2 Commas: The $multi-million exit show with Josh Comrie
Oct 7, 2026 · 25 min · 13 segments
A few years ago I bought a new website from a stranger. My own IT company could have built it. They just never told me they did. That small story is the whole problem in miniature. Your customers can…
Josh ComrieHost
So let me get something out of the way up front so that you know that this is actually hard to do.

It's just two very strong forces working on you and both of them feel like virtue.

When someone's been a good customer for years, you start to feel like you owe them something through their loyalty of yours for years.

They backed you, they've paid on time, they've probably even referred you other customers.

And so the idea of turning up and selling them something else could feel a little bit grubby.

But trying to expand an existing account feels like it puts the existing revenue that you have at risk.

So let me get something out of the way up front so that you know that this is actually hard to do.

It's just two very strong forces working on you and both of them feel like virtue.

When someone's been a good customer for years, you start to feel like you owe them something through their loyalty of yours for years.

They backed you, they've paid on time, they've probably even referred you other customers.

And so the idea of turning up and selling them something else could feel a little bit grubby.

But trying to expand an existing account feels like it puts the existing revenue that you have at risk.
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