Does the entry price matter?

By
Apr 29, 2026
/
min read
Category

I keep hearing the same thing over and over again.  

“If the startup becomes huge, the entry valuation doesn’t matter.”

It happened again at a conference I attended recently.
It’s one of those cliches. 

I’m a proud contrarian.
(The other one being you only win or lose when you sell)

But the truth is simple:

When a company becomes a massive winner…
That’s exactly when valuation matters the most.

• A 100x outcome is an investors dream
• A 200x outcome is not just double, it’s a 100 more x

The only difference?
Your entry price.

When the numbers are small, the gap barely moves the needle. A 2x vs. 3x rarely changes anything. 

And if a company folds? 

That’s exactly when the entry price doesn't matter. Your return is zero no matter your entry price.

But when the numbers get big…

Missing an extra 100x is not a rounding error.
It’s a whole different outcome.

Yet for some reason, people flip the logic.

They say the valuation “doesn’t matter” at the very moment it matters most.

What do you think?

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