Building Wealth Through Rental Properties with Joel Miller
Apr 17, 2025
In this episode of the DealQuest Podcast, I'm thrilled to welcome Joel Miller, a seasoned real estate investor who has been investing in rental property since 1978 and flipping houses since 1991. Joel has flipped over 100 houses and is now a hard money lender to other investors. What makes Joel's story particularly fascinating is that he built his real estate portfolio while maintaining a 35-year career as a full-time mobile DJ with 5,051 appearances before retiring from that profession in 2011.
Beyond his impressive real estate achievements, Joel has served in numerous leadership roles in professional and personal circles, teaches real estate investing at both beginner and advanced levels, and is the author of the bestselling book "Build Real Estate Wealth: Enjoy the Journey of Rental Property Investment." Today, we explore Joel's journey from accounting student to real estate investor, discussing everything from buying your first property to hard money lending. Let's dive in!
EARLY EXPERIENCES CAN SHAPE YOUR ENTREPRENEURIAL FUTURE
Joel's path to real estate investing began in his childhood when an investor built four apartment buildings on his paper route at the edge of his subdivision. As a junior high student, Joel found himself fascinated by the rental model, doing the mental calculations in his bedroom: "I see these people are gonna pay the guy that owns this more than it costs him to own it." He stuck that observation in his "back pocket" for the future.
At the same time, Joel developed an interest in being a disc jockey after one of the older kids in the neighborhood built a pirate radio station in their basement where Joel got to hang out. This dual interest shaped his career path – studying accounting in college ("because I knew you could use accounting in any business that you went into"), working at radio stations, and eventually pioneering the mobile DJ business in Northwestern Pennsylvania while simultaneously beginning his real estate investment journey.
Joel's book is written largely for "people who don't think real estate is for them necessarily, or they're wondering how they could add it to something that they already have going, some other business that they're passionate about." His own story demonstrates this approach – maintaining his passion for being a full-time entertainer while building wealth through real estate investments.
JUMP INTO REAL ESTATE WITH YOUR FIRST PROPERTY
Joel's first real estate investment in 1978 was a two-unit property that he immediately converted into three units. "I took one of the bedrooms and made it a bath and ended up with a two bedroom, one bath and a one bedroom efficiency on the first floor." Remarkably, he still owns this property after 47 years, calling it a "cash cow" with three garages behind it.
This property marked not only the beginning of his real estate journey but also taught him an important lesson about finding deals. It was "the first and last property that I ever bought that was listed on the multi-list." Every property he acquired afterward came through off-market deals, though he notes that for some flip properties, he bought at auctions or occasionally had a realtor bring him opportunities.
Joel prepared for his first investment through extensive self-education, reading hardback books by investors like Al Lowry and studying late-night real estate guru tape courses that came with binders and manuals. He would listen to these courses multiple times while driving or at home, taking detailed notes that he organized in a four-inch three-ring binder with 25 different tabbed sections.
EDUCATION IS KEY TO SUCCESSFUL REAL ESTATE INVESTING
Joel's real estate education journey was "nothing like the journey now when we have the internet and all kinds of seminars and conferences and gurus." He spent years reading hardback books by investors like Al Lowry and buying tape courses from late-night real estate gurus "that came in a binder with a manual to follow along while you listen to their cassette tapes."
Joel's dedication to learning was remarkable – he had "shelves full of those things" and still has "about a three or four inch three-ring binder notebook of all the notes that I took while I was listening." He would listen to the courses multiple times while driving or at home, organizing his notes with "about 25 different tabs" for easy reference. This binder was so valuable that Joel referenced it decades later when writing his own book.
His educational journey took a practical turn when his mother found an ad for a resident manager position at an apartment complex. Taking this job simultaneously with purchasing his first property meant Joel "went from zero to 99 units" in a single month – 96 in the complex and 3 in his own building. Though he didn't stay long in that management position (less than a year), it provided valuable experience while he was "building my DJ work and buying my own properties."
BALANCE YOUR PRIMARY CAREER WITH REAL ESTATE INVESTMENTS
One of the most valuable aspects of Joel's story is how he balanced his thriving mobile DJ career with his growing real estate portfolio. As "one of the few full-time professional mobile disc jockeys in this part of the country," Joel had a unique schedule that actually complemented his real estate activities.
