infrastructure names, including Hewlett Packard Enterprise and Marvell Technology, while Alphabet’s planned AI […]
Ask Tim: Selling the Family Business Without Blowing Up Holiday Gatherings
The family business. The estate plan. The charitable gift that sounded simple until taxes entered the room. Some planning conversations start with spreadsheets. Others start with a sibling saying, “Wait, how is that fair?” This week, we look at two decisions where the math matters, but the people matter more: passing down a business with […]