Why Most People Fail in Real Estate—and How Not to Be One of Them

Don DeRosa

Alright, welcome back to Expert Real Estate Secrets. I’m Don DeRosa, and as always, I’m here with Mia. Today, we’re diving into a topic that, honestly, trips up more investors than anything else—why most people fail in real estate, and how you can avoid being one of ‘em.

Mia Arnold

Hey everyone! I’m Mia, and Don, I gotta say, this is one of those episodes where I wish someone had sat me down and told me the truth when I started. Because, let’s be real, there are so many ways to make money in real estate—wholesaling, flipping, Airbnbs, lease options, you name it. It’s like a giant buffet, and everyone’s piling their plate way too high.

Don DeRosa

Yeah, and that buffet? It’s a trap. I had a student once—let’s call him Mike—who, in his first year, tried wholesaling, then jumped to lease options, then got distracted by Airbnbs, and even dabbled in land deals. Guess how much he made that year? Zero. Not a dime. Because he never stuck with one thing long enough to get good at it.

Mia Arnold

That’s so common. I mean, I get it—there’s this fear of missing out, right? Like, “What if I pick the wrong strategy?” But the truth is, you’re better off picking one and actually mastering it. So, Don, how do you help people figure out which lane to pick?

Don DeRosa

Great question. I always tell folks, ask yourself: What are your strengths? What’s your market like? Do you have time, money, or neither? If you hate talking to people, maybe wholesaling isn’t your thing. If you love numbers and systems, maybe rentals or notes are a better fit. But whatever you pick, stick with it. Don’t try to be a jack of all trades right out of the gate.

Mia Arnold

Yeah, and if you’re listening and feeling overwhelmed, just remember: focus creates momentum. You don’t have to do everything. You just have to do something—consistently.

Mia Arnold

So, let’s talk about the other big reason people fail—inaction. I’ll be the first to admit, I spent months in what I call “learning mode.” I was binging podcasts, reading every book, watching YouTube videos… but I wasn’t actually talking to sellers. I was just, you know, preparing to prepare.

Don DeRosa

Oh, you’re not alone. I see it all the time. People think if they just learn a little more, they’ll finally feel ready. But you never really feel ready. The only way to get comfortable is to get out there and do it. I always say, you can’t learn to swim by reading about it—you gotta get in the water.

Mia Arnold

Exactly! I remember the first time I actually picked up the phone and called a seller. My hands were shaking, my voice was all over the place, but you know what? I survived. And after that, it got easier. So, if you’re stuck in research mode, here’s a challenge: make one direct contact every day. Just one. It could be a call, a text, a DM—whatever feels doable.

Don DeRosa

And if you’re worried about what to say, keep it simple. “Hi, I saw your property at 123 Main Street. Are you open to selling?” That’s it. Don’t overthink it. And yeah, you might get rejected. That’s part of the game. But every ‘no’ gets you closer to a ‘yes.’

Mia Arnold

And honestly, the fear of rejection is way worse in your head than it is in real life. Once you get that first awkward call out of the way, you realize it’s not so bad. Progress over perfection, right?

Don DeRosa

So, let’s put it all together. The real formula for not failing? It’s not magic. It’s focus, action, and support. Pick one strategy, take daily action, and—this is key—find a mentor or a community to keep you accountable.

Mia Arnold

Yeah, and I’ve seen this firsthand in your mentorship group, Don. Remember Sarah? She was brand new, super nervous, but because she had the group checking in on her, she actually closed her first deal in under two months. That accountability made all the difference.

Don DeRosa

Absolutely. And look, sometimes you pick a strategy and it’s just not working. Maybe your market shifts, or you realize it’s not a good fit. That’s okay. But don’t jump ship after a week. Give it a real shot—at least 60 to 90 days. Track your actions, review your results, and if you need to pivot, do it with intention, not out of frustration.

Mia Arnold

And if you’re struggling to stay on track, get an accountability partner. Someone who’ll call you out if you start slacking. Even just texting a friend your daily action can make a huge difference.

