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Masters of Scale

When ‘genius’ becomes a trap, with author Ryan Holiday

Masters of Scale

WaitWhat

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

4.64.4K Ratings

🗓️ 30 October 2025

⏱️ 38 minutes

🧾️ Download transcript

Summary

For everyone from Superbowl-winning coaches to CEOs, Ryan Holiday’s writing has made the timeless wisdom of ancient Stoic philosophers accessible and relevant in a modern age. He joins host Jeff Berman to reveal how he scaled his audience at The Daily Stoic and why the four Stoic virtues (courage, discipline, justice and wisdom) feel more important than ever.

Wisdom Takes Work: https://store.dailystoic.com/products/wisdom-takes-work-learn-apply-repeat

Ryan also recommends: https://www.thepaintedporch.com/products/biography17

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Transcript

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0:00.0

If you're a Y-combinator founder hitting Series A, you could be hearing one phrase that keeps stalling big enterprise deals.

0:07.6

We love your product, but we need to see your SOC2 report to make sure our customer data is protected.

0:13.7

Compliance becomes a bottleneck.

0:15.9

But there's a shortcut, AWS.

0:18.7

AWS already maintains SOC2 compliance across more than 100 services, from Cloud Trail to

0:24.8

Security Hub, meaning instead of building it from scratch, you can inherit it and focus on

0:29.8

scaling.

0:30.7

It's the same playbook startups like Supabase and Substack used to unlock enterprise customers

0:35.6

fast.

0:37.0

Turn compliance from a roadblock into a competitive

0:39.6

advantage. Get up to $100,000 in AWS credits and a free SOC2 consult at startups.AWS.

0:49.4

Great leaders, you know, a Lincoln or something assembles a team of rivals versus a team of yes

0:55.1

men. And these are things that we have a lot of precedent over historically. You think you want

1:02.0

freedom of movement and supporters and advocates, but actually what you need is to be challenged,

1:09.7

and you need boundaries and you need is to be challenged, and you need boundaries, and you need limitations.

1:15.6

Ryan Holiday has made it his mission to bring the wisdom of ancient Stoic philosophers,

1:21.8

such as Roman Emperor Marcus Aurelius, into modern life.

1:26.8

Ryan believed the Stoics unlocked the source code for leading a meaningful life,

1:31.2

the four virtues.

1:33.4

We know what courage is, right?

1:35.0

Courage is when you brave danger.

1:37.7

But then what danger?

...

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