“The investor’s chief problem—and even his worst enemy—is likely to be himself.”
— Benjamin Graham
Did you know your brain is working against you when you invest?
Most people say they want to buy low and sell high.
But in reality, we do the exact opposite.
We chase what’s already gone up.
Then we panic when things go down.
I’ve seen this over and over again.
I’ve lived it myself.
That’s why psychology is such a huge part of investing.
If you don’t have a system, emotions will run the show every single time.
Today, I want to share the three prompts I personally use before making any investment decision.
These have helped me slow down, think clearly, and avoid costly mistakes.
Let’s get into it.
1. Slow the Brain Down With a Five-Minute Timer
One of the biggest mistakes investors make is moving too fast.
Emotion loves speed.
Clarity loves slowness.
Whenever I’m evaluating a deal, I set a five-minute timer.
Nothing fancy.
Just five minutes to pause.
During that time, I journal.
I ask one simple question:
What is my actual investment thesis here?
Why am I doing this deal?
What outcome am I expecting?
Most people never define success upfront.
And if you don’t define success, you’ll never know if you’ve actually achieved it.
You end up reacting instead of executing.
This is especially dangerous during hype cycles.
I’ve owned silver for years.
I bought it around $15.
At the time of recording this, it’s gone up more than 6x.
Now everyone wants in.
But usually, by the time something feels obvious, the easy money is already gone.
The five-minute timer forces you to step out of FOMO.
It gives your rational brain a chance to catch up.
Research backs this up.
According to behavioral finance studies, slowing decision-making reduces impulsive errors and improves long-term outcomes¹.
That small pause can save you years of regret.
2. Write the Case Against the Deal
This step is just as important—maybe more.
After I write my thesis, I do the opposite.
I write the antithesis.
In plain English:
How could this go wrong?
Where could I lose money?
Every deal has risks.
Pretending otherwise doesn’t make you smart.
It makes you vulnerable.
I’ve made money in deals.
I’ve also lost money.
The losses taught me more than the wins ever did.
When you write down the risks, you take power away from them.
You stop being surprised.
You start being prepared.
I’ll often go a step further and ask the operator directly:
“What do you see as the biggest risk in this deal?”
The answer is often different than what I expected.
That’s valuable.
Another trick I use is sending the operator my full “case against the deal.”
Five reasons I’m hesitant.
Five things that concern me.
A good operator won’t be offended.
They’ll respect the process.
You can even use ChatGPT to help pressure-test your assumptions.
The goal isn’t negativity.
The goal is realism.
History is full of examples where ignoring downside destroyed fortunes.
From tech bubbles to real estate cycles, the pattern is always the same.
Optimism without discipline leads to pain².
3. Create a Must-Be-True List
The final step is my favorite.
I call it the must-be-true list.
These are the assumptions that absolutely must hold for the deal to work.
For example:
Does this deal require rents to grow forever?
Does it assume constant market expansion?
Does it fall apart if interest rates stay high longer than expected?
If one or two assumptions fail, is the deal still okay?
Or does everything collapse?
This exercise exposes fragile deals quickly.
Strong investments can bend without breaking.
Weak ones rely on perfect conditions.
I want to know which one I’m looking at before I wire money.
This framework is especially important today.
A lot of investors are hesitant about multifamily right now.
Some have experienced real pain.
Ironically, that often creates opportunity.
But only if the fundamentals still work.
The must-be-true list forces honesty.
It replaces hope with structure.
And structure is what protects you when markets shift³.
Bringing It All Together
Here’s the full process I use:
Slow down with a five-minute timer.
Define your thesis.
Write the case against the deal.
List what must be true for success.
This doesn’t eliminate risk.
Nothing does.
But it dramatically reduces emotional decision-making.
It keeps you from buying at the top and selling at the bottom.
Most investors don’t fail because they lack intelligence.
They fail because they lack systems.
If you build a process that respects psychology, you give yourself a real edge.
I’d love to hear from you.
How do you stress-test deals?
What lessons have you learned from investments that didn’t go as planned?
Drop your thoughts in the comments and share this with someone who needs to hear it.
If you haven’t already, check out our Investment Club here.
My name is Bronson Hill, Bronson Equity.
My goal is to add value and help you find passive cash flow outside of Wall Street.
Thanks for being here.
Disclaimer: I am not your investment advisor. This is for educational purposes only. I am not giving specific advice on what you can do. I am simply giving my opinions.
Works Cited
- Kahneman, Daniel. Thinking, Fast and Slow. Farrar, Straus and Giroux, 2011.
- Shiller, Robert J. Irrational Exuberance. Princeton University Press, 2015.
- Graham, Benjamin. The Intelligent Investor. Harper Business, 2006.
