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When is the best time to get started in real estate investing?
"Is the market too hot right now?" "Should I wait until rates come down?" "Is it too late?" You've probably heard variants of thost question, and maybe wondered about them yourself. Each one of those questions really asks the same thing: what is everyone else doing, and is it safe to do that too? That instinct will get you middling results at best. Here's why. 𝗖𝗮𝘀𝗲 𝗶𝗻 𝗽𝗼𝗶𝗻𝘁, 𝗳𝗿𝗼𝗺 𝗮 𝗰𝗼𝗺𝗽𝗹𝗲𝘁𝗲𝗹𝘆 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁 𝗳𝗶𝗲𝗹𝗱: I've been rewarded with a recent pop in the value of my Bitcoin holdings. But, man there times when I was sorely tempted to cash in. All the news stories were negative. Day after day, the value kept dropping. And if felt crazy, but I kept buying. The thing that held me through was simply sticking with my convictions. And so far, so good. That's just what holding through a cycle looks like. Real estate runs on cycles too. Slower and quieter than crypto, but the same psychology. When it feels safe, it's already priced in. By the time the headlines turn positive, you're bidding against everybody else who reads headlines. Competition is what makes a market bad for you. Not interest rates, not the news. Fear thins the field. When everyone's scared, sellers pick up the phone. There are fewer offers on the ugly house. The guys who were in it for easy money are gone. That's not a worse market. That's a market with less traffic. Buffett's line gets quoted wrong. "Be fearful when others are greedy, greedy when others are fearful" isn't about bravery. It's about knowing what something is worth so other people's panic becomes information you can act on instead of a mood you catch. Courage without a number is just gambling with extra steps. Which is the other half of it: Fools rush in. Contrarian doesn't mean buying because it's cheap. It means buying because you ran the numbers, you can defend the price, and the crowd's opinion didn't sway you in either direction. Plenty of people bought the dip on things that kept dipping. The discipline is the whole edge. The contrarian part is just what the discipline looks like from the outside.
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5 Things to Remind Yourself of When You're About to Speak With a Motivated Seller
The call is won or lost in the 60 seconds before you dial or knock. Not in your script. Not in your comps. In your head. Today, as I was putting together content for a website, I pulled out some old testimonials of homeowners I'd helped out of a tough jam back the great mortgage debacle of '08-09. It reminded me that, sure money was made. But lives were made better. Relief, peace of mind and financial stability restored. That's a good thing to remember when meeting with a seller in distress. Lacking a positive self-image about making lowball offers to sellers in a jam can really hang you up. Of course, act ethically, honestly and within the letter of the law. But also don't forget, you're providing cash relief to help somebody out of a tough spot. Here are a few things you can run through before picking up the phone, or knocking the door: 1. NEVER RESCUE YOUR ADVERSARY This is a Jim Camp rule, and it's one of the hardest one to follow as a cash buyer. When a seller goes quiet, when they hesitate, when they say something that hangs in the air... Every instinct you have wants to fill that silence and make it comfortable again. No. That silence is where they're doing the work of deciding. Rescue him from it and you've taken the decision away from him, which means he'll have to make it all over again later. Usually after he's signed. 2. YOU'RE NOT THERE TO STEAL GRANNY'S EQUITY You're there to craft a deal you can both feel good about. If you can't say your offer out loud without flinching, that's not a negotiating problem, it's a conscience problem, and your voice will give you away. Sellers can 𝘴𝘮𝘦𝘭𝘭 it. The investors who last in this business are the ones who never need to talk themselves into their own offers. 3. YOU ARE THE BUYER. NEVER TRY TO SELL YOUR WAY INTO A DEAL The second you start pitching, you've handed over your leverage. Buyers ask. Sellers pitch. Get those backwards and now you're the needy one (another Jim Camp rule, "NO Neediness!), and they'll feel that shift before you finish your sentence.
