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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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The “join a hot company” career narrative is getting a lot of PMs into trouble. In Part 2 of our PM Career Framework for AI series, we get practical: how to pick the door that fits you — and spot when a prestigious logo is quietly costing you career momentum. We break down nearly 600 listener questions, then map the first set of doors, from Big Tech and public enterprise to the “quality middle” of elite private companies and recent IPOs.
Key topics
• The “doors” framework: building a personal stack rank
• Golden handcuffs: when staying in Big Tech is rational
• Why L7+ doesn’t translate to startups or AI labs
• The “step down” that’s actually a level up
• How to know if you’re a fit for AI-native companies
• Debunking the myth of “coasting” in Big Tech
• Why APM programs can be the fastest way to learn the craft
• The stay/leave test: can you produce a career story?
• Who is suited to public enterprise tech
• The “quality middle” sweet spot
What’s next (Part 3):
Next episode, we assess the doors everyone’s obsessing over: AI labs (OpenAI / Anthropic), hot AI startups, ex-growth mid-stage companies, and founding. We will also cover why the rules change dramatically once you move into the AI-native part of the market.
Where to find Nikhyl:
Where to find Carly:
Join The Skip:
Find The Skip:
Timestamps
(00:46) The “doors” framework: building a personal stack rank
(11:50) Golden handcuffs: when staying in Big Tech is rational
(17:12) Why promotion often doesn’t translate to your next job
(19:29) The “step down” that’s actually a level up: from learning to teaching
(22:55) How to upgrade your product intuition without quitting your job
(26:23) The Big Tech fit test: why some builders struggle (and some thrive)
(31:03) Early-career exception: why APM programs can accelerate you
(34:26) Career stories: opinion → ship → impact → learning (and how to collect them)
(39:17) Public enterprise tech: when stability + liquidity is the smart move
(42:30) The hard question: are you unlucky, or are you the problem?
(48:44) If your company is behind on AI: be the change agent or move on?
(53:49) The “quality middle” sweet spot: elite teams, near-liquidity, durable brands
(57:55) Domain expertise vs “chasing AI”: where you’ll have the most impact
(62:17) Builder vs fixer: choosing the work you’re actually signing up for
(65:03) Key takeaways + what’s coming in Part 3
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com
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