Reasonably unreasonable

"Never tell me the odds." – Han Solo, Star Wars.

What are the odds?

Yesterday, I watched my favorite hockey team (the Edmonton Oilers) lose to the Florida Panthers in the Stanley Cup finals.

Every season, all 32 NHL teams have the same goal: "Win the Cup." But only one team can win.

Even a strong team (like the Oilers) has only a ​12% chance of winning.

Put another way: they had an 88% chance of not winning.

What are your odds?

A founder building a new startup also faces daunting odds.

As Jason Cohen ​says​:

"[Startup success] is rare and risky. [Many] people who are equally smart, equally deserving, equally privileged, and work equally hard often don’t make it."

US data shows that only 20–30% of all new businesses are operating and profitable after 5 years.

Why play the game?

Given NHL playoff odds, what drives the Oilers captain, Connor McDavid, to strive for the Cup each year?

Likewise, given your odds of success as an entrepreneur, what should drive you to start companies?

Perhaps it's the same sentiment that drove NBA superstar Michael Jordan:

"I can accept failure; everyone fails at something. But I can't accept not trying."

What increases your odds of success?

I like ​Kevin Smith's answer​:

"[Success] requires a reasonable amount of unreasonability. Not like, "Hey, man. I'm going to jump off a building and fly without the aid of a jetpack." That's unreasonable unreasonability. Reasonable amount is just like, "You know, why not me?"

This is the first attribute: having just enough "unreasonable" belief in yourself.

The second attribute you'll need is similar. I'm going to call it:

"A reasonable amount of relentlessness."

Jason Cohen ​says​, "Before they were successful, every founder started out unsuccessful."

What distinguishes founders who were (finally) able to build a profitable startup? Relentlessness and drive, tempered by realism.

This means you're the kind of person who doggedly pursues a higher goal ("I'm going to build a profitable company to give me and my family a better life"), and you know it might take multiple bets to get there.

Also, these have to be reasonable bets; you can't afford to make bad bets (because every startup costs you time, energy, and money).

Finally, successful founders cultivate the skills, insights, connections, and resources they'll need to give them a shot at success.

So, if you "can't accept not trying," focus on being:

  • Reasonably unreasonable.

  • Relentless, with reasonable bets

  • Someone who collects skills and resources

Cheers,
Justin Jackson

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Published on June 18th, 2025
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