Identity Diversification May Be As Important As Investment Diversification

41 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 […]

Identity Diversification May Be As Important As Investment Diversification Read More »

The Ideal Length Of Time To Hold A Mortgage Until Paying It Off

32 Comments / Mortgages / By

Deciding whether to pay off a mortgage early—or how long to keep one—is ultimately a personal choice. In this post, I’ll share my perspective by drawing on both real-life experience and some numbers to frame the decision. In 2022, my wife and I finally paid off the mortgage on our Lake Tahoe vacation property. That

The Ideal Length Of Time To Hold A Mortgage Until Paying It Off Read More »

Being Truly FIRE Is Terrible For Entrepreneurship, But That’s OK

18 Comments / Entrepreneurship / By

In 2020, during the heart of the COVID pandemic, I remember listening to a FIRE-focused podcast hosted by two people who claimed to be financially independent and retired early. Even though it’s been over 16 years since I first started writing about FIRE, the topic still fascinates me. The journey toward financial independence is full

Being Truly FIRE Is Terrible For Entrepreneurship, But That’s OK Read More »

Purposefully Leaving A Rental Property Empty As A Luxury Move

57 Comments / Real Estate / By

If you own rental properties, this post may resonate with you. It’s about what to do with a property once a tenant gives notice: keep renting it out, sell and pay capital gains taxes, sell via a 1031 exchange to defer taxes, move back in to avoid taxes, or—most controversially—simply leave it empty. For most of

Purposefully Leaving A Rental Property Empty As A Luxury Move Read More »

The Upside of Grindcore Culture: Work Hard, Profit Harder

20 Comments / Career & Employment / By

The grindcore culture is back and grindier than ever. At least that’s what Are Kharazian, an economist at fintech startup Ramp, says. (Disclosure: I’m an investor in Ramp through the Innovation Fund.) For those unfamiliar, Ramp is a corporate card company that makes doing expenses easier. But here’s the fascinating part: according to Kharazian, usage of

The Upside of Grindcore Culture: Work Hard, Profit Harder Read More »

The End Of The Commercial Real Estate Recession Is Finally Here

11 Comments / Real Estate / By

Since 2022, commercial real estate (CRE) investors have been slogging through a rough downturn. Mortgage rates spiked as inflation ripped higher, cap rates expanded, and asset values fell across the board. The rally cry became simple: “Survive until 2025.” Now that we’re in the back half of 2025, it seems like the worst is finally over.

The End Of The Commercial Real Estate Recession Is Finally Here Read More »

How The Irrevocable Life Insurance Trust Saves Families From the Estate Tax Hammer

7 Comments / Taxes / By

Lately, I’ve been thinking more about estate planning. Part of it is just getting older. Part of it is having young children I want to protect no matter what. And part of it is watching the unsettling rise in political violence, which is a stark reminder that life can be cut short unexpectedly. As I

How The Irrevocable Life Insurance Trust Saves Families From the Estate Tax Hammer Read More »

Artificially Feeling Poor May Help You Grow Rich One Day

12 Comments / Budgeting & Savings / By

What if one of the best ways to get wealthy is to trick yourself into thinking you’re poor? It sounds counterintuitive, even ridiculous. But after decades of saving, investing, and observing how people behave around money, I’ve realized one thing: abundance often breeds complacency. When you feel flush, you spend more, work less, and get

Artificially Feeling Poor May Help You Grow Rich One Day Read More »