My sister texted me on September 28, 2025.

“Call me when you get a chance.”

This isn’t a normal text between my sister and I, so naturally my mind started racing.

Is everyone okay? Did something happen?

I called her back within seconds.

She answered in her usual bubbly voice and immediately asked:

"Should I buy Bitcoin?"

Facepalm.

I thought we had an emergency on our hands.

Maybe for my sister, this actually was an emergency.

At the time, Bitcoin was trading around $120,000.

It was everywhere.

CNBC was talking about it nonstop.

Friends and family were talking about it.

FOMO had fully arrived.

But instead of answering her question directly, I walked her through a simple exercise that you might find useful yourself.

I told her to pull up a 10-year Bitcoin chart.

I asked her:

"Looking at this chart… When do you wish you would've bought Bitcoin?"

Of course, she picked out the major lows.

2016… 2019… and 2023.

Then I told her:

"Now go find the Bitcoin headlines during those periods."

She searched the internet as I waited over the phone.

The results were exactly what you'd expect.

In 2016, Bitcoin headlines were scarce. And what she did find were about exchange failures, hacks, and whether crypto was already dead.

In 2019, headlines were again scarce. And what she could find focused on Bitcoin collapsing, retail investors getting wiped out, and the popping of the crypto bubble.

Then came 2023.

FTX had recently collapsed. Sam Bankman-Fried became the face of crypto fraud. Entire exchanges and lenders were imploding.

The point I was trying to make was that during the three times she wished she bought Bitcoin, either A) nobody was talking about Bitcoin, or B) the headlines surrounding Bitcoin were extremely negative.

That’s usually how great buying opportunities work.

The best time to buy an asset rarely feels good in the moment.

Nobody rings a bell at the bottom.

In fact, the opposite usually happens.

The media stops covering it.

Your friends stop talking about it.

And investors become embarrassed to admit they even own it.

By the time your sister texts you asking whether she should buy Bitcoin… a lot of the easy money has already been made.

That’s human nature.

People become interested in assets after they’ve already gone up. Not before.

And this isn’t unique to Bitcoin.

The same thing happens with stocks, real estate, gold, and virtually every other asset class.

Human beings are wired to chase what is already working.

We feel safest buying when everyone else is buying.

Unfortunately, that’s often when prices are the most expensive.

Hence why my sister texted me in late 2025 instead of 2016, 2019, 2023, or even now.

As I type, Bitcoin has fallen sharply over the last few days and now trades around $67,000.

Down nearly 50% since September.

I’ll be buying more Bitcoin on the pullback.

And I recommend you do, too.

Unsurprisingly though… my sister hasn’t texted me.

So I’ll be a good brother and send her this article.