The Unremarkable Entrepreneur

The Unremarkable Entrepreneur

The 50k Question: Why Most People Never Ask

And What Happened When I Finally Did

Dan Dowman's avatar
Dan Dowman
Nov 19, 2025
∙ Paid

There’s a reason most businesses fail that nobody talks about.

It’s not poor products, positioning, personal brand, bad timing, or a lack of hustle and hard work.

It’s simpler. More devastating. And way more stupid.

We never ask.

On Friday I sat down with my son on my knee and a microphone in my hand.

Because time was (and always is) in short supply, I’d dec…

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