What I Told a 20-Something Sitting on $5M in One Stock

What I Told a 20-Something Sitting on $5M in On...

We all want to believe we “knew” our company was going to the moon. But a $5M+ single‑stock position in your 20s isn’t genius. It’s concentration and luck. Here’s what...

What I Told a 20-Something Sitting on $5M in On...

We all want to believe we “knew” our company was going to the moon. But a $5M+ single‑stock position in your 20s isn’t genius. It’s concentration and luck. Here’s what...

How to Actually Get My Help (Without “Picking My Brain” for Free)

How to Actually Get My Help (Without “Picking M...

How to actually get my help on complex tax + portfolio cases.  Dozens of people hit my inbox every week asking to: • “Pick my brain” • Talk shop •...

How to Actually Get My Help (Without “Picking M...

How to actually get my help on complex tax + portfolio cases.  Dozens of people hit my inbox every week asking to: • “Pick my brain” • Talk shop •...

High Valuations Don’t Mean Run for the Exits

High Valuations Don’t Mean Run for the Exits

What I tell $5M+ families about diversifying when the S&P is priced for perfection. Short version: valuation risk is high, uncertainty is higher, so we diversify more intelligently - not...

High Valuations Don’t Mean Run for the Exits

What I tell $5M+ families about diversifying when the S&P is priced for perfection. Short version: valuation risk is high, uncertainty is higher, so we diversify more intelligently - not...

A $12M Case Study in Tax-Efficient Investing

A $12M Case Study in Tax-Efficient Investing

PE partner with a $12M portfolio in the 37% bracket Current mix (outside of his own PE deals): $2M in retirement accounts $10M in taxable accounts Portfolio is 100% long-only...

A $12M Case Study in Tax-Efficient Investing

PE partner with a $12M portfolio in the 37% bracket Current mix (outside of his own PE deals): $2M in retirement accounts $10M in taxable accounts Portfolio is 100% long-only...

How to Tell If Your Financial Advisor Is the Real Deal

How to Tell If Your Financial Advisor Is the Re...

Always untie your bow tie at the end of the night to show it was the real thing. None of that pre-tied nonsense. And now… here comes the analogy I...

How to Tell If Your Financial Advisor Is the Re...

Always untie your bow tie at the end of the night to show it was the real thing. None of that pre-tied nonsense. And now… here comes the analogy I...

How We Moved $750,000 Into a Roth IRA — With Zero Taxes

How We Moved $750,000 Into a Roth IRA — With Ze...

Most business owners don’t realize this: Your 401(k), IRA, cash balance plan, and deferred comp aren’t “tax shelters”… They’re ticking tax time-bombs waiting to explode later in life. Eventually, the IRS forces...

How We Moved $750,000 Into a Roth IRA — With Ze...

Most business owners don’t realize this: Your 401(k), IRA, cash balance plan, and deferred comp aren’t “tax shelters”… They’re ticking tax time-bombs waiting to explode later in life. Eventually, the IRS forces...