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How Warren Buffett Would Buy If He Had a Cash House Buying Bidness Today
If Buffett woke up tomorrow with a cash house buying business, a phone, and a list, he wouldn't out-hustle you. He'd out-wait you. That's the whole thing. His edge was never the deals he did. It was the ones he let go by. Today, I saw that principle play out on a land deal I've been working on all summer. It had an encroachment issue that required some diplomacy with a neighbor and a lot of nurturing for all parties involved, including the seller, a local realtor I'm working with, the local real estate closing attorney (It's in North Carolina and I'm in Colorado), a soils engineer... Well it's been quite the cast of characters. And I suppose you could say I'm the director. Long and short is, sometimes patience wins the game. For me, patiently playing every step resulted in a nearly 30% concession on pricing by the seller today. Elsewise, like Warren, I'd have walked. Here's why that holds up in our business and not just his. There are no called strikes. Baseball punishes you for watching. This game doesn't. You can let forty houses go past the plate and your bank balance is identical to where it started. Swing at one bad one and you're eight months deep explaining to your money guy why the sewer scope came back the way it did. The downside isn't symmetrical, so your behavior cannot be either, if you don't want to get kicked off the field. Knowing your numbers isn't just about math. It's at least part, er, shall we say... 𝘤𝘰𝘫𝘰𝘯𝘦𝘴? Anybody can run comps. Almost nobody can hold their number at the kitchen table when the seller pushes back and there's a voice in your head reminding you that you haven't closed anything since April. Running the number is the easy half. Owning it out loud is the part where you earn it. Saying what you want is a filter, not a negotiation. Too often buyers soften the offer before it ever leaves their lips. They pad it, hedge it, apologize for it. That tells you nothing. State it plain and the reaction tells you everything: whether this person is actually motivated, whether they've got a mortgage that makes your number impossible, whether you're the solution or the backup plan. The flinch is information you can't get any other way.
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The 4 Numbers That Beat Every Housing Headline
You've heard "all real estate is local" since day one. It's true. The national median price tells you nothing about what the 3/2 on Elm Street is worth, or whether that seller will take 70 cents on the dollar. Here's the half nobody says out loud. The national picture doesn't set your buy price. It sets how long you're going to own the thing. Which means you can ignore the headlines completely and still get hurt by what's behind them. Right now I've got a chunk of southern Colorado land for sale that's not performing as predicted. We like to see these deals turn in 60 days or less. We're barreling in on our 60th day as I write this, no offers in hand. Not like the land business of just 2-3 years ago when we were flipping deals in a matter of days, 48 hours after listing in one case. Read a sharp breakdown this week where an operator ran three viral "housing depression" claims against the primary sources. All three were technically true. All three fell apart on the trend. → "BIGGEST MONTHLY DROP OF 2026" in pending home sales. Real number: down 5.4% for the month, but only 0.3% year over year, and it was the first decline in five months. It was the biggest drop of the year because it was the only drop of the year. Same window, HousingWire's tracking showed pending single-family sales UP 4.1% year over year. Both sources correct. Different definitions. → "MORTGAGE APPS TANKING, NEAR ALL-TIME LOWS." Purchase applications rose 6% the very next week. The MBA (Mortgage Bankers Association) attributed the dip to the July 4th holiday adjustment. Their economists also noted growing inventory is supporting purchase activity, even at 6.69%. → "DELINQUENCIES AT 4.4%, HIGHEST IN YEARS." True. Also true: conventional loan delinquencies FELL 14 basis points, to 2.75%. The entire increase came from FHA (11.88%) and VA (4.99%), and part of that is an accounting artifact from pandemic-era FHA relief expiring in late 2025. That last one isn't a gotcha. It's a map. WHY THIS MATTERS MORE THAN THE HEADLINE DID
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Building a Reputation as a Professional Cash House Buyer Has Its Rewards
Most new investors think this business is about finding deals. It isn't. It's about becoming the person deals get brought to. You'll go find your first ten. The next hundred find you. The gap between those two phases is called reputation, and it's the only asset in this business that appreciates while you sleep. Here's what nobody tells beginners: in every market there are maybe a dozen buyers who actually close. Everybody else is noise — tire-kickers, retraders, "let me run it by my partner" guys. Sellers can't tell you apart on day one. But agents, title reps, and estate attorneys can. And they talk to each other constantly. Here's how you get on the right list. STEP 1 — PICK A LANE AND SAY IT THE SAME WAY EVERY TIME Beginners describe themselves five different ways in a single week. "I'm a real estate investor" means nothing to a homeowner — and to some of them it sounds predatory. Give them one sentence instead: "I buy houses in [County] with cash, as-is. You don't clean it out, you don't fix anything, and you pick the closing date." Write it down. Use it on the phone, on your card, in your voicemail greeting, on your site. Consistency is the cheapest form of credibility there is. STEP 2 — BUILD YOUR CREDIBILITY PACKET BEFORE YOUR FIRST APPOINTMENT Have this ready before you need it: - Proof of funds letter, current, correct entity name - Your title company or closing attorney, with your rep's direct number - Two or three references (a past seller, your title rep, an agent) - A one-page "here's exactly what happens next" timeline When the seller asks "how do I know you can actually close?" — and they will — you're not stammering. You're handing them paper. Most people you're competing against have none of this. STEP 3 — LEARN TO DEFEND YOUR NUMBER OUT LOUD An offer you can't explain is an offer that sounds like a lowball. Practice saying it: three comps, your repair estimate line by line, holding and closing costs, what's left. Sellers rarely love your number. They respect a number backed by math.
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