Deciding where to invest in real estate can make or break your financial freedom. In this episode of The Rich on Money Podcast, I walk you through a simple but powerful five-level framework for choosing the right market — even if your hometown is overpriced. You’ll learn how to use the 1% rule and 50% rule to instantly gauge whether a property will cash flow, and why “boots on the ground” — either your own or a trusted confidant’s — is the secret weapon most investors overlook.

From expensive markets like San Diego or Honolulu to hidden gems like Montgomery, Alabama, this episode shows you how to build wealth no matter where you live. I’ll break down what makes a city affordable, landlord-friendly, and scalable for long-term success. If you’ve ever wondered “Where should I actually buy my next rental?”, this is your blueprint to stop guessing and start investing like a pro.

Chasing shortcuts to wealth? This episode is your wake-up call. I break down the nine most common “get rich quick” strategies people fall for in investing and real estate—day trading hype, crypto fever, timing the market, no-money-down schemes, wholesaling traps, BRRRR fantasies, syndication hype, and even the sneaky sales pitch of whole life insurance. These approaches sound sexy, but they quietly destroy futures, savings, and relationships. I’ve watched smart people wipe themselves out chasing speed instead of sticking to the simple, proven, boring path to long-term wealth—and I’m here to make sure that’s not you.

If you want real financial freedom instead of YouTube-guru dreams and internet-hustler illusion, listen in. You’ll learn the no-nonsense strategy I’ve used for decades: slow, disciplined investing, index funds, and smart buy-and-hold real estate. This episode will save you from expensive mistakes, protect you from predatory “wealth hacks,” and put you on a path to steady compounding wealth—the same path that actually builds millionaires in the real world. Watch this before you let hype cost you years of your life and thousands of your dollars. Your wallet—and your future self—will thank you.

Most landlords fail at property management because they don’t know what questions to ask—or what red flags to watch for. In this episode, I lay out nine brutally practical tips to stop sucking at property management, drawn from two decades of experience and hard-won lessons from managing 20–30 properties with minimal effort. From understanding fee structures and tenant criteria to reading between the lines on maintenance charges, eviction processes, and referral checks, I explain how to vet a property manager like a pro—and how to catch the warning signs before they start costing you money.

Then, I share how I scaled from six to twenty cash-flowing properties while stationed overseas, using one capable property manager as the backbone of his operation. It’s a masterclass in systems, leverage, and trust—but also a reminder that nobody cares about your properties as much as you do. If you’ve ever wondered how to grow your portfolio without losing control, this episode shows you exactly how to build a team, hold them accountable, and finally make property management work for you—not against you.

Get everything you’ll ever need to manage rentals—in one 27-minute masterclass. I pull back the curtain on my no-nonsense system from 20+ years and 20–30 doors: airtight tenant criteria, bulletproof applications and leases, how to run self-showings safely, verify income and prior rentals, and spot the red flags that wreck cash flow. You’ll learn late-fee discipline that ends chronic lateness, exactly when and how to send pay-or-quit notices, and why an eviction attorney is your secret weapon. I cover move-in checklists, move-out and make-ready (paint, LVP, fixtures, pro cleaning), pet policy, smart rent raises, insurance shopping, practical thoughts on LLCs, clean accounting and paperless records, plus building a fast, fair contractor bench. It’s all tech-enabled, mostly by text, so you stay responsive while protecting your time. Watch once, and you’ll manage better than most “professionals,” keep great tenants longer, and make more money—confident, legal, and in control.

I had a very interesting path from military officer to financial independence. It's definitely not a get rich quick story. It's really a story of making more, spending less, and investing the difference like a boss. I maxed out retirement accounts as well investing wisely and consistently in brokerage accounts and, of course, real estate. Interestingly enough, I paid off my primary residence, and my first 20 investment properties were paid off 15 years into my military career. On one income.