Don DeRosa

Yeah, and don’t forget to actually track what you’re doing. Write it down. Numbers don’t lie. If you’re not getting results, look at your activity, not just your outcomes.

Mia Arnold

Alright, let’s talk about setbacks—because, let’s be honest, they’re gonna happen. The key is building resilience. Instead of seeing failure as, well, failure, try to see it as feedback. What can you learn from it?

Don DeRosa

Yeah, I mean, every deal that falls through, every seller that ghosts you, it’s all data. It’s not personal. I always tell my students, set aside time every week to review what worked, what didn’t, and why. That’s how you spot patterns and get better.

Mia Arnold

And don’t forget to celebrate the small wins. Maybe you didn’t close a deal this week, but you made five calls, or you got a seller to actually talk to you. That’s progress. Celebrate it. It keeps you motivated when things get tough.

Don DeRosa

Yeah, and honestly, if you’re not failing at something, you’re probably not pushing hard enough. The people who succeed in this business are the ones who keep going, even when it’s not easy.

Don DeRosa

So, let’s say you’ve got some momentum. You’re closing deals, you’re feeling good. How do you scale without burning out? First, you need a plan. Set clear milestones—like, “I want to close five deals this quarter,” or “I want to add two rentals this year.”

Mia Arnold

And don’t try to do it all yourself. Start building systems—use automation tools for follow-up, lead tracking, even scheduling. That way, you’re not glued to your phone 24/7. Free up your time for the stuff that actually grows your business.

Don DeRosa

Exactly. And as you grow, think about who you need on your team. Maybe it’s a virtual assistant, maybe it’s a contractor, maybe it’s a partner who’s good at the stuff you’re not. The goal is to fill your gaps, not just add bodies.

Mia Arnold

Yeah, and don’t be afraid to invest in people or tools that make your life easier. It’s not about doing more, it’s about doing better.

Mia Arnold

Now, let’s talk about staying ahead of the curve. The best investors I know are obsessed with data. They’re always looking at local market trends—what’s selling, what’s sitting, where are prices moving?

Don DeRosa

Yeah, and you don’t need to be a data scientist. Just start by tracking your own deals. What’s your average days on market? What’s your return on each property? And keep an eye on bigger economic indicators—interest rates, policy changes, stuff like that. It all impacts your strategy.

Mia Arnold

And don’t forget to regularly review your portfolio. Should you hold, sell, or maybe refinance? The market changes, and your plan should too. Stay flexible, and don’t get caught flat-footed.

Don DeRosa

Yeah, and if you’re not sure where to start, just look at your local MLS data, or even free public records. The info is out there—you just gotta use it.

Don DeRosa

Alright, last piece of the puzzle—mindset. I know it sounds a little woo-woo, but honestly, your mindset is what keeps you in the game long-term. I start every day visualizing my goals, practicing gratitude, and reminding myself why I do this.

Mia Arnold

Yeah, and if you catch yourself thinking, “I’m not cut out for this,” or “I’ll never get a deal,” challenge that. Replace it with, “I’m learning every day,” or “I’m getting closer.” It sounds cheesy, but it works.

Don DeRosa

And journaling—don’t underestimate it. Write down your wins, your setbacks, how you felt, what you learned. It helps you see your own growth, and it keeps you honest with yourself.

Mia Arnold

Totally. And remember, this is a marathon, not a sprint. If you keep showing up, keep learning, and keep your head in the right place, you’re already ahead of most people.

Don DeRosa

Alright, that’s a wrap for today. If you got value from this, share it with someone who needs a little push. And if you’re ready to get serious, check out our previous episodes—like the one on the top mistakes new investors make, or how to find deals for free. We’re here every week to help you win.

Mia Arnold

Thanks for hanging out with us. Don, always a pleasure. And to everyone listening, go take that next step—no matter how small. We’ll see you next time!

Don DeRosa

See you, Mia. See you, everyone. Stay focused, stay active, and go make something happen.