Since "the commitments for the DJ work was primarily in the evenings and weekends," Joel had weekdays free to work on properties. He acknowledges that this is different for most people: "I recognize that a lot of people are stuck if they want to keep their career working during the day, during the night. But so they would be forced to do more things in the evening or on the weekends... for messing around with properties, looking at properties, showing properties."
Unlike many investors, Joel chose to self-manage all his properties rather than using third-party management: "I have never used third party management on any of the properties. I've always been able to manage things myself." He describes the process as "a balancing act that you have to figure out for your own life," noting that some investors are "willing to really hit it hard because it's their objective to leave their full-time work ASAP," while others, like himself, maintain their primary career alongside real estate investments.
LEARN FROM BOTH SUCCESS AND FAILURE
While Joel's real estate career has been largely successful, he openly shares his biggest investment mistake: buying into a large commercial property partnership in 1988. The managing partner of an existing partnership had "put this deal together and run the conversion that went on in that building from a department store into an office building," then wanted out. Joel knew all three partners and was asked to replace the managing partner by buying into the partnership.
Within months of joining, disaster struck: "by November, the tenant that had the 51% of the space, in other words, our basically our anchor tenant went bankrupt. And then almost the same month, the restaurant that had another 25% also went bankrupt." This began a ten-year struggle to salvage the investment, which included keeping tenants "under a renegotiated lease," converting the restaurant's banquet space, and eventually "condominium-izing the building" to sell off individual office spaces. The experience was so challenging that Joel "gave my interest to the other two guys just to be out of it."
The silver lining? During this ordeal, Joel met his future wife. One of the tenants was a real estate brokerage where Joel kept an extra set of keys for the building. "The cute blonde that was the keeper of the keys became my wife." Despite this happy outcome, the experience taught Joel valuable lessons about commercial real estate: "with residential, you have little problems all the time... and they're easy to handle... when you have commercial real estate, especially when you have things like anchor tenants... you have no problem at all... And then when you have a problem, you have a big problem."
FOCUS ON YOUR INVESTMENT STRATEGY
Joel's difficult experience with commercial real estate shaped his investment strategy moving forward. Following that challenging deal, he admits: "I actually did not ever pursue commercial real estate after that." This wasn't because he believes commercial real estate is inherently bad, but because he recognized the different risk profiles between commercial and residential investments.
As Joel explains: "I'm not saying, 'Hey, everybody, avoid commercial property.' It's not my message. I'm just saying that that's an example of how something that happens to you with a certain type of property can shape the way you move forward." He adds that he wouldn't have turned down a good commercial opportunity in later years, but "it just didn't end up being my path."
This experience demonstrates how investors develop their personal strategies based on their experiences, skills, and risk tolerance. For Joel, residential properties proved to be the right fit, allowing him to build wealth while still pursuing his passion for entertainment as a DJ. As he notes about his book's focus, it's written for people who want to understand "how they could add it [real estate] to what they've already got going on, like we were talking about earlier."
SHARE YOUR KNOWLEDGE THROUGH TEACHING AND WRITING
When the pandemic hit, Joel had more available time and felt motivated to write his book, "Build Real Estate Wealth: Enjoy the Journey of Rental Property Investment." A significant motivation was his 19-year-old son who had expressed interest in following his path: "considering that he was expressing interest in following in what I had done, a lot of the motivation was to write it for him."
Joel approached writing the book "like I was trying to instruct my son," creating content "in a tender way and in an organized way and a really informative way... the same way that I would want my own kid to learn about how to invest in real estate." The subtitle's emphasis on "enjoying the journey" reflects Joel's philosophy that sustainable success requires finding satisfaction in the process: "if you don't enjoy it, you probably won't stick to it... it's commitment to get you to follow through that will bring you the success."
The book has become known as "the big book on income properties," serving as a comprehensive resource that reviewers say "is not the kind of book that you buy and read and say, 'oh, that was great,' and you put it on your shelf and you never really look at it again. This is the kind of book you buy and you park it on your desk because you're going to keep referring to it." It covers everything from mindset and entity formation to finding deals, managing properties, tax implications, and financial statements. With "over 150 checklists for everything from tenant screening questions to negotiating deals, to doing due diligence on property," it's designed to be a reference guide that readers will continually return to throughout their investment journey.
