Think back for a minute—what was your first thought the first time you saw one of those handwritten signs at the highway entrance? You know, the one that says, “Handyman Special Must Sale [sic] $87,000 555-5555”? Or the first time you saw a bandit sign that said, “I Buy Houses Close in 7 Days”?

Unless you happened to have encountered one of these messages for the first time after you’d already started studying real estate, your reaction was probably a mixture of:

• Suspicion (“Is this for real? Who tries to buy houses by putting a sign on a telephone pole?”)
• Confusion (“Handyman’s special WHAT? What are they trying to sale [sic] me, exactly?”)
• Mistrust (“How can they possibly buy a house in 7 days when it took my bank 45 to close?”)
• Curiosity (“Who puts these things up, agents?”)

Today, of course, you completely understand the goal of such marketing, because today you live in a bubble populated by other real estate entrepreneurs who eat, breath, and sleep deals. Now that you understand what a handyman’s special is, and that a 7-day closing is in fact possible with other people’s money, your emotional reaction is more likely to be one of jealousy (“Dang, I wish I’d put my sign there”) than of confusion.

But—and this is important—You. Are. Not. Your. Customer.

Your customer, especially your SELLER customer, is NOT familiar with the worl ... Read More…

Just this morning, I was having yet another conversation with a fellow educator about the frustration we have with students who have the brains, education, and resources to make deals—but who, month after month, do everything BUT make deals. 

We discussed people who spend big bucks on courses, set up their LLCs, draft land trusts, buy marketing/accounting/management software, attend REIA meetings religiously, have a color-coded filing system, get their real estate license, start a buyer’s list, concoct every conceivable question about every conceivable scenario in a deal… 

…in fact, do everything that it takes to be a successful real estate entrepreneur except make offers. 

Many of these people are successful in their other endeavors; many have good jobs, nice houses, great kids, you name it. But they can never seem to get to the point of actually buying a property, no matter what we tell them or how much time passes. 

What many of you seem to be waiting for is that NEXT bootcamp or the NEXT investor meeting or the NEXT meeting with their coach. 

And what you’re hoping for is that you’ll read something, hear something, or learn something that makes all the fear go away, makes you completely sure of yourself, and makes you 100% confident that the next step you take is the right one. 

I’m here to tell you, from the perspective of almost 2 decades’ experience, that the day you’re waitin ... Read More…

There’s a dark secret that many investors know but that no one seems to talk about much. It’s a secret that every full-time investor eventually discovers for himself or pays the consequences.  

To illustrate, let’s take 2 imaginary real estate entrepreneurs, Investor A and Investor B. For the sake of simplicity, let’s imagine that both investors start from the same place. Same income, same credit, same skill level. Then, both attend a real estate conference one weekend in hopes of finding a way to quit their jobs in short order and become full-time real estate entrepreneurs. 

The story of Investor A 

Investor A latches on to a landlording course. He’s attracted to the idea of building wealth and loves the tax-advantaged nature of rental properties. On Monday, he sets out to build a rental empire that will allow him to become financially independent in short order.  

“A” is very successful in finding under-priced rentals in his hometown. His typical deal looks like this:  

ARV:                     $150,000 

Repairs:                $20,000 

Purchase Price:    $85,000 

Rent/mo                $1,200   ... Read More…

Ya'll do realize the irony of asking the question, “I know you’re in a hurry, but is there any quick advice you can give me about how to get started?”, right?

Because I get asked some version of that question at least 100 times a year, always by a newer investor hoping that there's some wisdom I can drop on them in the time it takes to get from the elevator to my car when I'm running from one event to another. Wisdom, preferably, that will make their entry into the business rapid, painless, and above all profitable.

The irony is that there IS no single answer to the question, "How do I get started?".

In order to properly get into that topic, I'd need to know about you: your goals, resources, preferences, exit strategies, needs, wants, and and and...and in no circumstance would that be "quick" advice.

If there were such a thing as "quick" advice, there would be no need for mentoring programs like Fasttrack to Financial Independence. Or, for that matter, for 4-day bootcamps, or REIA groups, or any of the other support systems to which we are all so devoted.

Without knowing anything else about you other than that you don't seem like a crazy stalker who's following me out to my car to kill me, I can only tell you, GENERALLY, some of the things successful people when they get started. I can't tell you what deal to look for (until I know what you plan to do with it) or how to get money (until I know your credit score) or what to pay (until you give me ... Read More…

Does this sound like you? 

• You love going to association meetings and webinars, and hanging out in online fora reading about, asking questions about, and discussing real estate.
• You own several home study courses.
• You’ve been to multiple long-form workshops, seminars, and boot camps.
• You haven’t done a deal. 

If it does, I’ve got some good news and some bad news. 

The good news is, you’re not alone: 80% of all real estate newbies are in exactly this position. The bad news is, 80% of real estate newbies will never get out of this position. 

Now, I’ve never seen an actual study that says that only 20% of people who learn about real estate will ever do anything with that knowledge, but I CAN tell you that it’s a number that’s agreed upon by people who are in a position to observe (and fret about) the phenomenon. 

Group leaders and gurus who’ve been around for a while will tell you the same thing—about 1 out of 5 people who start their real estate education will never take it out into the real world and use it to make money. 

So what do we do with this sobering statistic? 

The first thing we should do is ask, “Why”? What is it that the 20% has or is or does that the other 80% doesn’t? 

Again, there aren’t studies that I know of that explain this, but I have a theory, and it goes like this: 

There are several psychological stages that a new i ... Read More…

An interesting thing happens when people become successful real estate investors:  like any true convert, they start to want to proselytize. And one of the primary characteristics of any good missionary is the desire to emphasize the good and de-emphasize the downsides of one’s religion.

