#94: How AI is enabling top operators to open-source their expertise | Casey Winters (Co-founder & CEO @ SuperMe, ex-Eventbrite & Pinterest)

Jan 26, 2026

Casey Winters, Co-founder and CEO of SuperMe and former growth lead at Pinterest and Eventbrite, builds AI-native tools to capture how top operators think. He explains interactive AI profiles trained on real artifacts. The conversation covers why nuance moved private, trust and redaction mechanics, automating personal branding, perspective search, and peer learning over traditional mentorship.

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INSIGHT

Perspective Search Replaces Single Answers

SuperMe builds interactive profiles trained on a person's real artifacts so you can 'talk to' an expert's thinking.
Casey calls this 'perspective search' because founders want multiple expert viewpoints, not a single AI answer.

INSIGHT

Expertise Moved Private Because Algorithms Favored Virality

Public platforms rewarded virality over nuance, so top operators moved knowledge into private channels.
That migration created an availability gap for high-quality business judgment on the open internet.

ADVICE

Ground AI Outputs With Source And Human Feedback

Source every AI-generated answer back to the original artifact and show timestamps so users can verify credibility.
Notify and surface conversations to the human so they can correct and improve the AI profile over time.

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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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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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