Founder Realities: Trade-offs and Emotional Toll

What if AI didn’t just give you answers—but helped you understand how the best operators actually think?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Casey Winters, former growth leader at Pinterest and Eventbrite, to unpack why he’s building SuperMe, an AI-native professional network designed around perspective, not content or virality.

Casey shares why meaningful expertise has disappeared from public platforms, how knowledge has moved into private networks, and why most AI tools miss the thing people actually want: judgment. The conversation explores how AI can responsibly capture a person’s thinking from real artifacts (conversations, writing, podcasts), how trust and consent must be designed into these systems, and why scaling access to expertise doesn’t mean replacing humans.

They also dive into mentorship, career leverage, and why peer learning often matters more than traditional top-down advice. If you’re a founder, operator, or product leader thinking deeply about AI, knowledge-sharing, and the future of professional networks, this episode offers a thoughtful and opinionated look at what comes next.

Big thanks to Adam Fishman for introducing us to Casey!

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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:

* (01:16) Casey explains SuperMe: an AI-native professional network with interactive profiles trained on your real artifacts (podcasts, docs, notes, etc.)

* (03:31) Why knowledge sharing moved private: algorithms reward virality over nuance, so the best operators stopped posting publicly

* (07:22) Trust mechanics: sourcing, timestamps, attribution, and feedback loops designed to make outputs feel credible

* (09:50) Why “answers” aren’t enough: founders don’t want one right answer—they want how different great people reason

* (12:53) Consent + effort reduction: SuperMe finds insights, redacts, and asks you to approve before adding to your profile

* (16:04) The discomfort factor: why new AI-native products feel “weird” at first—and why normalization takes time

* (24:03) Even top execs need help telling their story—profiles should communicate what you’re actually great at

* (33:26) Mentorship rethought: why “finding a mentor” is often the wrong frame—and why peer learning can be higher leverage

* (36:40) What changes when expertise is searchable: relationships, learning, and access to judgment compound differently

* (49:33) Strategy angle: network effects, defensibility, and why many AI tools are “one-trick ponies” vulnerable to incumbents

* (01:15:52) Casey’s gratitude story: Support system in Kevin Doyle and Apartments.com

* And more!

Links:

* Casey Winters: https://www.linkedin.com/in/caseywinters/

* Casey’s Blog: https://www.caseyaccidental.com/

* SuperMe: https://www.superme.ai/

* Kevin Doyle: https://www.linkedin.com/in/kevindoyle4/

* Michael Ricciardelli: https://www.linkedin.com/in/michaeljricciardelli/

* Cat Lee: https://www.linkedin.com/in/thecatlee/

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

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

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