MONEY

MONEY

How Big Your Stock Portfolio Should Be Before Buying A House

Housing affordability is at a crisis low. You’ve read that headline a hundred times. Either incomes rise or home prices crash to get back to pre-COVID levels. That’s true if.

Read More
MONEY

Buying A Mansion In Paradise Might Be Backwards

This summer I toured a couple of 6,000 to 7,000 square foot mansion in the Kahala neighborhood of Honolulu, all in preparation for a potential move in two or three.

Read More
MONEY

The Rise Of The Stay At Home Man (Boyfriend Or Husband)

According to an Indeed Hiring Lab analysis, women now hold more payroll jobs than men in America. It’s only the third time this has ever happened. The first two times,.

Read More
MONEY

A Tax Identification System For Determining Your Level of Freedom

Ever since two park rangers approached me at an empty public court while I was teaching my own children tennis, I’ve been thinking about how to make sure it doesn’t.

Read More
MONEY

Real Adults Are Not Financially Dependent On Their Parents

One of my biggest fears as a parent is raising kids who can’t launch into adulthood on their own. My hope is that by 26, three years after college to.

Read More
MONEY

How Much A Family Needs To Earn To Live Comfortably By City

Back in 2018, I wrote that households need to earn $300,000 a year to live a middle-class lifestyle in an expensive coastal city. The internet was not pleased. I was called out.

Read More
MONEY

What A 6-Month IPO Lockup Feels Like As A Startup Employee

Before I die, I have a whole bucket list I want to get through. One item is experiencing what it’s like to be a startup employee whose company goes public..

Read More
MONEY

The Dumbbell FIRE Investing Method To Safely Build Max Wealth

FIRE is ultimately about being set for life. You build a portfolio big enough to cover your expenses, and then your one job is to not blow it up. But.

Read More
MONEY

Summer YOLO Fund: Permission To Spend More and Save Less

In anticipation of investing in some YC Demo Day startups, I transferred $50,000 from my Fidelity brokerage account to my Citibank checking account. This was right after I’d already wired $56,100.

Read More
MONEY

The Incredible Satisfaction of Never Giving Up: A Lesson In Grit

Life is hard if you want to outperform average. To reach a USTA 5.0 level in tennis takes an endless amount of practice. To get promoted to Managing Director in banking, you.

Read More