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Masters of Scale

Asking the uncomfortable questions, w/ Michael Seibel, Y Combinator

Masters of Scale

WaitWhat

Diversity & Inclusion, Jeff Berman, Bob Safian, Startups, Business, Management, Entrepreneurship, Mindset, Reid Hoffman

4.6 β€’ 4.4K Ratings

πŸ—“οΈ 29 June 2021

⏱️ 38 minutes

🧾️ Download transcript

Summary

Barreling full-speed ahead isn't always the key to scale. For Michael Seibel, managing director at Y Combinator and co-founder of Justin.tv and Socialcam, action sometimes needs to take a back seat to asking: "Is this working?" Michael learned early on that by stopping to ask the counterintuitive question, he gained the wisdom – and avoided time lost to big mistakes – that ultimately propelled him forward. At Y Combinator, he's helping other founders ask themselves uncomfortable questions. The answers aren't always obvious, and sometimes they seem downright irrational. But following where they lead, he says, feeds efficiency, confidence, and ambition. That's why the ability to ask the right questions at the right times of the right people is an essential skill for every entrepreneur.

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Transcript

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0:00.0

Hi, it's Bob Safian. You've been hearing me as the host of rapid response in this feed for a few years now,

0:07.8

with short newsy interviews alongside the deeper dives of Masters of Scale. Well, I'm excited to share that rapid response is expanding into its own feed.

0:17.0

We'll be putting out shows twice a week, focusing on the urgent issues that business leaders are dealing with in real time.

0:24.7

So search for rapid response in your podcast player and subscribe to make sure you get all our episodes.

0:31.2

I'll see you on the other side.

0:34.0

Shogun is so interesting because there are all these situations that confront the two main

0:39.9

characters.

0:49.9

Where... characters where they're given two bad options. It's like here are your two two options. There are two items on the menu and they both kind of round to death.

0:57.0

That's Michael Seibel, managing director of Y-Cominator.

1:02.0

You know, the storied Strut of Accelerator that counts AirB&B, Dropbox,

1:06.4

Reddit, and Stripe among its many successful alumni companies. He's talking about one of

1:11.5

his and my favorite novels,

1:13.4

the classic samurai adventure, Shogun.

1:17.0

And the smarter of the two characters, Tornaga,

1:21.2

he always finds a way to introduce the third option, which is like, let's wait.

1:29.2

Let's wait.

1:32.2

How about we wait a day?

1:35.0

Even in the most pressing of circumstances,

1:38.0

Tornaaga takes the time to ask himself this question.

1:42.0

There was some order given for Tornaago to show up and see the

1:45.6

Emperor and then he's going to be killed. And his brother is dispatched I believe to

1:51.2

deliver this order, which I love. That's kind of a shm-y thing. But they're on this

...

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