Is AI making founders more anxious than ever, even in the heart of Silicon Valley? Behind the optimistic LinkedIn posts and fundraising announcements, some of the most successful people in tech are struggling with burnout and an overwhelming pace of change. So what does it actually take to build a resilient, successful startup in 2026?

In this episode, Yaniv is joined by Jess Mah, serial founder, Y Combinator alum, and venture creation powerhouse behind Mahway. Jess has founded more than 10 companies — collectively valued at over $1 billion — and was the youngest woman ever accepted into Y Combinator.

Fresh from dinners with Fortune 500 CEOs and unicorn founders in San Francisco, she shares what's really happening behind closed doors in the startup world, and why the founders who refuse to get hands-on with AI tools are now at a serious disadvantage.

In this episode, you will:

Discover why experienced, repeat founders are at the highest risk of falling behind in the AI era

Learn Jess's go-to interview question that instantly reveals whether a hire will stay relevant
Understand "role collapse", and what should replace traditional siloed positions when the boundaries between product managers, designers, and engineers break down

Hear why the best founders in 2026 are building clickable prototypes themselves instead of delegating to product teams
Find out why AI has made distribution and competitive moats harder, not easier, and what to do about it
Explore why domain expertise has become the most valuable startup superpower when building is cheap
Get an honest look at the anxiety, burnout, and 996 culture affecting even the top AI founders in the Bay Area
Learn the AI educators and resources Jess and Yaniv personally rely on to stay ahead

Connect with Jess: https://www.linkedin.com/in/jessmah/Resources mentioned in this episode:

Stratechery by Ben Thompson: https://stratechery.com/
Matthew Berman (YouTube): https://www.youtube.com/@matthew_berman
How I AI with Claire Vo: https://www.lennysnewsletter.com/s/how-i-ai
Steve Yegge / Gastown: https://www.linkedin.com/in/steveyegge/
Maven (cohort-based learning): https://maven.com/
Hacker News: https://news.ycombinator.com/

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Key links

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Learn more about Chris and Yaniv

Work 1:1 with Chris: http://chrissaad.com/advisory/

Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/

Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

Intro Voice: Jeremiah Owyang https://web-strategist.com/