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The #1 Reason New Flippers Fail
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The Mistake That Sinks New Investors

The #1 Reason New Flippers Fail
Here’s how to avoid it.
Ask ten new flippers what they're most afraid of and you’ll hear:
“Losing money,” “Buying a bad house,” or the very popular, “Contractors.”
But none of those are the real culprit.
After watching thousands of new investors try (and many fail), the #1 reason new flippers flame out is painfully simple:
They underestimate EVERYTHING.
Costs. Time. Complexity. Stress. Their own limitations. The laws of physics. All of it.
They underestimate the rehab budget because they think YouTube videos count as experience.
They underestimate timelines because on HGTV the house gets finished in 43 minutes including commercials.
They underestimate holding costs because they forget the bank still wants its money even when the project is “almost done.”
They underestimate the emotional toll because no one warned them that the county inspector speaks primarily in riddles.
And then they underestimate the importance of their first deal going well.
It’s amazing how many future empires never get built because Deal #1 took twice as long, cost twice as much, and sold for less than a hearty public apology.
So the solution isn’t complicated.
It just requires humility—something the Greek philosophers praised and new investors avoid like Brussels sprouts.
Let’s break it down.
1. Overestimate Your Rehab Budget (On Purpose)
If your rehab estimate is $40,000, assume $50,000. Or $55,000.
I’ve never seen a beginner say, “Wow, I spent less than I expected.”
Not once.
The house always has secrets.
Roofs leak. Floors sag. Electricians discover wiring that appears to have been installed by raccoons.
Budget the unknowns before they greet you personally.
2. Overestimate Your Timeline
If you think it’s an eight-week project, call it twelve.
Contractors don’t live in linear time.
They operate in what philosophers call “kairos”—the realm of vibes and possibility.
A longer timeline also gives you emotional breathing room.
You’ll be calmer, and calm investors make better decisions.
3. Add Holding Costs Like a Responsible Adult
Mortgage, taxes, insurance, utilities, interest, and donuts for the crew.
You must account for all of it.
Holding costs are silent but deadly—they’re the carbon monoxide of failed flips.
4. Over-communicate With Your Contractor
If you assume anything, you will be wrong.
Write it down.
Confirm it.
Walk the job.
Repeat.
A flipper who skips communication because they “don’t want to bother the contractor” is like a pilot who skips the pre-flight checklist because “the plane looked fine.”
5. Accept That Your First Flip Is an Education
Education is never free.
Whether you spend the money upfront (mentorship, training, preparation)
or during the flip (panic, tears, and extra dumpsters)
you’re going to pay.
Better to invest in preparation than repairs.
6. Remember the Goal: Live to Flip Another Day
The winners in this business aren’t the ones who hit a home run on their first swing.
They’re the ones who didn’t blow up the runway on takeoff.
If your first flip breaks even, that’s a win.
If it makes a little money, that’s a miracle.
If it makes a lot of money, write it down and frame it—you may never see that particular constellation of luck again.
Your real job is to learn, finish, recover, and improve.
Because once you stop underestimating, everything gets easier.
Costs get more accurate.
Timelines get real.
Your confidence grows.
And suddenly flipping isn’t chaos—it’s competence.
Avoid this one mistake, and you’ll be miles ahead of the crowd.
I took my first real estate investing course after I’d already completed 75 flips. I’d made money on all of them and felt pretty good about my skills.
But during that weekend course, I realized I had left money on the table on nearly every deal—mostly because of poor negotiation. When I added it up, it was close to $50,000 I could have earned without hurting anyone.
That’s when I knew I needed to improve. So I spent years reading, studying, practicing, and distilling everything down to a handful of principles I could remember in every conversation.
Side benefit: these skills didn’t just make me better in business. They made me a better husband, dad, and friend. Four simple ideas changed everything.
👉 If you want to learn them too, here’s the Negotiation mini-course — just $19
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