Let's talk through all the ways to legally cheat on your real estate when you sell. I'll cover the capital gains exclusion for primary residences, the 1031 exchange for investment properties, and to top it off, the stepped up basis strategy for paying no taxes on your real estate when you die. We'll also go over truth vs hype when it comes to LLCs!

Here is the entire closing process for a property that is purchased from a realtor's perspective. This goes all the way from making an offer, to a signed purchase contract, to actual closing. We will discuss inspections, title work, appraisal, and everything else along the entire process. You'll understand all the steps necessary to buy or sell a house and you'll probably know more about the process than most realtors do!

Perfect for new or newer realtors, but this is great for anyone.

I talk about the pros and cons of getting your real estate license - becoming a realtor, as a real estate investor. I talk about the costs associated with it, and what I've learned working as a real estate agent and realtor the last two years.

What happens if one of your rental properties catches on fire?

Or in my case, two or three fires over the course of a real estate investing career.

I'll talk about all aspects you need to consider in dealing with the insurance loss of a fire.

From dealing with tenants, renters insurance, your landlord policy, the fire department, and the city permit office. I'll give you everything you need to know to successfully deal with this difficult issue.

Stop getting ripped off by these investment advisors or money managers and their high fees.

I'll teach you about the most common fees they charge. You'll see how paying these fees can result is 7-figure losses over an investment lifetime!

Don't give all that money to a damn investment advisor. You can do it yourself and even make more money.

I'll show you what you should do with your money instead.

These are the 6 dangerous red flags that you must avoid if you are going to make money in real estate investing.

If you want to be a successful landlord, you need to avoid dangerous tenants, and anyone that falls into one of these six categories is a great place to start.

At the end of the day, having good rental criteria is the most important thing for being successful as a landlord.

This list will help you.

Here is the best money advice for teens you can get.

Warren Buffett and the S&P 500 index. That's the secret. I'll show you exactly what to do with that info.

Stay away from the lame hype like day trading and crypto.

Save early and often and retire with millions.

This is just me spouting some stories about various mistakes I've had in my life.

I think of these as some of the best things that have ever happened to me, because I learned from it.

In fact, if anything, I haven't failed enough in life. The most successful people try and fail a lot before they hit the things that work.

This is a podcast episode that is basically a collection of stories from my life.

Some are taken from my time in the military.

While I pretend I'm hoping to draw important lessons from each of these stories, I really just felt like telling these stories.

Who knows, maybe my girlfriend actually listens to these!

When you are newer to real estate, you are often tempted by a number of different strategies out there that are often talked about on podcasts. Somebody made tons of money fast by doing wholesaling, turnkey, flips, section 8, Airbnb, etc.While it's possible to do well in all these, they have their pitfalls for beginners. I'll talk about those pitfalls, as well as tell you what you should actually do as a newbie.

This is episode 7 of the Rich on Money Podcast.I talk about how to get a property rent ready, sometimes called a make ready. I also discuss how to flip a property. I give a lot of practical advise and even discuss the average prices for many big ticket capital expenditures items.

What is the best way to pay contractors who do big jobs?

There are a lot of different approaches to this, and I lay out several different options to consider.

I also talk about various other aspects of working with contractors as a real estate investor.

Don't let contractors take advantage of your inexperience. Find the best way to motivate them to finish your job on time.

I believe that if you figure out how to avoid late payments, you'll avoid most evictions.

I'll walk you through my 3 step process to ensure you avoid evictions.

Of course first you need to have great criteria.

Next you need to keep everyone's emotions in check, including yours.

And lastly, you need to work everything you do in tandem with a great eviction attorney.

I talk through all the different parts of my lease. I talk about clauses I've added and adjusted and why. This will help you understand what kind of things need to be in leases. It should help you develop your own. I'm not trying to sell my lease, but some of you will ask. It's $50. I think it's better for you to talk to an eviction/real estate attorney and use the lease they provide.

I talk about what I consider to be the two most important rules in real estate investing.The 1% rule and the 50% rule. Then I lay out my approach to investing in real estate which is essentially to invest from a financial position of strength and use proven, conservative methods.