Guide to One Rental at a Time

After spending a decade climbing the corporate ladder and successfully turning $7,000 into nearly $200,000 via aggressively trading tech stocks, I received a rude awakening by heavy losses very quickly. When the dot com bubble burst, I was left holding a portfolio that lost 80% seemingly overnight. This gigantic loss led me to read Rich Dad, Poor Dad, the book that would change my life. At the age of 30, I had never considered owning a rental property, knew nothing about rentals, and had no idea what was ahead, but I now knew I wanted to own at least one property.


I spent the next year consuming dozens of books on the topic and searching for rentals in the Bay Area, as the current wisdom was that you must “own in your backyard.”  Little did we know that there was little cash flow in the Silicon Valley market back then, and when confronted with that fact, we were left with a choice; we could give up, we could go out of state, or we could find a market within driving distance. We found our answer a 2.5 hour drive away, in Fresno, California. After refining a new buy box in Fresno, we bought Norris Drive at the end of 2002, and we were new landlords. If you read my first book, you know that our first tenant was a nightmare, but we pressed on.


I am a huge fan of real estate meetups as opportunities to get in a room and learn from the experts. One of these events with Bruce Norris in 2006 frankly saved our butts. Bruce spoke about the Affordability Index (which I had never heard of before), and it showed us that Fresno was grossly overvalued and set for a fall. This one event set us on a mission to sell all of our houses and 1031 exchange them into multi-family properties. We went from owning 8 to owning 80 doors, and you can get a breakdown of the process in my first book One Rental at a Time.


The Great Recession was in full swing by 2010, and real estate was on sale at below land value in many markets. We were active, but we turbo charged our buying by borrowing private money from friends and family. I was writing a blog about our investing at the time, and it piqued the interest of our friends and family, who started offering to lend us money. During the recession, investors were pulling their money from the market and earned nothing in the banks. We offered our friends and family 10% interest on guaranteed safe and secure properties, and everyone won. Building a reputation and track record allowed us to borrow millions of dollars and pay 10% interest for years!

After over 12 years of living wildly below our means, it was time to smell the roses a little bit. Olivia retired from her day job after we saved her income for a year to prove that we didn’t need it. It is embarrassing to admit that 2015 was the first year that I looked up and realized that the little trickle of cash flow had grown into something bigger. You see, we had been buying dilapidated properties for so long that it was pretty common for us to send in checks to cover remodel bills (for which we budgeted at purchase). In 2015, I remember asking Olivia why we hadn’t written any checks for our last few projects, and she told me that our cash flow covered the remodel. I was shocked! Because she ran the books and I looked for deals, I never thought to stop to look at our growing cash flow.


What a crazy year 2018 was. I can still remember heading to the office in early 2018, looking forward to the new year, only to return home one hour later as a retiree. After a couple weeks of excitement over my newfound freedom, I was left to ponder what exactly to do with my time, and I was getting very depressed.  My whole being and ego was wrapped up in being a hard-charging “Type A personality,” and now that I no longer had the motivating force of a career, I felt increasingly unmoored. I remember sitting at my kitchen table with Olivia thinking, “This sucks! I need to get a job!” Then I remembered what a complete and utter mistake that would be, as so many only dream of being retired at 45. That weekend I decided to launch One Rental at a Time and to start flipping properties by buying run-down slumlord-owned buildings  and creating pride-of-ownership rentals. We successfully flipped over 50 properties into pride-of-ownership rentals, which felt great. I also launched the One Rental at a Time YouTube channel (please like, comment, and subscribe).

If you know me at all, you would know that I have my strengths and some significant weaknesses. One of my weaknesses is writing. To be honest, I find writing not just difficult, but exhausting, as the words smash together and the letters seem jumbled in my head. I share this with you because despite this weakness, I managed to self-publish my first book One Rental at a Time, which became an Amazon Best Seller and has over 1,200 five star reviews. I’ve even had people tell me that the book changed their life, which is amazing to hear. If you own a copy of the book, I would love it if you would take a book selfie and tag me on Instagram! I have a corkboard in my office full of One Rental at a Time book selfies. Seeing that book take off and change lives has been one of the greatest joys of my life.


After the crazy success of One Rental at a Time, I wanted to expand my reach to help more hopeful investors. People were constantly asking me for advice and I could only do so much to assist them. That is when I decided to spend months creating the One Rental at a Time course on Teachable.  This is my no-nonsense, straight-to-the-work course that is helping thousands of investors do the work every day. I have gone on to add bonus sections and additional topics as I work with creators in new areas. All in all, the one thing I am most proud of is the private Facebook group I created for One Rental at a Time students! I originally thought it would become a FAQ repository, but boy was I wrong. It has become the happiest place on the internet, with folks sharing wins, asking questions, and networking. The group is free to join when you buy the course. Just search for the Facebook group titled “One Rental at a Time Works” and request to join.

 I knew great things would come out of my first course How to Get Started, as it gave people the understanding they needed to begin the investment process. However, it is my second course, Get your Money Right, that I am even more proud of. The course is anchored by three themes that were important to us on our journey but didn’t really fit neatly within my first course. It begins with a discussion of “needs” versus “wants,” which is a vital distinction that needs to be made in order to stay focused on understanding where your money goes. From there I try to help the student understand cost discretionary items in “time versus dollar” amount. For example, I explain that a new phone doesn’t cost you $1,000, it costs you 160 hours of working based on your discretionary take-home. Lastly, I ask students to review their lifestyle. I ask them to document their current lifestyle, their “minimum” lifestyle, and their ideal “baller” lifestyle. This is a great family exercise that really sparks conversation and helps students and their families develop a collaborative vision. 

Another amazing personal development in 2021 was the publishing of my second book, 15 Conversations with Real Estate Millionaires. While I was writing it, I had this vision of creating a book that I wished had existed during the first five years of my real estate investing journey. Investing in real estate is amazing, but boy can those first five years really suck while you are learning, making mistakes, and getting only a trickle of cash flow.  I wanted a book that any investor could hold on to and re-read as needed as a reminder that the journey is possible and worth it. I think I crushed it, and in it you will find 15 very different and distinct stories that are worth revisiting time and time again. If you read the book, please leave a 5 star review and take a book selfie. As an added bonus, Dion from Dion Talk did us the pleasure of narrating the audiobook on Audible! I still can’t believe he did that for us, and I am forever grateful! Thank you Dion!

We did something as a community that I had never dreamed of. We hosted the first ever ORaaT Mastermind event, with eight speakers and roughly 200 attendees, where we shared knowledge and answered questions. To everyone’s relief, there was nary a single PowerPoint slide in sight, and 90% of the event was audience driven. This event far exceeded my expectations and its success blew me away. I was so happy that I spent the extra money to record it, and now you too can experience it and see what everyone is raving about.

After returning from a 30 day trip to Southeast Asia, I realized that we are all better together and I need to do a better job of merging my growing Rolodex of experts and my One Rental at a Time family. I plan to host at least one virtual event a month with a capacity of 100 attendees to keep the interaction controlled and valuable for everyone. In addition, I hope to hit 50,000 YouTube Subscribers so we can start planning our Las Vegas Event and celebrate together.