Family Finances

Rolling Over Leftover 529 Funds Into A Roth IRA: Who Really Benefits?

A 529 plan is one of the best generational wealth transfer vehicles. Instead of just giving our kids or grandchildren money, it’s way better to give them the gift of education. Thanks to the SECURE Act 2.0, we will be able to roll over leftover 529 funds to a Roth IRA without taxes or penalties. […]

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How To Develop A Better Personality To Get Into An Elite University

Want to get into an elite university? Develop a better personality so you can receive a higher personality score during the admissions process. In the Supreme Court case regarding using race-conscious admissions (affirmative action) at Harvard University and UNC, we learn Harvard assigns a personality score to every applicant. By assigning a lower personality score

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Where Are All The Adult Athletes? Sports And Your Career

For over 20 years, I’ve been a tennis club member. Player levels range from beginner to ex-professionals. Everybody gets along and rallies around a sport they enjoy, no matter their level of wealth. But I just realized something odd. And the realization wouldn’t have come had I not become a father. After three years of

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When To Play The Status Game Again: Money, Fame, And Impact

Since 2012, I have tried hard to stop playing the status game. After all, leaving my job in banking meant losing status at age 34 when folks are usually coming into their own. After my career was over, I turned down multiple TV show appearances, podcast interviews, and speaking gigs. To be able to just

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Conduct A Regret Minimization Exercise To Help You Move Forward

One of the main reasons why I wrote my WSJ bestseller, Buy This, Not That was to help readers feel less regret by making wiser choices. Regret is one of the worst feelings, especially if it is a type of regret that could have been prevented through knowledge. The easiest way to stop saying, “If

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Overcoming The Trough Of Sorrow: Defeating An Emptiness Inside

Here in the San Francisco tech startup scene, we have a term called “the trough of sorrow.” The trough of sorrow refers to the sadness that comes after a setback or a big win. After a setback, you’re tasked with finding product-market fit to survive given your company has a limited runway of cash. You

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Vacation Property Comparison: Single-Family Mansion Vs. Resort Condo

If you’re in the market for a vacation property you will likely have to decide between purchasing a single-family home or a condo. However, what if you have enough money to buy a single-family mansion for $10+ million versus a condo at a luxury resort for $500,000+? I used to think a single-family mansion for

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How To Get Life Insurance For Free: Make More Money

Have you ever wondered how you can get life insurance for free? I’m not talking about getting free life insurance from work. The life insurance amount usually isn’t enough. I’m talking about how to get free life insurance outside of work. My wife and I have life insurance because with have two young children, a

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The Unexpected Financial Benefits Of Having Children

One of the main reasons why people delay having children is its cost. Rising prices for daycare, preschool tuition, and shelter plus the opportunity cost of not working, partially explains why our population replacement rate is declining.  The cost of raising children worried me so much that I actually had a $1 million net worth

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The Age Children Begin Loving Their Fathers As Much As Their Mothers

Are you a stay-at-home father or father who spends a lot of time with his children? If so, you may be second-guessing your decision to spend so much time with them during their early years. Without some reciprocating love, you might be wondering whether your effort is worth it. You see, the more time and

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