What New Investors Always Get Wrong (But Won’t Admit)
Real estate investing can be a goldmine or a landmine — and it all starts with your mindset. In this candid episode, we sit down with longtime investor Kevin Gaithier, who opens up about his early financial missteps, how he lost $14,000 on a single property, and what he learned that kept him coming back for more. We dive into the biggest mistakes new investors make — and rarely admit — including ignoring real math, relying on hype, and skipping essential reserve planning. Kevin shares his philosophy on long-term investing, avoiding emotional traps, and why having the right team makes investing out of state not just possible, but smart. Whether you’re a first-timer or trying to level up your game, this episode is packed with high-traffic real estate investing insights: from understanding cash-on-cash return to building a proper “Oh Beep” fund to protect your rental portfolio when tenants vanish or properties go sideways. If you’ve been burned, hesitant, or just overwhelmed by it all, this episode delivers the real talk most podcasts skip.
In today’s real estate investment landscape, too many new investors dive in with emotional expectations and seminar fantasies — and that’s exactly how they get burned. Kevin Gaithier shares why the biggest trap is believing you know enough before making a move. The truth? You don’t — but that’s okay. Real estate is a learn-by-doing game. Kevin talks through the evolution of his mindset, how fear almost held him back, and why trusting hype over hard math cost him dearly in his early investments. He explains how to recalibrate your approach with real numbers, smart calculations, and a focus on long-term return instead of short-term wins.
One of the most powerful lessons in this episode is about financial reserves. Most new investors don’t plan for what Kevin calls the “Oh Beep” fund — and that’s why many don’t survive their first bad tenant or surprise repair. He breaks down the importance of allocating for vacancies, maintenance, and capital expenditures, and gives a step-by-step on how he and his wife built six months of reserves per property — a move that saved them in the 2008 crash. This strategy separates professional investors from hopeful dabblers.
Another big takeaway: you don’t need to live near your properties to be successful. Kevin has invested for nearly two decades in Tennessee without stepping foot in any of his homes until recently. Why? Because he built a trustworthy team that includes his agent, property manager, inspector, title officer, lender, and insurance agent. He explains how to “trust but verify,” and how doing your own rent comps and inspections keeps you in control — even from a distance. The Memphis real estate market, with its slow but steady growth, emerges as a blue-chip cash flow rental option for out-of-state investors who want solid, dependable returns.
In this What New Investors Always Get Wrong (But Won’t Admit) episode:
- Emotional Investing Is Killing Your ROI – New investors often let emotions override smart investing. Kevin explains how fear, excitement, and ego lead to poor decisions — from buying the wrong properties to ignoring basic math. Learning to detach emotionally helps you see your investments as business decisions. It’s not about pride, it’s about profit.
- The Power of the “Oh Beep” Fund – Too many investors skip building reserves — until they need them. Kevin lays out why six months of expenses in reserve per property is essential, and how this one habit helped him survive the 2008 crash. He explains how to build your fund over time without cutting into your life or growth.
- Why Cash Flow Beats Hype Every Time – Forget beachfront dreams — your investment should be about what it puts in your pocket. Kevin shares how to use the 1% rule, cash-on-cash return, and hard data to evaluate rental properties. He reveals why markets like Memphis offer solid ROI while overpriced metros fail to deliver real returns.
- Out-of-State Success Depends on Teamwork – Kevin never visited his properties for over 18 years — because he didn’t need to. He built a trusted team of professionals: property managers, lenders, title officers, and inspectors. He talks about how to vet your team and why this makes investing from anywhere not only safe, but scalable.
- Avoiding the Seminar Investor Trap – Real investors do math. Seminar investors chase hype. Kevin breaks down the mentality that leads people to over-leverage, ignore risk, and chase unicorns in bad markets. He offers practical steps to ground your strategy in reality — not just Instagram dreams or PowerPoint promises.
This episode cuts through the hype and sugarcoated nonsense that surrounds real estate investing. Kevin Gaithier offers a no-BS blueprint for real success — built not on speculation, but on preparation. If you’re new to investing or even on your second or third property, this episode is your wake-up call. Investing in real estate isn’t about emotional wins or picture-perfect homes — it’s about smart math, strategic leverage, and surrounding yourself with a team that actually cares.
By walking us through his worst deal (a $14K loss), Kevin teaches the most important lesson: you don’t fail unless you quit. Every hit comes with experience, and that experience builds the kind of investor who doesn’t blink when the market shifts or a tenant trashes a unit. His advice to new investors? Jump in — but do it smart. Build reserves. Know your numbers. Choose properties that meet the 1% rule. And if you’re investing out of state, Memphis remains one of the strongest cash flow real estate markets because of its affordability, stability, and investor-friendly infrastructure.
Don’t wait for perfection. Real estate rewards those who move with intention, not those who hesitate forever. The key isn’t avoiding mistakes — it’s making sure you survive them, learn from them, and use them to build a smarter portfolio. This is the episode that will turn nervous rookies into confident, well-equipped investors.
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.
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