Part of the American dream is to climb the property ladder and live in the nicest neighborhood possible. We spend more than half our lives at home, so we want a neighborhood that offers as much peace, quiet, safety, and convenience as our budget allows. As an old man with young kids, long gone are the days […]
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I recently shared that I'm 49 and out of cash because a venture capital fund called capital much faster than I expected. I assumed a conservative 30% of my commitment would be called in year one. Instead, 46% was called in just six months. On a $1 million commitment, that's $460,000 out the door instead […]
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After stretching for the nicest house I could afford in 2023, I ended up living paycheck to paycheck for six months. It was stressful enough that I picked up a part-time consulting gig to shore up liquidity. Thankfully, stocks and real estate kept rebounding after a rough 2022, and the broke feeling faded. I promised myself I […]
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Once both our children began school full-time in 2024, my wife and I had more breathing room. At least six hours a day of free time. No more wrangling toddlers in the chaos of the early years. I used the time to finish Millionaire Milestones, which became a USA Today bestseller in 2025. Now I'm […]
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In 2012, two months before my 35th birthday, I engineered my layoff from a 13-year career in investment banking. At the time, it felt like the riskiest thing I had ever done. Was I really going to blow up my career right as my earning power was about to compound? It did not seem wise. […]
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Ever wonder why Honolulu, Hawaii has the highest median life expectancy of any city in America? Sunshine, moderate temperatures, walkability, and an unhurried pace do wonders for your mental and physical health. As a relatively low-stress guy who doesn't have to commute to a day job to sit in meetings all day, every time I […]
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Historically, I've viewed stocks as funny money. It's not real until it's converted into something you can use. Given the lack of utility for stocks, I've long preferred owning real estate. Being able to touch, see, and enjoy your investment without experiencing daily volatility is a huge win. And the feel good wealth effect of […]
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The other day I made $10 winning a set of tennis at a public park. It was a funny situation because I didn't set out to make money playing tennis. It just happened. I was hitting with my long-time buddy, Richard, next to a young man and a couple of regulars. We asked them if […]
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A neighbor across the street from my rental texted me at 3:35pm on a Saturday to say something had been beeping inside my property all day and my tenants appeared to be gone. I drove over, let myself in, and found three smoke alarms stacked on the garage floor with the top one screaming away. […]
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This summer, my new AI investment advisor, Mezzi, discovered roughly $300,000 of hidden stock exposure in Google I didn't know I had. It sounds a little absurd, given the amount. But I've been investing in Google for over 15 years, and with a complicated net worth it's hard to track everything accurately when your mind anchors […]
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Happy Labor Day weekend everyone. Perhaps some of you are in the market for a new car this weekend. I'm definitely not. After almost a year of deliberating between replacing my 2015 Range Rover Sport or continuing to fix it, I've finally decided to keep fixing it indefinitely. The main reason is that we may […]
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