Why Flipping Houses Isn’t Always Fast Money
In this episode, we sit down with Josh, a seasoned investor and good friend, to discuss his real-world journey from modular homeownership to flipping houses and building a solid rental portfolio. Starting out in North Dakota, Josh discovered the power of real estate when he turned his home into an income-producing asset by renting out rooms. His story takes us through cold-weather lineman work, flipping massive and often quirky houses, dealing with over-the-top renovation blunders, and the hard lessons learned from high-cost hard money lending. Now operating full-time as a franchisee with Firehouse Subs, Josh offers deep insight into how he balances entrepreneurship with a growing real estate investment portfolio. The conversation is packed with self-managing rental properties, flipping houses for profit, avoiding common investor pitfalls, and maximizing ROI in emerging markets like Memphis real estate.
One of the episode’s standout themes is Josh’s early entry into the real estate investing world through necessity, not strategy. Living in a town with limited rental options, Josh purchased land and a modular home, then generated income by renting out spare bedrooms. This grassroots entry gave him practical experience in cash flow generation, tenant management, and understanding the true potential of residential property as an investment. Josh transitioned into house flipping, and while his early projects yielded quick profits, the challenges of renovation budgeting and timeline control taught him the importance of estimating rehab costs correctly and the dangers of using hard money loans without a backup plan.
Another powerful segment of the episode centers around self-managing rental properties. Josh shares honest reflections about why he manages his Memphis properties remotely from North Dakota and how tools like Apartments.com simplify the entire process. He discusses how managing directly saves thousands annually in property management fees and gives him control over tenant relationships, maintenance, and finances. But this isn’t without its downsides—the phone never stops ringing, and emergencies like burst pipes can turn a profit center into a problem overnight. Yet for Josh, the autonomy and cost savings outweigh the hassle, especially when supported by reliable local contractors.
Finally, we dive into investment strategy and philosophy. Josh discusses why flipping isn’t always the fast-track to wealth and how transitioning to buy-and-hold rentals builds long-term stability. By leveraging the Memphis real estate market—known for its affordability and high rent-to-price ratios—Josh has structured a portfolio that yields strong monthly cash flow and long-term equity. He emphasizes the importance of the 1% rule in quickly vetting deals and explains how treating rental properties like a business, with proper reserve funds and repair oversight, makes the difference between a successful investor and a struggling one.
In this Why Flipping Houses Isn’t Always Fast Money episode:
- Self-Managing from a Distance – Josh explains how he effectively manages multiple properties in Memphis while living in North Dakota. By using modern property management tools and maintaining trusted contractor relationships, he saves significantly on fees and keeps operations streamlined. While the tradeoff includes frequent tenant calls and maintenance coordination, he believes the financial control and direct communication with tenants are well worth it.
- Flipping Isn’t Always Fast Money – While house flipping can be profitable, Josh shares how his first big flip—a sprawling 4,000-square-foot home—was a learning experience in managing timelines, budgets, and surprises. The use of hard money lending added to his stress and cut into profits. Josh now views flips as a way to generate capital, but not a sustainable long-term model without deep planning and risk control.
- Turning Renters into Revenue – Starting out by renting rooms in his own home, Josh turned a necessity into opportunity. That early move taught him about income streams and paved the way for his investment mindset. With later acquisitions, including a five-property package in Memphis, Josh strategically grew his portfolio to include high-yield, low-cost rental properties with long-term tenant potential.
- The Truth About Property Management Companies – Josh pulls no punches when evaluating traditional property managers, calling them “glorified secretaries” who charge hidden fees and often fail to act in the investor’s best interest. His take is backed by firsthand experience, including dodging a $7,000 invoice thanks to a simple breaker flip. His advice: manage your properties like a business, not like a blind investment.
This episode offers a rare blend of humor, honesty, and actionable insight from an investor who’s been there and done that. Josh walks us through his entire evolution—from DIY modular home ownership in North Dakota to flipping rap-star homes in Memphis, and ultimately to building a profitable rental portfolio. Along the way, he outlines the real-world challenges of using hard money loans, the risks and rewards of flipping houses, and the benefits of holding onto rental properties long term. Perhaps the most valuable takeaway is his take on self-management: it’s not for everyone, but the savings and control are real if you’re willing to answer the phone and do the legwork. The episode also emphasizes the critical importance of having an “oh shit” fund, being meticulous about repair bids, and vetting contractors and management partners. Whether you’re new to real estate investing or looking to scale your existing portfolio, this conversation is packed with high-traffic SEO strategies, smart investor tips, and lessons in how to thrive in the Memphis real estate market—one of the most investor-friendly markets in the country.
About 5 O’Clock Somewhere Real Estate Investor Podcast
5 O’Clock Somewhere Real Estate Podcast throws out the script, brings common sense back to real estate, and has casual conversations about the one and only market that matters – Memphis! We’re not interested in what some real estate expert from California has to say because we know the truth: Memphis is where the smart investors put their money. Forget about Vegas, Nashville, and the rest of the country, Memphis is the blue-chip stock of the real estate world. We’ll tell you everything you need to know about why Memphis is the safest and hottest place to buy rental real estate, and how you can be a part of a smart investment.
If you would like to join the conversation, participate in an upcoming recording, or just call to bounce ideas off one of our team, you can call or text us at 901-692-7401. Or if you prefer send us a message.