After months on the market, I finally got an offer on our Smoky Mountains vacation rental — but selling would mean a $150K loss. Do I sell now or hold and hope the market rebounds? Here’s how I’m weighing the decision between cash flow, taxes, peace of mind, and long-term strategy.

Caitlin and I have been out on the Podcast circuit again, guesting on some popular podcasts that will be out soon. Until those episodes are released, I thought I would revisit some of the other podcast interviews we’ve done – the good, bad, and the ugly.

The best time to sell is not what you think it is. There are three important factors to consider, and apply to your life.

When colleges lose government funding, they don’t just dim the dorm lights - they start selling off private assets in their endowments, and those moves can ripple down into our portfolios too.

There’s a phenomenon I’ve seen play out in every career I’ve had - across airports, government, coaching, and investing. When the world feels chaotic, people latch onto something tangible to direct their frustration, even if it doesn’t make logical sense.

Learn about depreciation recapture and how it can apply even if selling at a loss.

My experience on the Bigger Pockets Money podcast: why I was excited to share my FIRE experience, and what shocked me about the final cut.

I thought it would be interesting to do a post-mortem on our beach condo investment to show what went wrong and share some lessons learned.

Have you ever noticed the hoards people who make significant money online by selling advice on how to succeed, rather than by succeeding...

🏖️ Imagine this: you’re lounging by the pristine pool of your dream vacation home, the sun setting in a blaze of color behind you. It’s...

Private equity real estate funds and syndications can be a great way to make money, but they can also be a great way to lose all of your...

In the vast landscape of personal finance influencers, a growing chorus seems to sing the same tune: real estate is a bad investment. I'm...

This morning I was pondering whether to compose a dry (but very educational!) post about the Rule of 72 or delve into something a little...

What makes real estate investing worth it? In this article, we explore the differentiators in real estate investing versus the stock market.

When I bought my first rental property back in 2012, I didn’t belong to any real estate investing groups or socialize with other...

The beginning: I graduated from graduate school in 2005, ready to jump out into the world bright-eyed and bushy-tailed with tens of...

As women, we are often trapped in the societal expectation that we should be giving our time away for free – caring for children, caring...

Susan ​wrote recently​ about three main paths to achieving early financial freedom (extreme frugality & saving, growing a profitable...

Society tells us to follow the traditional path: 💪 Start working a 9-5 job when you’re young 💰 Diligently contribute to your 401k...

Breezy beach condos, cozy mountain cabins, and piles of money flooding in. This is the “HGTV” image of Short-Term Rentals (STRs) - and...