Making Money from Mistakes

How To Turn Mistakes Into Money

Most real estate entrepreneurs are so focused on the next deal and they forget to mine the gold in the last one.

You close. You celebrate. You move on.

But if you don’t extract lessons from that deal, you’re leaving money on the table every single time.

Experience is expensive. If you’re not learning from it, your organization is not getting smarter.

The best tool I’ve found for this is the After-Action Review.  It’s a simple system that comes from the military and it helps your business get smarter every time something goes right, wrong, or sideways.

There are three levels. Each one gives you a different layer of insight. But they all follow the same rule: the lesson isn’t complete until it updates a real process. If it doesn’t change something operational, it wasn’t worth capturing.

Level 1: 10-Second Capture

This is your real-time debrief. A seller just hung up on you. A contractor ghosted. A tenant blew up during a call. You're annoyed, frustrated, maybe even rattled. That's when you stop and ask three questions:

• What just happened?
• Why did it happen that way?
• What should I do differently next time?

No meetings. No spreadsheets. Just raw feedback, fast.

Example: You realize the seller bailed the moment you brought up price without asking about their timeline. Takeaway: lead with questions to understand their situation, then present your offer based on what matters to them.

This step is about pattern recognition and developing the habit of quick reflection.   Most problems in your business don't come from lack of knowledge. They come from repeating the same mistakes without realizing it.

This gives you clarity through repetition, not complexity.    But none of this matters if you don’t implement it.    Find the lowest friction way to document these quick insights.     

Use a note-taking app on your phone, jot down a note in your journal, or (my favorite way) send a Slack message to your Executive Assistant and ask them to capture it.       

Level 2: Deal Review

This is your structured review for completed projects. You just closed a flip, wrapped a marketing campaign, implemented a new software, etc.   Take the time to extract the lessons that will make your team better the next time.   

Your assistant can run this with minimal lift. Start by pulling numbers: budget versus actual, timeline, communication history, cost variances. Then send three questions to anyone involved:

• What exceeded expectations?
• Where did we lose time, money, or energy?
• What’s one change that would prevent most of that next time?

Answers should be short. Fast input, fast review.

Then make sure the lesson updates something real. That’s the entire point. If marketing underperformed, make changes to the data.   If a contractor failed, rewrite the onboarding checklist. If timelines slipped, change the SOP.

If no system gets updated, no lesson was learned. You didn’t grow. You just paid for another round of frustration.

Level 3: Strategic Decision Audit

This one is for big moves. You entered a new market. Hired your first leadership role. Restructured a partnership. Changed your business model.

Ninety days later, audit the decision and repeat every quarter.

Start with your original assumptions. What did you think would happen? What risks did you name? What results did you expect?

Then look at what actually happened. Which risks showed up? What surprised you? Were the outcomes better, worse, or just different than projected?

Now make the call. Double down. Pivot. Shut it down. Document the why. Assign a next step. Lock in a time to review it again.

Example: You entered into a new partnership expecting shared workload, faster growth, and complementary skill sets. Instead, communication has broken down, priorities aren't aligned, and decision-making has stalled.   Decision: pause new joint initiatives and revisit partnership terms. Action: draft a revised scope of roles and expectations, and schedule a reset conversation with clear next steps.

This level prevents months or years of pursuing the wrong course.     

Why This Works

Most people don’t learn from mistakes. They react. Then they repeat.

This fixes that because it forces implementation.

Every insight becomes an update. Every decision leaves a trail. Every error turns into a system fix. That’s how you stop spinning your wheels.

The cycle is simple:

• Structured Reflection

• Extract the lesson

• Update the process
   

Run this consistently and you stop making the same ten thousand dollar mistake every quarter. Your business compounds forward instead of sideways.

Start Where You Are

If you’re overwhelmed, just start with Level 1. Ten seconds. Three questions. Every time something breaks.

If your projects are inconsistent, build in Level 2. Make it part of your closeout process. Let someone on your team own it. 

If you’re making major moves, block one afternoon per quarter for Level 3. Get quiet. Audit your decisions. Adjust before it's too late.

You don’t need all three levels running today. But you need a loop that doesn’t live in your head. Work towards organizing this process into your system (we use ClickUp) to make sure you’re capturing the feedback and implementing it.