UNDERSTAND THE MINDSET FOR REAL ESTATE SUCCESS
Joel identifies "three main reasons why people don't invest in rental property," all rooted in mindset. First, "they have some preconceptions of rental property being all about bad tenants and broken toilets." Second, some people have unrealistic expectations, either thinking it's too difficult or too easy: "One person's thinking, 'oh, is all toilets and bad tenants.' And the other person's thinking, 'oh, this is easy... anybody could do this.' And then they get in trouble." Third, "they think they're gonna lose money."
Joel adds a fourth reason that many don't invest: "people think that they don't have the money." He firmly believes this is also a mindset issue, stating: "it's harder to find the deal than it is to find the money. If you can find a deal that makes sense, you will find some way to get the money." His book covers "a whole lot of ways to finance property," from paying cash (including sources people might not realize they have access to, like borrowing against a life insurance policy with cash surrender value) through conventional financing and hard money lending.
For those worried about tenant problems, Joel emphasizes that tenant selection skills dramatically improve the experience: "the better you are at selecting tenants, the better the tenants are." He also stresses that property maintenance doesn't require personal handyman skills – "you don't have to know how to do everything. You just have to know who to call."
LEVERAGE HARD MONEY LENDING FOR FASTER GROWTH
Joel began hard money lending in 2018 after accumulating "a little war chest of money" that he was mainly using himself for deals. He describes it as "actually the best business I've ever been in" because he enjoys "helping the other investors who are earlier in their journey, and providing the funding for their rentals or their flips."
Contrary to the perception that hard money is only for desperate investors, Joel explains: "I would dispute that because I have regular clients now that in many cases could use their own money to do what they're borrowing from me. But it's just their business plan that they want to keep their powder dry... keep some cash on hand for themselves for other things or emergencies."
Joel typically lends under two scenarios: "when the investor is borrowing the money to buy and/or rehab a single family home that they're going to sell to a third party who's gonna live there, which of course is a flip," or "when the investor is borrowing the money to buy and/or rehab a keeper rental property that the bank wouldn't lend on it the way it is." In many cases, he lends "100% of the money to buy the property... and in some cases we're also lending 100% of the rehab money." His loans are typically interest-only with terms of 12-18 months, plus a "six month automatic extension... like a no questions asked" if the project runs over. The primary advantage is avoiding bank underwriting and making cash offers: "we usually close two or three weeks after we even find out about the deal."
BUILD WEALTH THROUGH RELATIONSHIPS, NOT JUST TRANSACTIONS
Throughout the conversation, Joel emphasizes that true wealth comes from relationships, not just financial gains. When asked about what freedom means to him, he defines it as "being able to do what you want, when you want, with who you want, wherever you want, and be a good person when you're doing it." He explains that freedom isn't "taking advantage of everybody else and thinking that in order for you to win, somebody else has to lose."
In his book, Joel discusses "the difference between riches and wealth," explaining that wealth involves giving back to the community: "it's not just accumulating things and not having good relationships." He offers a memorable perspective on priorities: "if I had a choice of losing all my money or losing all of my relationships, I would lose my money in a heartbeat a hundred percent. Because my relationships will help me get my money back. And if I had a lot of money and no relationships, what fun would that be?"
This philosophy extends to his approach to hard money lending, where he builds relationships with borrowers rather than just evaluating deals. Before lending to new investors, Joel wants to "get to know them, see who they're hanging out with... who are they taking the cues from as far as what their business model's gonna be like." He specifically looks for borrowers who have "had some experience, like two or three deals of getting a project across a finish line" and, for landlords, participation in professional organizations. By focusing on relationships, Joel has built a lending business that allows him to help other investors while generating returns.
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FOR MORE ON JOEL MILLER
Joel Miller's LinkedIn
Joel Miller Books
FOR MORE ON COREY KUPFER
Corey Kupfer's LinkedIn
Corey Kupfer's Website
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
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