Pop quiz: You’re buying airline tickets to visit grandma for the holidays. She lives on the other side of the nation, too far away to drive. You’ve budgeted $400 for holiday travel, but you can’t find airfare for less than $575. What do you do? a) Tell grandma she’ll have to spend Christmas alone. b)…
Lately I’ve been getting emails from readers with the following situation: “I’ve pinched every penny and slashed every expense. But I still can’t pay my bills. Help!” If I accept your premise — if you’ve slaughtered your expenses to the brink of extinction — then you don’t have a spending problem. You have an income problem.
This article is Part 3 of The Airbnb Series. Before you read this, check out Part 1 and Part 2, and when you’re done, visit Part 4. Well, it’s happened. Eight crazy months, 42 guests, one police incident, and $19,000 in gross income. I’ve packaged the adventures, ideas and full disclosure of the numbers into…
A few days ago, I slept in my own bed for the first time in more than a month. I’ve been on the road nearly nonstop for the past few months — including trips to Costa Rica and Ireland — and the last 30 days really took the cake: from San Diego to New Orleans…
Despite the fact that I have the best roommates in the world, I’ll occasionally remark, “I’m tired of having roommates.” And Will replies: “Are you $1,700 per month tired of it?” I don’t need to respond. The answer is obvious. The minor inconveniences — sharing a refrigerator, waiting to use the washing machine — pale…
I’m about to tell you something that most travel and lifestyle bloggers are afraid to say. I’m going to reveal the truth about the “digital nomad” lifestyle. The term “digital nomad” (or the phrase “location independent”) refers to people (like me) who have the freedom to work from anywhere on the planet with an internet…
Myth: If you’re supporting 5 people on 1 income (and it’s not a high income), you’re screwed. You’ll never become a business owner or an investor. You’ll be lucky just to pay the bills. Fact: Ladies and gentlemen, meet success story: Rental Randy. In my last blog post, I re-emphasized that the best way for…
Moderation is not my strong suit. I don’t just eat one chocolate-chip cookie — I either eat zero, or I eat the whole batch. I don’t just travel for a weekend — I either stay at home, or I hit the road for weeks/months/years. And apparently, I can’t just buy one or two houses. Afford…
A few months ago, a startup videography team from Florida came knocking on my door. Mike and Lauren are a young married couple living in Sarasota, and in their spare time, they’ve started hustling: They’re under contract for their first rental property, devised a plan to retire by 2018, and they’ve launched an awesome YouTube…
I’ve been in Costa Rica for a week now; a few more days until I fly out. Believe it or not, I came here for work. I spoke at a blogging workshop for the first five days, at the invitation of a publishing company. About a dozen attendees came to learn about blog writing and…