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MS

Michael Seibel

02/24/23

@ Y Combinator

When someone asks for a deep dive, it often indicates they have underlying concerns about your understanding of the business.

Video

YC

The Hard Conversations Founders Don't Want to Have

@ Y Combinator

The Hard Conversations Founders Don't Want to Have

02/24/23

Related Takeaways

DG

Diane Greene

08/05/17

@ Y Combinator

When seeking investors, it's crucial to find those who deeply understand your business and can provide valuable insights.

JL

Jessica Livingston

06/27/24

@ Lenny's Podcast

Having deep domain expertise is crucial for founders, as it often leads to fewer pivots and a better understanding of the problems they are solving.

PR

Peter Reinhardt

09/06/18

@ Y Combinator

When testing for product-market fit, it's essential to ask customers deep, probing questions to truly understand their problems and needs.

DC

Dalton Caldwell

12/27/24

@ Y Combinator

If your answers to foundational startup questions are complicated, it may indicate a lack of focus; clarity in these areas is essential for progress.

MS

Michael Seibel

02/24/23

@ Y Combinator

In office hours, founders often come with a question that isn't the real issue; the actual question is often about their insecurities and seeking validation.

YC

Y Combinator Cast

09/24/24

@ Y Combinator

If investors are dictating actions to a founder, it indicates a deeper problem within the company structure that needs to be addressed.

YC

Y Combinator Cast

05/21/16

@ Y Combinator

When an investor doesn't understand your business, view it as an opportunity to educate them rather than taking it personally.

MS

Michael Seibel

11/29/18

@ Y Combinator

I often have to ask founders a tough question: why does your company deserve more money after spending 1 to 2 million dollars without finding product-market fit?

IF

Isa Fulford

05/08/25

@ Sequoia Capital

Deep Research begins by asking clarifying questions to ensure it understands the user's request and wants users to provide as much detail as possible upfront to ensure the output meets their expectations.