Have you ever noticed that most successful investors remember their early years in real estate as “not that hard”, or “scary, but doable”? Yet if you ask a new investor who’s in the midst of trying to find his first few deals, he’ll more than likely describe this time as “terrifying”, “overwhelming” or “nearly impossible”. 

Remember, dear readers, that your mentors and colleagues are (for the most part) not deceiving you intentionally, unless they’re trying to sell you something. It’s just that they want you to succeed as they’ve succeeded, and that, now that doing deals is second nature, they’ve honestly forgotten a lot of what it was like to struggle in the early years. You may have been guilty of this yourself: I know I’ve been. But unlike most of you, I have a forum from which to atone for my sins of omission. 

So, this one’s for every newbie who thought that he must be stupid for not being able to find a great deal his first week out, and for every old-timer who’s ever forgotten to mention to said newbie that, though a millionaire on paper, he’ ... Read More…

Long, navel-gazing post/manifesto ahead:

Anyone who's started a business will tell you that you HAVE to have a really big "Why"--bigger than 'the money' or the desire to not work for someone else--if you're going to get through all the hard work and disappointments and market cycles and fear.

For some people, it's the desire to spend more time with their children, or to create generational wealth, or to give, financially or in terms of time, in a big way to a cause they’re passionate about.

Since I don’t have children, my big why sort of falls into the latter category, but in a weird way.

I love real estate—it’s interesting, fun, creative, and the learning just never stops (which my ADHD brain loves). It also provides the financial freedom to spend a humongous amount of time on much HARDER thing that’s my real “Why”.

If you haven’t gathered this from talking to me or reading my posts, I’m a huge believer in and advocate for freedom in all of its forms—financial, personal, political, social, whatever.

It’s hard for people to feel, or be, free, or to want real freedom for other people, when they’re struggling financially. There needs to be a base level of financial security before humans can even start to creep out of survival mode and into “Impact” mode and “Betterment” mode.

The way *I* know how to get there, and I know how to CONVEY how to get there, is through owning and providing ... Read More…

I’m very slowly, very painfully, and with a lot of stops and starts, learning something uncomfortable about myself.

In my heart, I’m still the workhorse/get ‘er done/no one can outwork me, person I was 30 years ago.

I’m the one who’s always ready to jump in, take out the trash, move the chairs, stay up all night painting the unit for move-in tomorrow, stay late, handle the problem, make it work if it kills me.

And for a long time, that was a strength. It’s how I built credibility, survived early deals, got experience, and showed everyone that I wasn’t “above” anything and that I was useful.

But here’s the hard truth I keep running up against: that identity, that instinct, is now the thing holding me back.

Because every time I insist on doing work that someone else could do — even when I’m good at it, even when it feels virtuous — I’m stealing time and energy from the work that only I can do.

I have a lot of business (not something I necessarily recommend to others!) and that means a LOT of chances to jump in and fix things and be a team player and prove I’m not stuck up (which was the WORST thing someone could say about you on the Oakley Elementary School playground, and an accusation that still rings in my head lo these may years later).

It’s really, literally painful to think about saying things like, “I’m sorry you don’t have time to show that vacancy ... Read More…

If you got into real estate anytime in the last decade, you’ve spent most of your investing life in a market where prices went up, inventory stayed tight, and competition never really let up.

There are some real advantages to that kind of market. Flips, both wholesale and retail, sell fast. Renters are easy to find, and rents usually climb every year. The headlines are upbeat. Everyone feels smart.

It’s fun to be in the real estate business when the wind is always at your back.

The downside of that kind of market is, of course, that everyone wants to be in it. And that means that great deals are hard to come by.

When homeowners and investors are all racing to buy, prices get pushed up and profit margins get squeezed.

Finding deals that actually pencil out as long-term holds or really profitable flips becomes the hardest, most time-consuming part of the business. We find ourselves doing deals that are pretty marginal—because, well, they keep working out as long as the market stays hot, and prices keep going up.

But the one constant in the real estate market is change…and that’s what we saw in 2025.

Buyers hesitated. Inventory grew. Rents and house prices didn’t.

Logically, most of us get that lower sale prices and flatter rents aren’t a problem as long as purchase prices and payment terms come down even more.

Slower sales and less competition = more motivated sellers.

More motivated sellers = lower prices and better terms. ... Read More…

When I was 2 or 3 years old, my mother took me on trips to the library almost every week. While she checked out the latest mystery novels, I always went to the same shelf in the children’s section and pulled down the same worn, tea-colored book called “I Can’t, Said the Ant.” I must have made my mom check that book out 50 times. I had every word memorized, every illustration emblazoned on my brain, and every character befriended in my daydreams.

In case you missed out on this epic, the basic plot is that a teapot falls off the counter and breaks its spout, and if it isn’t put back up, it will die some horrible teapot death. All of the denizens of the kitchen—from the dinner bell to the pie to the pot—beg the (oddly, single) ant in the kitchen to get the teapot back to the counter and repair the broken spout.

Much rhyming ensues (“I can’t bear it, said the carrot” is one that still sticks with me), and ultimately, the ant, who initially, as you might guess from the title, doesn’t see how he can manage it, rounds up a work crew of insects and rescues the unlucky teapot from the floor.

Yes, this is going somewhere.

To this day, dozens of years later, I still think about that ant and his creative solutions to an impossible task when I think about the people I meet for whom “I can’t” is the final answer and the much smaller group of people I meet for whom “I can’t” is j ... Read More…