All Startup Advice Contradicts Itself

Steve Benjamins
2 min readFeb 13, 2016

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Read enough startup advice and you’ll notice contradictions:

  • Not hiring soon enough is a big mistake (Mark Suster) but don’t be afraid to spend 6 months making your first hire (Brian Chesky).
  • Start a company with mission and purpose (Intercom) and yet remember that startups are like jumping off a cliff and assembling an airplane on the way down (Reid Hoffman).
  • Don’t try to make everyone happy (Forbes) but be sure to listen to customer feedback (Eric Ries).
  • Adhering blindly to a plan is a surefire way to steer a company off a cliff (Richard Branson) and yet don’t let other possibilities or hazy dreams distract you from achieving your goal. (Richard Branson)

… What the hell? Are all these startup gurus dumb?

Nope. Definitely not. (In fact after reading Losing My Virginity I think Branson is a kind of maniac genius.)

Here’s what I think: I think that hard things — such as startups — are usually paradoxical.

Paul Graham says that determination is the most important thing for a founder. He also suggests that a founder have a blurry view of the future. Think about those two statements — Graham is suggesting a founder be determined towards a blurry future. How can you be determined towards a blurry future? Sounds kind of paradoxical right?

The point is to embrace paradoxes and avoid the easy lie that somewhere out there the “right answer” is waiting for you.

This is why Jeff Bezos says that powerful minds can contain powerful inconsistencies. Or why Reid Hoffman says that being a great founder is navigating what is apparent contradictions.

Paradoxes are hard. They make us squirm. They’re uncomfortable. But the ability to face up to and resolve paradoxes is what makes founding a startup hard.

What do you think? Let me know on Hacker News.

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