Should You Tax‑Loss Harvest a Stock You Love?

Should You Tax‑Loss Harvest a Stock You Love?

Should you tax-loss harvest a stock you love?This is a genuinely hard question for stock‑pickers.Let’s say you’re incredibly bullish on a company.The stock is down.You could:• Sell it• Capture the...

Should You Tax‑Loss Harvest a Stock You Love?

Should you tax-loss harvest a stock you love?This is a genuinely hard question for stock‑pickers.Let’s say you’re incredibly bullish on a company.The stock is down.You could:• Sell it• Capture the...

He Sold His Business for $17M in California. Now He’s Scrambling.

He Sold His Business for $17M in California. No...

I had a call with a guy who sold his business for ~$17M in CA two months ago. No tax planning. Now he’s staring at a massive tax bill and asking what we can...

He Sold His Business for $17M in California. No...

I had a call with a guy who sold his business for ~$17M in CA two months ago. No tax planning. Now he’s staring at a massive tax bill and asking what we can...

Why I Put SpaceX in My Roth IRA

Why I Put SpaceX in My Roth IRA

This is why I invested in SpaceX out of my Roth IRA.Whenever I have the opportunity to invest in private equity, I’m very careful about where I hold it.Let’s say...

Why I Put SpaceX in My Roth IRA

This is why I invested in SpaceX out of my Roth IRA.Whenever I have the opportunity to invest in private equity, I’m very careful about where I hold it.Let’s say...

Direct Indexing Has Two Superpowers

Direct Indexing Has Two Superpowers

This is why I love investing in individual stocksThe ability to tax‑loss harvest losers gets all the attention…But what about the winners?By definition, you’ll own some of the best-performing stocks...

Direct Indexing Has Two Superpowers

This is why I love investing in individual stocksThe ability to tax‑loss harvest losers gets all the attention…But what about the winners?By definition, you’ll own some of the best-performing stocks...

Your Bond Yield Doesn't Have to Be Taxed as Income

Your Bond Yield Doesn't Have to Be Taxed as Income

Most investors are unknowingly paying taxes they don’t have to.If you hold bonds in a taxable account, every monthly distribution gets taxed as ordinary income – up to 37% federally....

Your Bond Yield Doesn't Have to Be Taxed as Income

Most investors are unknowingly paying taxes they don’t have to.If you hold bonds in a taxable account, every monthly distribution gets taxed as ordinary income – up to 37% federally....

San Francisco Rents Are Up 22% And We’re Capitalizing On It

San Francisco Rents Are Up 22% And We’re Capita...

San Francisco rents are up 22%.Over the last few years, the consensus trade was:• Leave San Francisco• Work remotely• Move to Austin, Miami, Nashville, etc.But the companies creating the most...

San Francisco Rents Are Up 22% And We’re Capita...

San Francisco rents are up 22%.Over the last few years, the consensus trade was:• Leave San Francisco• Work remotely• Move to Austin, Miami, Nashville, etc.But the companies creating the most...