The Loss Worth Taking (Sometimes)
The Question A client is looking at a position worth $100,000 that cost $125,000. The instinct is to wait for it to come back. The CPA’s instinct is to sell it. The real question isn’t whether a loss is a loss. It’s whether a loss on paper is worth turning into one on purpose. That’s […]
Measured Against What?
The Question A portfolio is up for the year, but the index is up more. Or the portfolio is down, and the index is down less. Either way, the question comes up: are we behind? The real question isn’t “am I beating the market.” It’s “what am I measuring against, and does that measure have […]
Portfolio Insurance?
Everyone pays for insurance. Health insurance. Car insurance. Home insurance. Pet insurance. You name it, and there is insurance for it. But who has portfolio insurance? Why can’t the value of a portfolio be insured, in case of damage, like property or someone’s health? It turns out it can, and here’s how. The Mechanics – […]
The Pre-money Advisory Relationship
When in life does a person get to test something, of substantial value, before they buy it? In the world of founder and early-employee advisory services, it’s part of the design. The key is building a relationship so that when big decisions need to be made, trust has already been established. As discussed in other […]
Don’t Sleep on ESPP
Most people know about the 401K match. Contribute to the plan, your employer matches it, bank the extra funds until retirement. It’s one of the easiest paths to free money in the modern world. Fewer are familiar with the Employee Stock Purchase Plan, or known by its acronym, ESPP. In an ESPP employees purchase the […]
Who Is Your Quarterback?
It’s the beginning of a new football season. Everyone’s team has a chance to win it all. Spirits are high. Teams have their coaches, staff and roster prepped for a grueling season that punishes bad decisions and mistakes and rewards solid strategy and execution. Just as a football team has many moving parts to drive […]
The Obstacle That Created the Opportunity
In 1980, Nintendo hands a young designer named Shigeru Miyamoto a strange assignment: turn a warehouse of unsold arcade cabinets — leftover from a flopped game called Radar Scope — into something people will pay to play. Miyamoto has never designed a game before, but he has an idea: a love triangle. A hero, a […]
Vested Doesn’t Mean Yours Yet
The Question An employee leaves a private company holding vested stock options. Most assume there’s time to figure out what to do with them. There usually isn’t — the clock starts on the last day worked, not the day a decision gets made. Three Angles I. Exercise now, sort out the rest later. Locks in […]
The Clock Nobody Told You Was Running
The Question In a world where the average senior engineer is leaving the incumbent to start their own company, QSBS planning is more relevant — and running on a more compressed timetable — than ever before. A founder or early employee holds stock that might qualify for a full exclusion on the gain when it’s […]
The Compensation That Comes With Homework
The Question Equity compensation — can we spend it? It’s a fair question, and it comes up in more households than you’d think — tax season, a year-end statement, a stray mention of “vesting” at dinner. The number on the form is real. The account balance is also real. The gap between them isn’t a […]