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Crazy Idea? How to Make Your Dreams Happen Anyway

Stefan Loble

Stefan doing a dangerous handstand.


When I used to share my idea for starting Bluffworks with friends and acquaintances – before a single pair of pants was ever created – I became accustomed to people reacting in one of two ways:

#1 - Either my idea was insane — too far out there, crazy, bizarre. They’d say things like “Who would ever buy that?”

#2 - Or, it was old news — been done before, just isn’t special. “Don’t pants like that exist, and aren’t they called Dockers?”

But there was one comment that really stuck with me. The conversation went like this:

Me: “I want to make a new kind of wrinkle-free pant that instead of stodgy is really cool, and is so wrinkle resistant it can be worn for multiple days in a row without care.”

My friend: “That’s your idea?”

“Yeah. And I’m super excited about it, too.”

He said, “Do you have another 59 ideas lined up?”

“Huh? No, what do you mean?”

“Well, I read it takes the average entrepreneur 60 tries before they’re successful, so I’m wondering what you plan to do when your first idea fails?”


The thing is, I didn’t have 59 other ideas lined up. Or 59 bank accounts. Or 59 layers of stomach lining to survive the kind of stress it takes to launch a new venture. I was committed to this one.

But I couldn’t help wondering, could he be right? Does feedback like that have merit?

Looking back, I realized that with the rare exception of other entrepreneurs, my friends’ strong reactions weren’t about whether I could make my idea work. Rather, they put themselves in my shoes, to imagine if they could make it work. And when they did, the idea of launching a startup was overwhelming.

Either way, it’s easy to discard their reaction as worthless. But there’s a problem with that too, and it’s that their comments usually contain some kernel of truth...

Consider my friend and the 59 failures. There are a few key messages hidden in what he had to say:

  • Be careful not to wager too much before you’re certain an idea will succeed.
  • If this wasn’t your first startup, you’d make fewer mistakes. (Oh boy, was he right.)
  • When you hit bumps, successful entrepreneurs keep going.

And guess what? All those things are true.

I learned that when people offer feedback, you need to figure out how to hear the pearls of wisdom within what may just seem like criticism or fear. And this isn’t just for business. It’s family, travel, relationships. Any idea people aren’t ready for.

Maybe you want to take a year off to travel. Sail across the ocean. Buy an air ticket with no plans on the other end. Live in a country where you don’t speak the language. All completely possible, and have been done. It’s just whether you’re going to let other people’s fears slow you down.

Whatever your big idea is, only you can know if it’s going to fly.

Good luck… and Bluff On!

Stefan Loble


P.S. Regular Fit Chinos are shipping May 25th. You can order a pair here.


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