Millionaire Early Retirees Probably Shouldn’t Get Healthcare Subsidies

19 Comments / Insurance / By

If healthcare in America weren’t so egregiously expensive, more people would retire earlier and live better, happier lives. We’re one of the few countries in the world where affordable healthcare is tied to employment, making financial independence that much harder to achieve. Given the high cost of coverage, before you decide to retire early by […]

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How Empower’s Free Financial Review Helped Me Rethink Retirement

18 Comments / Retirement / By

After doing my first free Empower financial professional review back in 2014, I decided to do another investment portfolio review with them. Given the portfolio review is free for anyone with over $100,000 in investable assets, and my financial situation has changed so dramatically since then, I figured, why not spend a little time uncovering potential

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It Feels Like 1999 Again: Time To Party Without Blacking Out

22 Comments / Investments / By

1999 is back, and I’ve missed it. Ever since then, I’ve been chasing that next 50-bagger, the kind of life-changing winner that helped me come up with the down payment for my first property. But he’s been elusive. I still remember sitting on the international trading floor at Goldman Sachs at 1 New York Plaza,

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Vacations Just Aren’t As Great Anymore Once You Retire Early

30 Comments / Retirement / By

On October 8, 2025, we decided to go on a family vacation I was decidedly unexcited about. That entire week was supposed to be my time to attend the Fairfield Challenger tennis tournament every day with my buddy Richard. September and October are tennis paradise months in the Bay Area, with multiple tournaments and ideal

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The Cost To Prove Your Ethnicity And Heritage: Hawaiian Edition

25 Comments / Family Finances / By

So you’ve read my post on the growing importance of Identity Diversification and now you’re wondering what it actually takes to prove your ethnicity and heritage. Doing so can help you better navigate the shifting socioeconomic winds of society and, in some cases, even improve your odds of getting into school, landing a job, winning

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Turn a Government Shutdown Into an Opportunity to Thrive

6 Comments / Big Government / By

The government has shut down again, this time mostly over healthcare subsidies. We’ve seen shutdowns before, and we’ll see more in the future. As frustrating as they are, shutdowns remind us that uncertainty is the only constant. Instead of just surviving, I want to show you how to thrive during and after one. Out of

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Identity Diversification May Be As Important As Investment Diversification

40 Comments / Relationships, Retirement / By

As long-time investors, we all understand the importance of diversification when it comes to growing wealth. Bear markets and corrections are inevitable, which is why putting everything into a single asset class is not wise. But what about applying that same principle to our identities? What if “Identity Diversification” could help grow not just our

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