Founder Fit: Vision, Dissatisfaction, and Courage

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If you’re a product leader wondering whether climbing the ladder is still the best path - or sensing a shift in where the real leverage is in the age of AI - this episode will change how you think about your role.

Gokul Rajaram (DoorDash board member, ex-Square, Google, Facebook) joins Marc and Ben for a powerful conversation about why many senior product leaders are stepping back into IC roles—and why that might be the smartest move you can make in today’s tech landscape. They unpack how the AI-native era has redefined leverage, why hands-on experience is critical to building credibility and staying relevant, and how the best PMs are evolving into multi-skilled builders who blend product, design, analytics, and engineering.

They also explore what great product execution looks like today, how to hire (or become) a truly modern product leader, and what to prioritize if you’re joining a breakout company in a fast-moving space.

Whether you’re a CPO, aspiring founder, or senior PM eyeing your next move, this conversation offers deep clarity on navigating your career in the AI era.

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Interviewing at Uber, Figma, or Stripe?

Exciting news! If you’re a PM preparing for interviews at Uber, Figma, or Stripe… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (01:22) Why many product leaders are returning to IC roles in AI-native companies

* (05:05) What founders get wrong when hiring Heads of Product too early

* (09:16) How product execution is evolving: prototypes over PRDs

* (22:15) Building features vs driving measurable customer outcomes

* (28:48) Why most CPO hires fail and how to promote from within instead

* (34:17) How to evaluate which company to join: mission, trajectory, talent density, founder courage

* (43:09) The importance of joining a company with high talent density and visionary leadership

* (51:47) Should you optimize for company moats early on? Gokul’s contrarian take

* (56:06) The power of low ego, high energy, and grabbing work no one else wants

* (1:03:22) Why gratitude fuels energy and career momentum

* And more!

Links:

* Gokul’s X: https://x.com/gokulr

* Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

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