Handling public failure fears

Switching into product can feel like a one-way door, especially if you’re already successful in another function. But for Michael, the path from product marketing to product management wasn’t a leap of faith, it was a series of low-risk experiments, relationship-driven conversations, and intentional “spikes” he could bring to the PM role.

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Michael Chen (former PMM at LinkedIn, Slack, and Asana; now a PM at DoorDash) to break down exactly how he made the transition from marketing into product, and what made it work. They unpack the fears people don’t say out loud (title cuts, failing publicly, losing social capital), why internal moves are often more about timing + business need than a single ask, and how to frame the whole process as an exploration rather than a high-stakes bet.

Michael also shares how his go-to-market and storytelling background has become a real product advantage, especially in areas like pricing & packaging, subscription tiers, and helping customers “see and believe” the value before they ever click buy. If you’re a PMM, marketer, or operator who wants to become a builder, or a PM who wants stronger GTM instincts - this episode is a practical blueprint.

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Interviewing at Uber, Figma, Stripe, or DoorDash?

If you’re a PM preparing for interviews at Uber, Figma, Stripe, and DoorDash… 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:

* (1:30) Why PMM and PM are more cyclical than people think: understand needs → build → educate → drive success

* (3:40) The deeper origin story including consulting + “full brain thinking” + MBA + design/innovation foundation

* (9:16) The real fear: title/trajectory resets are real—acknowledging the risk without over-dramatizing it

* (11:34) Why internal transitions are uniquely de-risked by relationships, subject-matter context, and built-in support systems

* (16:10) The “spikes” framework: you need at least one clear advantage you can carry into PM (domain, customer, research, etc.)

* (22:05) “What if I fail publicly?” Why the stakes felt manageable (supportive manager, exploration mindset)

* (29:15) Treat big career moves as experiments—keep doing it if it works, stop if it doesn’t

* (37:25) How often to “check in” on opportunities

* (41:45) The advantage internal candidates have: tighter line to roadmap + ability to paint vision + make it a no-brainer hire

* (50:07) Switching companies and rebuilding credibility, learning culture, and giving yourself grace in a new environment

* (58:35) Why now is the best time to switch: AI + prototyping tools let customer-adjacent people show what they mean

* (1:03:05) Gratitude corner: Evan (LinkedIn), Ceci (Slack), Lily (Asana) and the “bet on how I think” theme

* And more!

Links:

* Michael Chen: https://www.linkedin.com/in/hashtagmichaelchen/

* Evan Ling: https://www.linkedin.com/in/evanling/

* Cecilia Stallsmith: https://www.linkedin.com/in/cecistallsmith/

* Lili Rachowin: https://www.linkedin.com/in/lilirachowin/

* 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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* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

* Preparing for Meta-style Product Sense & Analytical Thinking interviews? Check out Ben’s AI Practice Copilot for Meta-Style PM Interviews and top-rated Maven course: Product Sense & Analytical Thinking Bootcamp for Meta-Style PM Interviews (selected by Lenny as a top course in product 🔥). Get 25% off the course with promo code `suprainsider` (auto-applied here).

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