Brie Wolfson: Learning to Love Flounder Mode from Kevin Kelly (Hyperlegible 013)

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Jul 17, 2025

Brie Wolfson, CMO of Positive Sum and Colossus and co-founder of Stripe Press, shares her journey through 'Flounder Mode,' a playful term for career paths driven by curiosity. She discusses her mentorship experience with Kevin Kelly, exploring his profound influence on her creative journey. Brie reflects on the challenges of navigating a non-linear career while comparing it to her peers' more structured paths. The conversation highlights the importance of storytelling, innovative workplace dynamics, and the value of genuine connections in personal growth.

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ANECDOTE

Origin of "Flounder Mode" Title

Brie credits the editorial team for the catchy title "Flounder Mode," which was originally a joke that stuck.
They initially hesitated to use it but embraced its uniqueness to capture attention.

INSIGHT

Kevin Kelly's Multifaceted Influence

Kevin Kelly is a multifaceted innovator involved in projects spanning Wired magazine to the 10,000-year clock.
His influence extends broadly across tech, culture, and futurism without being center-stage.

ANECDOTE

Brie’s Curiosity Driven Career

Brie’s career at Stripe began in account management but quickly led to diverse, creative opportunities.
Saying "yes" to unusual projects became her retention strategy and way to engage with work she loved.

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How do I introduce Brie Wolfson?

Brie's website – briewolfson.com – is a good place to start. It's a treasure trove. She launched Stripe Press. She started The Kool-Aid Factory. Today, she's the CMO of Positive Sum and Colossus.

And there's so much more! She told a story on The Moth! She's written two novels. Everyone is now obsessed with "taste." Her essay, Notes on Taste, kicked off the craze. She even worked at Dandelion Chocolate just to make something with her hands.

But I'm talking to her today because she wrote a phenomenal, personal, and original essay on her day with Kevin Kelly, who's career is even more varied than Brie's.

She called it Flounder Mode.

Flounder Mode is a way of building a career by following your curiosity. It's winding, weird, and often illegible. I know something about this - I've been in Flounder Mode without having the words for it before reading Brie's essay.

The essay itself is unique. Brie spent a day at Kevin Kelly's house and had the chance to interview her hero. Instead of just writing a bunch of Kevin Kelly quotes, though, she writes about her own career, how odd it feels to be in Flounder Mode when your peers are climbing a sturdy ladder, and how comfortable Kevin Kelly seems to be working this way.

I would never have thought to write this essay this way, but it's perfect. Kevin Kelly has impacted so many peoples' careers. So it's only appropriate that Brie's profile is about how he impacted hers. By putting Kelly's words into the background, she infuses the whole essay with him.

In our conversation, we talk all about how to Flounder Mode, what it feels like, the difference between Flounder Mode and laziness, what it takes to do it well, and much more.

I've been a fan and admirer of Brie's for a long time, and I'm so happy we had a chance to get to chat.

At the end of our conversation, Brie makes a couple of recommendations:

Her favorite of her own essays: Notes on Taste⁠

One essay everyone should read: Being basic as a virtue by Nadia Asparouhova

And she gives a one-sentence takeaway from her time with Kevin Kelly: "Have fun!"

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Big thanks to Jim Portela for editing!